Showing papers on "Triterpene published in 1995"
TL;DR: All triterpenoids were remarkably active against the edema produced by TPA, and the presence of a C-28 or C-30 carboxylic group and an alcoholic group at C- 28 increases the activity in carrageenan- and EPP-induced edemas, respectively.
Abstract: In order to establish the possible relationship between their chemical structures and pharmacological properties, the oral and topical anti-inflammatory activities of ten triterpenoids belonging to the lupane, oleanane, and ursane series, were evaluated. All triterpenoids were remarkably active against the edema produced by TPA. While the basic carbon skeleton has no influence on the activity, the presence of a C-28 or C-30 carboxylic group and an alcoholic group at C-28 increases the activity in carrageenan- and EPP-induced edemas, respectively.
170 citations
TL;DR: From the roots of Clematis stans three new oleanane-type triterpenoid saponins named clemastanoside A, B and C, and two new lignan glycosides named Clemastanin A and B, have been isolated together with three known triterPenoid sap onins, huzhangoside B, C and D.
Abstract: From the roots of Clematis stans three new oleanane-type triterpenoid saponins named clemastanoside A, B and C, and two new lignan glycosides named clemastanin A and B, have been isolated together with three known triterpenoid saponins, huzhangoside B, C and D, and three known lignan glycosides, (+)-lariciresinol 4-O-beta-D-glucopyranoside, (+)-lariciresinol 4'-O-beta-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-beta-D-glucopyranoside. In addition, from the leaves, four new oleanane-type triterpenoid saponins, named clemastanoside D, E, F and G, have been isolated together with five known triterpenoid saponins, hederasaponin B, kizutasaponin K12, huzhangoside B, sieboldianoside B and huzhangoside D, and three known flavonoids, isoquercitrin, rutin and quercetin 3-O-beta-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows: clemastanoside A, 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-a lpha-L- arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-alpha-L-rhamnopyranosyl-(1-->4)-beta-D- glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (terminal rhamnosyl 4-O-acetate of huzhangoside B); clemastanoside B and C, 3-O-beta-D-xylopyranosyl- and 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L- rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl- (1-->6)-beta-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl- (1-->2)-alpha-L-arabinopyranosyl hederagenin 28-O-beta-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-a lpha-L- arabinopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta- D- glucopyranosyl ester, respectively; clemastanin A, (7S,8R)-3-methoxy-3',4,9,9'-tetrahydroxy-4',7-epoxy-5',8-lignan 3'-O-beta-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-beta-D-glucopyranoside.
81 citations
TL;DR: Two new lupane triterpenes, salacianone (lup-20(29)-en-3,21-dione) and salacicianol (21β-hydroxylup 20(29)en-1,3-3-one), have been isolated from the hexane extract of the stem bark of Salacia beddomei together with the known compounds lup20( 29)-en-(3,3)-one, friedelan-3-, 3,1)-one and sitosterol.
67 citations
TL;DR: The time courses of 27 haemolytic saponins out of 75 synthetic steroid and triterpene glycosides were compared and it was found that the ha Hemolytic rates of the steroids were fast while those of the triterpenoids were slow.
Abstract: The time courses of 27 haemolytic saponins out of 75 synthetic steroid and triterpene glycosides were compared. The haemolytic rates of the steroids were fast while those of the triterpenoids were slow.
66 citations
TL;DR: Two triterpenoids, 2α,3α-dihydroxy-urs-12-ene-24-oic acid and urs- 12ene-3α,24-diol, have been isolated from the gum resin of Boswellia serrata.
58 citations
TL;DR: In this paper, the separation of lanostane-type triterpene acids carrying an acetoxyl group from sclerotia of Poria cocos (hoelen) was effectively achieved by means of preparative HPLC of the phthalimidomethyl esters followed by selective hydrolysis of the PHTHM groupings.
54 citations
TL;DR: A new iridoid lactone, morindolide, and a newiridoid glucoside, morofficinaloside have been isolated from a Chinese natural medicine, Morindae Radix, the dried root of Morinda officinalis How.
Abstract: A new iridoid lactone, morindolide, and a new iridoid glucoside, morofficinaloside, have been isolated from a Chinese natural medicine, Morindae Radix, the dried root of Morinda officinalis How. together with a number of known compounds: five anthraquinones, four iridoid glucosides, a monoterpene glycoside, two sterols, an ursane-type triterpene, and a lactone compound. The chemical structures of the new compounds were determined on the basis of chemical and physicochemical evidence.
44 citations
TL;DR: In this article, the structures of Julibrosides I, II, and III, isolated from dried stem bark of Albizzia julibrissin DURAZZ (Albizziae Cortex), were characterized as complex triterpenoidal glycosides linked to the monoterpene glycoside dimer.
Abstract: The structures of Julibrosides I, II, and III, isolated from dried stem bark of Albizzia julibrissin DURAZZ (Albizziae Cortex), were characterized as complex triterpenoidal glycosides linked to the monoterpene glycoside dimer, mainly by means of an NMR spectroscopic method. These compounds have a common structure comprising from acacic acid, the (6S)-2-trans-6-hydroxy-2,6-dimethy1-2,7-octadienoyl-6-O-quinovopyranoside dimer, and α-L-arabinofuranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside. The diversity of the oligosaccharides attached to the C-3 hydroxyl group of acacic acid, an oleanane-type triterpene, makes a distinction between Julibrosides I, II, and III.
41 citations
TL;DR: E and Z-Senegasaponins a and b were found to exhibit potent inhibitory effects on alcohol absorption and hypoglycemic activity in the oral D-glucose tolerance tests in rats, and some structure-activity relationships of the acylated bisdesmoside-type saponins were clarified.
Abstract: E-Senegasaponins a, b, and c were isolated from Senegae Radix, the root of Polygala senega L. var. latifolia TORREY et GRAY, together with their Z-isomers of the 4"-methoxycinnamoyl moiety, Z-senegasaponins a, b, and c. The structures of E-senegasaponins a and b and Z-senegasaponins a and b have been elucidated on the basis of chemical and physicochemical evidence, and the geometrical isomeric structure of the 4"-methoxycinnamoyl group in each saponin was found to show tautomer-like behavior in methanol solution or under irradiation with fluorescent lamps. E and Z-Senegasaponins a and b were found to exhibit potent inhibitory effects on alcohol absorption and hypoglycemic activity in the oral D-glucose tolerance tests in rats, and some structure-activity relationships of the acylated bisdesmoside-type saponins were clarified.
40 citations
TL;DR: In this article, nine novel stereoisomeric triterpene dimers, xuxuarines Aα (1), Aβ (2), Bα (3), Bβ (4), Cα (5), Cβ (6), Dα (7), Dβ (8) and 7′,8′-dihydroxuxuarine Aβ(9), were isolated from a South American medicinal plant "xuxua" (Maytenus chuchuhuasca Raymond-Hamet et al.
40 citations
TL;DR: The structure of a brominated triterpenoid from the red alga Laurencia omaezakiana Masuda sp. ined was elucidated by spectroscopic analysis and chemical reactions of a degradation product.
Abstract: The structure of a novel brominated triterpenoid, designated enshuol, from the red alga Laurencia omaezakiana Masuda sp. ined. (Enshu-sozo) was elucidated by spectroscopic analysis and chemical reactions of a degradation product.
TL;DR: Six new oleanane-type triterpene saponins, called reiniosides A-F, were isolated from the roots of Polygala reinii Fr.
Abstract: Six new oleanane-type triterpene saponins, called reiniosides A-F, were isolated from the roots of Polygala reinii Fr. et Sav. and their structures were elucidated by spectroscopic and chemical means.
TL;DR: From the seeds of Trifolium alexandrinum, two new oleanene-type triterpene glycosides were isolated as their methyl esters, together with five known saponins, determined by NMR and mass spectral analyses.
TL;DR: From the roots of Silene jenisseensis a new trans-p-methoxycinnamoyl triterpene saponin has been isolated and exhibited only a weak inhibitory effect in the cyclooxygenase inhibition assay.
TL;DR: The usefulness of tandem mass spectrometry in the structural determination of oleanene-type triterpene bisdesmosides is also discussed.
Abstract: A continuing study of the ingredients of Puerariae Radix, the roots of Pueraria lobata (WILLD.) OHWI, which is one of the most important crude drugs, has resulted in the first isolation of four new oleanene-type triterpene glycosides, named kudzusaponins SA1, SA2, SA3 and C1 (1-4). Their structures were determined to be 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl soyasapogenol A (1), 3-O-beta-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl soyasapogenol A 22-O-alpha-L-arabinopyranoside (2), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-D- glucuronopyranosyl kudzusapogenol C 21-O-beta-D-glucopyranoside (4), respectively. The usefulness of tandem mass spectrometry in the structural determination of oleanene-type triterpene bisdesmosides is also discussed.
TL;DR: A tirucallane triterpene, (−)-leucophyllone, was isolated from the stem bark of Aglaia leucophylla and its structure was elucidated from spectral data as 23( Z )-25methoxy-tirucall-7,23-diene-3-one as discussed by the authors.
TL;DR: The latex of Euphorbia lathyris was shown to be capable of producing lanosterol, as well as cycloartenol, butyrospermol and hopenol B, via the enzymatic cyclization of 2,3-oxidosqualene.
TL;DR: In this paper, seven triterpenoid saponins were isolated from the seeds of Amaranthus caudatus (Amaranthaceae) and their structures were elucidated on the basis of spectral and chemical data.
Abstract: Seven new triterpenoid saponins were isolated from the seeds of Amaranthus caudatus (Amaranthaceae). Their structures were elucidated on the basis of spectral and chemical data to be (1) 3-β-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-2β,3β-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester, (2) 3-α-O-α-L-rhamnopyranosyl-(1→2)-6-O-methyl-β-D-glucopyranosyl-2β,3β-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester; (3) 3-β-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl-2β,3β-dihydroxy-23-oxoolean- 12-en-28-oic acid 28-O-β-D-glucopyranosyl ester; (4) 3-β-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-2β,3β,6α-trihydroxy-23-oxoolean12-en-28-oic acid 28-O-β-D-glucopyranosyl ester; (5) 2β,3β-dihydroxy-30-norolean-12,20(29)-diene-23,28-dioic acid 28-O-β-D-glucopyranosyl ester; (6) 2β,3β-dihydroxy-30-norolean-12,20(29)-diene-23,28-dioic acid 23,28-di-O-β-D-glucopyranosyl ester, (7) 3-O-β-D-glucopyranosyl-2β,3β-dihydroxy-30-norolean-12,20(29)-diene-23,28-dioic acid 23,28-di-O-β-D-glucopyranosyl ester
TL;DR: Cylindrin and lupeol methyl ether were isolated for the first time from Palmae leaf epicuticular waxes and a new triterpene methyl ether was isolated from O. phalerata wax.
TL;DR: Forty-two triterpenoids including eight novel compounds, gammacer-16-en-3β-yl acetate (1), Gammacer 16-en 3β-ol (2), gammceramide-15-en 2β-α-ol(3), gameramide-14-en 1β-γ-yl-acetate (4), grameramide-13-en.3-one (5), pichierenyl acetates (6), picris hieracioides subsp. japonica
Abstract: Forty-two triterpenoids including eight novel compounds, gammacer-16-en-3β-yl acetate (1), gammacer-16-en-3β-ol (2), gammacer-16-en-3α-ol (3), gammacer-16-en-3-one (4), pichierenyl acetate (5), pichierenone (6), isopichierenyl acetate (7) and isopichierenol (8), were isolated from the fresh roots of Picris hieracioides subsp. japonica, Compositae, and their structures were elucidated by means of spectroscopic analysis, and chemical correlations. Fifteen compounds were also obtained from the fresh aerial parts.
TL;DR: From the methylated trunk wood extracts of Myrianthus liberecus, six pentacyclic triterpenes have been isolated as their methyl esters as discussed by the authors, including the known methyl benthamate, methyl euscaphate and methyl tormentate.
TL;DR: In this paper, a new lupane triterpene and two new triterpingene caffeates were isolated from the bark of Rhoiptelea chiliantha.
TL;DR: A triterpene 3β-hydroxy-lup-20(29)-ene-23,28-dioic acid has been isolated from Mimusops elengi.
TL;DR: In this paper, a biomimetic approach towards the synthesis of chiral diepoxide was described. But this approach was aimed at the squalene tetraepoxide, and double Sharpless epoxidation led to the intermediate bisglycidic alcohol being subject to a stereochemical analysis.
TL;DR: In this paper, two triterpenoid glycosides, anemoclemosides A and B, were isolated from the roots of Anemoclema glaucifolium, along with four known compounds.
TL;DR: A new triterpene diglucoside terminolitin (23-deoxyarjunolitin) has been isolated from the fruits of Terminalia arjuna (Combretaceae) and was identified by IR, (1)H- and (13)C-NMR spectroscopy.
Abstract: A new triterpene diglucoside terminolitin (23-deoxyarjunolitin) has been isolated from the fruits of Terminalia arjuna (Combretaceae) and was identified by IR, 1 H- and 13 C-NMR spectroscopy.
TL;DR: In this paper, the new phenolic triterpenes, blepharodol (5) and 7α-hydroxy-blepharodorol (6) were isolated from Maytenus blepharis and canarol (8), 7α,hydrox-canarol, 7-hydoxy-6-oxoiguesterol (11), canaradial (12), and the triterpene methylene quinones iguesteroquinone (13), and were elucidated by means of 1H and 13
Abstract: The new phenolic triterpenes, blepharodol (5) and 7α-hydroxy-blepharodol (6) were isolated from Maytenus blepharodes and canarol (8), 7α-hydroxy-canarol (9), 7-hydroxy-6-oxoiguesterol (11), canaradial (12) and the triterpene methylene quinones iguesteroquinone (13) and 7α-hydroxy-7,8-dihydro-iguesterin (14) and were isolated from Maytenus canariensis. Their structures were elucidated by means of 1H and 13C NMR spectroscopic studies, including homo and heteronuclear correlations, DEPT, COSY, HMQC and HMBC experiments. These products are intermediates in the biogenetic pathway of methylene quinone triterpenes.
TL;DR: Four new triterpene esters were elucidated and nmr assignments have been made for two previously known compounds in this group of phorbol esters.
Abstract: Anti-HIV activity and the inhibition of phorbol ester receptor binding activity in two species of Maprounea were traced to small amounts of highly potent phorbol esters of the daphnane type The triterpenes previously isolated from this genus were found to be devoid of biological activity when scrupulously purified Four new triterpene esters were elucidated; two [3,4] were found in M africana, while three [4,6,7] were found in M membranacea Nmr assignments have also been made for two previously known compounds [2,5] in this group
TL;DR: Two bioactive novel triterpene glycosides named hovenidulciosides A1 and A2 have been isolated from a Chinese natural medicine and exhibited inhibitory activity on the histamine release from rat mast cells induced by compound 48/80 or calcium ionophore A-23187.
Abstract: Two bioactive novel triterpene glycosides named hovenidulciosides A1 and A2 have been isolated from a Chinese natural medicine, Hoveniae Semen Seu Fructus, the seeds and fruit of Hovenia dulcis Thunb. (Rhamnaceae). The absolute stereostructures of hovenidulciosides A1 and A2 with a migrated 16,17-seco-dammarane skeleton have been determined on the basis of chemical and physicochemical evidence which included the X-ray crystallographic analysis of the p-bromobenzoate of their common aglycone, hovenidulcigenin A. Hovenidulciosides A1 and A2 exhibited inhibitory activity on the histamine release from rat mast cells induced by compound 48/80 or calcium ionophore A-23187.