New bitter-tasting hemiterpene glycosides from the Japanese fern Hymenophyllum barbatum.

Hymenosides G--J were newly isolated from the Japanese fern Hymenophyllum barbatum, in addition to hymenosides A--F. The structures of hymenosides were elucidated by extensive two-dimensional nuclear magnetic resonance and/or chemical evidence. The structures of those aglycones were divided into three types, 1,4-dihydroxy-2-hydroxymethyl-but-2-ene, 1,4-dihydroxy-2-methyl-but-2-ene, and 3-hydroxy-5-hexanolide. The sugar moieties were also established by chemical and spectroscopic methods, which were acylated by phenylacetic acid derivatives. These glycosides had a bitter or weakly pungent taste.     

Hymenosides A-F, six new hemiterpene glucosides from the Japanese fern Hymenophyllum barbatum

In the course of investigation of the bitter-tasting substances of the Japanese fern Hymenophyllum barbatum belonging to the family Hymenophyllaceae, six new hemiterpene glucosides called hymenosides A-F (1-6) have been isolated from the methanol extract, together with an acyclic bis-bibenzyl derivative, perrottetin H. This paper deals with the structure elucidation of the newly isolated glucosides.     

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.     

New flavonoid oligoside fromAconitum barbatum Pers.

A new flavonoid oligoside,viz. 3-O-[3,4-)di-O-acetyl-β-xylopyranosyl)-α-rhamnopyranosyl]-7-o-(α-rhamnopyranosyl)kaempferol, was isolated from the above-ground part of the plantAconitum barbatum Pers. The product was identified by spectral methods. Published inIzvestiyu Akademii Nauk. Seriya Khimicheskaya. No. 11, pp. 1935–1937, November, 2000.     

New lignan glycosides from Glehnia littoralis

From the roots ethanol extract of Glehnia littoralis, two new lignan glycosides, named glehlinoside E (1) and F (2), were obtained. Their structures were determined to be (-)-secoisolariciresinol 4-O-β-D-(6-O-feruloyl) glucopyranoside (1) and (-)-secoisolariciresinol 4-O-β-D-(6-O-caffeloyl) glucopyranoside (2) by analysis of their spectral data, respectively.     

New pregnane glycosides from Cynanchum ascyrifolium

Two new pregnane glycosides, cynascyrosides D and E, were isolated from the roots of Cynanchum ascyrifolium. The structures of these compounds were determined on the basis of spectroscopic and chemical evidence as cynajapogenin A 3-O-alpha-L-cymaropyranosyl-(1-->4)-beta-D-digitoxopyranosyl-(1-->4)-beta-L-cymaropyranoside and cynajapogenin A 3-O-beta-D-glucopyranosyl-(1-->4)-alpha-L-diginopyranosyl-(1-->4)-beta-L-cymaropyranosyl-(1-->4)-beta-D-digitoxopyranoside.     

New farnesylhydroquinone glycosides from the gorgonian Euplexaura anastomosans

Euplexides F (3) and G (4), novel farnesylhydroquinone glycosides, have been isolated as minor constituents of the gorgonian Euplexaura anastomosans. The structures of these compounds have been determined by combined spectroscopic methods. These compounds exhibited moderate cytotoxicity and inhibitory activity against PLA2.     

New glycosides from plants of the genus Phlojodicarpus

From plants of the genusPhlojodicarpus have been isolated the new coumarins umbelliferone -D-apiosyl (1 6)--D-glucopyranoside (I) and 8-(2,3-dihydroxy-3-methylbutyl)umbelliferone 7-O--D-glucopyranoside (II) and also the flavone glycoside diosmetin 7-O--D-glucopyranoside (III). The result of IR, UV, PMR, and¹³C NMR spectroscopy are given.Institute of Chemistry, Academy of Sciences of the Mongolian Peoples' Republic, Ulan-Bator; Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 36–39, January–February, 1986.     

New phenylethanoid glycosides from Bacopa monniera

Three new phenylethanoid glycosides, viz. monnierasides I-III (1-3) along with the known analogue plantainoside B were isolated from the glycosidic fraction of Bacopa monniera. Their structures were elucidated mainly on the basis of two dimensional (2D) NMR spectral analyses.     

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 glycosides from the rhizomes of Tacca chantrieri

Five new glycosides, which are classified into two bisdesmosidic pseudofurostanol glycosides (1, 2), two new ergostanol glycosides (3, 4), and a new phenolic glycoside (5), were isolated from the rhizomes of Tacca chantrieri. The structures of 1-5 were determined on the basis of extensive spectroscopic analysis, including that of two-dimensional (2D) NMR data, as well as hydrolytic cleavage followed by spectroscopic and chromatographic analyses.     

New flavonoid glycosides from the leaves of Solidago altissima

Two new flavonoid glycosides kaempferol 3-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1), and quercetin 3-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), together with six known flavonoid glycosides were isolated from the leaves of Solidago altissima L. grown in Kochi of Japan. The structure elucidation of the isolated compounds was performed by acid hydrolysis and spectroscopic methods including UV, IR, ESI-MS, 1D- and 2D-NMR experiments.     

New oleanene glycosides from the leaves of Acanthopanax japonicus

The structures of 6 new oleanene glycosides (1--6) isolated from the leaves of Acanthopanax japonicus FRANCH et. SAVART (Araliaceae) were elucidated by mass, 1D, and 2D NMR spectroscopy. The structures of 1--6 were established as 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester of 3beta,23-dihydroxy-olean-12-en-28,29-dioic acid, 3beta,30-dihydroxy-olean-12-en-23,28-dioic acid, 3beta,29-dihydroxy-olean-12-en-23,28-dioic acid (=dianic aicd), 3beta-dihydroxy-olean-12-en-23,28-dioic acid (=gypsogenic acid), 3beta,29-dihydroxy-23-oxo-olean-12-en-28-oic acid, and 3beta-hydroxy-23-oxo-olean-12-en-28,29-dioic acid, designated acanjaposide D (1), E (2), F (3), G (4), H (5), and I (6), respectively.     

New secoiridoid glycosides from the roots of Picrorhiza scrophulariiflora

Three new secoiridoid glycosides, named picrogentiosides A (1), B (2) and C (3), have been isolated from the underground parts of Picrorhiza Scrophulariiflora, together with the two known compounds plantamajoside (4) and plantainoside D (5). Their structures were established by spectroscopic analyses and comparisons with data from related compounds. A pilot pharmacological study showed that picrogentiosides A (1) and B (2) have an immunomodulatory effect in vitro.     

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.     

New cholestane glycosides from the leaves of Cordyline terminalis

Four new cholestane glycosides (1-4) were isolated from the leaves of Cordyline terminalis (Agavaceae). The structures of the new compounds were determined on the basis of spectroscopic analysis and a few chemical transformations followed by chromatographic and spectroscopic analyses.     

New phenolic glycosides from the seeds of Cucurbita moschata

Five new phenolic glycosides, cucurbitosides A-E (1-5), were isolated from the seeds of Cucurbita moschata. Their structures were elucidated as 2-(4-hydroxy)phenylethanol 4-O-(5-O-benzoyl)-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (1), 2-(4-hydroxyphenyl)ethanol 4-O-[5-O-(4-hydroxy)benzoyl]-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (2), 4-hydroxybenzyl alcohol 4-O-(5-O-benzoyl)-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (3), 4-hydroxybenzyl alcohol 4-O-[5-O-(4-hydroxy)benzoyl]-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (4) and 4-hydroxyphenyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (5) on the basis of spectroscopic analysis and chemical evidence.