Alkaloids of Rauwolfia species growing in Vietnam

Reserpine, ajmaline, serpentine, ajmalicine, isoreserpiline, and other alkaloids have been isolated from the roots ofRauwolfia cambodiana Pierre ex Pitard,R. verticillata Baill. andR. serpentina Benth.R. vomitoria Afz. was the richest in alkaloids.Leningrad Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 813–816, November–December, 1991.     

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.     

Triterpenoids from Rhododendron caucasicum and Rh. ledebourii gas-liquid chromatography of rhododendron extracts

Conclusions FromGentiana olgae have been isolated gentiananine, gentianadine, and the new base gentianaine C₆H₇O₃N. The structural formula for the latter has been given.G. caucasica contains gentianine and gentiananine; andG. kaufmanniana contains gentianine, gentianaine, and gentiananine; gentianaine has been found in the mother liquors fromG. turkestanorum andG. olivieri.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 1, pp. 32–36, 1969     

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)-3-(-D-glucopyranosyloxy)-21-methoxy-21,23-epoxycycloart-24-ene-22,30-diol, C₃₀H₆₀O₁₀; squarroside A2 (II) — the (21S)-epimer of compound (I); squarroside B1 (III) (21R, 22S, 23R)-3gb-[O--L-rhamnopyranosyl-(1 6)--D-glucopyranosyloxy]-21-methoxy-21,23-epoxycycloart-24-ene-22,30-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.     

Metabolites of the pathogenic fungus Verticillium dahliae II. Components of the fraction of neutral lipids from the culture liquid

Summary Di-2-ethylhexyl phthalate has been isolated from the neutral lipids fraction of the culture liquid of the fungusVerticillium dahliae Kleb. Its¹H and¹³C magnetic resonance spectra have been obtained, and an assignment of the signals has been made.On the basis of their UV, IR, and ESR spectra, the chromogenic components of the neutral lipid fractions have been assigned to the melanins.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 689–693, November–December, 1975.     

Structures of four new triterpene glycosides from the holothurian Cucumaria japonica

Four new triterpene glycosides of the holostane series have been isolated from an alcoholic extract of the economically important Pacific Ocean holothurianCucumaria japonica: cucumariosides A₁-2 (I), A₂-3 (II), A₂-4 (III), and A₄-2 (IV). The structures of these substances have been established by the methods of carbohydrate chemistry and¹³C NMR spectroscopy.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 787–793, November–December, 1990.     

New diterpene lactones fromEuphorbia pallasii

Three new diterpene lactones have been isolated from a chloroform extract of the roots ofEuphorbia pallasii: pseudojolkinolide A psuedojolkinolide B, and 16-hydroxypseudojolkinolide B. Structures have been proposed for them on the basis of chemical transformations and IR, UV,¹³C and¹H NMR, and mass spectra.Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 337–345, May–June, 1985.     

Phytoecdysones ofSilene praemixta. I. Silenosterone

In addition to known ecdysteroids (2-deoxy--ecdysone and 2-deoxyecdysterone) fromSilene praemixta (Caryophyllaceae) we have isolated new ones — premixisterone and selenosterone (I), C₂₇H₄₂O₇, mp 115–117°C (from MeOH), [] _D ²⁸ +86.9 ± 2° (c 0.92, MeOH), yield 0.003%. The acetylation of (I) with (CH₃CO)₂O in Py gave 22-acetyl-selenosterone (II), C₂₉H₄₄O₆, mp 210–212°C (MeOH-C₆H₁₄), [] _D ²⁷ +45.5 ± 3° (c 0.16; MeOH). On the basis of physiocochemical and spectral characteristics it has been established that (I) has the structure of 14,22R,25-trihydroxy-5-cholest-7-ene-3,6-dione. The IR, PMR, and mass spectra of (I) and (II) are presented.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 793–797, November–December, 1979.     

Triterpene glycosides of Thalictrum squarrosum. III. Structures of squarrogenins 1 and 2

Two genins — squarrogenin 1 and squarrogenin 2 — have been isolated from nodding meadow rue by the hydrolysis of squarrosides A1 and A2. The compounds are epimeric at C-21 and have the following structures: 1 — (21R, 22S, 23R)-21-methoxy-21,23-epoxycycloart-24-ene-3,22-30-triol, C₃₁H₅₀O₅, mp 169–171°C (hexane-acetone), [] ₅₄₆ ²⁰ –11.06° (c 4.52; pyridine); and 2 — (21S, 22S, 23R)-21-methoxy-21,23-epoxycycloart-24-ene-3,22,30-triol, C₃₁H₅₀O₅, mp 190–193°C (hexane-acetone), [] ₅₄₆ ²⁰ +106.6° (c 0.3; pyridine). The results of¹H and¹³C NMR spectroscopy and of mass spectrometry for the new compounds are given.Irkutsk Institute of Organic Chemistry, Siberian Division of the USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 510–516, July–August, 1989.     

Steroid saponins and sapogenins ofAllium. XIX. The structure of karatavigenin C

Two new steroid glycosides of the spirostan series — karataviosides E and F — have been isolated from inflorescences ofAllium karataviense Regel. Smith degradation of these compounds has given a steroid sapogenin, karatavigenin C, which is (25S)-spirost-5-ene-2,3,24S-triol. Its structure was established from an analysis of spectral characteristics.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 736–740, November–December, 1983.     

Investigation of Aconite alkaloids

Summary The composition of the alkaloids in plants of the genus Aconitum —A. kirinense,A. altaicum, A. coreanum, andA. nemorosum — has been studied. Four new alkaloids of composition C₂₆H₄₁O₈N·HNO₃, C₃₅H₄₁O₁₀N·HBr, C₂₀H₂₅O₃N, and C₂₃H₂₉O₆N have been isolated.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 2, pp. 113–116, 1965.     

Structure of isoregecoline

The structure of the alkaloid isoregecoline (I) with the composition C₁₉H₂₃O₄N⁺, mp. 284–286°C, isolated previously fromColchicum kesselringii Regel growing in the flood plains of the R. Chirchik has been established. It has been shown by IR, PMR and mass spectroscopy and chemical transformations that (I) is an epimer of regecoline isolated from a plant of the same species.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 808–810, November–December, 1985.     

New quinone from a marine sponge of the order dictyoceratida

Two pigments of quinoid nature, one of which has been identified as ilimaquinone, have been isolated from a hexane extract of a marine spongeHyatella sp., family Spongiidae, order Dictyoceratida. The second was a new benzoquinone of the drimane series with the composition C₂₂H₃₂O₅, which has been called hyatoquinone. Its structure has been established on the basis of spectral characteristics and chemical transformations.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 793–796, November–December, 1987.     

The structure of majdine, pseudokopsinine, and vinervinine

Summary Three new bases have been isolated fromVinca erecta andV. major. The structures of majdine, pseudokopsinine, and vinervinine have been established.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 5, pp. 310–315, 1967     

Alkaloids of Aconitum coreanum VIII. Structure of coryphidine

A new C₂₀-diterpene alkaloid of the coryphine type has been isolated from the plantAconitum coreanum (Levl.) Rapaics, and it has been called coryphidine. Its structure has been established on the basis of an analysis of IR and¹H and¹³C NMR spectra. This is the second diterpene alkaloid having a hexahydro-N-methylindole fragment at C-17. Coryphidine contains an imide grouping, which is unusual for a diterpene skeleton.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 243–246, March–April, 1992.     

Glycosylation of triterpenoids of the dammarane series. VII. Dammar-24-ene-3α,12β,17α,20(S)-tetraol β-D-glucopyranosides

Glucosides have been synthesized from dammar-24-ene-3,12,17,20(S)-tetraol (betulafolienetetraol), isolated from the leaves ofBetula pendula. Condensation with -acetobromoglucose in the presence of silver oxide and silicate has given acetylated betulafolienetetraol 3- and 12- mono- and 3,12- and 3,20-di-O--D-glucopyranosides, the total yield of which amounted to 75–80%. The structures of the semisynthetic glycosides have been established on the basis of the results of IR,¹H and¹³C NMR spectroscopy.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 225–229, March–April, 1988.