Cardenolides of the seeds ofCoronilla glauca and ofC. scorpioides. New glycosides alloglaucoside and scorpiosidol

Two new glycosides have been isolated from the seeds ofCoronilla glauca L. and C. scorpioides Koch: 3-(0-D-glucopyranosyloxy)-14. 15-dihydroxy-19-oxo-5-card-20(22)-enolide (alloglaucoside) and 3-(-D-gluco-ucofuranosyloxy)-5,14,19-trihydroxy-5-card-20(22)-enolide (scorpiosidol), together with a glycoside previously unknown for theCoronilla genus — 3-(-D-glucopyranosylo)g)-14-hydroxy-5-card-20(22)-enolide (desglucouzarin) and known aglycons (corotoxigenin, alloglaucotoxigenin, coroglaucigenin) and glycosides (glucocorotoxigenin, coronillobioside, glucocoroglaucigenin, coronillobiosidol and scorpioside).Ukraine Pharmaceutical Academy, Kharkov–2. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 372–376, May–June, 1996. Original article submitted August 14, 1995.     

Structure of psolusoside B — A nonholostane triterpene glycoside of the holothurian genus Psolus

The structure of psolusoside B — a minor triterpene oligoglycoside from the holothurianPsolus fabricii and the main glycoside fromPsolus sp. has been determined by the methods of partial acid hydrolysis, methylation,¹³C NMR, and FAB mass spectrometry as 20S-acetoxy-3-{2-O-[O--D-glucopyranosyl-(1 4)-O--D-glucopyranosyl]-4-O-(6-O-sulfato--D-glucopyranosyl)--D-xylo-pyranosyloxy}holosta-7,25-diene-18,16-carbolactone. 3-[O-(3-O-Methyl-6-O-sulfato--D-glucopyranosyl)-(1 3)-O-(6-O-sulfato--D-glucopyranosyl)-(1 4)-O--D-quinovopyranosyl-(12)--D-xylopyranosyloxy]holosta-9(11),25-dien-16-one (psolusoside A), known previously forPsolus fabricii, has been identified in a holothurian —Psolus sp. — from Kraternaya Bay (island of Ushishir).Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 361–368, May–June, 1989.     

The triterpene glycosides ofpatrinia intermedia roem et schult

Conclusions It has been established that patrinoside D₁ is the -D-glucopyranosido(13) -D-xylopyranosido(12) -L-rhamnosido(14)--D-xylopyranoside (13) of oleanolic acidKhimiya Prirodnykh Soedinenii, Vol. 5, No. 2, pp. 84–89, 1969     

Transformations of solasodine

Solasodine (I) has been subjected to a number of transformations. The following compounds have been obtained from it by described procedures: 3-acetoxypregna-5,16-dien-20-one (II), 3-acetoxypregn-5-en-20-ol (III), and 3-acetoxypregn-5-en-20-ol (IV). The oxidation of (III) and (IV), the formation of an oxime, and the reduction of the oxime with sodium in ethanol, followed by Hess methylation, has led to 20-dimethylaminopregn-5-en-3-ol (IX) and to 20-dimethylaminopregn-5-en-3-ol (X). From compounds (IX) and (X), by analogy with (III) and (IV) by their oxidation and the preparation of oximes, which were then reduced and methylated, the following were obtained: 3,20-bisdimethylaminopregnane (XVII) and 3,20-bisdimethylaminopregnane (XVIII), and also quaternary salts of the latter.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 370–374, May–June, 1980.     

Proanthocyanidins ofPolygonum coriarium III. Structures of proanthocyanidins T1 and T2

The roots ofPolygonum coriarum have yielded two oligomeric proanthocyanidins, T1 and T2, and their structures have been established: 3-O-galloyl-7-O-[O-(6-O-galloyl)--D-glucopyranosyl]-(–)-epigallocatechin-(4-8)-(–)-epicatechin-(4-8)-(–)-epicatechin-(4-8)-(–)-epigallocatechin 3-O-gallate (T1) and (–)-epicatechin-(4-8)-[3-O-galloyl-(–)-epigallocatechin]-(4-8)-(–)-epicatechin-(4-8)-(+)-catechin (T2).The material of this paper were presented at the IInd International Symposium on the Chemistry of Natural Compounds (SCNC, Eskisehir, Turkey, October 22–24, 1996).Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 588–593, July–August, 1977.     

Synthesis of 2β, 3β, 14α-trihydroxy-Δ4,7-6-ketosteroids and their derivatives

A scheme using -sitosterol as an example for synthesizing 2, 3, 14-trihydroxy-^4,7-6-ketosteroids and their derivatives from 3-hydroxy-⁵-steroids was developed.Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141, Belarus, Minsk, ul, akad. Kuprevicha, 5/2. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 244–248, May–June, 2000.     

Retro-michael reaction of 28-methoxy-18,19-secolupane-18,19-dione derivatives

The interactions with KOH in boiling diethyleneglycol of 3,28-dimethoxy- and 3-acetoxy-28-methoxy-18,19-secolupane-18,19-diones have been studied. In the first case, 3-methoxy-19,20,21,22,29,30-hexanor-18,19-seco(17H)lupan-18-one and the corresponding 18-ol were isolated from the mixture of products, and in the second case 3-hydroxy-19,20,21,22,29,30-hexanor-18,19-seco(17H)lupan-18-one — which was also obtained by an analogous reaction from 3-acetoxy-18,19-secolupan-18,19-dione — and 3-hydroxy-19,20,21,22,28,29,30-heptanor-18,19-secolupan-18-one. Thus, it has been found that in this case the retro-Michael reaction is accompanied by 28-demethoxylation and partially by 28-demethoxy-methylation.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 210–215, March–April, 1992.     

Triterpene glycosides ofSalsola micranthera. I. Structures of salsolosides C and D

New triterpene glycosides — salsolosides C and D — have been isolated from the epigeal part ofSalsola micranthera Botsch. On the basis of chemical transformations and physicochemical measurements, salsoloside C has been assigned the structure of oleanolic acid 28-0--D-glucopyranoside 3-0-[0--D-xylopyranosyl-(1 4)--D-glucuropyranoside], and salsoloside D has the structure of hederagenin 28-0--D-glucopyranoside 3-0-[0--D-xylopyranosyl-(1 4)--D-glucuropyranoside].Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 727–732, November–December, 1983.     

Percolation Effects on the Surface of a Polyimide Film Modified with Aqueous Solutions of an Alkali and Acid

A cluster structure of the surface of a polypyromellitimide film was studied by the electron microscopy and ATR IR spectroscopy methods at different steps of consecutive treatment with aqueous solutions of an alkali and acid. The effective size and fractal dimension D of polyamidoacid clusters, as well as the degree _s of the filling of the surface with the latter were calculated from the data of the electron microscopy as a function of the degree of imide group conversion into amidoacid units on the film surface. The _s and D parameters were shown to increase with a rise in : _s = 0.1–0.3 and D = 1.3–1.4 at < _cr and _s 0.6 and D 1.7 at > _cr, where _cr is a critical degree of conversion, which corresponds to the formation of a continuous physical network of polyamidoacid macromolecules or a percolation cluster. In a region close to _cr (at < _cr), the correlation length land the concentration C of the clusters vary according to the laws of the percolation theory for two-dimensional lattices: l (_cr – )^– and C (_cr – ), where = 1.3 ± 0.1 and = 0.67 ± 0.05.     

Rearrangement ofα -trifluoromethyl-β-dialkylamino-β-fluoroacrylic acid N.N-dialkylamides

Conclusions When heated in the presence of a catalytic amount of BF₃ etherate,-trifluoromethyl--diethylamino--fluoroacrylic acid N, N-dimethylamide is reversibly isomerized to-trifluoromethyl--dimethylamino--fluoroacrylic acid N, N-diethylamide. The methyl esters of-trifluoromethyl--diethylammo--fluoroacrylic acid and-trifluoromethyl--phenoxy--fluoroacrylic acid N,N-dimethylamide are not isomerized under the same conditions.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No.1, pp.137–141, January, 1976.