Triterpene and steroid glycosides of the genusMelilotus and their genins IV. Trillin and dioscin from the seeds ofMelilotus tauricus

Two steroid glycosides belonging to the spirostan series — trillin and dioscin — have been isolated from the seeds of the plantMelilotus tauricus (Bieb.) Ser. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 770–772, November–December, 1994.     

Triterpene and steroid glycosides of the genusMelilotus and their genins III. Funkioside B and protodioscin from the seeds ofMelilotus tauricus

Two steroid glycosides belonging to the furostan series — funkioside B and protodioscin — have been isolated from the seeds of the plantMelilotus tauricus (Bieb.).Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 766–770, November–December, 1994.     

Triterpene and steroid glycosides of the genusMelilotus and their genins II. Melilotoside D from the roots ofMelilotus albus

A new triterpene glycoside of the oleanane series — melilotoside D — has been isolated from the roots of plantMelilotus albus Medik. (Leguminosae). Melilotoside D is a tetraoside of soyasapogenol B. Its structure has been shown on the basis of chemical transformations and spectral characteristics as soyasapogenol B 3-O-{[O-α-L-rhamnopyranosyl-(1→2)]-[O-α-L-arabinopyranosyl-(1→3)]-O-β-D-galactopyranosyl-(1→2)-α-L-arabinopyranoside}.     

Triterpene and steroid glycosides of theMelilotus genus and their genins I. Melilotosides A,B, and C from the roots ofMelilotus albus

Three new triterpene glycosides of the oleanane series — melilotosides A, B, and C — and the nonglycosylated soyasapogenol B have been isolated from the roots of the plant Melilotus albus Medik. (Leguminosae). The structures of the glycosides have been shown on the basis of chemical transformations and spectral results. Melilotoside A has the structure of soyasapogenol B 3-O-α-L-arabinopyranoside, melilotoside B that of soyasapogenol B 3-O-[O-β-D-galactopyranosyl-(1→2)-α-L-arabinopyranoside], and melilotoside C that of soyasapogenol B 3-O-[O-α-L-rhamnopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→2)-α-L-arabinopyranoside.     

Triterpene glycosides ofAstragalus and their genins

The roots of Astragalus taschkendicus Bunge (Leguminosae) have yielded the new cycloartane glycoside askendoside F which is 24R-cycloartan-3β,6α,16β,24, 25-pentaol 3-O-[O-α-L-arabinopyranosyl-(1→2)-β-D-xylopyranoside] 25-O-D-glucopyranoside, and D-3-O-methyl-chiro-inositol.     

Triterpene glycosides ofAstragalus and their genins. III. Cycloasgenin a fromAstragalus taschkendicus

The new isoprenoid cycloasgenin A has been isolated from the roots of the plantAstragalus taschkendicus C. Bge., and its structure has been established on the basis of chemical transformations and spectral characteristics as 6α,11α,16β, 25-tetrahydroxy-20(S), 24(R)-epoxycycloartan-3-one.     

Triterpene glycosides of Astragalus and their genins. XXXI. Cycloorbigenin B from Astragalus orbiculatus

Chemistry of Natural Compounds - A new methylsteroid of the cycloartane series has been isolated from the epigeal part ofAstragalus orbiculatus Ledeb. (Leguminosae); it has the structure of a...     

Triterpene glycosides of Astragalus and their genins XL. Cyclocarposide B from Astragalus coluteocarpus

In addition to cyclosieversigenin, -sitosterol -D-glucopyranoside, and cyclocarposide, we have isolated another three glycosides of triterpene nature from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). On the basis of chemical transformations and spectral characteristics, the structure of one of the new glycosides, which we have called cyclocarposide B, has been established as 20R,24S-epoxycycloartane-3,6,16,25-tetraol 6-O--L-(2-O-acetylrhamnopyranoside) 3-O--D-xylopyranoside.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 227–231, March–April, 1992.     

Triterpene glycosides of Astragalus and their genins. XXXI. Cycloorbigenin B from Astragalus orbiculatus

A new methylsteroid of the cycloartane series has been isolated from the epigeal part ofAstragalus orbiculatus Ledeb. (Leguminosae); it has the structure of a (23R,24S)-16,23; 16,24-diepoxycycloartane-3,6,25-tetraol.Institute of the Chemistry of Plant Substances, Uzbek SSR. Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, Vol. 6, pp. 809–812, November–December, 1989.     

Triterpene glycosides and their genins from Thalictrum foetidum. III. The structure of cyclofoetoside A

A new glycoside of the cycloartane series — cyclofoetoside A — has been isolated from the epigeal part ofThalictrum foetidum L., and its structure has been established on the basis of chemical transformations and spectral characteristics as 24S-cycloartane-3,16,24,25-tetraol 3-0--L-arabinopyranoside 16-0-[0--L-rhamnopyranosyl-(16)--D-glucopyranoside].Pyatigorsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR; Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 66–71, January–February, 1986.     

Triterpene glycosides ofAstragalus and their genins. XVII. Cycloasgenin B fromAstragalus tashkendicus

The roots ofAstragalus tashkendicus Bge. have yielded a new triterpenoid — cycloasgenin B – the structure of which has been established on the basis of chemical transformations and spectral characteristics as (24R)-6α,11α,16β,24,25-pentahydroxycycloartan-3-one.     

Triterpene and steroid glycosides of the genusMelilotus and their genins IV. Trillin and dioscin from the seeds ofMelilotus tauricus

Two steroid glycosides belonging to the spirostan series — trillin and dioscin — have been isolated from the seeds of the plantMelilotus tauricus (Bieb.) Ser.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 770–772, November–December, 1994.     

Triterpene glycosides ofTragacantha and their genins. Cyclostipulosides A and B fromTragacantha stipulosa

Two new triterpene glycosides of the cycloartane series, which have been called cyclostipulosides A and B, have been isolated in the individual form from the roots ofTragacantha stipulosa Boviss. Their structures have been established by physicochemical methods. Cyclostipuloside A is 24R-cycloartane-3β,6α,16β,24,25-pentaol 16-O-β-D-glucopyranoside 3-O-β-D-xylopyranoside, and cyclostipuloside B is 24R-cycloartane-3β,6α,16β,24,25-pentaol 6-O-α-L-arabinopyranoside 16-O-β-D-glucopyranoside 3-O-β-D-xylopyranoside. By the acid hydrolysis of cyclostipulosides A and B we have obtained the new glycoside 24R-cycloartane-3β,6α,16β,24,25-pentaol 16-O-β-D-glucopyranoside. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (371) 120 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 670–674, September–October, 1998.     

Triterpene glycosides and their genins fromThalictrum foetidum. IV. Structure of cyclofoetigenin B

A glycoside isolated from the epigeal part ofThalictrum foetidum (Ranunculaceae) has yielded a new genin — cyclofoetigenin B — the structure of which has been established on the basis of chemical transformations and spectral characteristics as 24S-cycloartane-3,16,24,25,30-pentaol.Irkutsk Institute of Organic Chemistry of the Siberian Branch of the Academy of Sciences of the USSR. Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 312–320, May–June, 1986.     

Triterpene glycosides and their genins fromThalictrum foetidum. V. Structure of cyclofoetoside B

A new glycoside (cyclofoetoside B) (I) has been isolated from the epigeal part of the plantThalictrum foetidum L. (Ranunculaceae). On the basis of chemical transformations and with the aid of physicochemical characteristics it has been established that cyclofoetoside B is 24S-cycloartane-3, 16, 24, 25, 29-pentaol 3-O--L-arabinopyranoside 16-O-[O--L-rhamnopyranoside-(1 6)--D-glucopyranoside], C₄₇-H₈₀O₁₇, mp 194–197°C (methanol); [] _D ²⁴ +15.7 ± 2° (c 0.88; pyridine). The enzymatic hydrolysis of (I) has yielded cyclofoetigenin B (III), 24S-cycloartane-3,16,24,25,29-pentaol 16-O--D-glucopyranoside, (IV), C₃₆H₆₂O₁₀, mp 223–225°C (acetone), [] _D ²⁴ +37 ± 2° (c 0.97; methanol) and 24S-cycloartane-3,16,24,25,29-pentaol 16-O-[O--L-rhamnopyranosyl-(1 6)--D-glucopyranoside, C₄₂H₇₂O₁₄, mp 229–231°C (methanol), [] _D ³⁰ +41 ± 2° (c 0.7; methanol). Details of the IR and¹H and¹³C NMR spectra of the compounds are given.Irkutsk Institute of Organic Chemistry, Academy of Sciences of the USSR. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Trashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 341–345, May–June, 1986.