Triterpene glycosides ofLeontice eversmannii

Conclusions The structure of leontoside D-a hederagenin pentaoside-has been established. The O-glycosidic moiety of leontoside D is O--D-glucopyranosido-(1 4)-O--L-arabopyranose, and the O-acyl moiety is O--L-rhamnopyranosido-(1 4)-O--D-glucopyranosido-(1 6)-O--D-glucopyranose.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 3, pp. 153–158, 1968     

Triterpene saponins of Caltha polypetala. Glycosides G and I

From the epigeal organs of the great march marigold (family Ranunculaceae) two triterpene glycosides, a tetra- and a pentaoside of hederagenin, have been isolated. Their chemical structures have been established by chemical methods of investigation and by¹H and¹³C NMR spectroscopy. Glycoside G is hederagenin 3-O--L-arabinoside 28-O-[O--L-rhamnopyranosyl-(1 4)-O--D-glucopyranosyl-(1 6)--D-glucopyranoside]. Glycoside I is hederagenin 3-O-[O--D-glucopyranosyl-(1 2)--L-arabinoside 28-O-[O--L-rhamnopyranosyl-(1 4)-O--D-glucopyranosyl-(1 6)--D-glucopyranoside].I. G. Kutateladze Institute of Pharmacochemistry, Georgian SSR Academy of Sciences, Tbilisi, Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 229–236, March–April, 1988.     

Triterpene glycosides ofHedera taurica. XI. Structures of taurosides St-G1, St-H1, and St-H2 from the stems of Crimean ivy

The previously known glycosides 3-O--L-arabinopyranosyl-28-O-[-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl]hederagenin and 3-O-[-L-rhamnopyranosyl-(12)-O--L-arabinopyranosyl]-28-O-[-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl]hederagenin and the new triterpene glycoside tauroside St-H₁ — 3-O--D-glucopyransyl-28-O-[-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl]hederagenin — have been isolated from the stems ofHedera taurica Carr.M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 571–579, July–August, 1993.     

Triterpene Glycosides of Tetrapanax papyriferum. II. Isolation and Structure Determination of Glycosides St-E2, St-F2, St-J2, and St-K2 from Stem Bark

Stem bark ofTetrapanaxpapyriferum yielded the new triterpene glycosides 3-O-[-D-glucopyranosyl-(13)]--D-galactopyranosyl-(12)-O--L-arabinopyranosides of oleanolic and echinocystic acids and their 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters. Their structures were established using chemical and physicochemical methods     

γ-Pyrone derivatives

3, 5-Dibromocomanic acid (3, 5-dibromo- -pyrone -2-carboxylic acid) VI and its ethyl ester, hitherto not described in the literature, are synthesized by the following route: diethyl acetonedioxalate (I) diethyl dibromochelidonate (III) (mono) ethyl dibromochelidonate (IV) diethyl 3, 5-dibromocomanate (V) VI. Direct bromination of diethyl bromochelidonate gives the ester III. 6-Bromocomenic acid and its ethyl ester are prepared, as well as 2-bromo-3-hydroxy - -pyrone. Bromocomanic acid (x-bromo--pyrone-2-carboxylic acid) XVI is synthesized by the following route: I (mono) ethyl chelidonate ethyl comanate comanic acid XVI. Oxonium salts are obtained: acid sulfates of comanic acid and ethyl comanate.For Part VII [1].     

Metal bioaccumulation by the freshwater algaScenedesmus quadricauda

Bioaccumulation of six metals (Cu²⁺, Cu⁺, Mo⁶⁺, Mn²⁺, V⁵⁺, Ni²⁺) and their combinations by algaScenedesmus quadricauda was determined by using radio nuclide X-ray fluorescence (RXFA). The metals were added into the cultivation medium in concentrations corresponding with EC₅₀ value for each metal. The obtained results indicate that Ni²⁺, Cu²⁺ and Cu⁺ were accumulated in high amounts (20%, 17.5% and 15.19%) the Mo⁶⁺ ion (<0.2%) was accumulated in the lowest amount. For metal-metal interactions in accumulation of metal ions by algaS. quadricauda three types of answers were determined: inhibition (MoCu²⁺, Ni, Mn, V; VNi, Mn; MnNi, Cu²⁺, Cu⁺; Cu⁺Ni; Cu²⁺Ni; NiMn, V), enhancement (VCu⁺; Cu²⁺Mn;Cu⁺V, Mn; MnV; NiCu²⁺, Cu⁺) and neutral effect (VMo; Cu²⁺Mo; Cu⁺Mo; MuMo; NiMo).     

Triterpene glycosides ofHedera helix I. The structures of glycosides L-1, L-2a, L-2b, L-3, L-4a, L-4b, L-6a, L-6b, L-6c, L-7a, and L7-b from the leaves of common ivy

The leaves of common ivy have yielded 11 triterpene glycosides: the 3-O--L-pyranosides of oleanolic acid (1), of echinocystic acid (2), and of hederagenin; the 3-O-[O--L-rhamnopyranosyl-(12)--L-arabinopyranoside]s of oleanolic acid (4), of echinocystic acid (5), and of hederagenin (6); the O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl ester of hederagenin 3-O--L-pyranoside (7); the O--D-glucopyranosyl-(16)-O--D-glucopyranosyl ester of hederagenin 3-O-[O--L-pyranosyl-(12)--L-arabinopyranoside] (9); and the O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters of oleanolic acid, echinocystic acid, and hederagenin 3-O-[O--L-rhamnopyranosyl-(12)--D-glucopyranoside]s (8), (10), and (11), respectively. This is the first time that compounds (1), (2), (5), (7), (9), and (10) have been found in this plant.Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 742–746, November–December, 1994.     

Coumarin glycosides ofHaplophyllum performatum. structures of haploperosides C,D, and E

New coumarin glycosides — haploperosides C, D, and E — have been isolated from the epigeal part of theHaplophyllum performatum (MB) Kar et Kir. On the basis of chemical transformations and spectral characteristics, haploperoside D has the structure of 6-methoxy-7-[0--L-rhamnopyranosyl-(1 2)--D-glucopyranosyloxy]-2H-benzopyran-2-one, and haploperoside C that of 6-methoxy-7-[0--L-rhamnopyranosyl-(1 6)-(2-0-acetyl--D-glucopyranosyloxy)]-2H-benzopyran-2-one. The structure of haploperoside E has been established as 7-[0--L-rhamnopyranosyl-(1 2)-0--L-rhamnopyranosyl-(1 6)--D-glucopyranosyloxy]-2H-benzopyran-2-one. The structures of haploperosides A and B have been refined. An assignment has been made of the carbon signals in the¹³C NMR spectra of haploperosides A, D, C, and E.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 27–35, January–February, 1985.     

Triterpene glycosides of Hedera taurica VI. Structures of hederosides G, H1, H2, and I from the berries of Crimean ivy

We have isolated from Crimean ivy berries in addition previously known triterpene glycosides — 3-O--L-arabinopyranosyl-28-O-[O--L-rhamnopyranosyl-(1 4)-O--D-glycopyranosyl-(1 6)--D-glucopyranosyl]hederagenin, 3-O-[O--L-rhamnopyranosyl-(1 2)--L-arabinopyranosyl]-28-O-[O--L-rhamnopyranosyl-(1 4)-O--D-glucopyranosyl-(1 6)--D-glycopyranosyl]hederagenin, the new triterpene glycosides hederoside H₂-3-O-[O--D-glycopyranosyl-(1 2)--D-glycopyranosyl-(1 2)--D-glucopyranosyl]-28-O-[O--D-glucopyranosyl-(1 6)--D-glucopyranosyl]oleanolic acid- and hederoside I-3-O-[O--D-glucopyranosyl-(1 2)--D-glucopyranosyl]-28-O-[O--D-glucopyranosyl-(1 6)--D-glucopyranosyl]hederagenin. Details of their¹³C NMR spectra are given.M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 779–783, November–December, 1990.     

Triterpene glycosides ofHedera helix II. Determination of the structure of glycoside L-6d from common ivy leaves

A new hederagenin pentaoside — glycoside L-6d — has been isolated from the leaves of common ivyHedera helix L., fam. Araliaceae, and its structure has been determined by using various NMR-spectroscopic methods. Glycoside L-6d is hederagenin 3-O-[O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl-(14)-O--L-rhamnopyranosyl-(12)--L-arabinopyranoside.Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 746–752, November–December, 1994.     

Triterpene glycosides ofSophora japonica seeds

We have isolated from the seeds of Sophora japonica the known soyasaponogenol B-3-[O--D-glucopyranosyl-(12)-O--D-glucopyranuronoside] (adzukisaponin II), soyasapogenol B [3-O--galactopyranosyl-(12)-O--L-glucopyranuronoside] (soyasaponin III), soyasapogenol B 3-(O--L-rhamnopyranosyl-(12)-O--L-glucopyranosyl-(12)-O--D-glucopyranuronoside] (adzukisaponin V), soyasapogenol B 3-(O--D-rhamnopyranosyl-(12)-O--D-galactopyranosyl-(12)-O--D-glucopyranuronoside] (soyasaponin I), and the new glycoside (1) — soyasapogenol B 3-[O--D-glucopyranuronoside]. The structure of this glycoside has been established on the basis of the results of enzymatic, complete, and partial hydrolyses and¹³C NMR spectra.Simferopol' State University and Kursk State Medical Institute, Kursk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 709–713, September–October, 1995. Original submitted March 3, 1995.     

Triterpene glycosides of Hedera taurica

From the leaves of Crimean ivy we have isolated the previously known glycosides 3-O--L-Ara_p-28-O-[O--L-Rha_p-(14)-O--D-Glc_p-(16)--D-Glc_p]hederagenin, 3-O-[O--L-Rha_p-(12)--L-Ara_p]-28-O-[O--L-Rha_p-(14)-O--D-Glc_p-(16)--D-Glc_p]oleanic acid and -hederagenin, and 3-O-[O--L-Rha_p-(12)--L-Ara_p]-28-O-[O--D-Glc_p-(16)--D-Glc_p]hederagenin and a new one: tauroside H₁ — 3-O-[O--L-Rha_p-(12)-O--L-Ara_p]-28-O-[O--L-Rha_p-(14)-O--D-Glc_p-(16)--D-Glc_p]echinocystic acid.M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 522–528, September–October, 1992.     

Polysaccharides of Saponin-Bearing Plants. XV. Structure of Glucoarabinogalactan from Acantophyllum Borszczowii Roots

The structure of the branched polysaccharide glucoarabinogalactan was investigated by periodate oxidation, methylation, and ¹³C NMR spectroscopy. The main chain consists of -16-bonded galactopyranoses. 12-Bonded D-glucopyranoses and 13-bonded D-galactopyranoses are located on the unreducing ends. There is a short side chain with -13-bonded L-arabinopyranoses.     

Transformed steroids. 121. Synthesis of the δ-lactone of 3β-acetoxy-16α-hydroxy-6-oxo-24-nor-5α-chol-17(20)-en-23-oic acid

The synthesis of the ¹⁷⁽²⁰⁾-16 analog of natural chiogralactone is described. Attempts to introduce a 6-oxo group directly into the -lactone proved unsuccessful, since the first stage — saponification — took place with the formation of three products: the 3-hydroxy--lactone, the 3-hydroxy-²⁰⁽²²⁾-lactone, and the 15,17(20)-dienoic acid. The synthesis of the desired compound was effected from the ethyl ester of the 5,16-dienoic acid by the scheme 3-acetate3-tosylate6-hydroxy-3,5-cyclosteroid6-oxo-3,5-cyclosteroid6-oxo-5H--lactone. It has been shown that the cyclopropane ring in the 3,5-cyclosteroid -lactone is extremely stable under the conditions of acid treatments.N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 184–187, March–April, 1981.     

Synthesis of bacterial antigenic polysaccharides and their fragments 6. Improved synthesis of β-D-mannopyranosyl-(1→4)-α-1-rhamnopyranosyl-(1→3)-D-galactose- the repeating unit of the specific polysaccharide of Salmonella Newington

Conclusions We have synthesized the trisaccharide-D-mannopyranosyl-(1 4)--L-rhamnopyranosyl-(1 3)-D-galactose using 1,2-O-isopropylidene-4,6-O-ethylidene--D-galactopyranose to form the 1 3 rhamnosylgalactose linkage.Part 5 [1].Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2578–2581, November, 1977.     

Steroid glycosides of the leaves of Yucca aloifolia

Two new steroid glycosides have been isolated from the leaves of aloe yucca and their structures have been established. Glycosides B and C are tigogenin penta-and hexaosides. Glycoside B, which we have called yuccaloeside B is (25R)-5-spirostan-3-ol 3-{[O--D-glucopyranosyl-(12)]-[O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(13)]-O--D-glucopyranosyl-(14)--D-galactopyranoside}, and glycoside C, which we have called yuccaloeside C is (25R)-5-spirostan-3-ol 3-{[(O--D-glucopyranosyl-(13)-O--D-glucopyranosyl-(12)]-[O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(13)]-O--D-glucopyranosyl-(14)--D-galactopyranoside}.N. G. Kutateladze Institute of Pharmacochemistry of the Georgian SSR Academy of Sciences, Tbilisi. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 537–542, July–August, 1987.     

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     

Proanthocyanidins of Polygonum coriarium. I

Six proanthocyanidins have been isolated from the roots ofPolygonium coriarium. The structures of three oligomeric proanthocyanidins have been established: taranin, consisting of [epigallocatechin gallate]-(48)-[epigallocatechin gallate]-(48)-[epigallocatechin-(48)-epigallocatechin₂-(48)-epigallocatechin; taranoside A - [epigallocatechin gallate]-7-0-[-(16)--D-Glcp]₃-(48)-[epigallocatechin-(48)-epigallocatechin]₂-(48)-gallocatechin; and taranoside B - [epigallocatechin gallate]-7-O-[-(16)--D-Glcp]₄-(48)-[epigallocatechin-(48)-epigallocatechin]₂-(48)-epigallocatechin-(48)-[epigallocatechin gallate).Institute of the Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 59–67, January–February, 1992     

Triterpene Glycosides of Tetrapanax papyriferum. I. Isolation and Structure of Glycosides St-H2 and St-I2 from Stem Bark

Stem bark ofTetrapanax papyriferumC. Koch., Araliaceae, yielded new triterpene glycosides 28-O--L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranosyl esters of the 3-O-[-D-glucopyranosyl-(13)-[-D-galactopyranosyl-(12)]-O--L-arabinopyranosides of oleanolic and echinocystic acids. The structures of these substances were established using chemical and physicochemical methods     

The electronic spectrum of acrylonitrile

The vapor absorption spectrum of acrylonitrile CH₂CHCN has been measured in the vacuum ultraviolet region. In addition, an all-valence-electron molecular orbital calculation has been used to calculate the electronic structure and spectrum of the molecule. On the basis of the MO calculation, as well as a vibrational analysis of the observed spectrum, several electronic transitions are assigned. The lowest energy absorption band (2107Å, = 150) is assigned as an n ^* transition. Absorption bands at 2030Å (=1600), 1725Å ( = 2100), and 1570Å ( = 1920) are assigned as 0–0 bands associated with transitions that are, respectively, ^*,^*, and ^* in character.

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Zusammenfassung Das UV-Absorptionsspektrum von dampfförmigen Acrylnitril wurde gemessen und eine CNDO/2-Rechnung für die Elektronenstruktur durchgeführt. Auf dieser Basis konnten unter Zuhilfenahme der Analyse der Schwingungsstruktur im beobachteten Spektrum mehrere Banden zugeordnet werden: die 2107-Å-Bande ( = 150) einem n^*-Übergang, die drei Banden bei 2030Å ( = 1600), 1725Å ( = 2100) und 1570 Å ( = 1920)0-0-Übergängen von ^*-, ^*- bzw. ^*-Banden.

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Résumé Mesure du spectre d'absorption en phase vapeur de l'acrilonitrile CH₂CHCN dans la région de l'ultraviolet. Par ailleurs, la structure électronique et le spectre de la molécule ont été calculés à l'aide d'une méthode des orbitales moléculaires semi-empirique pour tous les électrons de valence. Sur cette base, ainsi que sur une analyse vibrationnelle du spectre expérimental, on procède à l'attribution de plusieurs transitions électroniques. La bande d'absorption de plus basse énergie (2107 Å, = 150) est attribuée à une transition n ^*. Les bandes d'absorption à 2030Å ( = 1600), 1275Å ( = 2100) et 1570Å ( = 1920) sont considérées comme des bandes 0 - 0 associées à des transitions ^*, ^* et ^* respectivement.