Showing papers on "Triterpene published in 2004"
TL;DR: The triterpenoids are a large group of natural products derived from C(30) precursors and each of these structures is classified and mechanisms for their formation are provided.
500 citations
TL;DR: It is demonstrated that PgSS1 is a key regulatory enzyme not only for phytosterol but also for triterpene biosynthesis and overexpressing of Pg SS1 confers the hyperproduction of triterPene saponins to P. ginseng.
Abstract: ;Roots of Panax ginseng, one of the most famous medicinal plants, contain various phytosterols and bioactive triterpene saponins (ginsenosides). In P. ginseng, phytosterols and triterpenes share the common biosynthetic intermediate, squalene. Here, we investigate the regulatory role of Panax ginseng squalene synthase (PgSS1) on the biosynthesis of phytosterols and triterpene saponins. PgSS1 transcripts are expressed ubiquitously in the various plant tissues, but higher in shoot apex and root. The transcript levels of PgSS1 increased markedly in the adventitious roots during 12- to 96-h period after metyl jasmonate (MeJA) treatment; MeJA treatment induced the activation of the transcripts of squalene epoxidase (SE), β-amyrin synthase (bAS), but not cycloartenol synthase (CAS). Unlike MeJA treatment, overexpression of PgSS1 in adventitious roots of transgenic P. ginseng was followed by the up-regulation of all the downstream genes tested, such as SE, bAS, and CAS. The enhanced activity of PgSS1 enzyme resulted in remarkable increase of phytosterols as well as ginsenoside contents. These results demonstrate that PgSS1 is a key regulatory enzyme not only for phytosterol but also for triterpene biosynthesis and overexpressing of PgSS1 confers the hyperproduction of triterpene saponins to P. ginseng.
334 citations
TL;DR: Eight triterpene acids isolated from ethanol extracts of the leaves of red and green perilla exhibited strong antitumor-promoting activity in an in vivo two-stage carcinogenesis test of mouse tumor by using 7,12-dimethylbenz(a)anthracene (DMBA) as an initiator and TPA as a promoter.
Abstract: Nine triterpene acids, viz., six of the ursane type, ursolic acid (1), corosolic acid (2), 3-epicorosolic acid (3), pomolic acid (4), tormentic acid (5) and hyptadienic acid (6), and three of the oleanane type, oleanolic acid (7), augustic acid (8) and 3-epimaslinic acid (9), among which 1 constituted the most predominant triterpene acid, were isolated and identified from ethanol extracts of the leaves of red perilla [Perilla frutescens (L.) Britton var. acuta Kudo] and green perilla [P. frutescens (L.) Britton var. acuta Kudo forma viridis Makino]. These eight compounds, 1, 2, 4–9, were evaluated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 μg/ear) in mice. All the compounds tested showed a marked anti-inflammatory effect, with a 50% inhibitory dose (ID50) of 0.09–0.3 mg per ear. In addition, an evaluation against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA showed five compounds, 1–3, 5 and 9, with a potent inhibitory effec...
260 citations
TL;DR: A saponin-enriched fraction prepared from the MeOH extract of the roots of Clematis chinensis showed cytotoxic activity against HL-60 promyelocytic leukemia cells.
Abstract: A saponin-enriched fraction prepared from the MeOH extract of the roots of Clematis chinensis showed cytotoxic activity against HL-60 promyelocytic leukemia cells, from which five new triterpene saponins (1−5) based on oleanolic acid, along with three known saponins (6−8), were isolated. The structures of the new saponins were determined on the basis of spectroscopic analysis, including extensive 1D and 2D NMR data and hydrolysis followed by chromatographic and spectroscopic analysis. Among the isolated saponins, monodesmosidic saponins exhibited cytotoxic activities against cultured tumor cells.
106 citations
TL;DR: Eleven new triterpenoid saponins, scabiosaponins A-K, and hookerosides A, B, and prosapogenin 1b were isolated from the whole plants of Scabiosa tschiliensis and exhibited strong inhibition of pancreatic lipase in vitro.
Abstract: Eleven new triterpenoid saponins, scabiosaponins A-K (1-11), and hookerosides A (12) and B (13) were isolated from the whole plants of Scabiosa tschiliensis. The structures of the new compounds were established on the basis of extensive NMR (DEPT, DQF-COSY, HETCOR, TOCSY, HMQC, HMQC-TOCSY, HMBC, and NOESY) and MS studies coupled with chemical degradations. The biological activity of compounds 1-10, 12, and 13 and prosapogenin 1b were examined against pancreatic lipase. Scabiosaponins E, F, G, I (5, 6, 7, 9), hookerosides A, B (12, 13), and prosapogenin 1b all exhibited strong inhibition of pancreatic lipase in vitro.
98 citations
TL;DR: The drug samples derived from the same botanical origin revealed similar constituent patterns, in other words, each Panaxtaxon showed its own characteristic chromatographic profile, which appeared in the specific shape of an 11-direction radar graph constructed on the basis of the result of quantitative analysis.
Abstract: A comparative study on the triterpene saponins of 47 samples of Ginseng drugs derived from 12 Panax taxa was conducted using a reverse-phase high-performance liquid chromatography (HPLC)method. Eleven ginsenosides, which represent 4 types of typical sapogenins, were chosen as standards for quantitative determination in order to characterize the chemical constituent pattern of each Ginseng drug and investigate the relationship between genetic varieties and chemical constituent pattern. The results showed that the ginsenoside compositions in Ginseng drugs of different origins were of considerable variability. Total saponin contents varied by 10-fold from the highest drug to the lowest one. Chikusetsu-ninjin derived from P. japonicus (Japan) was found to have the highest content (192.80 - 296.18 mg/g) and Ginseng from P. ginseng to be the lowest (5.78 - 15.63 mg/g). Two main groups (I and II) suggested by phytochemical data were clearly observed; group I mainly containing dammarane saponins consisted of P. ginseng, P. quinquefolius, P. notoginseng, P. vietnamensis and P. vietnamensis var. fuscidiscus; and group II containing a large amount of oleanolic acid saponins was com-posed of P.japonicus (apan), P. zingiberensis, P.japonicus (China),P. japonicus var. angustifolius, P. japonicus var. major, P. japonicus var. bipinnatifidus and P. stipuleanatus. The ratios of the subtotal of dammarane saponins to that of oleanolic acid saponins (D/0) were found to be > 1.9 and < 0.25 for groups I and II, respectively. The drug samples derived from the same botanical origin revealed similar constituent patterns, in other words, each Panaxtaxon showed its own characteristic chromatographic profile,which appeared in the specific shape of an 11-direction radar graph constructed on the basis of the result of quantitative analysis. Similarities of chemical constitution were seen among the closely phylogenetically-related taxa, including P. ginseng and P.quinquefolius, P. vietnamensis and P. vietnamensis var.fuscidiscus,P. japonicus (China) and its varieties were demonstrated, except P. japonicus (Japan) and P. zingiberensis.
84 citations
TL;DR: One new and eight previously described lupane-type metabolites were isolated for the first time from Acacia mellifera (Leguminosae) and cytotoxicity of the isolated metabolites was evaluated on the NSCLC-N6 cell line, derived from a human non-small-cell bronchopulmonary carcinoma.
73 citations
TL;DR: The methanolic extract from guggul-gum resin, the resin of Balsamodendron mukul, was found to inhibit nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages and three new polypodane-type triterpenes were isolated together with 17 known compounds including progesterone and the related steroids.
61 citations
TL;DR: Three new oleanane-type triterpenes showed significant cytotoxicity against two human tumor cell lines, namely, oral epidermoid carcinoma KB and colorectal carcinoma HT29, and gave IC(50) values in the range 1.2-3.6 microM.
Abstract: Three new oleanane-type triterpenes, (23Z)-coumaroylhederagenin (1), (23E)-coumaroylhederagenin (2), and (3Z)-coumaroylhederagenin (3), together with two known triterpene acids, oleanolic acid and ursolic acid, have been isolated from the whole plant of Ludwigia octovalvis, and their structures have been elucidated by spectroscopic methods. All three new triterpenes showed significant cytotoxicity against two human tumor cell lines, namely, oral epidermoid carcinoma KB and colorectal carcinoma HT29, and gave IC50 values in the range 1.2−3.6 μM.
57 citations
TL;DR: A new triterpene and six known pentacyclic terpenoids were isolated from the methanol extract of the dried leaves from Mallotus apelta and their structures were determined to be 3α-hydroxyhop-22(29)-ene, hennadiol, friedelin, friedelanol, and epifriedelanol.
Abstract: A new triterpene (1) and six known pentacyclic terpenoids (2-7) were isolated from the methanol extract of the dried leaves from Mallotus apelta. Based on the spectral and chemical evidence, their structures were determined to be 3alpha-hydroxyhop-22(29)-ene (1), hennadiol (2), friedelin (3), friedelanol (4), epifriedelanol (5), taraxerone (6), and epitaraxerol (7).
54 citations
TL;DR: By adopting this HPLC method, the determinations of 11 ginsenosides in three Ginseng drugs derived from Panax ginseng, Panax vietnamensis var.
Abstract: A HPLC method for the simultaneous determination of 11 triterpene saponins with four-type aglycones (protopanaxadiol, protopanaxatriol, ocotillol and oleanolic acid types) in Ginseng drugs was developed and validated. Using a gradient of acetonitrile and 10 mM K-phosphate buffer (pH 5.80) as the mobile phase and UV detection at 196 nm, more than 18 ginsenosides with different aglycones were separated satisfactorily within 60 min. The detection limits (signal/noise> or =3) were 0.1 microg for ginsenosides Rb1, Rc, Rd, Re and Rg1, chikusetsusaponin III, and notoginsenoside R2, 0.2 microg for gisenoside Ro and chikusetsusaponin IVa, 0.3 microg for chikusetsusaponin IV, and 3 microg for majonoside R2. The calibration curve of each saponin had a correlation coefficient close to 1. Intra- and interday precisions were less than 2.1% (n=5) and 3.3% (n=15), respectively. The recovery rates of extraction were in the range of 96.4-102.7% for all ginsenosides. By adopting this method, the determinations of 11 ginsenosides in three Ginseng drugs derived from Panax ginseng, Panax vietnamensis var. fuscidiscus and Panax japonicus (Japan) were achieved.
TL;DR: The isolates were investigated for their radical scavenging abilities through a spectrophotometric assay involving reduction of 2,2-diphenyl-picryl hydrazyl (DPPH) and elucidated by interpretation of their spectral data, including gHMQC and gHMBC experiments.
TL;DR: The triterpene mixture was inactive against Escherichia coli and possessed moderate activities against Staphylococcus aureus, Candida albicans, and Trichophyton mentagrophytes and there was no significant decrease in blood glucose levels (bgl) in alloxan-induced diabetic mice after administration of the triterPene mixture.
TL;DR: Two lanostane-type triterpene and a terpenic δ-lactone have been isolated from the roots of Zizyphus vulgaris Lam and characterized as lanosta-25 (26)-en-9α-ol-21-oic acid and lanosta (26-en-22β-ol(19)-olide, respectively, on the basis of spectroscopic techniques and chemical means.
Abstract: A lanostane-type triterpene, zizyphulanostane-21-oic acid, and a terpenic δ-lactone, zizyphulanostan-18-oic acid, have been isolated from the roots of Zizyphus vulgaris Lam. (syn. Z. sativa Gaertn., Z. mauritina. Lam.) and characterized as lanosta-25 (26)-en-9α-ol-21-oic acid and lanosta-25 (26)-en-22β-ol-18-oic acid 3(19)-olide, respectively, on the basis of spectroscopic techniques and chemical means.
TL;DR: Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase beta, resulted in the isolation of the four new lupane triterpenoids 1-4 and the seven known compounds lupeol.
TL;DR: Free cucurbitacin B is presumed to be formed in vivo by an enzyme-mediated scission of esters 2a-c, thus constituting a chemical weapon that protects the mushrooms against parasites and predators.
Abstract: In addition to the known bioactive triterpene cucurbitacin B (1), two new cucurbitane triterpenoids, namely, leucopaxillones A (3) and B (4), exhibiting a new oxygenation pattern among cucurbitacins, have been isolated from the mushroom Leucopaxillus gentianeus (syn. L. amarus). Cucurbitacin B (1) imparts a bitter taste to the flesh of the fungus; however, it occurs in the fruiting bodies mainly esterified as tasteless fatty acid esters 2a-c. In vitro growth inhibitory effects of compounds 1-4 on proliferation of four different human tumor cell lines (A549, CAKI-1, HepG2, MCF-7) were evaluated by using a 1-day MTT assay. Only cucurbitacin B was highly active on all lines. Free cucurbitacin B is presumed to be formed in vivo by an enzyme-mediated scission of esters 2a-c, thus constituting a chemical weapon that protects the mushrooms against parasites and predators. Compounds 1-4 are structurally different from the other few cucurbitacins isolated from Basidiomycetes, being, instead, more similar to those occurring in plants. In particular, cucurbitacin B (1) seems to represent an interesting example of secondary metabolite convergence between distant taxa such as fungi and vascular plants, where they likely exert a similar role of protection. The structures of the compounds were established by means of spectroscopic methods and X-ray diffraction on a single crystal. The absolute configuration of leucopaxillone A has been assigned on the basis of CD chirality rules.
TL;DR: In this paper, six triterpene saponins bearing an oxygen bridge between C-13 and C-28 and with pronounced anti-leishmanial activity were isolated from the methanolic extract of leaves of the Vietnamese medicinal plant Maesa balansae.
TL;DR: The observed results confirm the structural specificity of the I. paraguariensis triterpenoids and reinforce a previous proposal to detect mate adulteration by triter penoid analysis.
Abstract: From the leaves of Ilex affinis and Ilex buxifolia, two adulterant species of "erva mate" (Ilex paraguariensis), three new triterpenoid glycosides were isolated. Affinoside 1 (3beta-O-[beta-D-glucopyranosyl-(1-->3)-[2-O-acetyl-(1-->2]]-alpha-L-arabinopyranosyl pomolic acid 28-O-beta-D-glucopyranosyl ester, 1) was isolated from I. affinis, while buxifolioside I (28-O-beta-D-glucopyranosyl ester of (20S)-3alpha,19alpha-dihydroxyurs-12-ene-23,28-dioic acid, 7) and buxifolioside II (28-O-beta-D-glucopyranosyl ester of (20S)-3beta,19alpha-dihydroxyurs-12-en-24,28-dioic acid, 8) were isolated from I. buxifolia. Along with these new compounds, ilexoside II (2), ursolic acid (3), 28-nor-ursolic acid (4), 3beta-O-acetylursolic acid (5), and uvaol (6) were also isolated. The observed results confirm the structural specificity of the I. paraguariensis triterpenoids and reinforce a previous proposal to detect mate adulteration by triterpenoid analysis. In addition, the in vitro antitrypanosomal activity of some Ilex triterpenoids is also reported.
TL;DR: In this paper, eight major triterpene saponins have been isolated from the aerial parts of Medicago arabica and their structures elucidated by FAB-MS and NMR analysis.
Abstract: Eight major triterpene saponins have been isolated from the aerial parts of Medicago arabica and their structures elucidated by FAB-MS and NMR analysis. Three of them are new compounds and are identified as 3-O-(alpha-L-arabinopyranoside) bayogenin, 3-O-(alpha-L-arabinopyranosyl), 28-O-(beta-D-glucopyranoside) bayogenin, and 3-O-[alpha-L-arabinopyranosyl(1-->2)-beta-D-glucuronopyranosyl], 28-O-beta-D-glucopyranoside 2-beta-hydroxyoleanolic acid. Two saponins, identified as 3-O-(alpha-L-arabinopyranoside) hederagenin and 3-O-(alpha-L-arabinopyranosyl), 28-O-(beta-D-glucopyranoside) hederagenin are known compounds but not previously reported as saponin constituents of Medicago species, while three other saponins, being mono- and bidesmosides of hederagenin, have been previously isolated from roots of M. sativa.
TL;DR: 1beta,2alpha,3beta,11alpha-Tetrahydroxyurs-12-ene, the most abundant compound in the extract, was found to be highly cytotoxic to renal, non-small cell lung, and breast cancer cell lines.
Abstract: The three new triterpenes (1−3) and five known triterpenes and a sterol were isolated from the acetone extract of a Turkish collection of Salvia kronenburgii. The structures of the new triterpenes were established as 1β,2α-dihydroxy-3β-acetoxy-11-oxours-12-ene (1), 2α,20β-dihydroxy-3β-acetoxyurs-9(11),12-diene (2), and 1β,2α-dihydroxy-3β-acetoxyurs-9(11),12-diene (3) on the basis of spectral analyses, including 1D and 2D NMR and mass spectroscopy. It is probable that compounds 2 and 3 are artifacts from dehydration of the corresponding allylic alcohols. 1β,2α,3β,11α-Tetrahydroxyurs-12-ene (5), the most abundant compound in the extract, was found to be highly cytotoxic to renal, non-small cell lung, and breast cancer cell lines.
TL;DR: In this article, a biphasic liquid system composed of n−hexane−n−butanol saturated by 0.05 m NaOH was used as the stationary phase, and the upper phase was changed systematically into 1:1, 1:2 and 1:4.
Abstract: Pentacyclic triterpene aglycones and glycosides of the ursane type were successfully separated from 600 mg of a polar extract from Centella asiatica (Apiaceae) by high speed countercurrent chromatography (HSCCC), applying a mobile phase gradient with a step‐wise increase of elution strength. The lower phase of the biphasic liquid system composed of n‐hexane–n‐butanol–0.05 M NaOH (5:1:6, v/v/v) was used as the stationary phase, the upper phase was used as the initial mobile phase. The mobile phase was changed systematically into 1:1, 1:2 and 1:4 consisting of n‐hexane–n‐butanol saturated by 0.05 M NaOH. The separation mainly yielded five fractions with asiatic acid (18 mg), madecassic acid (13 mg), asiaticoside (140 mg), and madecassoside (75 mg). The chemical structures of the four compounds were confirmed by means of electrospray ionization ion trap multiple mass spectrometry (ESI–MS–MS) and NMR analysis.
TL;DR: Five new lanostane-type triterpenes, named fomefficinic acid A-E (1-5), were isolated from the dried sclerotium of Fomes officinalis, respectively.
Abstract: Five new lanostane-type triterpenes, named fomefficinic acid A—E (1—5), were isolated from the dried sclerotium of Fomes officinalis, respectively. Their structures were established as 24-methylene-3-oxo-lanost-8-en-21-oic acid (1), 3α,15α-dihydroxy-24-methylene-lanosta-7,9(11)-dien-21-oic acid (2), 3α,15α-dihydroxy-24-methylene-lanost-8-en-21-oic acid (3), 15α-hydroxy-3-oxo-24-methylenelanost-8-en-21-oic acid (4), 15α-acetoxy-3-oxo-24-methylenelanosta-7,9(11)-dien-21-oic acid (5), by spectral analysis and chemical methods as well as comparison with known compounds.
Patent•
11 Oct 2004
TL;DR: In this paper, a novel use of the triterpene compounds represented by the Formula 1 for improving decreased memory and a pharmaceutical composition for improving brain functions comprising of the triethyltetrameric compounds was described.
Abstract: The present invention relates to the triterpene compounds improving in brain functions. In particular, the present invention relates to a novel use of the triterpene compounds represented by the Formula 1 for improving decreased memory and a pharmaceutical composition for improving brain functions comprising the triterpene compounds represented by the Formula 1.
TL;DR: Triterpene cyclases constitute a family of enzymes that catalyze diverse and complex carbocationic cyclization/rearrangement reactions of squalene and (3S)-2,3-oxidosqualene (OS) to generate a distinct array of sterols and triterpenes as mentioned in this paper.
Abstract: Triterpene cyclases constitute a family of enzymes that catalyze diverse and complex carbocationic cyclization/rearrangement reactions of squalene and (3S)-2,3-oxidosqualene (OS) to generate a distinct array of sterols and triterpenes. A major determinant for the triterpenoid diversity is believed to be the precise control of conformation between substrate and enzyme, as well as the position of the carbocation intermediate formation. For example, both oxidosqualene-lanosterol cyclase (ERG7, EC 5.4.99.7) and oxidosqualene-cycloartenol synthase (CAS, EC 5.4.99.8) bind oxidosqualene in a chair–boat– chair conformation, initiate and propagate cyclization to form a protosteryl cation, and then promote 1,2-shifts of hydride and methyl groups to the lanosteryl C8 cation. The lanosterol formation is accomplished through the final deprotonation, abstracting a proton originally at C9 or after a hydride shift from C9 to C8. Cycloartenol is formed after a hydride shift from C9 to C8, followed by 9b,19-cyclopropane ring closure. Elegant molecular-genetic and bioorganic investigations have recently identified several amino acid residues that are critical in probing putative active sites and determining prod-
TL;DR: Quinovic acid glycosides were microbially deglycosylated by a Nocardia sp. to their aglycon quinovic acids and its biogenetic counterpart, cincholic acid (3) via an unprecedented carbon skeleton as discussed by the authors.
TL;DR: Eight new oleanane and lupane saponins as well as two new benzyl glycosides (9 and 10) were isolated from the aerial parts of Schefflera rotundifolia (Ten) Frodin (Araliaceae) together with two known benzyl Glycosides.
Abstract: Eight new oleanane and lupane saponins (1-8) as well as two new benzyl glycosides (9 and 10) were isolated from the aerial parts of Schefflera rotundifolia (Ten) Frodin (Araliaceae) together with two known benzyl glycosides. Their structures were established using 1D- and 2D-NMR spectroscopy and mass spectrometry. The antiproliferative activity of all compounds was evaluated using three continuous murine and human culture cell lines J774.A1, HEK-293, and WEHI-164. Compounds 7 and 8, having betulinic acid as aglycone, were the most active constituents.
TL;DR: A new dammarane-type triterpene monoglucoside, named isoginsenoside-Rh3, has been isolated from the fruits of Panax ginseng C. A. Mey and the structure has been elucidated as 3-O-β-d-glucopyranosyl-dammarane-(E)-20(22),24-diene-3β,12 β-diol (1).
TL;DR: Bioassay-guided fractionation of the rhizomes of Astilbe chinensis afforded four cytotoxic pentacyclic triterpenoids, which may be responsible, at least in part, for the antineoplastic action of the traditional crude drug Rhizoma Astil be chinensis.
TL;DR: Two new oleanane-type triterpenoids (1 and 2) were isolated from the stem bark of Liquidamber styraciflua and showed strong cytotoxicity against a disease-oriented panel of 39 human cancer cell lines, although compounds 2, 3, and 4 showed weaker activity compared to 1.
Abstract: Two new oleanane-type triterpenoids (1 and 2), together with two known compounds, 6β-hydroxy-3-oxo-lup-20(29)-en-28-oic acid (3) and 3,11-dioxoolean-12-en-28-oic acid (4), were isolated from the stem bark of Liquidamber styraciflua. The structures of 1 and 2 were determined to be 25-acetoxy-3α-hydroxyolean-12-en-28-oic acid (1) and 3α,25-dihydroxyolean-12-en-28-oic acid (2) on the basis of spectroscopic methods and chemical conversion. Compound 1 showed strong cytotoxicity against a disease-oriented panel of 39 human cancer cell lines, although compounds 2, 3, and 4 showed weaker activity compared to 1.
TL;DR: Seven new oleanane-type triterpenoid saponins, hydrocotylosides I-VII (1-7), and one known saponin, udosaponin B (8), were isolated from the methanol extract of the whole plants of Hydrocotyle sibthorpioides.
Abstract: Seven new oleanane-type triterpenoid saponins, hydrocotylosides I-VII (1-7), and one known saponin, udosaponin B (8), were isolated from the methanol extract of the whole plants of Hydrocotyle sibthorpioides.The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.