Showing papers in "Chemistry of Natural Compounds in 1974"
TL;DR: The structure of triterpene glycosides from the roots of potmarigold calendula (C. officinalis) has been established as discussed by the authors, including oleanolic acid 3-{[galactopyranosido-(1→3)] [glucopyranoid(1→2)]-β-D-glucopy-ranoside} (calenduloside C) and the 28-acyl-β-, β-D-,glucopeyranoside C(calendulooside D)
Abstract: The structure of new triterpene glycosides from the roots of potmarigold calendula (C. officinalis) has been established: oleanolic acid 3-{[galactopyranosido-(1→3)] [glucopyranosido-(1→2)]-β-D-glucopy-ranoside} (calenduloside C) and the 28-acyl-β-D-glucopyranoside of calenduloside C (calenduloside D).
13 citations
10 citations
TL;DR: In this paper, a comprehensive study of Chenopodium botrys L. (Jerusalem oak goosefoot), family Chenopodiaceae, growing in the valley of the river Issyk, Alma-Ata oblast, was conducted.
Abstract: Continuing a comprehensive study of Chenopodium botrys L. (Jerusalem oak goosefoot), family Chenopodiaceae, growing in the valley of the river Issyk, Alma-Ata oblast [1, 2], we have studied the flavonoid compounds from its epigeal part. The combined flavonoids were obtained by e x t r a c t i o n with m~thanol, followed by purification. By chromatography on a polyamide sorbent with fractional crystallization and preparative chromatography on paper we isolated three flavonoid substances. To determine the nature of these compounds we studied the physicochemical properties of the initial substances and of the products of their hydrolysis.
8 citations
TL;DR: In this article, descending paper chromatography (LM paper) was used to identify acids from butan-l-ol saturated with 25% ammonia solution using markers; the indicator was a 0.1% ethanolic solution of Bromothymol Blue.
Abstract: The acids isolated from the oil by means of sodium bicarbonate were investigated by descending paper chromatography (LM paper) in butan-l-ol saturated with 25% ammonia solution using markers [1]. The indicator was a 0.1% ethanolic solution of Bromothymol Blue. Acetic acid (Rf 0.17), propionic acid (Rf 0.22), isovaleric acid (Rf 0.57), and enanthic acid (Rf 0.78) were identified. The phenols were extracted from the oil with a 5% solution of caustic soda.
8 citations
7 citations
TL;DR: From the epigeal part of the plant collected in July 1972, in the Ashtarak region in theflowering phase, by aqueous extraction, followed by the chromatography of the total extract on a column of alumina (activity grade IV) with elution by benzene, this paper obtained a crystalline substance (1), CisHi804, mp 167-168°C [~]~-36.5~5 °, (c 2.0; methanol), tool. wt. 262 (mass spectrometrically).
Abstract: From the epigeal part of the plant collected in July, 1972, in the Ashtarak region in thefloweringphase, by aqueous extraction [2] followed by the chromatography of the total extract on a column of alumina (activity grade IV) with elution by benzene we have obtained a crystalline substance (1), CisHi804, mp 167-168°C [~]~-36.5~5 °, (c 2.0; methanol), tool. wt. 262 (mass spectrometrically). The IR spectrum of (1) has absorption bands in the following regions, cm-l: 3450 (OH stretching vibrations), 2980 (olefinic hydrogens), 1745 (carbonyl of an ~,fl-unsaturated V lactone), 1680 and 1635 (ketonic carbonyl conjugated with a double bond), and 1165, 1030, and 1060 cm -i (C-O bonds of ester and alcohol groups).
7 citations
TL;DR: In this paper, four cardiac glycosides have been isolated from the leaves of Erysimum crepidifolium Rchb. Three of them have been identified as erysimin, erysIMoside, and erycordin.
Abstract: Four cardiac glycosides have been isolated from the leaves ofErysimum crepidifolium Rchb. Three of them have been identified as erysimin, erysimoside, and erycordin. The fourth glycoside, which has been named glucostrophalloside, is new, and it consists of strophanthidin 3β-O-[4′-O-β-D-glucopyranosyl-β-D-allomethylopyranoside].
7 citations
7 citations
TL;DR: In this article, a comparative mass-spectrometric investigation of five isomeric and stereoisomeric abienols has been performed and it has been shown that all five can be identified from their mass spectra.
Abstract: 1. The synthesis of the previously undescribed Δ13-trans-neoabienol has been performed. 2. A comparative mass-spectrometric investigation of five isomeric and stereoisomeric abienols has been performed. 3. It has been shown that all five abienols can be identified from their mass spectra.
7 citations
TL;DR: It has been shown that BOC derivatives of amino acids can be obtained by the tert-butoxy carbonylation of amino acid salts with di-tert-butylpyrocarbonate in aqueous organic solutions as mentioned in this paper.
Abstract: It has been shown that BOC derivatives of amino acids can be obtained by the tert-butoxycarbonylation of amino-acid salts with di-tert-butylpyrocarbonate in aqueous organic solutions.
7 citations
TL;DR: The structure of the flavone C-glycoside vaccarin, isolated from the seeds of Vaccaria segetalis (Neck.) Carcke, has been determined.
Abstract: The structure of the flavone C-glycoside vaccarin, isolated from the seeds ofVaccaria segetalis (Neck.) Carcke, has been determined.
TL;DR: From the roots ofFerula mogoltavica, two new terpenoid coumarins have been isolated as mentioned in this paper, and also one known one, gummosin, has been identified.
Abstract: From the roots ofFerula mogoltavica, two new terpenoid coumarins have been isolated — mogoltavidin and mogoltavicin — and also one known one — gummosin.
TL;DR: In the literature available to us, we have found no information on the chemical composition of the epigeal part of Acorus calamus as mentioned in this paper, and only statements on the finding of an essential oil In the leaves and some information on its chemical composition.
Abstract: Th~ roots of Acorus calamus L., family Araceae (drug sweetflng) are widely used in medicine [1]. In the preparation of the raw material , the epigeal part, the weight of which is several times that of the rhizome, is discarded. In the l i terature available to us, we have found no information on the chemical composition of the epigeal part. There are only statements on the finding of an essential oil In the leaves and some information on its chemical composition [2].
TL;DR: From the methanolic mother solntion obtained in the crystallization of acetylpectoltnarin audpectolinarin, by repeated chromatography on columns of polyamide the authors have isolated, in addition to pectolinarlgenin and linaroside, three other minor components.
Abstract: From the methanolic mother solntion obtained in the crystallization of acetylpectoltnarin audpectolinarin [1] from Linaria kurd,ca by repeated chromatography on columns of polyamide we have isolated, in addition to pectolinarlgenin and linaroside [2] three other minor components. A chloroform eluate contained the flavone aglycone (I), CleH12Os, mp 258-260°C, tool wt. 284 (mass spectrometry), NMR spectrum: doublet at 7.69 ppm, J = 8 Hz, 2 H (H-2', 6'); doublet at 6.84 ppm, J = 8 Hz; 2 H (H-3', 5'); doublet at 6.41 ppm, J = 2.5 Hz, 1 H (R-6); single, at 6.37 ppm, 1 H (H-3); doublet at 6.07 ppm, J = 2.5 Hz, 1 H (H-8); and singlet at 3.77 ppm, 3 H (CHsO group) [3].
TL;DR: The following alkaloids have been isolated from the epigeal part of Sophora alopecuroides in the flowering phase: sophoridine, sophoramine, sophocarpine, aloperine, and a new base C15H20N2O, which is called neosophoramine and for which the structure of the A/B and B-cis, A/C-trans isomer of Sophoramine is proposed.
Abstract: The following alkaloids have been isolated from the epigeal part ofSophora alopecuroides in the flowering phase: sophoridine (0.06%), sophoramine (0.036%), sophocarpine (0.051%), aloperine (0.03%), a liquid base C19H23NO3 (0.00057%), and a new base C15H20N2O (0.0025%) which we have called neosophoramine and for which the structure of the A/B and B/C-cis, A/C-trans isomer of sophoramine is proposed.
TL;DR: Litvinenko and N. P. Geissman as mentioned in this paper, The Chemis t ry of Flavonoid Compounds, Pergamon P r e s s, New York (1962), p. 415.
Abstract: M. F. Denikeeva, V. I. Litvinenko, and L. I. Borodin, Khim. Pr i rodn . Soedin., 534 (1970). I. L. Kovalev and V. I. Litvinenko, Khim. Pr i rodn . Soedin., 233 (1965). V. I. Litvinenko and N. P. Maksyutina, Khim. Pr i rodn . Soedin., 420 (1965). T. A. Geissman, The Chemis t ry of Flavonoid Compounds, Pergamon P r e s s , New York (1962), p. 107. J. Gripenberg, ~Flavones,\" in: The Chemis t ry of Flavonoid Compounds, (ed. by T. A. Geissman), Pergamon P r e s s , New York (1962), p. 415.
TL;DR: From a methanolic extract of the roots ofPrangos biebersteinii Karjag, in addition to substances found previously, two other components of the coumarin series have been isolated as mentioned in this paper.
Abstract: 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.
TL;DR: In this article, a new diterpenoid of the kaurane series, called stachysic acid, was isolated from Stachys silvatica L. (family Labiatae) and the structure of 6β-acetoxy-(−)-kaur-16-en-18β-oic acid was established.
Abstract: In addition to 6-hydroxy- and 6,18-dihydroxy-(—)-kaurenes, fromStachys silvatica L. (family Labiatae) we have isolated a new diterpenoid of the kaurane series which we have called stachysic acid and for it we have established the structure of 6β-acetoxy-(—)-kaur-16-en-18β-oic acid.
TL;DR: Two terpenoid coumarins, mogoltadone and mogoltadin, have been isolated from the roots of Ferula mogoltavica as mentioned in this paper, and they have been shown to be the ether of umbelliferone and 3-oxo-4,4,10-trimethyl-8-vinyldecalin-9-ylmethanol.
Abstract: Two new terpenoid coumarins — mogoltadone and mogoltadin — have been isolated from the roots ofFerula mogoltavica. Mogoltadone has the composition C24H28O4, [α]
D
21
-41.7° (c 1.1; chloroform). On the basis of spectral characteristics, it has been shown that it is the ether of umbelliferone and 3-oxo-4,4,10-trimethyl-8-vinyldecalin-9-ylmethanol with the trans linkage of rings A and B and the equatorial orientation of the substituent at C9. Mogoltadin has the composition C24H30O4, [α]
D
21
-55° (c 1.0; ethanol) and is the ether of umbelliferone and 3-hydroxy-4,4,10-trimethyl-8-vinyldecalin-9-ylmethanol with the trans linkage of rings A and B and the diequatorial arrangement of the substituents at C3 and C9.
Abstract: From a methanolic extract of the roots ofPrangos ferulacea (L) Lindl., growing in the Nakhichevan ASSR, in addition to the compounds found previously, another six substances (I–VI) have been isolated, of which (I) and (VI) have been identified as, respectively, meransin hydrate monoacetate, found for the first time in nature, and umbelliferone: and in the study of a crystalline mixture obtained from the resin of the roots of the plant under investigation collected in Armenia, two coumarins — (VII) and (VIII) — have been isolated.
TL;DR: In this article, another lactone with the composition C24H3204, M + 382, mp 189-190°C (methanol), Rf 0.21 [petroleum e the r -e thy l acetate (5 : 1) system] was identified by the absence of depression of the melting point in a mixture with 7-hydroxycoumarin.
Abstract: Continuing a study of the coumarins of the above-named plant, from the ethereal fraction after the elimination of the galbanic acid [1] we have isolated another lactone, with the composition C24H3204, M + 382, mp 189-190°C (methanol), [a]~ + 63 ° (c 1.0; chloroform), Rf 0.21 [petroleum e the r -e thy l acetate (5 : 1) system]. From its chemical composition and UV spectrum [244,255, and 327 nm (log £ 3.64, 3.38, and 4.29, respectively)] it belongs to the 7-hydroxycoumarin derivatives. Its IR spectrum contains absorption bands at (cm-1): 1733 (carbonyl of an ~-pyrone), 1617, 1562 (aromatic nucleus), 2990, 2965, 2940, and 1380-1360 (C-methyl groups), and 1.713 (carbonyl group of a saturated ketone). Acid hydrolysis of the lactone gave umbelliferone CsH603 with mp 229-231°C (from water), which was identified by the absence of a depression of the melting point in a mixture with 7-hydroxycoumarin.
TL;DR: The triol (IV) (C20Hs6Os, mp 69-71°C, IR spectrum: 3450, 3100, 1640, 990 cm -1) was obtained from stachylone by reduction with sodium tetrahydroborate in admixture with products as mentioned in this paper.
Abstract: The hydrogenation of stachylone in ethyl acetate over Pd/BaSO 4 took place with the absorption of one mole of hydrogen and gave dihydrostachylone (III), which was identical f rom its IR spectrum, melting point, and mixed melting point with the tetrahydrostachysolone described previously [2]. Another confirmation of this was the triol (IV) (C20Hs6Os, mp 69-71°C, IR spectrum: 3450, 3100, 1640, 990 cm -1) obtained from stachylone by reduction with sodium tetrahydroborate in admixture with products (V) (C20H3602, mp 47-50\"C; IR spectrum: 3450, 1650, 990 can -1) and (VI) (C20Hs403, mp 79-81°C; IR spectrum: 3450, 1670, 1645, 990, 830 cm-1), isolated previously from stachysolone on its reduction with sodium in butanol [3].