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-3β, 6α, 16β, 25-tetraol 3-0-[0-α-L-rhamnopyranosyl-(1 → 2)-β-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.     

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 XXXV. Cycloaraloside C from Astragalus amarus

A new triterpene glycoside of the cycloartane series (cycloaraloside C) has been isolated from the roots of the plantAstragalus amarus Pall. (Leguminosae). Cycloaraloside C is a bioside of cyclosieversigenin including one D-glucose residue and one D-apiose residue. The structure of the glycoside has been shown on the basis of the chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3β,6α,16β,25-tetraol 3-O-[O-(D-apio-β-D-furanosyl)-(1 → 2)-β-D-glucopyranoside]. This is the first time that D-apiose has been found among cycloartane glycosides. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 783–787, November–December, 1990.     

Synthesis of 24-ethylcholesta-7, 22E-diene-3β, 5β-triol — A natural trihydroxysteroid from the bryozoan Myriapora truncata

24-Ethylcholesta-7, 22E-diene-3β,5α,6β-triol — a natural trihydroxysteroid from the bryozoanMyriapora truncata — has been synthesized from stigmasterol. Institute of Bioorganic Chemistry, Academy of Sciences of the Belorussian SSR, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 664–669, September–October, 1989.     

α- and β-scopodonnines from Datura inoxia seeds

A mixture of two alkaloids, d, ℓ-α- and β-scopodonnines, known earlier as synthetic products, has been isolated for the first time from the seed ofDatura inoxia. The spatial structure of β-scopodonnine dimethiodide has been established by the x-ray structural method. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 532–537, July–August, 1991.     

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

In addition to β-sitosterol, cyclosieversigenin, and β-sitosterol β-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-3β,6α,16β,25-tetraol 3-O-β-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 alfalfa. V. Medicoside H

A new triterpene glycoside — medicoside H — has been isolated from the roots ofMedicago sativa L. (Fabaceae), and on the basis of chemical transformations and spectral characteristics its structure has been established as medicagenic acid 3-O-β-D-glucopyranoside 28-O-[O-α-L-rhamnopyronosyl-(1 → 2)-β-L-arabino-pyranoside]. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 673–677, September–October, 1989.     

Triterpene glycosides of Astragalus and of their genins. X. Cyclogalegigenin from Astragalus galegiformis

The flowers of the plantAstragalus galegiformis L. have yielded a new isoprenoid — cyclogalegigenin — the structure of which has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3,6,16,25-tetraol.I. G. Kutateladze Institute of Pharmacochemistry, Academy of Sciences of the Georgian SSR, Tbilisi. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 332–339, May–June, 1983.     

Steroids of the spirostan and furostan series from plants of the genus Allium. XXVI. Structure of anzurogenin and anzuroside from the collective fruits of Allium suvorovii and Allium stipitatum

A new steroid glycoside of the spirostan series, anzuroside, has been isolated from the collective fruits of the cocultivatedAllium suvorovii Rgl. andA. stipitatum Rgl. (family Liliaceae, local name “anzur”). Enzymatic cleavage of the glycoside has given the previously undescribed steroid sapogenin anzurogenic C, which has the structure of (24S, 25S)-2α,3β,5,24-tetrahydroxy-5β-spirostan-6-one. Anzuroside is the 24-O-β-D-glucopyranoside of anzurogenin C. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 505–510, July–August, 1989.     

Phytoecdysteroids of Rhaponticum carthamoides. II. Rhapisterone B

A new ecdysteroid (rhapisterone B) has been isolated from the seeds ofRhaponticum cathamoides (Willd.) Iljin. (familyCompositae). It has been shown that it is 2β, 3β, 11α, 14α, 20R, 24ξ-hexahydroxy-5β-cholest-7-en-6-one. Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 806–808, November–December, 1991.     

Molecular and crystal structure of the germacranolides salonitenolide and hanphyllin

A sesquiterpene lactone of the germacrane type, salonitenolide, has been isolated for the first time from the epigeal part ofCentaurea pseudomaculosa Dobrocz (spotted centaurea) and has been identified. The structures of the germacranolides and hanphyllin have been determined by the method of x-ray structural analysis: salonitenolide is 8-hydroxy-6β,8β(H)7α(H)-germacra-1(10),4,11(13)-trien-6,12-olide and hanphyllin is 3-hydroxy-3α,7α(H),6β(H)-germacra-1(10),4,11(13)-trien-6,12-olide. It has been established that the ten-membered rings of salonitenolide and hanphyllin are of the chair-chair type,₁D¹⁴,¹⁵D₅. On the basis of the results of CD spectroscopy, the chiral centers in the hanphyllin molecule have been assigned the 3S, 6R, and 7S configurations. Institute of Organic Synthesis and Coal Chemistry, Kazakh SSR Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Heteroorganic Compounds, USSR Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 781–785, November–December, 1989.     

Molecular and crystal structure of the germacranolide argolide from Artemisia glabella

The new germacranolide argolide has been isolated from the epigeal part ofArtemisia glabella, and its structure has been shown by its conversion into oxopelenolide B. From the results of an x-ray investigation it is suggested that argolide has the spatial structure of 3-oxo-4α,7α,6β(H)-germacra-1(10),11(13)-dien-6,12-olide. Institute of Organic Synthesis and Coal Chemistry, Kazakh Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Organometallic Chemistry, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–657, September–October, 1991.     

Steroids of the spirostan and furostan series from nolina microcarpa III. Structure of nolinofurosides G and H

Two new glycosides which have been called nolinofurosides G(I) and H(III), have been isolated from the leaves ofNolina microcarpa. Nolinofuroside G is the sodium salt of 26-β-D-glucofuranosyloxy-(25S)-furost-5,20(22)-diene-1β, 3β-diol 1-sulfate, and nolinofuroside H is the sodium salt of 1-β-D-fucopyranosyloxy-26-β-D-glucopyranosyloxy-(25S)-furost-5,20(22)-dinen-1β-3β-ol 3-sulfate. M. V. Frunze Simferopol' State University. Institute of the Chemistry of Plant Substances, Uzbek. Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 801–806, November–December, 1991.     

A new component of Artemisia fragrans

A new component C₁₅H₂₂O₃, has been isolated from the epigeal part ofArtemisia fragrans. On the basis of chemical transformations and spectral characteristics it has been established that it has the structure of 1α-hydroxy-5,7αH,6,11βH-eudesm-3,4-en-6,12-olide (I). V. L. Komarov Institute of Botany, Academy of Sciences of the Azerbaidzhan SSR, Baku. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 632–635, September–October, 1990.     

Withasteroids of Physalis. IX. Physangulide — The first natural 22S-withasteroid

A new withasteroid — physangulide — has been isolated from the leaves ofPhysalis angulata L. It has been shown that physangulide is the first natural 22S-withanolide. Its structure has been determined as 3β,4β,20,24,25-pentahydroxy-1-oxo-5β,6β-epoxy-20R,22S,24S,25R-withanolide. Its¹H and¹³C NMR spectra, confirming this interpretation, are given. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 366–371, May–June, 1990.     

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.     

Molecular and crystal structure of jurineolide — A germacrane lactone from Jurinea multiflora

By extraction with chloroform, followed by treatment of the total extractive substances with hexane and chromatography of the resulting precipitate, the epigeal part ofJurinea multiflora has yielded a sesquiterpene lactone of the germacrolide type, jurineolide. The following spatial structure is proposed for jurineolide: 8α-(4′-hydroxytigloyloxy)-6β,7α(H)-germacra-trans-1(10),trans-4(5),11(13)-trien-6,12-olide. Institute of Organic Synthesis and Coal Chemistry, Central Kazakhstan Branch, Academy of Sciences of the Kazakh SSR. Translated from Khimiya Prirodnykh Soedinii, No. 4, pp. 490–494, July–August, 1991.     

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.     

Withasteroids of Physalis. X. Circular dichroism of withasteroids from plants of the genus Physalis

The circular dichroism method has been used to establish the stereochemical features of the structure of the withasteroids. The 22S-configuration of the asymmetric center has been confirmed for physangulide. The 22R-configuration has been confirmed for 14α-hydroxyixocarpanolide, vamonolide, ixocarpanolide, 24,25-epoxywithanolide D, and withanolide T. On the basis of changes in the circular dichroism spectra in acid and alkaline media it is suggested that in compounds having a 4β-hydroxy-1-oxo-5β,6β-epoxy-2,3-ene grouping the Δ^2,3 bond disappears, while in compounds having a 5α-hydroxy-1-oxo-6α,7α-epoxy-2,3-ene grouping dehydration takes place at C-4-C-5. These characteristics can be used in the identification of the withasteroids. The isolation of withanolide T from the leaves ofPhysalis angulata L. is described and its spectral characteristics are given. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 371–376, May–June, 1990.     

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.