Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXXIX. Askendoside H from <Emphasis Type="Italic">Astragalus taschkendicus</Emphasis>

A new triterpene glycoside of the cycloartane series that was called askendoside H was isolated from roots of Astragalus taschkendicus Bunge (Leguminosae). Its structure was elucidated based on chemical transformations and spectral data. Askendoside H was a bisdesmoside of cycloorbigenin C, 23R,24Rcycloartan-3β,6α,16β,23,24,25-hexaol 3-O-[(α-L-arabinopyranosyl)(1 → 2)-β-D-xylopyranoside] 23-O-βD-glucopyranoside.     

A new furostanol glycoside with fatty acid synthase inhibitory activity from <Emphasis Type="Italic">Ophiopogon japonicusa</Emphasis>

A new furostanol glycoside, named ophiopogonin J (1), was isolated from the fibrous root of Ophiopogon japonicas. The structure of the compound was established as (25R)-26-[(O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl)]-20α -hydroxyfurost-5, 22-diene-3-O-α-L-rhamnopyranosyl-(1 → 2)-[β-D-xylopyranosyl(1 → 4)]-β-D-glucopyranoside on the basis of spectroscopic methods, including HR-ESI-MS and 1D and 2D NMR experiments.     

A new flavonoid glycoside from <Emphasis Type="Italic">Galium verum</Emphasis>

A new flavonoid glycoside, an apigenin 7-O-(3,4-di-O-acetyl)-α-L-rhamnopyranosyl-(1 → _6)-β-D- glucopyranoside (1), was isolated from the 95% ethanol extract of Galium verum L. Its structure was elucidated by spectroscopic analysis.     

New triterpene glycoside from <Emphasis Type="Italic">Cyclamen adzharicum</Emphasis> tubers

Nine pure glycosides were isolated from total saponins of Cyclamen adzharicum Pobed. (Primulaceae). The total chemical structure of cyclamen F, 3β-O-[β-D-Xylp(1→2)]-[β-D-Glcp(1→2)]-(β-D-Glcp(1→4)-α-L-Arap)-16α-hydroxy-13,28-epoxy-30,30-dibutoxyolean, was elucidated using modern physicochemical and spectral methods (NMR, ¹H, ¹³C, HMBC, HMQC, DEPT, COSY, MS). A glycoside with the cyclamen F chemical structure has not been reported and, therefore, is a new organic compound.     

Identification of a new flavone glycoside from <Emphasis Type="Italic">Codonopsis nervosa</Emphasis>

A new flavone glycoside, luteolin 7-O-[(6″′-caffeoyl)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranoside (1), was isolated from Codonopsis nervosa, along with three other known compounds, luteolin 7-O-β-D-glucopyranoside (2), luteolin 7-O-gentiobioside (3), and tangshenoside VI (4). Their structures were determined on the basis of 1D and 2D NMR, IR, and HR-ESI-MS.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXXV. Structure of cyclomacroside E

The structure of a new cycloartane-type triterpene glycoside, cyclomacroside E, which was isolated from roots of Astragalus macropus Bunge (Leguminosae), was established as 3-O-α-L-rhamnopyranoside,24-O[(β-D-xylopyranosyl)(1→2)-β-D-xylopyranoside]-24R-cycloartan-1α,3β,7β,24,25-pentaol.     

A new flavone glycoside from the aerial part of <Emphasis Type="Italic">Scutellaria schachristanica</Emphasis>

The new flavone glycoside schachristanoside was isolated from the aerial part of Scutellaria schachristanica Zuz. (Lamiaceae). Spectral data and chemical transformations found that schachristanoside had the structure chrysin-7-O-[α-L-arabinopyranosyl-(1 → 6)]-β-D-glucopyranoside.     

Minor asterosaponin archasteroside C from the starfish <Emphasis Type="Italic">Archaster typicus</Emphasis>

A new minor asterosaponin (20S)-6-O-{β-d-fucopyranosyl-(1→2)-[β-d-fucopyranosyl-(1→4)-β-d-quinovopyranosyl-(1→2)]-β-d-quinovopyranosyl-(1→3)-β-d-quinovopyranosyl}-3β,6α,20-trihydroxycholest-9(11)-en-23-one 3-sulfate (archasteroside C) was isolated from the starfish Archaster typicus collected in shallow coastal waters of Vietnam. The structure of archasteroside C was determined by 2D NMR spectroscopy and electrospray ionization (ESI) tandem mass spectrometry.     

A new hederagenin glycoside from <Emphasis Type="Italic">Nephelium lappaceum</Emphasis>

A new oleane-type triterpene oligoglycoside, hederagenin 3-O-(3-O-acetyl-β-D-xylopyranosyl)-(1→3)-α-L-arabinopyranoside (2), together with four known compounds, hederagenin (1), hederagenin 3-O-(4-O-acetyl-α-L-arabinopyranosyl)-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (3), hederagenin 3-O-α-L-arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (4), hederagenin 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-D-xylopyranoside (5), was isolated from the hull of Nephelium lappaceum. All the isolates were obtained from the hull of rambutan for the first time.     

Flavonoid oligosides from georgian <Emphasis Type="Italic">Astragalus falcatus</Emphasis>

New flavonoid oligosides were isolated from leaves and flowers of Astragalus falcatus Lam. It was found on the basis of chemical transformations, UV, IR, PMR, ¹³ C NMR, HMBC, HSQC, 1D-TOCSY, and mass spectral properties that falcoside C had the structure quercetin 3-O-[β-D-glucopyranosyl(1 → 3)-α-Lrhamnopyranosyl(1 → 6)]-β-D-galactopyranoside 7-O-β-D-glucopyranoside; falcoside D, isorhamnetin 3-O-[β-D-xylopyranosyl(1 → 3)-α-L-rhamnopyranosyl(1 → 6)]-β-D-galactopyranoside 7-O-α-Lrhamnopyranoside.     

Furostane-Type Steroidal Saponin from <Emphasis Type="Italic">Digitalis ciliata</Emphasis>

A new furostane-type steroidal glycoside and derivative of tigogenin (1) was isolated from aqueous wastes from production of the cardiac drug acetyldigitoxin from leaves of Digitalis ciliata Trautv. (Scrophulariaceae) and characterized. The structure of the glycoside was established using physical constants, chemical transformations, and spectral data as 3-O-β-D-glucopyranosyl-(1→3) [β-D-fucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl-(25R)-5α-furostan-3β,22α,26-triol-26-O-β-D-glucopyranoside.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXXII. Cyclomacroside B,a new glycoside

The structure of the new cycloartane glycoside cyclomacroside B that was isolated from Astragalus macropus Bunge (Leguminosae) was shown to be 1,7-di-O-acetyl-24R-cycloartan-1α,3β,7β,24,25-pentaol 3-O-α-Lrhamnopyranoside-24-O-β-D-xylopyranoside.     

Triterpene glycosides from <Emphasis Type="Italic">Lonicera</Emphasis>. Isolation and structural determination of seven glycosides from flower buds of <Emphasis Type="Italic">Lonicera macranthoides</Emphasis>

The structures of seven triterpene glycosides (1–7), of which the 23-O-acetyl, 28-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin 3-O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside (2) was new, from the flower buds of Lonicera macranthoides were established using chemical and NMR spectroscopic methods. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 32–34, January–February, 2008.     

A new triterpene glycoside from <Emphasis Type="Italic">Premna microphylla</Emphasis>

A new triterpene glycoside, namely 28-O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranoside tormentic acid ester, was isolated from the leaves of Premna microphylla, together with two known triterpenes, i.e., arjunolic acid (2) and hyptatic acid A (3). Its structure was established by mass-spectrometric and spectroscopic methods, especially 2D NMR techniques. This is the first report of the isolation of triterpenes from this plant. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 173–174, March–April, 2009.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXX. Cyclomacroside D,a new bisdesmoside

The structure of the new cycloartane glycoside cyclomacroside D, which was isolated from Astragalus macropus Bunge (Leguminosae) and is 24R-cycloartan-1α,3β,7β,24,25-pentaol 3-O-α-L-rhamnopyranoside–24-O-β-D-xylopyranoside, was proved. Presented at the 7th International Symposium on the Chemistry of Natural Compounds (SCNC, Tashkent, Uzbekistan, October 16–18, 2007). Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 48–50, January–February, 2009.     

A new flavanone glycoside from <Emphasis Type="Italic">Clausena pentaphylla</Emphasis>

From the ethyl acetate extract of the roots of Clausena pentaphylla, a flavanone glycoside, 5,7-dihydroxy3',4'-dimethoxyflavanone 6-C-[α-rhamnopyranosyl-(1 → 6)]-β-glucopyranoside (1), was isolated. The isolated compound was characterized by UV, IR, and NMR (¹H, ¹³C) studies.     

Phenolic constituents from the stems of <Emphasis Type="Italic">Acanthopanax senticosus</Emphasis>

A new phenolic glycoside was isolated from the stems of Acanthopanax senticosus together with sixteen known compounds. The structure of the new compound was determined to be 2,6-dimethoxy-4-[(1E)-3,3-dimethoxy-1-propenyl]phenyl β-D-glucopyranoside (1) by means of physical, chemical, and spectroscopic methods. Of the known compounds, salvadoraside (7), (7R,8S)-dihydrodehydrodiconiferyl alcohol 4,9′-di-O-β-D-glucopyranoside (8), 3-(4-O-β-D-glucopyranosylferuloyl)quinic acid (15), rel-5-(1R,5S-dimethyl-3R,4R,8S-trihydroxy-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (16), and lycoperodine-l (17) were first reported from the title plant. The inhibitory activities of the isolated compounds against α-glucosidase from rat intestine were also reported.     

Polar steroidal compounds from the Far-Eastern starfish <Emphasis Type="Italic">Lethasterias fusca</Emphasis>

Nine steroidal compounds including three new steroidal glycosides, viz., sodium (24S)-3,24-di-O-(β-D-xylopyranosyl)-5α-cholestane-3β,6β,8,15α,24-pentol 15-sulfate (fuscaside A), (24S)-3,24-di-O-(β-D-xylopyranosyl)-5α-cholestane-3β,6β,8,15α,24-pentol (fuscaside B), and (22E,24R)-24-O-(β-D-xylopyranosyl)-5α-cholest-22-ene-3β,6α,8,15β,24-pentol (desulfated minutoside A); three previously known glycosides, viz., distolasterosides D₁ and D₂ and pycno-podioside A; two previously known polyhydroxysteroids, viz., 5α-cholestane-3β,6α,8,15β,16β,26-hexaol and 5α-cholestan-3β,4β,6α,7⇇8,15β,16β,26-octol; and the known sodium 24,25-dihydro-marthasterone 3-sulfate were isolated from the Far-Eastern starfish Lethasterias fusca. The structures of these compounds were elucidated by NMR spectroscopy and mass spectrometry. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 196–200, January, 2008.     

Furostanol Glycosides from leaves of the Chinese plant <Emphasis Type="Italic">Tribulus terrestris</Emphasis>

The structures of five furostanol glycosides (1–5), of which the 26-O-β-D-glucopyranosyl-(25S),5α-furost20(22)-en-12-one-2α,3β,26-triol-3-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1) was new, from the leaves of Tribulus terrestris L. were established using chemical and NMR spectroscopic methods.     

New neolignan glycosides and a new cerebroside from <Emphasis Type="Italic">Symplocos caudata</Emphasis>

A phytochemical investigation of the roots of Symplocos caudata Wall (Symplocaceae) resulted in the isolation and characterization of two optical isomers of a neolignan glycoside (1) and a new cerebroside (2). Their structures were elucidated as (7R,8S)-erythro-7,9,9'-trihydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside, (7S,8R)-erythro-7,9,9'-trihydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan-4-O-β-Dglucopyranoside (1), and 1-O-β-D-glucopyranosyl-(2S,3S,4R,8Z,12E)-2-N-[(2'R)-2'-hydroxyheptacosanoyl]-8,12-docosadiene-1,3,4-triol (2), respectively, on the basis of spectroscopic data (1D and 2D NMR, MS and CD).