Cycloaddition to 3h-1,2-dithiole-3-thiones. X-ray structural investigation of 2,3,4′,5′-tetracarbonmthoxy-5-methyl-6-phenylthio-pyran-4-spiro-2′-(1,3-dithiole)

Treatment of 4-methyl-5 -phenyl-3H-1,2-dithiole-3-thione with dicarbomethoxyaceotene gave 2,3,4,5-tetra-carbomethoxy-5-methyl-6-phenylthiopyran-4-spiro-2-(1,3-dithiole) whose structure was proved by x-ray investigation.K. A. Timiryazev Agricultural Academy, Moscow 127550. A. N. Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow 117813. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 908–914, July, 1994.     

Triterpene glycosides of Dianthus deltoides. I

Summary FromDianthus deltoides L. we have isolated three new triterpene glycosides: dianthosides A, B, and C. It has been shown that dianthoside A is the 3-O--glucopyranoside and dianthoside B the 3-O-[O--D-glucopyranosyl-(1 6)--glucopyranoside] of gypsogenic acid. Some information on the structure of dianthoside C — a new glycoside of gypsogenin — has been obtained.A. E. Arbuzov Institute of Organic and Physical Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 33–38, January, 1971.     

Conjugates of trans-coniferyl alcohol in propolis and its sources

In a study of the composition of propolis of the aspen type and its source — secretions of the axillary buds of thePopulus tremula — three new conjugates have been isolated and identified: the ferulate, p-coumarate, and p-hydroxy-benzoate of trans-coniferyl alcohol. The structures of the compounds were shown by the methods of NMR and low- and high-resolution mass spectrometry.Vitaminy Scientific-Industrial Association, Moscow. M. M. Shemyakin Institute of Bioorganic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 319–324, May–June, 1989.     

Triterpene glucosides of Dipsacus azureus. III. Structure of dipsacobioside

A new triterpene glycoside — dipsacobioside — has been isolated from the root of theDipsacus azureus Schrenk. By chemical transformation and spectral methods its structure has been established as hederagenin 3-O-[O--L-rhamnopyranosyl-(14)--L-arabinopyranoside].Institute of Organic Chemistry, Kirgiz SSR Academy of Sciences, Frunze. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 204–207, March–April, 1989.     

Alkaloids of the Monolian flora. IV. Turcosine — A new alkaloid from Aconitum turczaninowi

As the result of a further study of the total alkaloids from the epigeal part ofAconitum turczaninowi we have isolated beiwutine and delcaroline and also a new alkaloid, which has been called turcosine. The structure of turcosine as 6,16-dimethoxy-4-methoxymethyl-1,7,8,10,14-pentahydroxy-N-ethylaconitane has been shown from a study of the IR, mass, PMR, and¹³C NMR spectra of the alkaloid and of the triacetate obtained from it.Institute of Chemistry, Mongolian People's Republic Academy of Sciences. Institute of the Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedeninii, No. 1, pp. 60–62, January–February, 1993.     

A chemical study of the roots of Paeonia anomala

The new phenolic glycoside paeonovicinoside (methyl salicylate 6--L-arabino-pyranosyl--D-glucopyranoside), and also paeoniflorin, -sitosterol, benzoic acid, and gallic acid and its methyl ester have been isolated from the roots ofPaeonia anomala.All-Union Scientific-Research Institute of Medicinal Plants Scientific Production Combine, Moscow. D. I. Ul'yanov Kuibyshev Medical Institute. All-Union Scientific-Research Institute of Pharmacy, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 55–59, January–February, 1992.     

The structure of seselirin: A new chromone from the roots ofSeseli sessiliflorum

Conclusions From the roots ofSeseli sessiliflorum Schrenk a new chromone has been isolated for which the structure of 2,2-dimethyl-3-(3-methylthioacryloyloxy)-3,4-dihydropyrano-5,6:6,7-(5-hydroxy-2-methyl) chromone has been proposed. It is the first representative of this group of natural compounds containing sulfur.Khimiya Prirodnykh Soedinenii, Vol. 6, No. 4, pp. 412–415, 1970     

A bioglycan from the gastropod mollusc Rapana thomasiana

A bioglycan — rapanan — has been isolated from the mantle of the gastropod molluscRapana thomasiana, the main carbohydrate chain of which is constructed of -(1 4)-bound D-glucose residues with a small number of side chains attached by -(1 6)-glucosidic bonds to the main chain of the bioglycan.Pacific Ocean Institute of Bioorganic Chemistry of the Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 25–28, January–February, 1986.     

Unusual result of modification of anemonotoxin RTX-III by malonaldehyde

The modification of the arginine residues of neurotoxin RTX-III fromRadianthus macrodactylus with malonaldehyde led to the formation of a derivative with a maximum in the UV spectrum at 340 nm in place of the expected N-(pyrimidin-2-yl)ornithine with absorption at 315 nm. On the basis of chemical transformations and the results of absorption spectroscopy, it has been concluded that the product obtained was an intermediate of the reaction — a Schiff's base. It has been shown that the stabilization of the reactive intermediate is due to the influence of steric factors. The further conversion of the toxin derivative taking place in neutral and alkaline media has been investigated; it is connected with a rearrangement of the malonaldehyde residue of the enol-enamine type.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Division, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 383–387, May–June, 1989.     

A study of the herb Aerva lanata. III. Alkaloids

Four new alkaloids — aervine (10-hydroxycanthin-6-one), methylaervine (10-methoxycanthin-6-one), aervoside (10--D-glucopyranosyloxycanthin-6-one), and aervolanine (3-(6-methyoxy--carbolin-1-yl)propionic acid), and also the known alkaloids canthin-6-one and 3-(-carbolin-1-yl)propionic acid have been isolated from the herbAerva lanata Juss. Their structures have been established on the basis of chemical and spectral characteristics.All-Union Scientific-Research Institute of Medicinal Plants Scientific Production Combine, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 388–394, May–June, 1991.     

Molecular and crystal structure of the germacranolide argolide from Artemisia glabella

The new germacranolide argolide has been isolated from the epigeal part ofArtemisia glabella, and its structure has been shown by its conversion into oxopelenolide B. From the results of an x-ray investigation it is suggested that argolide has the spatial structure of 3-oxo-4,7,6(H)-germacra-1(10),11(13)-dien-6,12-olide.Institute of Organic Synthesis and Coal Chemistry, Kazakh Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Organometallic Chemistry, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–657, September–October, 1991.     

Synthesis of α-neryl and α-geranyl propionates — Components of the sex pheromone of San Jose scale

Summary An effective synthesis of -neryl and -geranyl propionates has been performed by the two-stage E/Z-C₅ homologization of 3-methylbut-3-en-1-yl iodide.N. D. Zelinskii Institute of Organic Chemistry, Moscow. All-Union Scientific-Research Institute of Biological Methods of Plant Protection, Kishinev. Institute of Chemistry, Bashkir Scientific Center, Urals Division, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 422–424, May–June, 1989.     

Synthesis of regular polypeptides including lysine,proline, and alanine residues

Summary From the epigeal part ofThermopsis alterniflora, in addition to the alkaloids found previously, argentine, argentamine, and a new alkaloid, dimethamine, which is a representative of the bimolecular series, have been isolated. The structure of 3-(3,4-dihydro-N-methylcytisin-5-yl)-N-methylcytisine has been proposed for dimethamine on the basis of IR, UV, mass, and NMR spectra and also from its conversion products.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 218–222, March–April, 1972.     

Synthesis of an analogue of the phospholipid platelet activation factor from a natural ethanolamine plasmalogen

The synthesis has been performed of an analogue of the phospholipid platelet activation factor — 1-0-(alk-1-enyl)-2-acetyl-sn-glycero-3-phospho-N-(N-acetylglycylethanolamine). In concentrations of 10^–7-10^–6 M, the analogues so obtained inhibited the aggregation of human platelets stimulated by the phospholipid activation factor.Scientific-Research Institute of Biomedical Technology, USSR Ministry of Health, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 325–330, May–June, 1990.     

Alkaloids ofPetilium raddeana. V. Structure of petisidinone

From the epigeal part ofPetilium raddeana have been isolated the known alkaloids edpetiline and edpetine and the new base petisidinone with mp 217–219°C, []_D 0° (c 0.169; chloroform), C₂₇H₃₉NO₃ (I). When the known alkaloid petisidine was oxidized, a product identical with petisidinone (I) was obtained. Thus, the structure of (I) has been established as 26,23-nitrilocholestane-3,6,22-trione. Details of the IR, PMR, and mass spectra of (I) are given.Institute of the Chemistry of Plant Substances of the Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh soedinenii, NO. 5, pp. 620–622, September–October, 1986.     

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.