Two new triterpene glycosides from the holothurian Duasmodactyla kurilensis

Two new glycosides have been isolated from the total triterpene glycosides of the holothurianDuasmodactyla kurilensis: kurilosides A (III) and C (IV). It has been established that (III) is 16-acetoxy-3-{[O--D-glucopyranosyl-(1 4)-O--D-quinovopyranosyl-(1 2)]-[O-(3-O-methyl--D-glucopyranosyl)-(1 3)-O-(6-O-(sodium sulfato)--D-glucopyranosyl)-(1 4)]--D-xylopyranosyloxy}-4,4,14-trimethylpregen-9(11)-en-20-one, while the minor glycoside (IV) is 16-acetoxy-3-{O--D-quinovopyranosyl-(1 2)-[O-(3-O-methyl--D-glucopyranosyl-(1 3)-O-(6-O-(sodium sulfato)--D-glucopyranosyl)-(1 4)]--D-xylopyranosyloxy}-4,4,14-trimethylpregn-9(11)-en-20-one.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 221–226, March–April, 1991.     

New triterpene glycosides from the holothurian Cladolabes sp.

Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 764–765, September–October, 1988.     

Structures of four new triterpene glycosides from the holothurian Cucumaria japonica

Four new triterpene glycosides of the holostane series have been isolated from an alcoholic extract of the economically important Pacific Ocean holothurianCucumaria japonica: cucumariosides A₁-2 (I), A₂-3 (II), A₂-4 (III), and A₄-2 (IV). The structures of these substances have been established by the methods of carbohydrate chemistry and¹³C NMR spectroscopy. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 787–793, November–December, 1990.     

Structures of four new triterpene glycosides from the holothurian Cucumaria japonica

Four new triterpene glycosides of the holostane series have been isolated from an alcoholic extract of the economically important Pacific Ocean holothurianCucumaria japonica: cucumariosides A₁-2 (I), A₂-3 (II), A₂-4 (III), and A₄-2 (IV). The structures of these substances have been established by the methods of carbohydrate chemistry and¹³C NMR spectroscopy.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 787–793, November–December, 1990.     

Structure of pseudostichoposide A — The main triterpene glycoside from the holothurian Pseudostichopus trachus

A holostane oligoglycoside — pseudostichoposide A — has been isolated from the holothurianPseudostichopus trachus Sluiter, collected on the oceanic side of the island of Urup (Kurile Islands). Its structure has been established with the aid of¹³C and¹H NMR spectroscopy and partial acid hydrolysis with sulfuric acid in the presence of butanol as 3β-{O-(3-O-methyl-β-D-quinovopyransoyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-β-D-quinovopyranosyl-(1 → 2)-[4-O-(sodium sulfato)-β-D-xylopyranosyloxy]}-holost-7-en-22-one. Its native genin, which has been called urupogenin (3β-hydroxyholost-7-en-22-one) was obtained on partial hydrolysis in the form of an individual compound. It is a new holostane derivative.     

New glycosides from the holothurian Cucumaria japonica

Four new compounds have been isolated from the fraction of weakly polar triterpene glycosides of the holothurianCucumaria japonica: cucumariosides A₁-2 (I), A₀-1 (II), A₀-2 (III), and A₀-3 (IV). The structures of these substances have been established by chemical and physical methods.Deceased.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Russian Academy of Sciences, Vladivostok. Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 242–248, March–April, 1993.     

Structure of psolusoside B — A nonholostane triterpene glycoside of the holothurian genus Psolus

The structure of psolusoside B — a minor triterpene oligoglycoside from the holothurianPsolus fabricii and the main glycoside fromPsolus sp. has been determined by the methods of partial acid hydrolysis, methylation,¹³C NMR, and FAB mass spectrometry as 20S-acetoxy-3-{2-O-[O--D-glucopyranosyl-(1 4)-O--D-glucopyranosyl]-4-O-(6-O-sulfato--D-glucopyranosyl)--D-xylo-pyranosyloxy}holosta-7,25-diene-18,16-carbolactone. 3-[O-(3-O-Methyl-6-O-sulfato--D-glucopyranosyl)-(1 3)-O-(6-O-sulfato--D-glucopyranosyl)-(1 4)-O--D-quinovopyranosyl-(12)--D-xylopyranosyloxy]holosta-9(11),25-dien-16-one (psolusoside A), known previously forPsolus fabricii, has been identified in a holothurian —Psolus sp. — from Kraternaya Bay (island of Ushishir).Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 361–368, May–June, 1989.     

New triterpene glycoside from the holothurianNeothyonidium magnum

The main component of the triterpene glycosides from the holothurianNeothyonidium magnum — neothyonidioside C — has been isolated and its structure has been determined by physical and chemical methods as 16-acetoxy-3-[O-(3-O-methyl-6-O-(sodium sulfato)--D-glucopyranosyl-(1 3)-O--D-xylopyranosyl-(1 4)-O--D-quinovopyranosyl-(1 2)-(4-O-(sodium sulfato)--D-xylopyranosyloxy)]holosta-7,25-diene.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 53–57, January–February, 1990.     

Structures of cucumariosides C1 and C2 — Two new triterpene glycosides from the holothurian Eupentacta fraudatrix

Two new triterpene glycosides — cucmariosides C₁ and C₂ — have been isolated from the Far Eastern holothurianEupentacta (=Cucumaria)fraudatrix Djakonov et Baranova. Their structures have been established with the aid of¹³C NMR and PMR spectroscopy, partial acid hydrolysis, periodate oxidation, and methylation as 16β-acetoxy-3-{[3-O-methyl-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)] [β-D-xylopyranosyl-(1→2)]-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyloxy}holosta-7,23,24(cis)-triene and 16β-acetoxy-3-{[3-O-methyl-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)] [β-D-xylopyranosyl-(1→2)]-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyloxy}holosta-7,22,24(trans)-triene, respectively.     

New triterpene glycosides from Camptosorus sibiricus

Two new cycloartane glycosides were isolated from the whole herbs of Camptosorus sibiricus Rupr. By means of chemical and spectroscopic methods (1D and 2D NMR, HRMS, ESI-MS), the structures were established as (24R)-3beta,7beta,24,25,30-pentahydroxycycloartane-30-O-coumaroyl-3-O-beta-D-glucopyranosyl-24-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranoside (1) and (24R)-3beta,7beta,24,25,30-pentahydroxy-1-ene-cycloartane 24-O-beta-D-glucopyranoside (2). The two new compounds were inactive in vitro against A375-S2 and Hela human tumor cell lines using the MTT method.     

New lanostane-type triterpene acids from wolfiporia extensa

ABSTRACT: BACKGROUD: Dried sclerotia of Wolfiporia extensa (Polyporaceae) is used to invigorate the spleen and to tranquilize the mind in Chinese herbal medicine. Lanostane-type triterpene acids were regard as major secondary metabolites from dried sclerotia of W. extensa. RESULTS: Three new lanostane-type triterpene acids, 3-epi-benzoyloxyl-dehydrotumulosic acid (1), 3-epi-(3'-O-methyl malonyloxy)-dehydrotumulosic acid (2) and 3-epi-(3'-hydroxy-3'-methylglutaryloxyl)-dehydrotumulosic acid (3), were isolated from the sclerotia of W. extensa, together with 3 known lanostane derivatives (4-6). Their structures were elucidated on the basis of spectroscopic analysis, including 1D and 2D-NMR techniques. CONCLUSION: Six lanostane derivatives including three new triterpene acids and three known compounds were reported from the sclerotia of W. extensa in this paper.     

New antitumor triterpene saponin from Lysimachia capillipes

One new saponin, named capilliposide D (1), and a known saponin, candidoside (2), were isolated from the whole plants of Lysimachia capillipes. Their structures were determined by 1D and 2D NMR, MS techniques, and chemical methods. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 268–270, May–June, 2006.     

New triterpene diglycosides from the rhizome of Cimifuga foetida

Five new 9,19-cycloartane triterpene diglycosides, which have been named cimiaceroside C (1), and cimifosides A-D (2-5) together with the known compounds cimiracemoside D (6), cimidahurine (7) and alpha-D-glucopyranosyl-l-beta-D-fructofuranoside (8) were isolated from the rhizome of Cimicifuga foetida. The new triterpene diglycosides 1-5 were identified as cimiacerol-3-O-beta-D-xylopyranosyl-(1'-->3')-beta-D-xylopyranoside, 12beta-hydroxycimigenol-3-O-beta-D-xylopyranosyl-(1'-->3')-beta-D-xylopyranoside, 25-Oacetylcimig-enol-3-O-beta-D-xylopyranosyl-(1'-->3')-beta-D-xylopyranoside, 24- acetylhydroshengmanol-3-O-beta-D-xylopyranosyl-(1'-->3')-beta-D-xylopyranoside and 26-deoxyacetylacteol-3-O-beta-D-xylo- pyranosyl-(1'-->3')-beta-D-xylopyranoside, respectively, based on analysis of their spectral data and chemical reactions.     

New triterpene peroxides from Pseudolarix kaempferi

The first study of the chemical constituents of the leaves of Pseudolarix kaemferi revealed three new triterpene peroxides, pseudolarolides Q (1), R (2), S (3). The stereochemical structures of these new compounds were elucidated on the basis of spectral and single-crystal X-ray analyses.     

New antifeedant triterpene glycosides from the Caribbean sponge Erylus formosus

Two groups of antifeedant triterpene glycosides were identified from the Caribbean sponge Erylus formosus. The structure of formoside B, a novel N-acetyl amino derivative of the known penasterol tetrasaccharide formoside, was elucidated using NMR and mass spectral data. Four triterpene hexasaccharides and two triterpene trisaccharides, characterized by a 31-carbon aglycone, proved difficult to isolate and therefore only the structure of their aglycone was determined. Gas chromatographic analysis of derivatized saccharides from these mixtures established the carbohydrate content of these compounds. All of the triterpene glycosides isolated contributed to the chemical defenses of this sponge, although with differing activities.     

New triterpene glucosides from the roots of Rosa laevigata Michx

Two new ursane-type triterpene glucosides, 2alpha,3alpha,24-trihydroxyurs-12,18-dien-28-oic acid beta-D-glucopyranosyl ester (1) and 2alpha,3alpha,23-trihydroxyurs-12,19(29)-dien-28-oic acid beta-D-glucopyranosyl ester (2), were isolated from the roots of Rosa laevigata, together with three known compounds: 2alpha,3beta,19alpha-trihydroxyurs-12-en-28-oic acid beta-Dglucopyranosyl ester (3), 2alpha,3alpha,19alpha-trihydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (4) and 2alpha,3beta,19alpha,23-tetrahydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (5). The structures of new compounds were established on the basis of detailed 1D and 2D NMR spectroscopic analyses. Compounds 2 and 5 exhibited modest in vitro antifungal activities against Candida albicans and C. krusei.     

Triterpene glycosides from the holothurian Cucumaria frondosa

Two triterpene glycosides have been isolated from an alcoholic extract of the holothurianCucumaria frondosa collected in the Kola littoral, Barents Sea: the main component of the glycoside fraction — frondoside A (I) — and a minor component — frondoside A₁ (II).Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Russian Academy of Sciences, Vladivostok. Murmansk Marine Biological Institute. Russian Academy of Sciences, Dal'nie Zelentsy, Murmansk province. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 260–263, March–April, 1993.