Cardiac glycosides of Cheiranthus allioni. IX

Summary From the seends ofCheiranthus allioni hort. another three cardiac glycosides have been isolated. One of them has been identified as cheirotoxin. It has been established that in cheirotoxin the D-glucose is attached to C₄ of the D-gulomethylose and this glycoside therefore has the structure of strophanthidin 3-O-[4-O--D-glucopyranosyl--D-gulomethylopyranoside]. The two other glycosides, which have been named sarmentogulomethyloside and gulosarmentoglucoside are new and are, respectively, sarmentogenin-3-O--D-gulomethylopyranoside and sarmentogenin 3-O-[4-O--D-glucopyranosyl--D-gulomethylopyranoside].For Communication VIII see [1].Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 607–611, September–October, 1974.     

The crystal structure of gummosin

Summary The reaction of 3,3,5,7-tetraacetylquercetin with tetraacetylglucopyranosyl bromide has given quercetin 4-O--D-glucopyranoside, and the substance has been characterized.Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 577–578, September–October, 1974.     

Coumarins ofHaplophyllum ramosissimum

Summary 7-(3,3-Dimethylallyloxy)-6-methoxycoumarin and two new coumarins — ramosin and ramosinin — have been isolated from the epigeal part ofHaplophyllum ramosissimum.On the basis of IR, PMR, and mass spectroscopy and chemical reactions, the structure of 8-(3,3-dimethylallyl)-7-(3,3-dimethylallyloxy)coumarin (II) has been proposed for ramosin and that of 3-(1,1-dimethylallyl)-8-(3,3-dimethylallyl)-7-methoxycoumarin (III) for ramosinin.Leningrad Sanitary-Hygienic Medical Institute. Institute of Chemistry, Academy of Sciences of the Turkmen SSR, Ashkhabad. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 15–17, January–February, 1979.     

Hydroxystilbenes of the inner bark of Pinus sibirica

Summary In addition to pinostilbene and resveratrol, two new stilbene glycosides have been isolated from the phloem ofPinus sibirica R. Mayr, and their structures have been established as 3,4-dihydroxy-5-methoxy-stilbene 4--D-glycopyranoside (pinostilbenoside) and 3,4,5-trihydroxystilbene 4--D-glycopyranoside (resveratroloside).Irkutsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 677–682, November–December, 1975.     

Cardiac glycosides of Cheiranthus allioni. XIII. Glucoerycordin

From plains erysimum (Cheiranthus allioni) Hort., (Erysimum asperum) a new cardiac glycoside has been isolated which has been called glucoerycordin. Its chemical structure has been established mainly by stepwise hydrolysis and the identification of the hydrolysis products. Glucoerycordin C₄₁H₆₄ O₁₉, mp 131–135°C, [] _D ²⁰ –22.2 ± 3° (c 0.65; methanol) is 3-[O--D-glucopyranosyl-(1 4)-O--D-glycopyranosyl-(1 4)-gulomethylopyranosyloxy]-14,19-dihydroxy-5, 14-card-20(22)-enolide.All-Union Scientific-Research Institute of Drug Chemistry and Technology, Khar'kov. Khar'kov State Pharmaceutical Institute. Translated from Khimiya Prirodnykh, No. 1, pp. 73–75, January–February, 1989.     

The structure of the alkaloid nitraramine fromNitraria schoberi

The spatial structure of the alkaloid nitraramine has been determined by x-ray structural analysis. This has shown that it has the structure of 2,1-epoxy-1,3-propanoperhydrobenzo [3,2-d]-1,8-naphthyridine. Its reactivity has been studied.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 692–698, September–October, 1985.     

Structure of bucharaine

Conclusions From the plantHaplophyllum bucharicum Litv. have been isolated skimmianine, folifine, haplopine, and a new base, bucharaine.Bucharaine has the structure 4-(6-hydroxy-5-hydroxyisopropylhept-3-enloxy)quinol-2-one.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 5, pp. 394–397, 1969     

Mass-spectrometric study of esters of marmesin and saturated acids

Summary From a methanolic extract of the roots ofPrangos biebersteinii Karjag., in addition to substances found previously, two other components — (I) and (II) — of the coumarin series have been isolated.The results of a study of their IR, NMR, and mass spectra, and also their chemical properties have enabled (I) to be identified as the known coumarin umbelliferone and the structure of 5-(1,2-dihydroxy-isopropyl)-4,5-dihydrofuro-2,3:7,6-coumarin to be proposed for (II), which has been named prandiol.Leningrad Sanitary-Hygenic Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 574–577, September–October, 1974.     

Structure of vasicol

The structure of bromovasicol has been established on the basis of the results of x-ray structural analysis as 4-bromo-2-(3-hydroxy-2-oxypyrrolinomethl)aniline. Vasicol was isolated from the plantPeganum harmala in the form of 2-(3-hydroxy-2-oxopyrrolidinomethyl)aniline.Institute of the Chemistry of Plants Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 18–23, January–February, 1989.     

Isoflavones and stilbenes of the heartwood ofMaackia amurensis

The isoflavin retusin, squalene, 3,4,5-trihydroxystilbene (resveratrol), 3,3,4,5-tetrahydroxystilbene, and a new compound constructed of fragments of retusin and 3,3,4,5-tetrahydroxystilbene have been isolated for the first time from an ethanolic extract of the heartwood ofMaackia amurensis Rupr. et Maxim (Fabaceae) growing in Maritime Territory. The high-molecular-weight polyphenols that impart the characteristic coloration to macckia wood are present in an amount of 7%. The majority of the phenolic compounds isolated showed a high antiradical and antioxidant activity.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. 775–781, November–December, 1985.     

A new coumarin, pranferol, from the roots ofPrangos ferulacea

Summary A new coumarin, pranferol C₁₆H₁₆O₅, has been isolated from the roots ofPrangos ferulacea (L.) Lindl.The structure 5-(2-hydroxy-3-methylbutoxy)furo-2,3:7,6-coumarin has been proposed for pranferol.Khimiya Prirodnykh Soedinenii, Vol. 9, No. 5, pp. 310–315, 1966     

Chrysin and its derivatives in plants of the genusScutellaria

Summary 1. A glycoside (II) identified by chrysin 7--glucopyranosiduronic acid has been isolated from the epigeal part ofScutellaria scordiifolia in a yield of 2.0–2.2%.2. A glycoside (IV), characterized as 2-methoxychrysin 7--D-glucopyranosiduronic acid has been isolated from the roots ofS. granulosa.3. This is the first time that chrysin and 2-methoxychrysin and their 7-glucuronides have been isolated from theScutellaria species mentioned.Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Ukrainian Zonal Research Station for Medicinal Plants, Poltava. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 730–735, November–December, 1976.     

New glycosides from plants of the genus Phlojodicarpus

From plants of the genusPhlojodicarpus have been isolated the new coumarins umbelliferone -D-apiosyl (1 6)--D-glucopyranoside (I) and 8-(2,3-dihydroxy-3-methylbutyl)umbelliferone 7-O--D-glucopyranoside (II) and also the flavone glycoside diosmetin 7-O--D-glucopyranoside (III). The result of IR, UV, PMR, and¹³C NMR spectroscopy are given.Institute of Chemistry, Academy of Sciences of the Mongolian Peoples' Republic, Ulan-Bator; Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 36–39, January–February, 1986.     

Floroselin, a new coumarin from the roots of Seseli sessiliflorum

Conclusions A new coumarin has been isolated from the roots ofSeseli sessiliflorum for which the structure of 3-angeloyloxy-2,2-dimethyl-4-(trans-3-methylthioacryloyloxy)-3, 4-dihydropyrano-5,6:8,7-coumarin has been proposed. This is the first time that esters of 3-methylthioacrylic acid have been found in the coumarin series.All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 517–521, September–October, 1970.     

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     

Application of the Arbuzov reaction to establish the structure of D-mannitol tricyclic triethyl triphosphite

Conclusions The previously expressed theory that the tricyclic triethyl triphosphite of D-mannitol is 2-ethoxy-4, 5-bis-(2-ethoxy-1, 3, 2-dioxaphospholan-4-yl)-l,3,2-dioxa-4-phospholane was corroborated on the basis of the differential-thermal analysis and³¹P NMR data.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1390–1395, June, 1972.     

Structure of the sesquiterpene lactone tanacin

Summary From the leaves ofAtraphaxis pyrifolia Bge. we have isolated a new flavonoid glycoside. By chemical and spectroscopic investigations its structure has been established as 3,4,5,8-tetrahydroxy-7-methoxy-flavonol 3-O--L-rhamnopyranoside.S. M. Kirov Kazakh State University. Translated from Khimiya Prirodnykh Soedenenii, No. 2, pp. 136–140, March–April, 1975.