Showing papers on "Triterpene published in 1998"
TL;DR: The present studies have revealed that distinct OSC exists for triterpene formation in higher plants, and the high level of similarity with cycloartenol synthase indicates close evolutional relationship between sterol and triterPene biosynthesis.
Abstract: β-amyrin, a typical pentacyclic triterpene having an oleanane skeleton, is one of the most commonly occuring triterpenes in nature and is biosynthesized from (3S)-2,3-oxidosqualene. The enzyme, β-amyrin synthase, catalyzing the cyclization of oxidosqualene into β-amyrin, generates five rings and eight asymmetric centers in a single transformation. A homology-based PCR method was attempted to obtain the cDNA of this enzyme from the hairy root of Panax ginseng which produces oleanane saponins together with dammarane-type saponins. Two sets of degenerate oligonucleotide primers were designed at the regions which are highly conserved among known oxidosqualene cyclases (OSCs). Nested PCRs using these primers successfully amplified the core fragment which revealed the presence of two OSC clones PNX and PNY. Specific amplification of each clone by 3′-RACE and 5′-RACE was carried out to obtain the whole sequences. The two clones exhibited 60 % amino acid identity to each other. A full-length clone of PNY was ligated into the yeast expression vector pYES2 under the GAL1 promoter to give pOSCPNY . β-amyrin production was observed with the mutant yeast lacking lanosterol synthase, transformed by this plasmid. The sequence of pOSCPNY contains an open reading frame of 2289 nucleotides which codes for 763 amino acids with a predicted molecular mass of 88 kDa. Sequence comparison with other OSCs showed a high level of similarity with lanosterol, cycloartenol and lupeol synthases. The other clone, pOSCPNX, was shown to be cycloartenol synthase by similar expression in yeast. The present studies have revealed that distinct OSC exists for triterpene formation in higher plants, and the high level of similarity with cycloartenol synthase indicates close evolutional relationship between sterol and triterpene biosynthesis.
294 citations
TL;DR: Two new lanostane-type triterpenes, lucidumol A and ganoderic acid beta, were isolated from the spores of Ganoderma (G.) lucidum and showed significant anti-human immunodeficiency virus (anti-HIV)-1 protease activity with IC50 values of 20-90 microM.
Abstract: Two new lanostane-type triterpenes, lucidumol A and ganoderic acid beta, were isolated from the spores of Ganoderma (G) lucidum, together with a new natural one and seven that were known The structures of the new triterpenes were determined as (24S)-24,25-dihydroxylanost-8-ene-3,7-dione and 3 beta,7 beta-dihydroxy-11,15-dioxolanosta-8,24(E)-dien-26-oic acid, respectively, by chemical and spectroscopic means The quantitative analyses of 5 fruiting bodies, antlered form and spores of G lucidum were performed by high performance liquid chromatography and demonstrated that ganoderic alcohol and acid contents were quite high in the spore Of the compound isolated, ganoderic acid beta, (24S)-lanosta-7,9(11)-diene-3 beta,24,25-triol (called lucidumol B), ganodermanondiol, ganodermanontriol and ganolucidic acid A showed significant anti-human immunodeficiency virus (anti-HIV)-1 protease activity with IC50 values of 20-90 microM
260 citations
TL;DR: Twelve new derivatives of bisamides, including two cyclopenta[b]benzofurans (flavaglines), pannellin (15) and pannella 1-O-acetate (16), displayed very strong insecticidal activity against Spodoptera littoralis and Lymantria dispar, comparable with the activity of azadirachtin.
Abstract: Twelve new derivatives of bisamides [piriferinol (5), edulimide (7)], lignans [lariciresinol acetat (10)], triterpenes [4-bis-norcycloartane-type triterpenes (11a, 12a+b, 13a+b)], cyclopenta[b]benzofurans [pannellin (15), pannellin 1-O-acetate (16), 3'-methoxypannellin (17)], and an aromatic butyrolactone [aglalactone (18)] were isolated and identified from lipophilic leaf, stem, and root extracts of Aglaia spp. elaeagnoidea, edulis, grandis, silvestris, and tomentosa. Two cyclopenta[b]benzofurans (flavaglines), pannellin (15) and pannellin 1-O-acetate (16), displayed very strong insecticidal activity against Spodoptera littoralis and Lymantria dispar, comparable with the activity of azadirachtin.
109 citations
TL;DR: From the leaves and roots of Polyscias fruticosa, eight new oleanolic acid saponins named polysciosides A to H were isolated together with three known saponin structures by means of spectral data, particularly NMR, which included COSY, HSQC, HMBC, HOHAHA and ROESY techniques.
85 citations
Patent•
20 May 1998
TL;DR: In this paper, a carboxyl group present on the 3-O-glucuronic acid of triterpene saponin was used to attach a lipophilic moiety to the residue of non-acylated or desacylated tritetrpene saponin.
Abstract: The present invention is directed to novel chemical compounds in which a lipophilic moiety such as a lipid, fatty acid, polyethylene glycol or terpene is covalently attached to a non-acylated or desacylated triterpene saponin via a carboxyl group present on the 3-O-glucuronic acid of the triterpene saponin. The attachment of a lipophile moiety to the 3-O-glucuronic acid of a saponin such as Quillaja desacylsaponin, lucyoside P, or saponin from Gypsophila, Saponaria and Acanthophyllum enhances their adjuvant effects on humoral and cell mediated immunity. Additionally, the attachment of a lipophile moiety to the 3-O-glucuronic acid residue of non- or des-acylsaponin yields a saponin analog that is easier to purify, less toxic, chemically more stable, and possesses equal or better adjuvant properties than the original saponin.
68 citations
TL;DR: In this paper, the dichloromethane extracts of Kielmeyera coriacea leaves and stems were analyzed by high performance liquid chromatography coupled with a photodiode array detector (LC-UV) and thermospray liquid-chromatography-mass spectrometry (TSP/LC-MS) revealed the presence of several xanthones.
68 citations
TL;DR: Investigation of the bark from Terminalia macroptera led to the isolation of two novel esterified triterpenes, identified as 23-galloylarjunolic acid and its β- d -glucopyranosyl ester.
66 citations
TL;DR: Three new cycloartane-type triterpene glycosides, brachyosides A, B, and C, from the roots of Astragalus brachypterus have been isolated together with five known saponins, astragalosides I, II, and IV, cyclocanthoside E, and cycloastragenol.
Abstract: Three new cycloartane-type triterpene glycosides, brachyosides A (1), B (3), and C (2), from the roots of Astragalus brachypterus and one new glycoside, cyclocephaloside II (4), from the roots of Astragalusmicrocephalus have been isolated together with five known saponins, astragalosides I, II, and IV, cyclocanthoside E, and cycloastragenol. The structures of the new compounds were established as 3-O-[beta-D-xylopyranosyl(1-->3)-beta-D-xylopyranosyl-6-O-beta-D-gluc opyranosyl-3beta,6alpha,16beta,24(S),25-pentahydrox ycycloartane (1), 3-O-beta-D-xylopyranosyl-6-O-beta-D-glucopyranosyl-24-O-beta-D-glucop yranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxyc ycloartane (2), 20(R),24(S)-epoxy-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta , 25-tetrahydroxycycloartane (3), and 20(R), 24(S)-epoxy-3-O-(4'-O-acetyl)-beta-D-xylopyranosyl-6-O-beta-D-glucopy ranosyl-3beta,6alpha,16beta,25-tetrahydroxycycloart ane (4). For the structure elucidations, 1D- and 2D-NMR experiments and FABMS were used.
53 citations
TL;DR: Three known dammarane triterpenes, 3-epi-ocotillol, eichlerianic acid and shoreic acid, together with two new ones, foveolins A and B, have been isolated from the bark of Aglaia foveolia by 2D NMR experiments.
48 citations
TL;DR: These compounds exhibited clear selectivity (parameters and species) over germination and growth of monocotyledon species with average of inhibition of −50% on the germination of Hordeum vulgare, and average of stimulation of 30% on that of Allium cepa.
44 citations
TL;DR: Two new hydroperoxy triterpene groups were isolated as hepatoprotective agents from Sedum sarmentosum and their structures were elucidated by spectral analysis and chemical reactions.
TL;DR: A triterpene, 9,19-cyclolanost-20(21)-en-24-ol-3-one, named neriifolione, and cycloartenol were isolated from the latex of Euphorbia nerifolia and their structures were elucidated with the help of chemical and physical data as discussed by the authors.
TL;DR: In this article, three oleanane-type triterpenes have been isolated from the wood of Viburnum awabuki and their structures have been elucidated as 3β,28-dihydroxy-12-oleanene-1-one, 3 β, 28-Dihydrox-12 -oleanene11-11-one and 13,28 -epoxy-11 -oxygenene-3-one by extensive analysis of spectroscopic data.
TL;DR: A set of friedelane triterpenoids has been isolated from the stem bark exudates of Maytenus macrocarpa and includes a new friedelan triterpene, which showed weak activity against aldose reductase and did not display antitumor activity against P-388 lymphoid neoplasm, A-549 human lung cancer, HT-29 human colon carcinoma, or MEL-28 human melanoma cell lines.
Abstract: A set of friedelane triterpenoids has been isolated from the stem bark exudates of Maytenus macrocarpa. It includes a new friedelan triterpene (1), together with the known compounds friedelin, 3-oxo-29-hydroxyfriedelane, 3-oxofriedelan-25-al, and canophyllol. The structures of these compounds were elucidated by spectroscopic and chemical evidence. Complete 1H and 13C assignments were achieved by 2D NMR spectroscopy. The new compound showed weak activity against aldose reductase. It did not display antitumor activity against P-388 lymphoid neoplasm, A-549 human lung carcinoma, HT-29 human colon carcinoma, or MEL-28 human melanoma cell lines.
TL;DR: Three new bisdesmosidic triterpene saponins, zygophylosides I, L and M, and three known quinovic acid glycosides were isolated from Zygophyllum gaetulum by use of 1D and 2D NMR techniques.
Abstract: Three new bisdesmosidic triterpene saponins, zygophylosides I (1), L (2) and M (3), and three known quinovic acid glycosides were isolated from Zygophyllum gaetulum. The new compounds were determined to be 3β-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→2)-β-d-glucopyranosylurs-20(21)-en-28-oic acid 28-O-[β-d-2-O-sulfonylglucopyranosyl] ester (1), 3β-O-[α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→2)-β-d-glucopyranosyl]urs-20(21)-en-28-oic acid 28-O-[β-d-glucopyranosyl] ester (2), and 3β-O-β-d-quinovopyranosyl-27-nor-olean-12-en-28-oic acid 28-O-β-d-glucopyranosyl ester (3) by use of 1D and 2D NMR techniques.
TL;DR: Four new oleanane-type triterpene glycosides, proceraosides A-D (1-4), were isolated from the seeds of Albizia procera by extensive NMR experiments and chemical methods.
Abstract: Four new oleanane-type triterpene glycosides, proceraosides A−D (1−4), were isolated from the seeds of Albizia procera Their structures were established by extensive NMR experiments and chemical m
TL;DR: A new lupane triterpene glycoside, acantrifoside A, was isolated from the leaves of Acanthopanax trifoliatus and A. koreanum as discussed by the authors.
TL;DR: A new A-ring contracted triterpene, rosamultic acid, was isolated from the roots of Rosa multiflora, together with five known triterpenes as mentioned in this paper.
TL;DR: Seven novel cycloartane-type triterpenes were isolated from Combretum quadrangulare and their structures were elucidated on the basis of spectral analysis, and they exhibited potent cytotoxicity against murine colon 26-L5 carcinoma cells.
TL;DR: The antinociceptive effects of 20 triterpene sapogenins from cacti were examined by the acetic acid-induced writhing method and alamosenogenin, bridgesigenins B and C, gummosogenins, thurberogenin and pachanol C showed the activity.
Abstract: The antinociceptive effects of 20 triterpene sapogenins from cacti were examined by the acetic acid-induced writhing method. The isolation of some triterpenes from the hydrolysate of MeOH extracts of three cacti was also described, and alamosenogenin, bridgesigenins B and C, gummosogenin, thurberogenin and pachanol C, showed the activity.
TL;DR: From the roots of Clematis terniflora, nine new oleanolic acid 3,28-O-bisdesmosides called clematernosides A, B, E, F, G, H, I, J and K, and two new hederagenin 3, 28- O-bis Desmosides C and D, have been isolated and the structures of the new saponins have been elucidated based on chemical and spectral evidence.
Abstract: From the roots of Clematis terniflora, nine new oleanolic acid 3,28-O-bisdesmosides called clematernosides A, B, E, F, G, H, I, J and K, and two new hederagenin 3,28-O-bisdesmosides called clematernosides C and D, have been isolated together with two known saponins, huzhangoside B and clematichinenoside C. The structures of the new saponins have been elucidated based on chemical and spectral evidence. Among the new spaonins, clematernosides I and J have a nonasaccharide moiety and a total of twelve monosaccharide moieties in the molecule. This is the first report of the isolation and structure elucidation of such "big" glycosides.
TL;DR: A mixture containing a new triterpene, chamaedrydiol (urs-12-ene-2α,3β-diol), and three known triterpenes (lup-20(29)-ene- 2α, 3β-Diol, castanopsol and epigermanidiol) was isolated from Marsypianthes chamaeds as discussed by the authors.
TL;DR: In this article, two lupane-triterpene glycosides, acankoreoside A (I) and B (2), were isolated from the leaves of Acanthopanax koreanum NAKAI (Araliaceae).
Abstract: Two new lupane-triterpene glycosides, acankoreoside A (I) and B (2), were isolated from the leaves of Acanthopanax koreanum NAKAI (Araliaceae). Based on spectroscopic data, the chemical structures of 1 and 2 were determined as 3α-hydroxy-lup-20(29)-en-23,28-dioic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester and 3α,11α,23-trihydroxy-lup-20(29)-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively.
TL;DR: A triterpene glycoside, ulososide B (1), was isolated from the sponge Ulosa sp and its structure was elucidated on the basis of spectroscopic data and obtaining of genuine aglycone after acid hydrolysis as discussed by the authors.
TL;DR: Two new diterpenoids, 3-oxo-12-methoxy-14-hydroxyabieta-8,11,13-triene and 6-oxy-12 peroxyabietas-8.11, 13-trienes, a new steroid brassicasterone and a new aromatic ester 4,4′- bis benzoic acid heptyl ester were obtained from the roots of Salvia multicaulis.
TL;DR: A novel 3,4-seco-triterpene alcohol was isolated from the non-saponifiable lipid of sasanqua oil from the seeds of Camellia sasqua, the first example of naturally occurring triterpene with a D:B-friedobaccharane skeleton.
TL;DR: In this article, the methanolic extract of Ficus pumila L. fruit (Moraceae) was used to obtain sterols, triterpenoids and a furocoumarin (psoralene).
Abstract: From the methanolic extract of Ficus pumila L. fruit (Moraceae), two new sterols, (24S)-stigmast-5-ene-3β,24-diol, (24S)-24-hydroxystigmast-4-en-3-one, two new cycloartane-type triterpenoids, (24RS)-3β-acetoxyeycloart-25-en-24-ol, (23Z)-3β-acetoxycycloart-23-en-25-O and a new euphane-type triterpenoid, (23Z)-3β-acetoxyeupha-7,23-dien-25-ol were obtained along with known sterols, triterpenoids and a furocoumarin (psoralene). The structures of the new compounds were determined by spectral methods.
TL;DR: Two new triterpenes were isolated from the leaves of Larix kaempferi together with two known compounds, 24- methylenecycloartanone and 24-methylenecYcloArtanone, and these new compounds were characterized as cycloarts-3,24-dione and lanost-9(11)-en-3alpha,24S,25-triol on the basis of chemical and spectroscopic evidence.
TL;DR: Two new diarylheptanoid glycosides, hirsutanonol 5-O-(6-O-galloyl)-β-D-glucopyranoside and 3-deoxohirsutanol 5 -O-β -D-gene, were isolated from fresh leaves of Alnus japonica together with three known triterpenes and quercitrin this article.
Abstract: Two new diarylheptanoid glycosides, hirsutanonol 5-O-(6-O-galloyl)-β-D-glucopyranoside and 3-deoxohirsutanonol 5-O-β-D-glucopyranoside, were isolated from fresh leaves of Alnus japonica together with three known diarylheptanoids [hirsutanonol, hirsutanonol 5-O-β-D-glucopyranoside and hirsutenone], five known triterpenes [β-amyrin, 3-O-acetyl-β-amyrin, 3-O-acetyltaraxerol, glutinone and lupenone] and quercitrin. One more new diarylheptanoid glycoside, 3-deoxohirsutanonol 5-O-(6-O-β-D-apiosyl)-β-D-glucopyranoside was also isolated from bark together with 3-deoxohirsutanonol 5-O-β-D-glucopyranoside, two known diarylheptanoids [hirsutoside and hirsutanonol 5-O-D-glucopyranoside and four known triterpenes [glutinol, glutinone, lupenone and taraxerone]. Their structures were determined on the basis of spectroscopic and chemical evidence.
TL;DR: Eight pentacyclic triterpenoids have been isolated from the aerial parts of Rubus xanthocarpus and four of them are new compounds and their structures were elucidated on the basis of spectral data and chemical transformations.