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Find video protocols related to scientific articles indexed in Pubmed.
Synthesis and biological evaluation of oseltamivir analogues from shikimic acid.
Nat Prod Commun
PUBLISHED: 09-19-2014
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New oseltamivir analogues were designed and synthesized, starting from shikimic acid. Biological evaluation against three human cancer cell lines (KB, MCF7 and Lu-1) showed that many of them exhibited cytotoxic activity. Azides 5 are more active than the corresponding amines 6. Thus, the reduction of the azide group into amine led to the loss of cytotoxicity. The compounds with a cyclohexanemethyloxy group at C-3 were more active than the other investigated compounds belonging to the same series. This cyclohexanemethyloxy group seems to be critical for the cytotoxic activity of this class of compounds. The synthetic oseltamivir analogues 6a-e had no inhibition activity, even at the concentration of 50 microM when they were evaluated for their in vitro influenza A neuraminidase inhibitory activity by an enzymatic assay.
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Two novel iridoids from Morinda longifolia.
Nat Prod Commun
PUBLISHED: 09-19-2014
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Six secondary metabolites, including two novel iridoids, longifolides A (1) and B (2), were isolated by various chromatographic methods from a methanol extract of branches and leaves of Morinda longifolia Craib. The structures of the compounds were determined on the basis of NMR spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY) and FTICR-MS data, as well as by comparison of them with literature values.
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Steroidal Constituents from the Edible Sea Urchin Diadema savignyi Michelin Induce Apoptosis in Human Cancer Cells.
J Med Food
PUBLISHED: 09-12-2014
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Abstract Bioassay-directed fractionation and purification were used to isolate 12 steroids (1-12) from a CH2Cl2 extract of the edible Vietnamese sea urchin Diadema savignyi Michelin. The cytotoxic activity of the CH2Cl2 extract and 12 steroids was evaluated in three human cancer cell lines (HL-60, PC-3, and SNU-C5). Relative to the effects of the positive control, mitoxantrone, the CH2Cl2 extract (with an inhibitory concentration of 50% [IC50] values ranging from 1.37±0.15 to 3.11±0.15 ?g/mL) and compounds 2 (with IC50 values ranging from 5.29±0.11 to 6.80±0.67 ?M) and 11 (with IC50 values ranging from 4.95±0.07 to 6.99±0.28 ?M) exhibited potent cytotoxic effects against all three tested human cancer cell lines. In addition, the CH2Cl2 extract and compounds 2 and 11 were found to induce apoptosis. The induction of apoptosis was accompanied by alterations of the apoptosis-related protein expression, inactivation of ERK1/2 mitogen-activated protein kinase signaling, and decreased c-Myc expression. These data suggest that compounds 2 and 11 from the edible sea urchin D. savignyi may have potential for the treatment of colon cancer, leukemia, and prostate cancer as complementary cancer remedies.
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New isoflavone glycosides from the stems of Dalbergia vietnamensis.
Nat Prod Commun
PUBLISHED: 08-14-2014
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Two new isoflavone glycosides, dalspinosin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1) and caviunin 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), and two known compounds, caviunin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3) and caviunin (4) were isolated from the stems of Dalbergia vietnamensis. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparing with the NMR data reported in the literature.
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Chemical components of Ardisia splendens leaves and their activity against coxsackie A16 viruses.
Nat Prod Commun
PUBLISHED: 07-17-2014
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Using a combination of chromatographic methods, one new flavonol glycoside, myricetin 3,7-di-O-alpha-L-rhamnopyranoside (1), and nine known compounds myricitrin (2), quercetin 3,7-di-O-alpha-L-rhamnopyranoside (3), quercitrin (4), desmanthin-l (5), myricetin 3-O-(3"-O-galloyl)-alpha-L-rhamnopyranoside (6), (+)-catechin (7), benzyl O-1-D-glucopyranoside (8), 2-phenylethyl O-beta-D-glucopyranoside (9), and corilagin (10) were isolated from the leaves of Ardisia splendens Pit. Based on an in vitro test against Coxsackie viruses A16 by SRB assay, only compounds 2, 5, and 10 exhibited activity against Coxsackie viruses A16 with IC50 values of 40.1, 32.2, and 30.5 microM, respectively. This result suggested that compounds 2, 5, and 10 might be potential agents for treating hand, foot and mouth diseases.
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Triterpene saponins from the sea cucumber Stichopus chloronotus.
Nat Prod Commun
PUBLISHED: 07-17-2014
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Sea cucumbers have been used as a dietary delicacy and important ingredient in Asian traditional medicine and functional foods over many centuries. Using combined chromatographic methods, six triterpene saponins (1-6), including a new compound, stichloroside F (1), were isolated from a methanol extract of the sea cucumber Stichopus chloronotus Brandt. Their structures were determined on the basis of spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1lH COSY, ROESY) and FTICR-MS data and by comparison with literature values.
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Endiandric acid analogues from Beilschmiedia ferruginea as dual inhibitors of Bcl-xL/Bak and Mcl-1/Bid interactions.
J. Nat. Prod.
PUBLISHED: 06-05-2014
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A rapid screening by (1)H and (1)H-(13)C HSQC NMR spectroscopy of EtOAc extracts of Endiandra and Beilschmiedia species allowed the selection of Beilschmiedia ferruginea leaves and flowers extract for a chemical investigation, leading to the isolation of 11 new tetracyclic endiandric acid analogues, named ferrugineic acids A-K (1-11). Their structures were determined by 1D and 2D NMR spectroscopic analysis in combination with HRMS data. These compounds were assayed for Bcl-xL and Mcl-1 binding affinities. Ferrugineic acids B, C, and J (2, 3, and 10) exhibited significant binding affinity for both antiapoptotic proteins Bcl-xL (Ki = 19.2, 12.6, and 19.4 ?M, respectively) and Mcl-1 (Ki = 14.0, 13.0, and 5.2 ?M, respectively), and ferrugineic acid D (4) showed only significant inhibiting activity for Mcl-1 (Ki = 5.9 ?M).
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Cytotoxic aryltetralin lignans from fruits of Cleistanthus indochinensis.
Planta Med.
PUBLISHED: 06-04-2014
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Eight new aryltetralin lignans, cleisindosides A-F (1-6), picroburseranin (7), and 7-hydroxypicropolygamain (8), were isolated from the fruits of Cleistanthus indochinensis (Euphorbiaceae). The structures of the isolates were established on the basis of their one- and two-dimensional NMR spectral data, as well as their mass spectrometric data. Compound 7 was found to have potent cytotoxicity against oral epidermoid carcinoma cells with an IC50 value of 0.062 µM, whereas glycosylation to 3 (IC50 7.5 µM) and stereochemical changes to 8 (IC50 10.8 µM) led to marked decreases in biological activity. Thus, it was determined that the C-7 and C-8' positions are critical for the biological activity of the lignans from this plant.
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Styryllactones and acetogenins from the fruits of Goniothalamus macrocalyx.
Nat Prod Commun
PUBLISHED: 05-30-2014
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Two new styryllactones, macrocalactone (1) and 3-deoxycardiobutanolide (2), were isolated from the fruits of Goniothalamus macrocalyx Ban (Annonaceae), together with seven known compounds including four acetogenins, annonacin (3), solamin (4), isoannonacin (5), trans-murisolinone (6), and three other compounds, 7-acetylaltholactone (7), beta-caryophyllene-8R,9R-oxide (8) and 2-(2'-hydroxytetracosanoylamino)-octadecane-1,3,4-triol (9). Their structures were determined by spectroscopic and MS analysis. The absolute configuration of 1 was determined by X-ray crystallographic analysis. The structures of the acetogenins were confirmed by liquid chromatography coupled to a hybrid quadrupole-time of flight mass spectrometer, using post-column lithium infusion. The results were compared with the fragmentation obtained with a hybrid linear trap-orbitrap mass spectrometer. Compound 7 had cytotoxicity against KB, HepG2, Lu, and MCF7 cell lines with IC50 values of 13.1, 23.7, 26.3 and 60.2 microM, respectively, whereas annonacin (3) was selectively active against KB cells (IC50 value of 6.5 microM). The discovery of 3-deoxycardiobutanolide (2) from the fruits of this plant revealed that G. macrocalyx could be a valuable natural resource to obtain this compound as it has been previously reported to have a significant cytotoxicity against different cancer cell lines, especially HL-60 cells.
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Secondary metabolites from Vietnamese marine invertebrates with activity against Trypanosoma brucei and T. cruzi.
Molecules
PUBLISHED: 04-04-2014
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Marine-derived natural products from invertebrates comprise an extremely diverse and promising source of the compounds from a wide variety of structural classes. This study describes the discovery of five marine natural products with activity against Trypanosoma species by natural product library screening using whole cell in vitro assays. We investigated the anti-trypanosomal activity of the extracts from the soft corals and echinoderms living in Vietnamese seas. Of the samples screened, the methanolic extracts of several marine organisms exhibited potent activities against cultures of Trypanosoma brucei and T. cruzi (EC50 < 5.0 ?g/mL). Among the compounds isolated from these extracts, laevigatol B (1) from Lobophytum crassum and L. laevigatum, (24S)-ergost-4-ene-3-one (2) from Sinularia dissecta, astropectenol A (3) from Astropecten polyacanthus, and cholest-8-ene-3?,5?,6?,7?-tetraol (4) from Diadema savignyi showed inhibitory activity against T. brucei with EC50 values ranging from 1.57 ± 0.14 to 14.6 ± 1.36 ?M, relative to the positive control, pentamidine (EC50 = 0.015 ± 0.003 ?M). Laevigatol B (1) and 5?-cholest-8(14)-ene-3?,7?-diol (5) exhibited also significant inhibitory effects on T. cruzi. The cytotoxic activity of the pure compounds on mammalian cells was also assessed and found to be insignificant in all cases. This is the first report on the inhibitory effects of marine organisms collected in Vietnamese seas against Trypanosoma species responsible for neglected tropical diseases.
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Cucurbitane-type triterpene glycosides from the fruits of Momordica charantia.
Nat Prod Commun
PUBLISHED: 04-03-2014
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Four new cucurbitane-type triterpene glycosides, charantosides D-G (1-4) were isolated from a methanol extract of Momordica charantia fruits. The structures of these compounds were determined by chemical and spectroscopic methods to be (19R)-5 beta,19-epoxy-25-methoxycucurbita-6,23-diene-3 beta,19-diol 3-O-beta-D-glucopyranoside, (19R)-5 beta, 19-epoxy-25-methoxycucurbita-6,23-diene-3 beta,19-diol 3-O-beta-D-allopyranoside, 7 beta-methoxycucurbita-5,23E,25-triene-3 beta-ol 3-O-beta-D-allopyranoside, and 3 beta,7 beta-dihydroxycucurbita-5,23E,25-triene- 19-al 3-O-beta-D-allopyranoside.
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New schiartane-type triterpene from Kadsura heteroclita and their cytotoxic activities.
Nat Prod Commun
PUBLISHED: 04-03-2014
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One new schiartane-type triterpene, heteroclitalactone N (1), and four known compounds (2-5), seco-coccinic acid F, dihydroguaiaretic acid, schizanrin F, and kadsuralignan B were isolated from the stems of Kadsura heteroclita. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D-, 2D-NMR, and CD spectra as well as by comparing with the NMR data reported in the literature. The cytotoxic activities of all isolated compounds were evaluated on three human cancer cell lines. Compound 3 exhibited moderate to weak cytotoxic activities on three human cancer cell lines, OVCAR, HT-29, and A-549, with IC50 values ranging from 16.2 to 36.4 microM.
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Anti-influenza sesquiterpene from the roots of Reynoutria japonica.
Nat Prod Commun
PUBLISHED: 04-03-2014
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One new flavonol glycoside, 4'-O-methylmyricitrin 3'-O-beta-D-glucopyranoside (1), one new sesquiterpene, reynoudiol (11), as well as the 12 known compounds (2-10, 12-14) quercetin 3-O-methyl ether (2), quercitrin (3), isorhamnetin 3-alpha-L-rhamnopyranoside (4), tamarixetin 3-alpha-L-rhamnopyranoside (5), myricitrin (6), 4'-O-methylmyricitrin (7), isorhamnetin 3-O-beta-D-xylopyranosyl (1-2)-O-beta- D-glucopyranoside (8), isorhamnetin 3-O-beta- D-apiofuranosyl(1-2)-O-beta- D-glucopyranoside (9), (+)-catechin (10), 7-drimene-3,11,12-triol (12), clovane-2 beta,9 alpha-diol (13), and a-cadinol (14), were isolated from the methanol extract of Reynoutria japonica roots. Based on in vitro screening of the anti-influenza activity of the isolated compounds, reynoudiol showed significantly higher activity than that of oseltamivir phosphate at the same concentration, and did not induce any detectable cytopathic effect in MDCK cells. The CC50 of reynoudiol was above 50 micro M and could inhibit influenza virus infection with an IC50 of 0.29 +/- 0.01 microM. The therapeutic index (TI) of reynoudiol against influenza infection was 172.4, and thus, this compound can be potentially used to treat oseltamivir-resistant influenza virus infection.
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Five new quassinoids and cytotoxic constituents from the roots of Eurycoma longifolia.
Bioorg. Med. Chem. Lett.
PUBLISHED: 03-18-2014
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Eurycoma longifolia has been widely used for various traditional medicinal purposes in South-East Asia. In this study, five new quassinoids, eurylactone E (1), eurylactone F (2), eurylactone G (3), eurycomalide D (4), and eurycomalide E (5), along with ten known quassinoids (6-15) were isolated from the roots of E. longifolia. Their structures were determined by extensive spectroscopic methods, including 1D and 2D NMR, and MS spectra data. Among the isolated compounds, 13?-methyl,21-dihydroeurycomanone (6) has been reported as a synthetic derivative. However, it was isolated from the natural product for the first time in this study. The cytotoxic activities of fifteen compounds were evaluated against human lung cancer cell line, A549 and human cervical cancer cell line, HeLa.
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NF-?B inhibitory activity of polyoxygenated steroids from the Vietnamese soft coral Sarcophyton pauciplicatum.
Bioorg. Med. Chem. Lett.
PUBLISHED: 02-10-2014
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Chromatographic purification of the methanolic extract from the soft coral Sarcophyton pauciplicatum led to the isolation of three polyhydroxylated steroids 1-3, including a new compound, sarcopanol A (1). Their structures were elucidated by spectroscopic analysis and by comparison of the spectroscopic data with those of similar compounds previously reported in literature. The anti-inflammatory effects of isolated compounds were evaluated using nuclear factor kappa B (NF-?B) luciferase and reverse transcription polymerase chain reaction (RT-PCR). The effect of isolated compounds on cell growth was evaluated by MTS assays. Compounds 1 and 2 significantly inhibited TNF?/INF?-induced NF-?B transcriptional activity in human keratinocyte (HaCaT) cells in a dose-dependent manner, with EC50 values of 8.27±3.28 and 26.07±5.59 ?M, respectively. Furthermore, the transcriptional inhibition of these compounds was confirmed by a decrease in cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS), and intercellular adhesion molecule-1 (ICAM-1) gene expression levels in HaCaT cells.
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Triterpenoid saponins from the roots of Rosa rugosa Thunb. as rat intestinal sucrase inhibitors.
Arch. Pharm. Res.
PUBLISHED: 02-07-2014
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Medicinal plants constitute an important source of potential therapeutic agents for diabetes. The purpose of present study is to investigate the effect of root extract of Rosa rugosa Thunb. on inhibition of sucrase related to diabetes mellitus (DM). Bioassay-guided fractionation of the methanol extract led to the identification of 13 triterpenoid saponins (1-13). Their structures were elucidated on the basis of extensive spectroscopic analysis, including 1D, 2D NMR, and MS. The n-butanol fraction showed potent rat intestinal sucrase inhibitory activity with value of 87.62 ± 5.84 % inhibition compared to the positive control acarbose (50.96 ± 2.97 % inhibition at 0.02 mM). Subsequently, compounds 11-13 (1.0 mM) exhibited significant sucrase inhibitory activity, with inhibition percentage values of 41.17 ± 3.52, 46.80 ± 4.00, and 39.39 ± 4.19 %, respectively. Whereas, compounds 2-6, 8, and 10 showed moderate sucrase inhibitory activity (ranging from 13.26 ± 7.00 to 32.08 ± 6.04 % inhibition) at a same concentration. The data provide a starting point for creating new sucrase inhibitors, which may be useful for the development of effective therapies for the treatment of DM.
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Two new neoclerodane diterpenoids from Scutellaria barbata D. Don growing in Vietnam.
J Asian Nat Prod Res
PUBLISHED: 02-05-2014
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Various chromatographic separations of the aerial parts of Scutellaria barbata afforded two new neoclerodane diterpenoids, scutebatas S and T (1 and 2), along with scutebata D (3). Their structures were elucidated by spectroscopic methods including high-resolution electrospray ionization mass spectrometry, 1D and 2D NMR and comparison with the literature values. Compounds 1 and 3 exhibited moderate cytotoxic activities against HL-60 (promyeloblast) human cancer cells. Weak cytotoxic effects toward four tested human cancer cell lines including KB (epidermoid carcinoma), LU-1 (lung adenocarcinoma), MCF7 (breast cancer), and Hep-G2 (hepatoma cancer) were observed for 1 and 3; whereas 2 was inactive on all five tested cell lines.
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Asterosaponins from the Starfish Astropecten monacanthus suppress growth and induce apoptosis in HL-60, PC-3, and SNU-C5 human cancer cell lines.
Biol. Pharm. Bull.
PUBLISHED: 02-05-2014
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Using various chromatographic experiments, six asterosaponins (1-6) were isolated from the MeOH extract of the Vietnamese starfish Astropecten monacanthus. The cytotoxic activities of the MeOH extract and six asterosaponins were evaluated on three human cancer cell lines, HL-60 (promyelocytic leukemia), PC-3 (prostate cancer), and SNU-C5 (colorectal cancer). Relative to the effects of the postitive control mitoxantrone, the MeOH extract (with IC50 values ranging from 0.84±0.03 to 3.96±0.14?µg/mL) and astrosterioside D (5) (with IC50 values ranging from 4.31±0.07 to 5.21±0.15?µM) exhibited potent cytotoxic effects against all three tested human cancer cell lines. In addition, the MeOH extract and astrosterioside D (5) have an effect on leading to apoptosis. Interestingly, the apoptosis of induction was accompanied by down-regulation of phosphatidyl inositol 3-kinase (PI3K)/AKT signaling and extracellular signal-regulated kinase (ERK) 1/2 mitogen-activated protein kinase (MAPK) signaling, and decrease of c-myc expression. Further studies are required to establish use of the asterosaponins from A. monacanthus as remedial and/or nutraceutical purposes.
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Cembranoid diterpenes from the soft coral Lobophytum crassum and their anti-inflammatory activities.
Chem. Pharm. Bull.
PUBLISHED: 02-05-2014
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Nine cembranoid diterpenes 1-9, including four new compounds, crassumols D-G (1-4), were isolated from the methanol extract of the Vietnamese soft coral Lobophytum crassum. Spectroscopic methods were used to elucidate the structures of these compounds. Compound 5 exhibited a potent inhibitory effect on tumor necrosis factor-alpha (TNF?)-induced nuclear factor-kappa B (NF-?B) transcriptional activation in HepG2 cells and significantly inhibited the mRNA expression of cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) in a dose-dependent manner.
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In vitro evaluation of the antioxidant and cytotoxic activities of constituents of the mangrove Lumnitzera racemosa Willd.
Arch. Pharm. Res.
PUBLISHED: 01-28-2014
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This study performed phytochemical and bioactive assessments of the mangrove Lumnitzera racemosa Willd. leaves. Bioassay-guided fractionation of the methanolic extracts led to the identification of thirty-six compounds (1-36), their structures were elucidated using detailed NMR spectroscopic and MS analysis. The extracts, fractions, and the isolated compounds were screened for potential antioxidant and cytotoxic activities. Antioxidant assays were performed using peroxyl radical-scavenging and reducing assays, whereas cytotoxicity was measured using MTT assays in HL-60 and Hel-299 cell lines. The methanolic extract, CH2Cl2 and n-BuOH fractions (10.0 ?g/mL) exhibited potent antioxidant activity, with Trolox equivalent (TE) values of 24.94 ± 0.59, 28.34 ± 0.20, and 27.09 ± 0.37 (?M), respectively. In addition, the isolated compounds exerted cytotoxic effects in a dose-dependent manner; compounds 1 and 14 exhibited the most potent cytotoxicity in HL-60 cells, with IC50 values of 0.15 ± 0.29 and 0.60 ± 0.16 ?M, respectively. To clarify the mechanism(s) behind these cytotoxic effects, we measured the time-dependent changes in apoptotic markers including the condensation and fragmentation of nuclear chromatin, and the downregulation of p-ERK1/2, p-AKT, and c-Myc levels.
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Peroxisome proliferator-activated receptor transactivational effects in HepG2 cells of cembranoids from the soft coral Lobophytum crassum Von Marenzeller.
Arch. Pharm. Res.
PUBLISHED: 01-28-2014
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Peroxisome proliferator-activated receptors (PPARs) are ligand-activated transcription factors that regulate the expression of multiple genes involved in metabolic, anti-inflammatory, and developmental processes. This study evaluated the PPARs transactivational effects of thirteen cembranoid diterpenoids 1-13 from the soft coral Lobophytum crassum, using PPAR-responsive elements-luciferase reporter and GAL4-PPAR chimera assays. All isolated compounds activated the transcription of PPARs in a dose-dependent manner, with EC50 values ranging from 2.07 ± 1.73 to 130.20 ± 1.85 ?M. Moreover, compounds 6-9 affected the transactivation of all three PPAR types, PPAR?, ?, ?(?), in a dose-dependent manner, with EC50 values in a ranging from 11.92 ± 1.23 to 122.50 ± 2.12 ?M. These results provide a scientific rationale for further studies on the soft coral L. crassum and its diterpenoid constituents to develop medicinal products against inflammatory and metabolic diseases.
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Rat intestinal sucrase inhibition of constituents from the roots of Rosa rugosa Thunb.
Bioorg. Med. Chem. Lett.
PUBLISHED: 01-03-2014
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A new octanordammarane triterpene, 3?,15?-dihydroxymansumbinol (1) and a novel A-ring contracted oleanane triterpenoid, 2-formyl-(A)1-19?-hydroxy-1-norolean-2,12-dien-28-oic acid (2) were isolated from the roots extract of Rosa rugosa along with fifteen known compounds (3-17). Their structures were elucidated by extensive spectroscopic analysis, including 1D and 2D NMR, and FTICRMS. The MeOH extract, as well as CH2Cl2 and EtOAc fractions at a concentration of 0.5mg/mL showed potent sucrase inhibitory activity, with inhibition percentage values of 84.67±5.37%, 87.50±2.78%, and 81.91±2.90%, respectively. In addition, compounds 7-13 (1.0 mM) showed potent sucrase inhibitory activity (61.88±3.19% to 84.70±3.07% inhibition), which was comparable to that of the positive control, acarbose, with an inhibition percentage value of 50.96±2.97%. Compounds 1, 2, 4, and 14-17 showed moderate and/or weak inhibitory activities at the same concentration. The ?-glucosidase inhibitory activities of the extracts and purified compounds may provide a novel opportunity to develop a new class of antidiabetic agents.
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Biscembranoids from the marine sponge Petrosia nigricans.
Nat Prod Commun
PUBLISHED: 11-27-2013
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One new biscembranoid, petronigrione (1), and five known compounds, methyl tortuoate B (2), lobophytone U (3), lobophytone H (4), (24S)-ergostane 3beta, 5alpha, 6beta, 25 tetraol-25-monoacetate (5), and (24S)-ergostane-1beta, 3beta, 5alpha, 6beta, 25-pentaol-25-monoacetate (6), were isolated from the methanol extract of the marine sponge Petrosia nigricans. Their structures were established on the basis of spectral and chemical evidence. The cytotoxicity of all compounds was evaluated by MTT assay on four human cancer cell lines, HepG2, KB, LU-1, and MCF-7. Compounds 1 and 2 exhibited moderate cytotoxic activities on the four human cancer cell lines with IC50 values ranging of 20.7 - 28.9 microg/mL.
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New anti-inflammatory cembranoid diterpenoids from the Vietnamese soft coral Lobophytum crassum.
Bioorg. Med. Chem. Lett.
PUBLISHED: 10-13-2013
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Four new cembranoid diterpenes lobocrasols A-D (1-4), were isolated from the methanol extract of the soft coral Lobophytum crassum. Their structures were elucidated by spectroscopic analysis and by comparison of the spectroscopic data with those of similar compounds previously reported in literature. The anti-inflammatory effects of isolated compounds were evaluated using NF-?B luciferase and reverse transcription polymerase chain reaction (RT-PCR). Compounds 1 and 2 significantly inhibited TNF?-induced NF-?B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values of 6.30±0.42 and 6.63±0.11?M, respectively. Furthermore, the transcriptional inhibition of these compounds was confirmed by a decrease in cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) gene expression levels in HepG2 cells.
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Steroidal constituents from the starfish Astropecten polyacanthus and their anticancer effects.
Chem. Pharm. Bull.
PUBLISHED: 10-04-2013
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Using various chromatographic methods, four new steroids, astropectenols A-D (1-4), along with three known compounds (5-7) were isolated from a methanol extract of the starfish Astropecten polyacanthus. The structure elucidation was confirmed by spectroscopic methods, including one dimensional (1D)-, 2D-NMR and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS). The CH2Cl2 fraction and compound 7 exhibit potent cytotoxic effects against HL-60 human leukemia cells with the IC50 of 8.29 µg/mL and 2.70 µM, respectively, comparing to the positive control, mitoxantrone (IC50=6.80 µM). When HL-60 cells were treated with the CH?Cl? fraction or compound 7, several apoptosis events like chromatin condensation and the increase of the population of sub-G1 hypodiploid cells were observed. Investigations for the possible mechanism underlying the induction of apoptosis showed that CH?Cl? fraction or compound 7 induced apoptosis through down-regulation of Bcl-2, up-regulation of Bax, cleavage of caspase-9, cleavage of caspase-3 and cleavage of poly(ADP-ribose) polymerase (PARP) in HL-60 cells. Furthermore, the apoptosis induction of HL-60 cell by CH?Cl? fraction or compound 7 was attended by the decreasing of phospho-extracellular signal-regulated kinase (ERK) 1/2 and C-myc. These results indicated that the CH?Cl? fraction and compound 7 could induce the apoptosis of HL-60 cells via the inactivation of ERK 1/2 and the decrease of C-myc. Our finding suggested the potential using of the CH?Cl? fraction and compound 7 for leukemia treatment.
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Anti-inflammatory asterosaponins from the starfish Astropecten monacanthus.
J. Nat. Prod.
PUBLISHED: 09-18-2013
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Four new asterosaponins, astrosteriosides A-D (1-3 and 5), and two known compounds, psilasteroside (4) and marthasteroside B (6), were isolated from the MeOH extract of the edible Vietnamese starfish Astropecten monacanthus. Their structures were elucidated by chemical and spectroscopic methods including FTICRMS and 1D and 2D NMR experiments. The effects of the extracts and isolated compounds on pro-inflammatory cytokines were evaluated by measuring the production of IL-12 p40, IL-6, and TNF-? in LPS-stimulated bone marrow-derived dendritic cells. Compounds 1, 5, and 6 exhibited potent anti-inflammatory activity comparable to that of the positive control. Further studies are required to confirm efficacy in vivo and the mechanism of effects. Such potent anti-inflammatory activities render compounds 1, 5, and 6 important materials for further applications including complementary inflammation remedies and/or functional foods and nutraceuticals.
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Inhibitors of ?-glucosidase and ?-amylase from Cyperus rotundus.
Pharm Biol
PUBLISHED: 09-18-2013
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Abstract Context: A methanol extract of Cyperus rotundus L. (Cyperaceae) rhizomes showed inhibitory activity against ?-glucosidase and ?-amylase, two enzymes involve in carbohydrate digestion. Objective: Identification of compounds from C. rotundus rhizomes responsible for the inhibition of ?-glucosidase and ?-amylase. Materials and methods: Compounds were identified by a phytochemical investigation using combined chromatographic and spectroscopic methods. ?-glucosidase and ?-amylase inhibitory activities were evaluated by in vitro enzyme inhibition assays. Results: A new (2RS,3SR)-3,4,5,6,7,8-hexahydroxyflavane (1), together with three known stilbene dimers cassigarol E (2), scirpusin A (3) and B (4) were isolated. Compound 2 inhibited both ?-glucosidase and ?-amylase activities while the flavane 1 only showed effect on ?-amylase, and compounds 3 and 4 were active on ?-glucosidase. All four compounds showed significant 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity. Discussion: The inhibitory activities against ?-amylase and ?-glucosidase of the C. rotundus rhizomes were reported for the first time. Stilbene dimers are considered as potent inhibitors of ?-glucosidase and promising antihyperglycemic agents. Conclusion: The isolated compounds may contribute to the antidiabetic property of C. rotundus.
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Muurolane-type sesquiterpenes from marine sponge Dysidea cinerea.
Magn Reson Chem
PUBLISHED: 08-06-2013
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Seven new muurolane-type sesquiterpenes, (4R,5R)-muurol-1(6),10(14)-diene-4,5-diol (1), (4R,5R)-muurol-1(6)-ene-4,5-diol (2), (4R,5R,10R)-10-methoxymuurol-1(6)-ene-4,5-diol (3), (4S)-4-hydroxy-1,10-seco-muurol-5-ene-1,10-dione (4), (4R)-4-hydroxy-1,10-seco-muurol-5-ene-1,10-dione (5), (6S,10S)-6,10-dihydroxy-7,8-seco-2,8-cyclo-muurol-4(5),7(11)-diene-12-oic acid (6), and (6R,10S)-6,10-dihydroxy-7,8-seco-2,8-cyclo-muurol-4(5),7(11)-diene-12-oic acid (7) were isolated from the marine sponge Dysidea cinerea. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D-NMR, 2D-NMR, and CD spectra as well as by comparing the NMR data with those reported in the literature. Copyright © 2013 John Wiley & Sons, Ltd.
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Antifouling 26,27-cyclosterols from the Vietnamese marine sponge Xestospongia testudinaria.
J. Nat. Prod.
PUBLISHED: 07-05-2013
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Three new C29 sterols with a cyclopropane ring cyclized between C-26 and C-27 of the side chain, aragusterol I (1), 21-O-octadecanoyl-xestokerol A (4), and 7?-hydroxypetrosterol (5b), were isolated from the Vietnamese marine sponge Xestospongia testudinaria, along with the known compounds, aragusterol B (2), xestokerol A (3), 7?-hydroxypetrosterol (5a), 7-oxopetrosterol (6), and petrosterol (7). The structures of the new compounds were established by analysis of spectroscopic data including 1D and 2D NMR, and high-resolution electrospray ionization mass spectrometry (HRESIMS). Their capacity to inhibit the adhesion of isolated bacteria from marine biofilms was evaluated against the bacterial strains Pseudoalteromonas sp. D41, Pseudoalteromonas sp. TC8, and Polaribacter sp. TC5. Aragusterol B (2) and 21-O-octadecanoyl-xestokerol A (4) exhibited the most potent antifouling activity with EC50 values close to these reported in the literature for tributyltin oxide, a marine anti-biofouling agent now considered to be a severe marine pollutant. Due to its comparable activity to tributyltin oxide and its absence of toxicity, the new 26,27-cyclosterol, 21-O-octadecanoyl-xestokerol A (4) constitutes a promising scaffold for further investigations.
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Inhibition of NF-?B transcriptional activation in HepG2 cells by diterpenoids from the soft coral Sinularia maxima.
Arch. Pharm. Res.
PUBLISHED: 06-28-2013
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Anti-inflammatory transcriptional effects of nineteen compounds (1-19) from the soft coral Sinularia maxima were evaluated using NF-?B luciferase and reverse transcriptase polymerase chain reaction. Compounds 1, 2, 4, 8, 15, 17, and 18 significantly inhibited TNF?-induced NF-?B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 15.81 ± 2.29 to 29.10 ± 1.54 ?M. Furthermore, the transcriptional inhibitory function of these compounds was confirmed by a decrease in intercellular adhesion molecule-1 and inducible nitric oxide synthase gene expression levels in HepG2 cells. These results provide a scientific rationale for the use of the soft coral S. maxima warrant further studies to develop new agents for the prevention and treatment of inflammatory.
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Anti-inflammatory components of the starfish Astropecten polyacanthus.
Mar Drugs
PUBLISHED: 06-20-2013
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Inflammation is important in biomedical research, because it plays a key role in inflammatory diseases including rheumatoid arthritis and other forms of arthritis, diabetes, heart disease, irritable bowel syndrome, Alzheimers disease, Parkinsons disease, allergies, asthma, and even cancer. In the present study, we describe the inhibitory effect of crude extracts and steroids isolated from the starfish Astropecten polyacanthus on pro-inflammatory cytokine (Interleukin-12 (IL-12) p40, interleukin-6 (IL-6), and tumor necrosis factor ? (TNF-?)) production in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs). Among those tested, compounds 5 and 7 showed potent inhibitory effects on the production of all three pro-inflammatory cytokines with IC50 values ranging from 1.82 ± 0.11 to 7.00 ± 0.16 ?M. Potent inhibitory activities were also observed for compound 1 on the production of IL-12 p40 and IL-6 with values of 3.96 ± 0.12 and 4.07 ± 0.13 ?M, respectively, and for compounds 3 and 4 on the production of IL-12 p40 with values of 6.55 ± 0.18 and 5.06 ± 0.16 ?M, respectively. Moreover, compounds 2 (IC50 = 34.86 ± 0.31 ?M) and 6 (IC50 = 79.05 ± 2.05 ?M) exhibited moderate inhibitory effects on the production of IL-12 p40, whereas compounds 3 (IC50 = 22.80 ± 0.21 ?M) and 4 (IC50 = 16.73 ± 0.25 ?M) moderately inhibited the production of TNF-? and IL-6, respectively.
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Inhibitory effects of oleanane-type triterpenes and saponins from the stem bark of Kalopanax pictus on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells.
Arch. Pharm. Res.
PUBLISHED: 02-27-2013
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Kalopanax pictus (Araliaceae) is a deciduous tree distributed in Korea, Japan, and China. The stem bark of K. pictus has been functionally used as a traditional crude drug for the treatment of various inflammatory diseases. In the present study, we describe the inhibitory effects of oleanane-type triterpenes and saponins isolated from the stem bark of K. pictus on production of pro-inflammatory cytokines in LPS-stimulated bone marrow-derived dendritic cells. Of the compounds tested, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3?,6?,23-trihydroxyolean-12-en-28-oic acid 28-O-?-D-glucopyranoside (3), nipponogenin E (6), 3?,6?,23-trihydroxyolean-12-en-28-oic acid (7), and caulophyllogenin (19) significantly inhibited the production of IL-12 p40 and IL-6 with IC50 values ranging from 3.3 to 9.1 ?M. Compounds 2, 3, 7, and 19 significantly suppressed the secretion of TNF-? with IC50 ranging from 8.8 to 20.0 ?M. These data provide scientific support for the use of K. pictus stem bark and its triterpene and saponin components in the inhibition of pro-inflammatory cytokine secretion, including IL-12 p40, IL-6, and TNF-?, and for prevention and treatment of inflammatory diseases.
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Pyrrole and furan oligoglycosides from the starfish Asterina batheri and their inhibitory effect on the production of pro-inflammatory cytokines in lipopolysaccharide-stimulated bone marrow-derived dendritic cells.
Bioorg. Med. Chem. Lett.
PUBLISHED: 01-04-2013
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Three new pyrrole oligoglycosides, astebatheriosides A-C (1-3), and a new furan oligoglycoside, astebatherioside D (4), were isolated from the starfish Asterina batheri by various chromatographic methods. Their structures were elucidated by spectroscopic and chemical methods. Compounds 2, 3, and 4 moderately inhibited IL-12 p40 production in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs) with IC50 values of 36.4, 31.6, and 22.8?M, respectively.
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Oleanolic triterpene saponins from the roots of Panax bipinnatifidus.
Chem. Pharm. Bull.
PUBLISHED: 11-02-2011
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Ten oleanane-type saponins (1-10), including three new compounds, namely bifinosides A-C (1-3), were isolated from the roots of Panax bipinnatifidus SEEM. Their structures were elucidated on the basis of chemical and spectroscopic methods.
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Toxicity and anticancer effects of an extract from Selaginella tamariscina on a mice model.
Nat. Prod. Res.
PUBLISHED: 10-14-2011
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The toxicity and antitumour effect of the ethanol extract of Selaginella tamariscina (STE), a plant widely used in folk medicine, were examined in a mice model. In the single-dose acute toxicity test, an oral administration of 10,000?mg?kg(-1) STE did not cause any lethality. The sub-acute toxicity study showed that the treatment by 250,?1000 and 3000?mg?kg(-1?)day(-1) for 30 continuous days did neither alter the body weights nor the haematological parameters in BALB/c mice. The anticancer effect of STE was evaluated in BALB/c mice inoculated with Lewis lung carcinoma cells. Oral administration of STE could not prevent the tumour formation but provided strong inhibition of tumour growth.
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Chemical constituents of the rhizomes of Hedychium coronarium and their inhibitory effect on the pro-inflammatory cytokines production LPS-stimulated in bone marrow-derived dendritic cells.
Bioorg. Med. Chem. Lett.
PUBLISHED: 07-25-2011
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The rhizomes of Hedychium coronarium have been used for the treatment of inflammation, skin diseases, headache, and sharp pain due to rheumatism in traditional medicine. From this plant, three new labdane-type diterpenes 1-3, named coronarins G-I as well as seven known 4-10, coronarin D, coronarin D methyl ether, hedyforrestin C, (E)-nerolidol, ?-sitosterol, daucosterol, and stigmasterol were isolated. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance spectroscopy. They were evaluated for inhibitory effects on lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Among of them, compounds 1, 2, and 6 were significant inhibitors of LPS-stimulated TNF-?, IL-6, and IL-12 p40 productions with IC(50) ranging from 0.19±0.11 to 10.38±2.34 ?M. The remains of compounds showed inactivity or due to cytotoxicity. These results warrant further studies concerning the potential anti-inflammatory benefits of labdane-type diterpenes from H. coronarium.
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Oleanane-type triterpene saponins from the bark of Aralia elata and their NF-?B inhibition and PPAR activation signal pathway.
Bioorg. Med. Chem. Lett.
PUBLISHED: 06-22-2011
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Two new oleanane-type triterpene saponins, tarasaponin IV (1) and elatoside L (2), and four known; stipuleanoside R(2) (3), kalopanax-saponin F (4), kalopanax-saponin F methylester (5), and elatoside D (6) were isolated from the bark of Aralia elata. Kalopanax-saponin F methyl ester was isolated from nature for the first time. Their chemical structures were elucidated using the chemical and physical methods as well as good agreement with those of reported in the literature. Oleanane-type triterpene saponins are the main component of A. elata. All compounds were investigated the anti-inflammatory activity. We measured their inhibition of NF-?B and activation of PPARs activities in HepG2 cells using luciferase reporter system. As results, compounds 2 and 4 were found to inhibit NF-?B activation stimulated by TNF? in a dose-dependent manner with IC(50) values of 4.1 and 9.5 ?M, respectively, when compared with that of positive control, sulfasalazine (0.9 ?M). Compounds 2 and 4 also inhibited TNF?-induced expression of iNOS and COX-2 mRNA. Furthermore, compounds 1-6 were evaluated PPAR activity using PPAR subtype transactivation assays. Among of them, compounds 4-6 significantly increased PPAR? transactivation. However, compounds 4-6 did not activate in any other PPAR subtypes.
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Effect of triterpenes and triterpene saponins from the stem bark of Kalopanax pictus on the transactivational activities of three PPAR subtypes.
Carbohydr. Res.
PUBLISHED: 06-16-2011
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Kalopanax pictus (Araliaceae) is a deciduous tree that grows in East Asian countries. Its stem bark and leaves have been used in traditional medicine to treat rheumatic arthritis, neurotic pain, and diabetes mellitus. A phytochemical study on a methanol extract of the stem bark of K. pictus resulted in the isolation of three new compounds, 6?,16?-dihydroxy-hederagenin 3-O-?-D-glucuronopyranoside (1), 3-O-?-D-glucuronopyranosyl-28-O-?-D-glucopyranosyl-6?,16?-dihydroxy-oleanolic acid (2), and 3-O-?-D-galactopyranosyl(1?3)-?-L-arabinopyranosyl hederagenin 28-O-?-D-glucopyranosyl-(1?6)-?-D-glucopyranosyl ester (3), along with eight known compounds (4-11). Their structures were established on the basis of chemical and spectroscopic methods (IR, 1D and 2D NMR, and HRESITOFMS). Compounds 1-6 and 8-10 upregulated PPARs transcriptional activity in a dose-dependent manner in HepG2 cells, with EC(50) values in the range 0.20-15.5 ?M. Moreover, the specific PPAR transactivational effects of compounds 1-6 and 8-10 on separate PPAR subtypes, PPAR?, -?, and -?(?) were further investigated. Compounds 4, 5, 8, and 10 showed significant PPAR? transactivational activity, with EC(50) values of 7.8, 8.0, 10.3, and 17.3 ?M, respectively. Compounds 2, 4, 6, and 8-10 exhibited PPAR? dose-dependent transactivational activity, with EC(50) values of 14.7, 15.5, 14.8, 10.9, 17.1, and 16.3 ?M, whereas compounds 8 and 10 significantly upregulated PPAR?(?) transcriptional activity, with EC(50) values of 15.7 and 17.7 ?M, respectively.
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Sanggenon C and O inhibit NO production, iNOS expression and NF-?B activation in LPS-induced RAW264.7 cells.
Immunopharmacol Immunotoxicol
PUBLISHED: 05-26-2011
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The NO production through the iNOS induction by activation of nuclear factor (NF-?B) is known to involve in various inflammatory conditions. Sanggenon C and O, two Diels-Alder type adducts isolated from Morus alba, a plant has been used for the anti-inflammatory purpose in the Oriental medicine, were investigated for their effect on the NO production, iNOS expression and NF-?B activity.
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Anti-inflammatory effects of fatty acids isolated from Chromolaena odorata.
Asian Pac J Trop Med
PUBLISHED: 05-11-2011
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To identify inhibitors of nitric oxide production and NF-?B activity from Chromolaena odorata (C. odorata).
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Inhibitory activity of Plantago major L. on angiotensin I-converting enzyme.
Arch. Pharm. Res.
PUBLISHED: 05-06-2011
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Eight compounds were isolated from methanol extract of Plantago major L. leaves and investigated for their ability to inhibit angiotensin I-converting enzyme activity. Among them, compound 1 showed the most potent inhibition with rate of 28.06 ± 0.21% at a concentration of 100 ?M. Compounds 2 and 8 exhibited weak activities. These results suggest that compound 1 might contribute to the ability of P. major to inhibit the activity of angiotensin I- converting enzyme.
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Cytotoxic steroidal alkaloids from Kibatalia laurifolia.
J. Nat. Prod.
PUBLISHED: 03-28-2011
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Four new steroids, 3-epi-gitingensine (1), N-acetylgitingensine (6), kibalaurifoline (7) and kibalaurifenone (8), along with the known paravallarine (2), 7?-hydroxyparavallarine (3), gitingensine (4), and N-methylgitingensine (5) were isolated from the leaves of Kibatalia laurifolia. Their structures were determined primarily from mass spectrometry and 2D NMR analyses. On the basis of the known absolute configurations of 2 and 4, the absolute configurations of the new compounds were proposed. Due to the structural relationships of compounds 1-8, a biosynthetic pathway was suggested. Compound 2 was cytotoxic to KB cells (IC50 12.8 ?M), followed by 1 with IC50 21.2 ?M.
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Anti-inflammatory activity on LPS-stimulated dendritic cells of lupanetype triterpenoids from the leaves of Acanthopanax koreanum.
Arch. Pharm. Res.
PUBLISHED: 03-27-2011
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Acanthopanax koreanum is well known herb in traditional Korean, Chinese, and Japanese anti-inflammatory action without any adverse effects. In the current study, we investigated the inhibitory effects of isolated compounds 1-13 from the leaves of A. koreanum on the lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Of these lupane-type triterpenoids, 1 exhibited particularly high inhibitory effect on lipopolysaccharide-stimulated TNF-?, IL-6, and IL-12 production with the values ranging from 45.0 to 84.5% at a concentration of 50 ?M. These results warrant further studies concerning the potential anti-inflammatory benefits of medicinal foods containing the leaves of A. koreanum.
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Chemical constituents and antioxidant activity of Ficus callosa.
Nat Prod Commun
PUBLISHED: 03-24-2011
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One new megastigmane glycoside, ficalloside (1), and eleven known compounds, were isolated from methanol extract of Ficus callosa leaves by repeated column chromatography. Their structures were established on the basis of spectral and chemical evidence. The antioxidant activities of these compounds were measured using the oxygen radical absorbance capacity (ORAC) assay. Compound 8 exhibited potent antioxidant activity of 10.6 microM trolox equivalents at the concentration of 2 microM. At this concentration, compounds 4-7 and 9-12 showed significant antioxidant activity with ranging of 2.1-6.1 microM trolox equivalents.
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Cytotoxic and PPARs transcriptional activities of sterols from the Vietnamese soft coral Lobophytum laevigatum.
Bioorg. Med. Chem. Lett.
PUBLISHED: 01-26-2011
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A new unusual sterol, named lobophytosterol (1), and five known metabolites (2-6) were isolated from the methanol extract of the soft coral Lobophytum laevigatum. Their chemical structures were elucidated by extensive spectroscopic analysis and comparison with those reported in the literature. The absolute stereochemistry of 1 was determined using a modified Moshers method. Compounds 1-3 showed cytotoxic activity against HCT-116 cells with IC(50) values of 3.2, 6.9 and 18.1 ?M, respectively. Compound 1 additionally displayed cytotoxic effects on A549 and HL-60 cells with IC(50) values of 4.5 and 5.6 ?M, respectively. Treatment of these cells with compound 1 resulted in an induction of apoptosis evident by chromatin condensation in treated cells. Besides, compounds 2, 4, and 6 significantly upregulated PPARs transcriptional activity dose-dependently in Hep-G2 cells. Taken together, these data suggest that compound 1 might inhibit the growth of the cancer cells by the induction of apoptosis, and compounds 2, 4, and 6 might act as specific agonists for PPAR?, PPAR?, and PPAR? and may therefore regulate cellular glucose, lipid, and cholesterol metabolism.
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Phenylpropanoids from the leaves of Acanthopanax koreanum and their antioxidant activity.
J Asian Nat Prod Res
PUBLISHED: 01-22-2011
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By various chromatographic methods, one new phenylpropanoid, acanthopanic acid (1), and three known compounds, 1,2-O-dicaffeoylcyclopenta-3-ol (2), (4S)-?-terpineol 8-O-?-D-glucopyranoside (3), and rutin (4), were isolated from the methanol extract of the Acanthopanax koreanum leaves. Their structures were elucidated on the basis of spectroscopic analyses, and their antioxidant activities were evaluated by the intracellular reactive oxygen species (ROS) radical scavenging 2,7-dichlorofluorescein diacetate assay. Among them, compounds 1, 2, and 4 showed significant scavenging capacity with IC(50) values of 3.8, 2.6, and 2.9 ?M, respectively, and compound 3 showed weak scavenging capacity with the inhibition rate of 37% at 40 ?M.
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A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-? in activated RAW 264.7 cells.
Bioorg. Med. Chem. Lett.
PUBLISHED: 01-18-2011
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One new ursane-type triterpenoid glycoside, asiaticoside G (1), five triterpenoids, asiaticoside (2), asiaticoside F (3), asiatic acid (4), quadranoside IV (5), and 2?,3?,6?-trihydroxyolean-12-en-28-oic acid 28-O-[?-L-rhamnopyranosyl-(1?4)-?-D-glucopyranosyl-(1?6)-?-D-glucopyranosyl] ester (6), and four flavonoids, kaempferol (7), quercetin (8), astragalin (9), and isoquercetin (10) were isolated from the leaves of Centella asiatica. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. The structure of new compound 1 was determined to be 2?,3?,23,30-tetrahydroxyurs-12-en-28-oic acid 28-O-[?-L-rhamnopyranosyl-(1?4)-?-D-glucopyranosyl-(1?6)-?-D-glucopyranosyl] ester. The anti-inflammatory activities of the isolated compounds were investigated on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Asiaticoside G (1) potently inhibited the production of nitric oxide and tumor necrosis factor-? with inhibition rates of 77.3% and 69.0%, respectively, at the concentration of 100 ?M.
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Cytotoxic and antioxidant activities of diterpenes and sterols from the Vietnamese soft coral Lobophytum compactum.
Bioorg. Med. Chem. Lett.
PUBLISHED: 01-17-2011
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Two new diterpenes, lobocompactols A (1) and B (2), and five known compounds (3-7) were isolated from the methanol extract of the soft coral Lobophytum compactum using combined chromatographic methods and identified based on NMR and MS data. Each compound was evaluated for cytotoxic activity against A549 (lung) and HL-60 (acute promyelocytic leukemia) human cancer cell lines. Among them, compound 5 exhibited strong cytotoxic activity against the A549 cell line with an IC(50) of 4.97 ± 0.06 ?M. Compounds 3, 4, and 7 showed moderate activity with IC(50) values of 23.03 ± 0.76, 31.13 ± 0.08, and 36.45 ± 0.01 ?M, respectively. The cytotoxicity of 5 on the A549 cells was comparable to that of the positive control, mitoxantrone (MX). All compounds exhibited moderate cytotoxicity against the HL-60 cell line, with IC(50) values ranging from 17.80 ± 1.43 to 59.06 ± 2.31 ?M. Their antioxidant activity was also measured using oxygen radical absorbance capacity method, compounds 1 and 2 exhibiting moderate peroxyl radical scavenging activity of 1.4 and 1.3 ?M Trolox equivalents, respectively, at a concentration of 5 ?M.
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Lignans and other constituents from the roots of the Vietnamese medicinal plant Pseuderanthemum palatiferum.
Planta Med.
PUBLISHED: 01-17-2011
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Two new lignans, palatiferin A (1) and palatiferin B (2), were isolated from the roots of Pseuderanthemum palatiferum, together with five known triterpenes, epifriedelanol (3), lupeol (4), lupenone (5), betulin (6), pomolic acid (7), and a dipeptide asperglaucide (8). Their structures were established from 2D?NMR and mass spectroscopy. The absolute configuration of 1 and 2 was proposed based on the comparison of their optical rotation activities with those of compounds with similar structures such as wodeshiol and paulownin. The new lignans, palatiferin A (1) and palatiferin B (2) exhibited a moderate cytotoxicity against KB and HepG2 cell lines. However, betulin and lupeol, two abundant compounds from the roots of P. palatiferum, showed cytotoxic and antimicrobial activities.
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Cytotoxic and anti-inflammatory cembranoids from the Vietnamese soft coral Lobophytum laevigatum.
Bioorg. Med. Chem.
PUBLISHED: 01-14-2011
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Four new cembranoids, namely laevigatol A-D (1-4), and six known metabolites (5-10), were isolated from the Vietnamese soft coral Lobophytum laevigatum. The structures of these compounds were elucidated by extensive spectroscopic analyses, and the absolute stereochemistry of 1 was determined using the modified Moshers method. Compounds 5, and 7-10 exhibited cytotoxic activity against selected human cancer cell lines. Compounds 1, 2, 8, and 9 showed dose-dependent inhibitory effects on the TNF?-induced NF-?B transcriptional activity in Hep-G2 cells. Moreover, compounds 1, 2, 8, and 9 significantly inhibited the induction of COX-2 and iNOS mRNA dose-dependently, indicating that these compounds attenuated the synthesis of these transcripts at the transcriptional level.
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A new monoterpenoid glycoside from Myrica esculenta and the inhibition of angiotensin I-converting enzyme.
Chem. Pharm. Bull.
PUBLISHED: 10-09-2010
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One new monoterpenoid glycoside, myresculoside (1), and eleven known compounds, were isolated from methanol extract of Myrica esculenta leaves by repeated column chromatography. The effects of these compounds on angiotensin I-converting enzyme (ACE) inhibition were investigated. Compounds 3 and 4 showed the most potent ACE inhibition with rates of 29.97% and 25.63% at concentration of 100 µM, respectively. Compounds 5, 6, and 11 showed weak activity with inhibitory rates of 0.07-1.41% at concentration of 100 µM.
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Antioxidant activity of a new C-glycosylflavone from the leaves of Ficus microcarpa.
Bioorg. Med. Chem. Lett.
PUBLISHED: 09-26-2010
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By bioactive-guided fractionation of methanol extract of the Ficus microcarpa leaves, one new C-glucosylflavone, ficuflavoside (1), one new megastigmane glycoside, ficumegasoside (8), and twelve known compounds including flavonoids (2-6), phenylpropanoids (7), megastigmanes (9-11) and sterol derivatives (12-14) were isolated. Their chemical structures were elucidated by mass, 1D, and 2D NMR spectroscopies. The antioxidant activities of these compounds were measured using the oxygen radical absorbance capacity methods. Compounds 1-6 exhibited potent antioxidant activities of 6.6-9.5?M Trolox equivalents at the concentration of 2.0?M. The results indicated 2, 3, and 5 having meaningful reducing capacity of copper (I) ions concentration of 6.1-8.4?M.
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Steamed ginseng-leaf components enhance cytotoxic effects on human leukemia HL-60 cells.
Chem. Pharm. Bull.
PUBLISHED: 08-06-2010
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Three new dammarane-type glycosides, named ginsenosides SL(1)-SL(3) (1-3), and eleven known compounds (4-14) were isolated from the heat-processed leaves of Panax ginseng. Their structures were elucidated on the basis of extensive chemical and spectroscopic methods. Cytotoxic-activity testing of compounds 1-14 against human leukemia HL-60 cells showed that ginsenosides Rh(3) (11) and Rk(2) (12) exhibited potent effects with IC(50) values of 0.8 and 0.9 microM. In addition, ginsenosides SL(3) (3), 20S-Rg(2) (7), F(4) (10), 20S-Rh(2) (13) displayed strong activity with IC(50) values of 9.0, 9.0, 7.5, and 8.2 microM, respectively. This is the first report on chemical components of the steamed ginseng leaves.
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Cytotoxic prenylated flavonoids from Morus alba.
Fitoterapia
PUBLISHED: 06-16-2010
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A phytochemical fractionation of the methanol extract of the Morus alba leaves led to the isolation of eleven flavonoids (1-11). The structure of the new 3-geranyl-3-prenyl-2,4,5,7-tetrahydroxyflavone (1) was elucidated by means of spectroscopic methods. The cytotoxicity of the isolated compounds against human cervical carcinoma HeLa, human breast carcinoma MCF-7, and human hepatocarcinoma Hep3B cells was evaluated. Of note, morusin (9) was the most potent with an IC(50) value of 0.64 ?M against HeLa cells.
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alpha-Glucosidase inhibition properties of cucurbitane-type triterpene glycosides from the fruits of Momordica charantia.
Chem. Pharm. Bull.
PUBLISHED: 05-13-2010
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Fourteen cucurbitane-type triterpene glycosides (1-14) were isolated from a methanol extract of Momordica charantia fruits, including three new compounds, charantosides A-C (1, 5, 6). Their structures were elucidated by chemical and spectroscopic methods. All isolated compounds were evaluated for alpha-glucosidase inhibitory effect. Of which, 12 and 13 showed moderate inhibitory activity against alpha-glucosidase. Whereas, 2, 3, 6-11, and 14 showed weak inhibitory activity, and 1, 4, and 5 were inactive.
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A new lignan dimer from Mallotus philippensis.
Nat Prod Commun
PUBLISHED: 04-28-2010
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A new lignan dimer, bilariciresinol (1), was isolated from the leaves of Mallotus philippensis, along with platanoside (2), isovitexin (3), dihydromyricetin (4), bergenin (5), 4-O-galloylbergenin (6), and pachysandiol A (7). Their structures were elucidated by spectroscopic experiments including 1D and 2D NMR and FTICR-MS.
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Triterpenoids from aerial parts of Glochidion eriocarpum.
Nat Prod Commun
PUBLISHED: 04-28-2010
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From the aerial parts of Glochidion eriocarpum, a new triterpene, glochieriol (1), three new triterpenoid saponins, glochieriosides C - E (2 - 4), together with four known triterpenes (glochidonol, glochidiol, lupeol, and 3-epi-lupeol) were isolated by using combined chromatographic separations. The structures of the new compounds were elucidated on the basis of spectroscopic data, including FTICR-MS, 1D and 2D NMR.
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Structure-activity relationship of lupane-triterpene glycosides from Acanthopanax koreanum on spleen lymphocyte IL-2 and IFN-gamma.
Bioorg. Med. Chem. Lett.
PUBLISHED: 04-11-2010
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Phytochemical investigation resulted in the isolation of three new lupane-triterpene glycosides acankoreosides M-O (1, 2 and 8) together with eight known lupane-triterpene glycosides (3-7, 9-11) from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D and 2D NMR spectroscopy. The effect of eleven lupane-triterpene glycosides on Con A-induced splenolytic production of IL-2 and IFN-gamma were measured as markers of acquired immune responses. Compounds 4, 5, 7, and 11 (5, 25, and 100 microM) significantly increased IFN-gamma and IL-2 release in spleen cells.
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Inhibitors of osteoclastogenesis from Lawsonia inermis leaves.
Bioorg. Med. Chem. Lett.
PUBLISHED: 03-23-2010
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Ten phenolic compounds (1-10) were isolated from a methanol extract of Lawsonia inermis leaves including two new ones, lawsoniasides A (1) and B (2). Their structures were elucidated by spectroscopic methods (NMR and FTICRMS) in combination with acid hydrolysis and GC analyses. Compounds 4 and 5 showed a significant inhibition on receptor activator for nuclear factor-kappaB ligand-induced osteoclast formation in murine bone-marrow macrophages.
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Cucurbitane-type triterpene glycosides from the fruits of Momordica charantia.
Magn Reson Chem
PUBLISHED: 03-13-2010
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The chemical study of Momordica charantia fruits led to the isolation of three new cucurbitane triterpene glycosides, momordicosides U, V, and W (1-3). The structures of these compounds were determined to be (19R, 23R)-5beta, 19-epoxy-19-methoxycucurbita-6,24-diene-3beta, 23-diol 3-O-beta-D-allopyranoside (1), (23R)-5beta, 19-epoxycucurbita-6,24-diene-3beta, 23-diol 3-O-beta-D-allopyranoside (2), and (19R)-5beta, 19-epoxy-19,25-dihydroxycucurbita-6,23(E)-diene-3beta-ol 3-O-beta-D-glucopyranoside (3), by chemical and spectroscopic methods.
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Two new C-glucosyl benzoic acids and flavonoids from Mallotus nanus and their antioxidant activity.
Arch. Pharm. Res.
PUBLISHED: 02-24-2010
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Two new 2-C-beta-D-glucopyranosyl benzoic acid derivatives named mallonanosides A (1) and B (2) were isolated from the methanolic extract of the leaves of Mallotus nanus along with five known flavonoids, kaempferin (3), juglanin (4), quercitrin (5), myricitrin (6), and rhoifolin (7). Their structures were established on the basis of spectral and chemical evidence. Their antioxidant activities were shown to depend on the number of hydroxyl groups, and the location and species of sugar moiety.
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A potential inhibitor of rat aortic vascular smooth muscle cell proliferation from the pollen of Typha angustata.
Arch. Pharm. Res.
PUBLISHED: 01-28-2010
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By various chromatographic methods, three flavonoids, (2S)-naringenin (1), isorhamnetin 3-O-(2-O-?-L-rhamnopyranosyl) ?-D-glucopyranoside (2), typhaneoside (3), and two sterol glycosides, ?-sitosterol-3-O-(6-octadecanoyl) ?-D-glucopyranoside (4) and ?-sitosterol-3-O-(6-octadeca-9Z,12Z-dienoyl) ?-D-glucopyranoside (5), were isolated from the pollen of Typha angustata. Their structures were determined on the basis of spectroscopic analyses. The flavonoids (1-3) were evaluated for their effects on the viability and proliferation of rat aortic smooth muscle cells. (2S)-naringenin (1) significantly inhibited cell proliferation in a dose-dependent manner without cytotoxic at concentrations of 30, and 50 ?M; it reduced the number of cells following PDGF-BB treatment to 1.83 ± 0.30 × 10(4) and 2.20 ± 0.60 × 10(4) cells/well, respectively. These findings suggest that (2S)-naringenin has antiproliferative effects on aortic smooth muscle cells.
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Chemical components from the Vietnamese soft coral Lobophytum sp.
Arch. Pharm. Res.
PUBLISHED: 01-21-2010
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Chromatographic separation resulted in the identification of one new squalene derivative, named lobophytene (1), three cembranoid diterpenes (2-4), and two sterols (5 and 6) from the Vietnamese marine soft coral Lobophytum sp. Their structures were identified on the basis of extensive spectroscopic data and comparison of those with reported data. Compounds 1 and 2 showed significant cytotoxic activities against lung (A549) and colon (HT-29) cell lines with IC(50) values of 8.2 and 5.6 microM for 1; 5.1 and 1.8 microM for 2, respectively.
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Dammarane-type saponins from Gynostemma pentaphyllum.
Phytochemistry
PUBLISHED: 01-15-2010
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Dammarane-type saponins, gypenosides VN1-VN7 (1-7), were isolated from the total saponin extract of Gynostemma pentaphyllum aerial parts, with their structures elucidated on the basis of spectroscopic and chemical methods. These compounds showed moderate cytotoxic activity against four human cancer cell lines, A549 (lung), HT-29 (colon), MCF-7 (breast), and SK-OV-3 (ovary), with IC(50) values ranging from 19.6+/-1.1 to 43.1+/-1.0 microM. Regarding the HL-60 (acute promyelocytic leukemia) cell line, compounds 1, 5, and 6 showed weakly active with IC(50) values of 62.8+/-1.9, 72.6+/-3.6, and 82.4+/-3.2 nM, respectively, while 2, 3, 4, and 7 were less active with IC(50) values>100 microM.
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Two new sesquiterpenes from Sarcandra glabra.
Nat Prod Commun
PUBLISHED: 01-07-2010
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Phytochemical study of the ethanol extract of Sarcandra glabra resulted in the isolation of two new sesquiterpenes, glabranols A (1) and B (2). Their structures were elucidated as 8alpha,9alpha,15-trihydroxylinden-4,7(11)-dien-12,8beta-olide (1) and 1beta,4alpha,7beta,11-tetrahydroxyeudesmane (2), by spectroscopic methods including 1D- and 2D-NMR and FTICR-MS.
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Aporphine alkaloids, clerodane diterpenes, and other constituents from Tinospora cordifolia.
Fitoterapia
PUBLISHED: 01-06-2010
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Phytochemical investigation of the methanol extract of Tinospora cordifolia aerial parts led to the isolation of four new and seven known compounds. The structures of two new aporphine alkaloids, N-formylasimilobine 2-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside (tinoscorside A, 1) and N-acetylasimilobine 2-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside (tinoscorside B, 2), a new clerodane diterpene, tinoscorside C (3), and a new phenylpropanoid, sinapyl 4-O-beta-D-apiofuranosyl-(1-->6)-O-beta-D-glucopyranoside (tinoscorside D, 6) were determined by extensive spectroscopic methods including FTICR-MS and 1D and 2D NMR.
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Unusual 22S-spirostane steroids from Dracaena cambodiana.
Nat Prod Commun
PUBLISHED: 10-17-2009
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From the methanol extract of Dracaena cambodiana roots two unusual 22S-spirostane steroids (1beta,3beta,14alpha,20R,22S,25R)-spirost-5-ene-1,3,14-triol (1) and (lbeta,3beta,14alpha,15alpha,20R,22S,25R)-spirost-5-ene-tetrol (2) have been isolated, together with a known 22R-spirostane compound, namogenin B (3). Their structures were elucidated by spectroscopic and spectrometric methods, including HRMS and extensive 1D and 2D NMR spectroscopy. Compound 1 showed significant antimicrobial activity against Pseudomonas aeruginosa, Staphylococcus aureus and Fusarium oxysporum, with MIC values of 45.0, 25.0 and 50.0 microg/mL, respectively.
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Inhibitors of osteoclast formation from rhizomes of Cibotium barometz.
J. Nat. Prod.
PUBLISHED: 09-11-2009
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Eight compounds (1-8) were isolated from a methanol extract of Cibotium barometz rhizomes including two new furan derivatives, cibotiumbarosides A (1) and B (2), and a new glycoglycerolipid, cibotiglycerol (4). Their structures were elucidated by chemical and spectroscopic methods. Compounds 2-5 each showed inhibition of osteoclast formation with no affect on BMM cell viability.
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Two new megastigmane sulphonoglucosides from Mallotus anisopodus.
Nat Prod Commun
PUBLISHED: 09-08-2009
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Phytochemical study of the methanol extract of Mallotus anisopodus led to the isolation of two new megastigmane sulphonoglucosides, namely anisoposides A (1) and B (2), along with junipetrioloside A (3), bergenin (4), os-tocopherol, and N1-methyl-2-pyridone-5-carboxamide. Their structures were deduced by spectroscopic and spectrometric methods including 1D-, 2D-NMR, ESI-MS, and HRESI-MS.
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