The structure of xanthalin

Conclusions From the roots ofXanthogalum purpurascens growing in the Transcaucasus, we have isolated a new coumarin, C₂₄H₂₆O₇ with mp 111–113°C, [] _D ²⁰ –164.2° (c 0.97; ethanol) which we have called xanthalin. On the basis of the NMR spectrum it has been established that xanthalin is 3, 4-diangeloyl-2, 2-dimethyl-3, 4-dihydropyrano-5, 6:6, 7-coumarin.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 5, pp. 280–283, 1968     

Culcitoside C1 from the starfishCulcita novaeguineae andLinckia guildingi

By repeated chromatography on Polikhrom-1, silica gel, and Florisil, ethanolic extracts of two species of starfish,Culcita novaeguineae andLinckia guildingi, have yielded the new steroid glycoside culcitoside C₁ (I): 5-cholestan-3,4,6,8,15,24-hexaol 24-O-[2,4-di-O-methyl--D-xylopyranosyl-(12)--L-arabinofuranoside], C₃₉H₆₈O₁₄, mp 245–248°C, []_D -35.8°, c 0.6; methanol). Its structure was shown by the results of acid hydrolysis, acetylation and methylation, and¹H and¹³C NMR spectroscopy.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 801–804, November–December, 1985.     

Cardiac glycosides of Erysimum contractum

The cardenolide composition ofErysimum contractum Somm. et Lew. familyBrassicaceae (Cruciferae) has been investigated. The seeds of this plant have yielded strophanthidin, erysimin, erysimoside, erycordin, and new cardiac glycoside which has been called nigrescigenin digitoxoside. It has mp 141–145°C, []_D ²⁰+16.0±2° (c 0.75; methanol), C₂₉H₄₂O₁₀. On the basis of chemical transformations and spectral investigations it has been established that the new glycoside is 3--D-digitoxopyranosyloxy-5,11,14-trihydroxy-19-oxo-5,14-card-20(22)-enolide. The total content of cardiac glycosides in the seeds of this plant amounted to 3.2%, including 1.26% of erysimoside.All-Union Scientific-Research Institute of the Chemistry and Technology of Drugs, Kharkov. G. S. Skovroda Kharkov State Pedagogic Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 58–62, January–February, 1991.     

Triterpene glycosides ofSilphium perfoliatum. IV. Structure of siliphioside C

The epigeal part ofSilphium perfoliatum has a yielded a new triterpene glycoside, silphioside C — C₅₀H₈₀O₁₉, mp 207–210°C (from aqueous methanol), []_D ²⁵ +19.3 ± 2°C (c 0.88; methanol). On the basis of acid hydrolysis, mild alkaline saponification, and the results of GLC and of IR, mass, and¹H and¹³C spectroscopy the structure of silphioside C had been established as 28--D-glucopyranosyl 3-O-[O--D-glucopyranosyl-(12)-(6-O-acetyl--D-glucopyranosyl)oleanolate.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pyatigorsk Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii. No. 4, pp. 519–522, July–August, 1985.     

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 alfalfa. III. Medicoside I

On the basis of chemical transformations and with the aid of physicochemical results, the structure of glycoside I isolated from the roots of the plantMedicago sativa has been established as hederagin 3-O-[O--L-arabinopyranosyl-(1 2)--D-glucopyranosyl-(1 2)--L-arabinopyranoside] 28-O--D-glucopyranoside. Compound (I), C₅₂H₈₄O₂₂, mp 210–212°C, [] _D ²¹ +38.4° (c 1.48; methanol). Acid hydrolysis of (I) led to hederogenin (II) — C₃₀H₄₈O₄, mp 326–330°C, [] _D ²³ +84.2° (c 0.19; pyridine. The Hakomorimethylation of glycoside (I) yielded the permethylate (IV) — C₆₅H₁₁O₂₂ [] _D ²³ +41.6° (c 1.79; methanol). The GLC analysis of the products of the methanolysis of compound (IV) showed the presence of 3,4,6-tri-O-methyl-D-glucopyranose, 2,3,4,6-tetra-O-methyl-D-glucopyranose, 3,4-di-O-methyl-L-O-arabinopyranose, and 2,3,4-tri-o-methyl-L-arabinopyranose. The alkaline hydrolysis of glycoside I gave compound (III) with mp 230–233°C, [] _D ²¹ +35.2° (c 0.21; methanol), which was identified as medicoside C. Details of the PMR spectrum are given for compound (IV) and of the IR spectrum for compound (I).Institute of the Chemistry of Plant Substances of the Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 607–610, September–October, 1986.     

Structure of korselimine

The new base korselidine with mp 272–274°C (methanol), []_D-75°, C₂₇H₄₃NO₂ (I), (ethanol), composition C₂₇H₄₃NO₂, has been isolated from the total alkaloids of the epigeal part ofKorolkowia sewerzowii Regel. As a result of the study of the chemical properties of the alkaloid itself and of its products of its transformation, the structure and partial configuration of korselamine have been established as (1,3,-dihydroxy-^8,14)-cevanene.Institute of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 44–46, January–February, 1989.