Phytoecdysteroids of plants of the genusSilene XX. Integristerone A 25-acetate fromSilene brahuica

A new ecdysteroid—integristerone A 25-acetate—has been isolated from the roots ofSilene brahuica Boiss. Its structure has been determined on the basis of chemical transformations and spectral characteristics.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 40 64 75. Translated from Khimiya Prirodnykh Soedinenii, No 4, pp. 492–493, July–August, 1999.     

Phytoecdysteroids of plants of the genusSilene XIV. Brahuisterone fromSilene brahuica

A new ecdysteroid with the composition C₂₇H₄₄O₆ which has been called brahuisterone has been isolated from the epigeal part of the plantSilene brahuica Boiss. Its chemical and complete spatial structures have been established by spectral studies and the x-ray structural method (diffractometer, Cu-K_α radiations, 996 reflections, direct method, R=0.119).     

Phytoecdysteroids of plants of the genusSilene. VII. Sileneoside D — ecdysterone 3-O-α-D-galactopyranoside fromSilene brahuica

A phytoecdysteroid, sileneoside D, has been isolated from the roots ofSilene brahuica Boiss. and it has been shown to be ecdysterone 3-O-α-D-galactopyranoside.     

Phytoecdysteroids of plants of the genusSilene XII. 5α-Ecdysterone 22-O-benzoate fromSilene scabrifolia

The new phytoecdysteroid 5α-ecdysterone 22-O-benzoate (I), C₃₄H₄₈O₃, mp 262–274°C (methanol-water) [α] _D ²⁰ +45.8° (methanol), has been isolated from the epigeal organ ofSilene scarbiofolia Kom. The alkaline hydrolysis of (I) led to 5α-ecdysterone (II) and benzoic acid. The isomerization of ecdysterone (0.6% KHCO₃ in CH₃OH) has yielded (II). Details of the IR, mass, and NMR spectra of compound (I) are given.     

Phytoecdysteroids of the plants of the genusSilene XV. Silenoside F — Brahuisterone 3-O-β-D-glucopyranoside fromSilene brahuica

A new brahuisterone glycoside — silenoside F — has been isolated from the epigeal part ofSilene brahuica Bois. (fam. Caryophyllaceae). Its structure has been established by an analysis of spectral characteristics: 3β,5,14α,22R,25-pentahydroxy-5β-cholest-6-one 3-O-β-D-glucopyranoside. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 734–737, November–December, 1994.     

Phytoecdysteroids of plants of the genusSilene. V. Sileneoside B — An ecdysterone digalactoside fromSilene brahuica

The phytoecdysteroid sileneoside B has been isolated from the roots ofSilene brahuica Boiss.; it is ecdysterone 3,22-di-O-α-D-galactopyranoside.     

Phytoecdysteroids of plants of the genusSilene

Ecdysteroids produced by plants of the genusSilene are considered. The discussion covers 17 species of plants, from which 45 ecdysteroids have been isolated. It has been shown that ecdysterone is the most characteristic representative of the biosynthesis of ecdysteroids in theSilene series.     

Phytoecdysteroids of plants of the genusSilene. IV. Sileneoside C — A galactoside of intergristerone A fromSilene brahuica

The phytoecdysteroid sileneoside C has been isolated from the roots ofSilene brahuica Boiss. It has been shown that sileneoside C is intergristerone A 22-0-α-D-galactoside.     

Phytoecdysteroids of plants of the genusSilene. VI. α-Ecdysone 22-sulfate — A new ecdysteroid fromSilene brahuica

A phytoecdysteroid consisting of the sodium salt of α-ecdysone 22-sulfate has been isolated from the roots ofSilene brahuica Boiss.     

Phytoecdysteroms of plants of the genusSilene. XVII. Tomentesterone fromSilene tomentella

The new ecdysteroid tomentesterone A has been isolated from the epigeal part ofSilene tomentella Schischk. Its structure has been established by spectral studies and chemical transformations.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 714–719, September–October, 1995. Original article submitte March 27, 1995.     

Phytoecdysteroids of plants of theSilene genus. XVIII. Tomentesterone fromSilene tomentella

A new ecdysteroid — tomentesterone B — has been isolated from the epigeal part of Silene tomentella. Its structure has been established by chemical transformations and spectral investigations.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 59–61, January–February, 1996. Original article submitted September 4, 1995.     

Phytoecdysteroids of plants of the genus Silene. XVIII. 2-Deoxyecdysterone 20,22-monoacetonide from Silene brahuica

In addition to the known 2-deoxy--ecdysone, 2-deoxyecdysterone, 2-deoxy--ecdysone-22-O-acetate, ecdysterone, integristerone A, and sileneoside A, B, and C, the new ecdysteroid 2-deoxyecdysterone 20,20-monoacetonide has been isolated from the roots of the plantSilene brahuica Boiss.Institute of Chemistry of Plant Substances Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 241–244, March–April, 1991.     

Phytoecdysteroids of plants of the genusSilene XVI. 5α-sileneoside E FromSilene brahuica

Derivatives of derrusnin and also its benzodioxane and benzodioxepane analogs have been synthesized. The structures of the compounds obtained have been confirmed by spectral studies.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 226–230, March–April, 1994.     

Phytoecdysteroids of plants of the genus Silene. XI. 2-Deoxy-α-ecdysone 3-acetate from Silene scabrifolia

From the epigeal organs ofSilene scabrifolia Kom. has been isolated the new phytoecdysteroid 2-deoxy-α-ecdysone 3-acetate (II) (0.0011%), C₂₉H₄₆O₆, mp 216–218°, [α] _D ²⁰ +131.9° (methanol). The enzymatic hydrolysis of (II) led to 2-deoxy-α-ecdysone (I). The acetylation of 2-deoxy-α-ecdysone (I) yielded (II) and the 22-monoacetate (III) and 3,22-diacetate (IV) of 2-deoxy-α-ecdysone, which have been described previously. Details of the IR, UV, CD, mass, and NMR spectra are given for (I) and of the IR, mass, and NMR spectra for (III).     

Phytoecdysteroids of plants of the genusSilene X. Sileneoside E — 2-Deoxy-α-ecdysone 3-O-β-D-glucopyranoside — FromSilene brahuica

A new ecdysteroid has been isolated from the epigeal organs ofSilene brahuica Boiss. — 2-deoxy--ecdysone 3-O--D-glucopyranoside (I), C₃₃H₅₄O₁₀, mp 195–196°C, [] _D ²⁰ + 44.4° (methanol). The enzymatic hydrolysis of (I) led to 2-deoxy--ecdysone. Details of the IR, UV, mass, and¹H and¹³C NMR spectra of all the compounds are given.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 323–326, May–June, 1986.     

Phytoecdysteroids of plants of the genusSilene. III. Sileneoside A — A new glycosidic ecdysteroid ofSilene brachuica

Ecdysterone (I), viticosterone E, polypodine B, and integristerone A (II) have been isolated from the epigeal part of the plantSilene brachuica Boiss. In addition to substances (I) and (II), the phytoecdysteroid sileneoside A has been isolated from the root of this plant. It has been shown that sileneoside A is ecdysterone 22-O-α-D-galactoside.     

Phytoecdysteroids ofSilene nutans. II. 22-Deoxyecdysterone and features of its mass spectrum

Using high-performance liquid chromatography, 22-deoxyecdysterone has been isolated from the butanolic fraction of the extractive substances from the epigeal part ofSilene nutans L. Characteristic features of the mass spectrum of 22-deoxyecdysterone due to the absence of an oxygen function at C-22 are discussed.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 62–66, January–February, 1985.     

Phytoecdysteroids of plants of the genus Melandrium I. Polypodin B 22-acetate from Melandrium turkestanicum

Known ecdysteroids — ecdysterone, ecdysterone 22-acetate, polypodin B, integristerone A, and sileneosides A and D — and a new phytoecdysteroid — polypodin B 22-acetate — have been found in the epigeal parts of the plantMelandrium turkestanicum (Rg1.) Vved. (family Caryophyllaceae).Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 480–483, July–August, 1990.