Studies on the constituents of Swertia japonica MAKINO I. On the structures of new secoiridoid diglycosides

Eight new secoiridoid diglycosides, 6'-O-alpha-L-arabinopyranosylswertiamarin (1), 3'-O-beta-D-glucopyranosylswertiamarin (2), 4'-O-beta-D-glucopyranosylswertiamarin (3), 3'-O-beta-D-galactopyranosylswertiamarin (4), 6'-O-alpha-D-galactopyranosylswertiamarin (5), 6'-O-alpha-D-mannopyranosylswertiamarin (6), 6'-O-beta-D-fructofuranosylswertiamarin (7) and 5'-O-beta-D-glucopyranosylamaroswerin (12), were isolated, together with five known compounds from the whole plants of Swertia japonica MAKINO. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence. Compounds 6 and 7 are the first naturally occuring iridoid diglycosides having an alpha-D-mannopyranosyl unit and beta-D-fructofuranosyl unit, respectively.     

Studies on the constituents of Lonicera species. XVII. New iridoid glycosides of the stems and leaves of Lonicera japonica THUNB

Four new iridoid glycosides, named L-phenylalaninosecologanin (1), 7-O-(4-beta-D-glucopyranosyloxy-3-methoxybenzoyl)secologanolic acid (2), 6'-O-(7alpha-hydroxyswerosyloxy)loganin (3) and (Z)-aldosecologanin (5), were isolated, together with a known one, newly named (E)-aldosecologanin (4), from the stems and leaves of Lonicera japonica. Their structures were established on the basis of chemical and spectral data.     

番红花化学成分研究 III. 番红花花粉中的番红花新苷甲和乙的结构

从番红花(crocus sativus L.)花粉中分到两个新苷, 命名为番红花新苷甲(1)和乙(2)。经理化性质和对它们的IR、UV、^1HNMR和MS数据的分析, 鉴定1为异鼠李素-4'-O-α-L-鼠李吡喃(1→2)β-D-葡萄吡喃糖苷, 2为β-对羟基苯基-乙醇-α-O-α-L-鼠李吡喃糖(1→2)-β-D-葡萄吡喃糖苷。     

Two new iridoid glycosides from the Tibetan folk medicine Swertia franchetiana

Two new iridoid glycosides designated as senburiside III (2) and senburiside IV (3), together with one known iridoid glycoside senburiside I (1) and three known secoiridoid glucosides swertiamarin (4), gentiopicroside (5) and sweroside (6), were isolated from the whole plant of Swertia franchetiana. The structures of the two new compounds were elucidated by spectroscopic methods.     

Two new xanthone glycosides from Swertia punicea Hemsl. and their anti-inflammatory activity

Abstract

Two new xanthone glycosides (1–2), together with seven known analogues (3–9), were isolated from whole herb of Swertia punicea. The structures of these metabolites were established on the basis of detailed spectroscopic analysis and comparison with data reported in the literature. In an in vitro test, all isolates were evaluated for their anti-inflammatory activity. The results revealed that all of them showed significant anti-inflammatory activity with IC₅₀ values ranging from 1.237 to 3.319?mM. Compounds 3, 4, and 5 (IC₅₀ values in the range 1.237–1.987?mM) displayed more potent anti-inflammatory activity than the positive control, indomethacin (IC₅₀ value of 2.004?mM).     

Triterpene glycosides ofFatsia japonica. I. Isolation and structure of glycosides fromFatsia japonica seeds

The known triterpene glycosides hederagenin 3-O--L-arabinopyranoside, hederagenin 3-O-\-D-glucopyranoside, oleanolic acid 3-O--sophoroside, hederagenin 3-O--sophoroside, and their 28-O--gentiobiosyl esters, respectively, in addition to the new triterpene glycoside 3-O--sophorosyl-28-O--L-rhamnopyranosyl-(14)-O--gentiobiosyl hederagenin are isolated fromFatsia japonica (Araliaceae) seeds. The structures of these glycosides are established using chemical and spectral methods.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 131–133, March–April, 2000.     

Studies on the constituents of Syringa species. X. Five new iridoid glycosides from the leaves of Syringa reticulata (Blume) Hara

Five new iridoid glycosides, (8Z)-ligstroside (1), (8Z)-nüzhenide (3), 6'-O-alpha-D-glucopyranosylsyringopicroside (4), 3'-O-beta-D-glucopyranosylsyringopicroside (5) and 4'-O-beta-D-glucopyranosylsyringopicroside (6) were isolated, together with a known one, (8E)-nüzhenide (2), from the leaves of Syringa reticulata. Their structures were established on the basis of chemical and spectral data. Compounds 1 and 3 are the first findings of a (8Z)-oleoside-type secoiridoid. Compound 4 is the first naturally occurring iridoid di-glycoside having an isomaltose.     

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.