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 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.     

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.     

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.     

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.     

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 furostan and spirostan series from Nolina microcarpa II. structures of nolinospiroside D and nolinofurosides D,E, and F

In addition to the know steroid sapogenin (25S)-ruscogenin (I), three new glycosides have been isolated from the leaves ofNolina microcarpa S. Wats. (family Dracaenacea), and the following structures are suggested for them: (25S)-spirost-5-ene-1β,3β-diol 1-O-β-D-fucopyranoside (nolinospiroside C, II), (25S)-furost-5-ene-1β,3β,22α,26-tetraol 1-O-β-D-fucopyranoside (nolinofuroside A, III), and (25S)-furost-5-ene-1β, 3β, 22α, 26-tetraol 1-O-β-D-fucopyranoside 26-O-β-D-glucopyranoside (nolinofuroside C, V). M. V. Frunze Simferopol' State University. Institute of Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 672–678, September–October, 1991.     

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.     

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.     

Triterpene glycosides of Thalictrum squarrosum. IV. Structures of squarrosides A1, A2, B1, and B2

Four new cycloartane glycosides have been isolated from a methanolic extract ofThalictrum squarrosum Stephan ex Willd.: squarroside A1 (I) — (21R, 22S, 23R)-3β-(β-D-glucopyranosyloxy)-21α-methoxy-21,23-epoxycycloart-24-ene-22β,30-diol, C₃₀H₆₀O₁₀; squarroside A2 (II) — the (21S)-epimer of compound (I); squarroside B1 (III) (21R, 22S, 23R)-3gb-[O-α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranosyloxy]-21α-methoxy-21,23-epoxycycloart-24-ene-22β,30-diol, C₄₃H₇₀O₁₄; and squarroside B2 (IV) — the (21S)-epimer of compound (III). The proposed structures were determined on the basis of¹H and¹³C NMR spectroscopy, FAB mass spectrometry, and chemical transformations. Irkutsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 516–523, July–August, 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.     

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.     

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.     

Alkaloids ofAconitum kirinense. Structure of akiramidine

A new alkaloid called akiramidine is isolated from the aerial part ofAconitum kirinense. The structure 6β,14α,16β-trimethoxy-1α,4β,8β-trihydroxy-N-ethylaconitane is proposed based on spectral data and confirmed by chemical transformation from akiramine. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 774–776, November–December, 1999.     

Insect phermones and their analogues XXXVIII. Synthesis of (±)-3-methylheneicosan-2-one and (±)-2-acetoxy-3,7-dimethylpentadecane using the reductive β-vinylation of α-olefins

Schemes are proposed for the synthesis of (±)-3-methylheneicosan-2-one and (±)-2-acetoxy-3,7-dimethylpentadecane — racemic analogues of the sex pheromones of the common cockroach (Blatella germanica) and of plane sawflies of the generaDiprion andNeodiprion, respectively, using the reductive β-vinylation of α-olefins. Institute of Chemistry of the Bashkir Scientific Center, Urals Division of the Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 567–571, September–October, 1992.     

Insect pheromones and their analogues XLII. Synthesis of 2,6-dimethyloct-1-yl formate — A mimic of the aggregation pheromone of flour beetles

2-6-Dimethyloctan-1-ol, the formate of which is a mimic of the aggregation pheromone of the flour beetlesTribolium confusum andT. castaneum, has been synthesized by the hydroboration of 2,6-diemthyloct-1-ene, obtained from β-methylvaleric acid. Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 571–573, September–October, 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.     

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.     

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.