Showing papers in "Chemistry of Natural Compounds in 1980"
TL;DR: In this article, a hexane extract of the dry lichen was used to identify six anthraquinones: chrysophanol (I), islandicin (II), cynodontin (III), emodin (IV), and pentahydroxymethylanthraquinone (VI).
Abstract: From a hexane extract of the dry lichen we have isolated six anthraquinones: chrysophanol (I), islandicin (II), cynodontin (III), emodin (IV), a tetrahydroxymethylanthraquinone (V), and a pentahydroxymethylanthraquinone (VI). The structures of (I) and (IV) were confirmed by direct comparison with authentic samples. The structures of (II) and (III) were established by the aid of UV, IR, PMR, and mass spectra. Pigments (V) and (VI) were isolated from a carbonate extract. Pigment (V): mp > 320°C; UV spectrum (nm) 258, 283, 310, 447, 500, 533; mass spectrum: 286 (M+ 100%), 270, 258, 257, 241, 229, 216, 213, 212, 211, 201, 161, 155, 137, 115, 105, 97. Pigment (VI): mp 315°C; UV spectrum (nm): 247, 261, 302, 500, 540, 565, 578; IR spectrum (cm−1): 1587, 3492; mass spectrum: 302 (M+, 100%), 286, 274, 245, 228, and the metastable ions 248.6, 219.1, and 192.5. The positions of the β-hydroxyls in the molecules of (V) and (VI) have not been definitively established.
12 citations
TL;DR: In this article, a triterpene (I) was isolated from the unsaponifiable fraction of an ethereal extract of the leaves ofBetula mandschurica to which, on the basis of the results of a physicochemical investigation and a comparison of the13C spectra with the spectra of known triterpenes, the structure of 20(S),24(S)-dihydroxydammar-25-3n-3-one has been assigned.
Abstract: A new triterpene (I) has been isolated from the unsaponifiable fraction of an ethereal extract of the leaves ofBetula mandschurica to which, on the basis of the results of a physicochemical investigation and a comparison of the13C spectra with the spectra of known triterpenes — ocotillone (II) and 20(S)-hydroxydammar-24-en-3-one (III) — the structure of 20(S),24(S)-dihydroxydammar-25-3n-3-one has been assigned. An approach to the determination of the configuration of the asymmetric center at C24 in 24-hydroxy derivatives of tetracyclic triterpenoids with an open side chain by the use of13C NMR spectroscopy is proposed.
12 citations
TL;DR: In this article, the relative acidities of 22 flavonoids have been studied in water, methanol, acetone, dimethylformamide, and dimethyl sulfoxide.
Abstract: In order to choose a solvent for performing potentiometric titration, the relative acidities of 22 flavonoids have been studied in water, methanol, acetone, dimethylformamide, and dimethyl sulfoxide. It has been established that the conditions of titration improve on passing from water in the following sequence of organic solvents: methanol < dimethylformamide < acetone < dimethyl sulfoxide.
10 citations
TL;DR: In this article, Ledum palustre L, collected in July in Kostroma province, was isolated in the form of light yellow crystals with mp 188-190°C (from ethanol), with the composition C19H18O8.
Abstract: From the herbLedum palustre L., collected in July in Kostroma province we have isolated β-sitosterol, the triterpenoids taraxerol, uvaol, and ursolic acid, the coumarin fraxetin, the known flavonoids quercetin, hyperoside, and 3,3′,7-tri-O-methylquercetin, and a new natural flavonoid. The latter was isolated in the form of light yellow crystals with mp 188–190°C (from ethanol), with the composition C19H18O8. On the basis of IR, UV, NMR, and mass spectroscopy the structure of 4′,5-dihydroxy-3,3′,5′,7-tetramethoxyflavone has been suggested for it.
8 citations
TL;DR: In this paper, a review of the steroid alkaloids of plants of the genera Veratrum, Petilium, and Korolkowia is presented, and some methods for determining their structures are considered.
Abstract: The review is devoted to a study of the steroid alkaloids of plants of the generaVeratrum, Petilium, andKorolkowia. Characteristic reactions, spectra, and some chemical transformations of the alkaloids subdivided into groups according to structure are discussed. Some methods for determining their structures are considered.
7 citations
TL;DR: In this article, the structure of 1,3,8-trihydroxy-7methoxyxanthone is proposed for isogentiakochianin, and that of 1 2,3-trihexyl-7,8dimethoxyanthone for swertiaiberin.
Abstract: From the roots ofSwertia iberica, together with the previously known swertiaperennin decussatin, gentiakochianin, and norswertianin, we have isolated two new xanthones — isogentiakochianin and swertiaiberin. On the basis of UV, IR, PMR, and mass spectroscopy, the structure of 1,3,8-trihydroxy-7-methoxyxanthone is proposed for isogentiakochianin, and that of 1,2,3-trihydroxy-7,8-dimethoxyanthone for swertiaiberin.
7 citations
TL;DR: In this article, the structure of 7-[6-(β-carboxyethyl)-5-isopropylidene-1,2-dimethylcyclo-hexylmethoxy]coumarin has been proposed for galbanic acid.
Abstract: On the basis of the1H NMR spectrum at 300 MHz and the results of chemical degradation, the structure of 7-[6-(β-carboxyethyl)-5-isopropylidene-1,2-dimethylcyclo-hexylmethoxy]coumarin has been proposed for galbanic acid.
7 citations
TL;DR: The composition of the triacylglycerols of oiticica oil has been studied by enzymatic hydrolysis with pancreatic lipase and it has been established that the majority of TAGs of the 96 types present have a mixed character.
Abstract: The composition of the triacylglycerols (TAGs) of oiticica oil has been studied by enzymatic hydrolysis with pancreatic lipase. It has been established that the majority of TAGs of the 96 types present have a mixed character. The four main types make up 60% of the total TAGs and the remainder consist of minor components. A high content of TAGs with octadeca-9,11,13-trienoic acids (including licanic) in the extreme positions has been detected.
6 citations
TL;DR: The structure of the new alkaloid aconifine, which has been isolated from the tubers and epigeal part of Aconitum karakolicum Rapcs. has been established on the basis of the results of chemical transformations and spectral characteristics.
Abstract: The structure of the new alkaloid aconifine, which has been isolated from the tubers and epigeal part ofAconitum karakolicum Rapcs. has been established on the basis of the results of chemical transformations and spectral characteristics. Some features of the selective acetylation of aconitine and aconine have been elucidated.
6 citations
TL;DR: In an extract of spore-bearing stems of Equisetum arvense L. (field horsetail) saponaretin, apigenin 5-glucoside, luteolin 5-GLU, kaempferol 3-sophoroside, quercetin 3-glUCOSI, 4-hydroxy-6-(2-hydroxylethyl)-2,2,5,7-tetramethylindanone, and a compound of ketonic nature, isolated previously from an extract from an
Abstract: In an extract of spore-bearing stems ofEquisetum arvense L. (field horsetail) saponaretin, apigenin 5-glucoside, luteolin 5-glucoside, kaempferol 3-sophoroside, quercetin 3-glucoside, 4-hydroxy-6-(2-hydroxyethyl)-2,2,5,7-tetramethylindanone, and a compound of ketonic nature, isolated previously from an extract of the herbage of the field horsetail, have been identified by high-performance liquid chromatography. The characteristics of the chromatographic behavior of glycosylated flavones under the conditions of reversed-phase liquid chromatography have been studied and it has been shown that the glycosylation of flavones at position 5 of the molecule causes a greater fall in the affinity for a nonpolar stationary phase than in position 7 of the molecule.
6 citations
TL;DR: In this paper, the composition of the mono-and sesquiterpenoids of the oleoresin of two species of conifers of the Pinaceae family has been studied.
Abstract: The composition of the mono- and sesquiterpenoids of the oleoresin of two species of conifers of thePinaceae family has been studied. In the oleoresin ofPinus koraiensis Sieb. et Zucc. 10 oxidized monoterpenoids, 18 sesquiterpene hydrocarbons, and six sesquiterpene alcohols have been identified. In theoleoresin ofPinus pumila (Pall.) Rg1. 10 monoterpene hydrocarbons, six oxidized monoterpenoids, 14 sesquiterpene hydrocarbons, and four sesquiterpene alcohols have been found. The structure of 1β,4αH,7αH,10βH-guaiane-5α,14-diol, one of the hydroboration-oxidation products of an unidentified sesquiterpene alcohol isolated from both oleoresins, has been determined by x-ray structural analysis.
TL;DR: Two coumarins have been isolated from an ethanolic extract of the epigeal part of Haplophyllum obtusifolium Lebed: capensin (I) and the new coumarin Obtusicin, C5H16O6, (II), mp 81-91°C (CH3OH).
Abstract: Two coumarins have been isolated from an ethanolic extract of the epigeal part ofHaplophyllum obtusifolium Lebed.: capensin (I) and the new coumarin obtusicin, C5H16O6, (II), mp 81–91°C (CH3OH). The acid hydrolysis of (I) and (II) leads to fraxetin. On the basis of the results of a study of acetylation products and the spectral characteristics (IR, UV, PMR, and mass spectra) it has been established that obtusicin has the structure of 8-hydroxy-7-(4′-hydroxy-3′-methyl-but-2′-enyloxy)-6-methoxycoumarin.
TL;DR: It has been shown that the coumarin composition of the plants changes with the growth site, and suitable structures have been established for the new compounds tenuidin, villosin, and tenudiol.
Abstract: The results are given of an investigation of three species of the genusHaplophyllum: H. villosum, H. kowalenskyi, andH. tenue, fromwhich five substances of coumarin nature have been isolated. Of them, two substances (I and II) have been identified as scopoletin and lomatin isovalerate, respectively, while suitable structures have been established for the new compounds tenuidin, villosin, and tenudiol. It has been shown that the coumarin composition of the plants changes with the growth site.
TL;DR: In this paper, a new route to the synthesis of a number of attractants of Lepidoptera (Argyrotaenia velutinana, Mamestra configurata, and Lycorea ceres ceres) has been developed.
Abstract: A new route to the synthesis of a number of attractants of Lepidoptera(Argyrotaenia velutinana, Mamestra configurata, andLycorea ceres ceres) have been developed. These substances are acetates of enols with the cis configuration: tetradec-11-en-1-ol, hexadec-11-en-1-ol, and octadec-11-en-1-ol, respectively. The constants of the substances obtained agree completely with those given in the literature. The method is based on the coupling of the C3, C5, and C7 aldehydes with methyl 11-bromoundecanoate (I) by the Wittig reaction. To obtain compound (I) from methyl undeca-2E,5E,10-trienoate or methyl undeca-10-enoate we used hydroboration according to Brown followed by hydrogenation and bromination of the alcohol obtained. The advantage of this method is the use as starting materials of esters of unsaturated acids readily obtained by the homogeneous catalytic co-oligomerization of 1,3-dienes with acrylates.
TL;DR: In this article, a new steroid glycoside of the spirostan series, taccaoside (I), has been isolated from an ethanolic extract of the roots of Tacca cheancer (familyTaccaceae).
Abstract: A new steroid glycoside of the spirostan series — taccaoside (I) — has been isolated from an ethanolic extract of the roots ofTacca cheancer (familyTaccaceae). An acid hydrolysate was found to contain the aglycone diosgenin (II) and the sugars D-glucose and L-rhamnose in a ratio of 1:2. By methylation and hydrolysis of the permethylate (IV) it has been established that the two terminal L-rhamnose residues are attached at C-2 and C-3 of the D-glucose molecule which, in its turn, substitutes the hydroxy group at C-3 of diosgenin. Glycoside (I) has the structure of (25R)-spirost-5-en-3β-ol 3-0-{[0-α-L-rhamnopyranosyl-(1→2)][0-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside}.
TL;DR: In this article, the coumarins scopoletin (I), scopocletin 7-0-β-D-glucopyranoside (II) and coumarin glycoside haploperoside A (III) were isolated from the epigeal part of Haplophyllum perforatum.
Abstract: From the epigeal part ofHaplophyllum perforatum we have isolated the coumarins scopoletin (I), scopoletin 7-0-β-D-glucopyranoside (II) and the new coumarin glycoside haploperoside A (III), mp 212–213°C, [α]
D
22
−37° (c 0.24, CH3OH). The acid hydrolysis of (III) formed (I) and the monosaccharides D-glucose and L-rhamnose. Partial hydrolysis of (III) with 10% acetic acid led to (II) and L-rhamnose. On the basis of the results of a study of UV, IR, and PMR spectra, and also periodate oxidation and polarimetric analysis the structure of 6-methoxy-7-[0-α-L-rhamnopyranosyl-(2→1)-β-D-glucopyranosyloxy] coumarin has been established for (III). Details of the IR, UV, PMR, and mass spectra are given.
TL;DR: The epigeal part of Haplophyllum perforatum has yielded a new acylated flavonol glycoside, haploside A, for which the structure of 3,4′,5,7,8-pentahydroxy-3′-methoxyflavone 7-O-(6″-O-acetyl-β-D-glucopyranoside) has been established as mentioned in this paper.
Abstract: The epigeal part ofHaplophyllum perforatum has yielded a new acylated flavonol glycoside, haploside A, for which the structure of 3,4′,5,7,8-pentahydroxy-3′-methoxyflavone 7-O-(6″-O-acetyl-β-D-glucopyranoside) has been established. The aglycone of the glycoside isolated — 3,4′,5,7,8-pentahydroxy-3′-methoxyflavone — has also proved to be new and it has been called haplogenin. The structures of the compounds mentioned have been established on the basis of UV, IR, PMR, and mass spectra and the products of acetylation and of acid and alkaline hydrolysis.
TL;DR: In this paper, a new compound 6-chloroapigenin, C15H9C105, M+ 304, mp 305-306°C, λmax 274, 336 (methanol) has been isolated from the ether-soluble fraction of a methanolic extract of the field horsetail.
Abstract: A new compound 6-chloroapigenin, C15H9C105, M+ 304, mp 305–306°C, λmax 274, 336 (methanol) has been isolated from the ether-soluble fraction of a methanolic extract of the field horsetail. On the basis of the results of UV and PMR spectroscopy and mass spectrometry, the structure of 6-chloro-4′,5,7-trihydroxyflavone has been established for this compound.
TL;DR: In this paper, the structure and configuration of 3-keto-4β, 6β(H)-germacra-1(10), 11·(13)-dien-6,12-olide has been established.
Abstract: Cumambrins A and B, artecalin, rupicolins A and B, and the new sesquiterpene lactone tansanin have been isolated from the epigeal part ofTanacetum santolina C. Winkl. For tansanin the structure and configuration of 3-keto-4β, 6β(H)-germacra-1(10), 11·(13)-dien-6,12-olide has been established.
TL;DR: The total alkaloids of the roots of Convolvulus subhirsutus collected in the period of vigorous growth close to the village of Dzhilga, Chimkent province, have been studied.
Abstract: The total alkaloids of the roots ofConvolvulus subhirsutus collected in the period of vigorous growth close to the village of Dzhilga, Chimkent province, have been studied. From the phenolic fraction of the total alkaloids of this species of plant we have isolated phyllalbine and convolidine for the first time. From the nonphenolic fraction of the combined bases we isolated convolvine, which has been found previously, the new alkaloid confoline, and an unidentified base (III). On the basis of spectral characteristics and some spectral transformations it has been established that confoline has the structure of (+)-N-formylconvolvine.
TL;DR: From the epigeal part and roots of Glaucium fimbrilligerum 22 alkaloids have been isolated, of which three have proved to be new.
Abstract: From the epigeal part and roots ofGlaucium fimbrilligerum 22 alkaloids have been isolated, of which three have proved to be new — d-isocorytuberine, dehydrocorydine, and corydine N-oxide.
TL;DR: In this paper, two esters of the roots of Ferula stylosa have been isolated: chimganin and a new one, stylosin, which is suggested as the ester of 4-hydroxy-3-methoxybenzoic acid and the monoterpene alcohol fenchol.
Abstract: From the total extractive substances of the roots ofFerula stylosa two esters have been isolated: chimganin and a new one — stylosin. The structure of stylosin is suggested as the ester of 4-hydroxy-3-methoxybenzoic acid and the monoterpene alcohol fenchol.
TL;DR: Using the buffer capacity method, a study has been made of the protolytic properties of three flavonoids isolated from pea chloroplasts: KG, KGC, and quercetin 3-D-triglucoside p-coumarate (QGC) as mentioned in this paper.
Abstract: Using the buffer capacity method, a study has been made of the protolytic properties of three flavonoids isolated from pea chloroplasts: kaempferol 3-D-triglucoside (KG), kaempferol 3-D-triglucoside p-coumarate (KGC), and quercetin 3-D-triglucoside p-coumarate (QGC). It has been shown that the curves of the buffer capacities of solutions of the flavonoid investigated have from two to four peaks of dissociation constants. When the substances participate in photobiochemical reactions, they are capable of manifesting protonophoric properties.
TL;DR: The lipid composition of the roots of Bryonia alba (Cucurbitaceae) have been studied: it consists of fractions of 3-acyloxy-24-alkyl(alkenyl)-cholest-7-enes (I), triacylglycerols (II), 1,2-diacyl-3-monoglycopyranosyl-sn-glycerol (III), 1-2-dimacyl -3-diglycopyrano-sn glycerols(IV), 1.3-bis(3-
Abstract: The lipid composition of the roots ofBryonia alba (Cucurbitaceae) have been studied: It consists of fractions of 3-acyloxy-24-alkyl(alkenyl)-cholest-7-enes (I), triacylglycerols (II), 1,2-diacyl-3-monoglycopyranosyl-sn-glycerols (III), 1,2-diacyl-3-diglycopyranosyl-sn-glycerols (IV), 1,3-bis(3-sn-phosphatidyl)glycerols (V), 3-sn-phosphatidylethanolamines (VI), 3-sn-phosphatidylcholines (VII), and methyl esters of fatty acids (VIII). The amount of unsaturated fatty acids in the lipid fractions (I–VIII) is 60–94%, the main component being linolenic acid.
TL;DR: The single maximum triterpenoids in sulfuric acid solutions at 310 nm are due to the formation of a carbocation as mentioned in this paper, which is the same as the case of oleanolic acid at the COOH group and Δ12 C=C bond.
Abstract: The single maximum of triterpenoids in sulfuric acid solutions at 310 nm is due to the formation of a carbocation. Under the action of sulfuric acid, oleanolic acid undergoes lactonization at the COOH group and the Δ12 C=C bond.
TL;DR: A complete x-ray structural investigation of the alkaloid parfumine has been performed as mentioned in this paper, where the lengths of the bonds and the valence angles have the usual values, and the benzene rings A and D are planar, B a distorted half-chairC(6)HN, and rings C and E are flattened envelopes, EC(14 andC(19)E, respectively.
Abstract: A complete x-ray structural investigation of the alkaloid parfumine has been performed. The lengths of the bonds and the valence angles have the usual values. Benzene rings A and D are planar, B a distorted half-chairC(6)HN, and rings C and E are flattened envelopes, EC(14) andC(19)E, respectively.
TL;DR: In this article, the authors developed methods for obtaining water-soluble cholesterol and sitosterol derivatives which consist in the reaction of the sterol chloroformate with dimethyl aspartate followed by saponification or in the reactivity of sterol with anhydroacetylcitric acid chloride and hydrolysis.
Abstract: Methods have been developed for obtaining water-soluble cholesterol and sitosterol derivatives which consist in the reaction of the sterol chloroformate with dimethyl aspartate followed by saponification or in the reaction of the sterol with anhydroacetylcitric acid chloride and hydrolysis.
TL;DR: The complete chemical composition of the oleoresin of the larchLarix cajanderi M. growing in Kamchatka has been studied in this article, showing that among the monoterpenes α- and β-pinenes, their amounts being 66.3% and 18.3%, respectively.
Abstract: The complete chemical composition of the oleoresin of the larchLarix cajanderi M. growing in Kamchatka has been studied. Fifty-four terpene compounds have been isolated and identified. It has been shown that among the monoterpenes the main constituents are α- and β-pinenes, their amounts being 66.3% and 18.3%, respectively. Among the sesquiterpene hydrocarbons the main components are δ-cadiene and γ-elemene (15 and 17%). Diterpenoids are represented mainly by bicyclic labdane compounds — epimanool (∼15%), larixylacetate (∼28%), and larixol (∼40%). In the acidic fraction of the oleoresin, isopimaric acid (40%) predominates.
TL;DR: In this paper, the 13C NMR spectra of pentacyclic oxindole alkaloids of the heteroyohimbine group of the allo and epiallo series have been studied and an assignment has been made of the CSs of the carbon atoms.
Abstract: The13C NMR spectra of pentacyclic oxindole alkaloids of the heteroyohimbine group of the allo and epiallo series have been studied and an assignment has been made of the CSs of the carbon atoms. Characteristic differences have been noted in the13C CSs of the C2, C3, C7, C14, C15, and C19 carbon atoms that may be useful for solving stereochemical problems in new bases of this series from their13C NMR spectra.
TL;DR: The first time that edulinine and ferulic acid have been detected in plants of the genus Haplophyllum foliosum Vved (family Rutaceae) was reported in this paper.
Abstract: The alkaloids skimmianine, dubinidine, foliosidine, graveoline, and compounds (I) and (II) have been isolated from the epigeal part of the plantHaplophyllum foliosum Vved (family Rutaceae) On the basis of the spectral characteristics of (I) and its 0-isopropylidene derivative it has been established that the compound is the alkaloid edulinine Substance (II) was identified as ferulic acid by direct comparison with an authentic sample This is the first time that edulinine and ferulic acid have been detected in plants of the genusHaplophyllum