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 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 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 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 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 glycosides of Astragalus and their genins XLI. Cycloexoside from Astragalus exilis

In addition to known glycosides of the cycloartane series — cyclosieversiosides A, E, and F — a new acetylated compound of glycosidic nature — cycloexoside — has been isolated from the roots ofAstragalus exilis A. Kor. (Leguminosae). On the basis of chemical transformations and spectral characteristics, the structure of cycloexoside has been established as 20R,24S-epoxycycloartane-3,6,16,25-tetrol 3-O-(2,3-di-O-acetyl--D-xylopyranoside).Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Pamir Biological Institute, Tadhikistan Academy of Sciences, Khorog. Translated from Khimiya Prirodnykh Soedinenii, Nos. 3,4, pp. 356–360, May–August, 1992.     

Triterpene glycosides of Astragalus and their genins. XX. Cycloorbigenin from Astragalus orbiculatus

A new genin — cycloorbigenin (I), C₃₀H₄₈O₅, mp 217–219°C, [] _D ²⁰ +28.3° (c 1.19; ethanol) has been obtained from a glycoside isolated from the epigeal parts of the plantAstragalus orbiculatus (Leguminosae), and on the basis of chemical transformation and spectral characteristics its structure has been established as 16,23:16,24-diepoxy-23(R),24(S)cycloartane-3,7,25-triol. The acetylation of (I) with acetic anhydride in pyridine yielded its diacetate (II), C₃₄H₅₂O₇, mp 148–150°C, [] _D ²⁰ +32.6° (c 0.92; methanol) and its triacetate (III), C₃₆H₅₄O₈, mp 137–139°C, [] _D ²⁰ +75° (c 0.4; methanol). The Jones oxidation of (I) led to a diketone (IV), C₃₀H₄₄O₅, mp 155–158°C, [] _D ²⁰ -73° (c 0.63; methanol). Details of the PMR, IR, and mass spectra are given for all the compounds.Institute of The Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 455–460, July–August, 1986.     

Triterpene glycosides of Astragalus and their genins. XXIII. Cyclocanthogenin from Astragalus tragacantha

The epigeal part of the plantAstragalus tragantha Habl. (Leguminosea) has yielded (in addition to cyclosieversigenin, cyclocyclosiversioside F, and β-sitosterol β-D-glucopyranoside) a new methylsteroid of the cycloartane series — cyclocanthogenin — the structure of which has been established on the basis of chemical transformations and spectral characteristics, and also of a chemical correlation with the structure of cycloasgenin C, as 24S-cycloartane-3β,6α,16β,24,25-pentaol.     

Triterpene glycosides of Astragalus and their genins. XXIII. Cyclocanthogenin from Astragalus tragacantha

The epigeal part of the plantAstragalus tragantha Habl. (Leguminosea) has yielded (in addition to cyclosieversigenin, cyclocyclosiversioside F, and -sitosterol -D-glucopyranoside) a new methylsteroid of the cycloartane series — cyclocanthogenin — the structure of which has been established on the basis of chemical transformations and spectral characteristics, and also of a chemical correlation with the structure of cycloasgenin C, as 24S-cycloartane-3,6,16,24,25-pentaol.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 817–824, November–December, 1987.     

Triterpene glycosides of Astragalus and their genins XXXII. Cyclocarposide from Astragalus coluteocarpus

A new triterpene glycoside of the cycloartane series, which has been called cyclocarposide, has been isolated from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). The structure of cyclocarposide has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3β,6α,16β,25-tetraol 6-0-α-L-rhamnopyranoside 3-0-α-D-xylopyranoside. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pamir Biological Institute, Academy of Sciences of the Tadzhik SSR, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–656, September–October, 1990.     

Triterpene glycosides of Astragalus and their genins XXXII. Cyclocarposide from Astragalus coluteocarpus

A new triterpene glycoside of the cycloartane series, which has been called cyclocarposide, has been isolated from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). The structure of cyclocarposide has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3,6,16,25-tetraol 6-0--L-rhamnopyranoside 3-0--D-xylopyranoside.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pamir Biological Institute, Academy of Sciences of the Tadzhik SSR, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–656, September–October, 1990.     

Triterpene glycosides of Astragalus and their genins. XX. Cycloorbigenin from Astragalus orbiculatus

A new genin — cycloorbigenin (I), C₃₀H₄₈O₅, mp 217–219°C, [α] _D ²⁰ +28.3° (c 1.19; ethanol) has been obtained from a glycoside isolated from the epigeal parts of the plantAstragalus orbiculatus (Leguminosae), and on the basis of chemical transformation and spectral characteristics its structure has been established as 16β,23:16α,24-diepoxy-23(R),24(S)cycloartane-3β,7β,25-triol. The acetylation of (I) with acetic anhydride in pyridine yielded its diacetate (II), C₃₄H₅₂O₇, mp 148–150°C, [α] _D ²⁰ +32.6° (c 0.92; methanol) and its triacetate (III), C₃₆H₅₄O₈, mp 137–139°C, [α] _D ²⁰ +75° (c 0.4; methanol). The Jones oxidation of (I) led to a diketone (IV), C₃₀H₄₄O₅, mp 155–158°C, [α] _D ²⁰ -73° (c 0.63; methanol). Details of the PMR, IR, and mass spectra are given for all the compounds.     

Triterpene glycosides ofAstragalus and their genins. IV. Cyclosieversioside E — A new diglycoside fromAstragalus sieversianus

A new glycoside of the cycloartane series has been isolated from the roots of the plantAstragalus sieversianus Pal.; it is cyclosieversigenin 3,6-di-O-β-xyloside.     

Triterpene glycosides of Astragalus and their genins XXX. Cycloaraloside A from Astragalus amarus

In addition to -sitosterol, cyclosieversigenin, and -sitosterol -D-glucopyranoside, the roots of the plantAstragalus amarus Pall. (Leguminosae) have yielded a new triterpene glycoside of the cycloartane series — cycloaraloside A, which has the structure of 2OR,24S-epoxycycloartane-3,6,16,25-tetraol 3-O--D-glucopyranoside.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 806–809, November–December, 1989.     

Triterpene glycosides of Astragalus and their genins XXXIX. Cycloaraloside D from Astragalus amarus

The structure of a triterpene glycoside of the cycloartane series — cycloaraloside D, isolated from the roots ofAstragalus amarus Pall. (Leguminosae) — has been established on the basis of chemical transformations and spectral characteristics. Cycloaraloside D is 20R, 24S-epoxycycloartane-3, 6, 16, 25-tetraol 3-0-[0--L-rhamnopyranosyl-(1 2)--D-glucopyranoside].Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 526–528, July–August, 1991.