NATURAL POLYACETYLENE COMPOUNDS
- Authors: Konovalov D.A1
-
Affiliations:
- Pyatigorsk Medical and Pharmaceutical Institute-a branch of Volgograd State Medical University
- Issue: Vol 2, No 4 (2014)
- Pages: 23-48
- Section: Articles
- URL: https://journal-vniispk.ru/2307-9266/article/view/111233
- ID: 111233
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Abstract
Polyacetylenes (polyynes) are compounds which contain two or more triple bonds in its structure. About 2 000 different polyacetylenes and biogenetically related substances were identified in 24 families of higher plants. However, most of these compounds were found in seven families of flowering plants: Apiaceae (Umbelliferae), Araliaceae, Asteraceae (Compositae), Campanulaceae, Olacaceae, Pittosporaceae and Santalaceae . Polyacetylenes are relatively unstable, chemically and biologically active compounds, and present in fungi, micro-organisms, marine invertebrates and other organisms except for plants. Acetylenes form distinct specialized group of chemically active natural compounds, which are biosynthesized in plants of unsaturated fatty acids. In addition to widespread aliphatic polyacetylenes thiophenes dithiacyclohexadienes (thiarubrines), thioethers, sulphoxides, sulphones, alkamides, chlorohydrins, lactones, spiroacetal enol ethers, furans, pyrans, tetrahydropyrans, isocoumarins, aromatic acetylenes were also found in plant species. Polyacetylenes are localized in different plant organs, and can be found both individually and as a compound with carbohydrates, terpene, phenolic and other compounds. Many polyacetylenes are found in the composition of the essential oils of plants and it confirms their strongly marked ecological functions. From biological point of view these compounds are often synthesized by plants as toxic or bitter antifeedants, allelopathic compounds, phytoalexins or broadly antibiotic components. Polyynes are strong photosensitizers. They exhibit anti-inflammatory, anti-coagulant, anti-bacterial, anti-tuberculosis, anti-fungal, anti-viral, neuroprotective and neurotoxic activity. Immunostimulatory influence associated with certain allergenicity of some of these substances was established. Therefore, without a doubt polyacetylenes are of interest for the modern pharmacy and medicine.
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##article.viewOnOriginalSite##About the authors
D. A Konovalov
Pyatigorsk Medical and Pharmaceutical Institute-a branch of Volgograd State Medical University
Email: konovalov_da@pochta.ru
References
- Антимикробные свойства эфирного масла и его компонентов из Artemisia scoparia Waldst. et Kit. / В.В.Адгина, С.А.Вичканова, Б.В.Белякова и др.// Фитонциды. Бактериальные болезни растений: материалы науч. конф. 11-13 сент. 1990 г. - Львов, 1990. - Ч. 1. - С. 24.
- Гольмов В.П., Афанасьев Н.М. Природные соединения с тройными связями // Успехи химии. 1958. Т. 27, вып. 7. С. 785-816.
- Коновалов Д.А. Ароматические полиацетиленовые соединения сем. Asteraceae и их хемотаксономическое значение // Растительные ресурсы. - 1996. - Т.32, вып. 4. - С.84-98.
- Коновалов Д.А. Цитотоксические свойства полиацетиленовых соединений растений. (I) // Растительные ресурсы. - 2014. - Т. 50, вып. 1. - С. 153-171.
- Коновалов Д.А. Цитотоксические свойства полиацетиленовых соединений растений. (II) // Растительные ресурсы. - 2014. - Т. 50, вып. 2. - С. 279-296.
- Состав эфирного масла Artemisia scoparia Waldst. et Kit./ О.А. Коновалова, Д.А. Коновалов, В.С. Кабанов и др.// Растительные ресурсы. - 1989. - Т. 31, вып. 3. - С. 404-410.
- Кучеров В.Ф., Мавров М.В., Держинский А.Р. Природные полиацетиленовые соединения. М.: Наука, 1972. 390 с.
- Насухова А.М., Коновалов Д.А. Природные полиацетиленовые соединения. Обзор начального этапа исследований // Фармация и фармакология. 2014. №1. С. 3-8.
- Использование лекарственных растений в восстановительной медицине и фитотерапии онкозаболеваний, пострадиационных поражениях и геронтологии. / А.Н. Разумов, А.И. Вялков, В.Г Сбежнева. и др. - М.: Издательство «МВД», 2008. - 376 с.
- Растительные ресурсы СССР: Цветковые растения, их химический состав, использование. Сем. Asteraceae (Compositae). - СПб.: Наука, 1993. - 352 с.
- Харборн Дж. Введение в экологическую биохимию. - М., 1985. - 312 с.
- Antifungal compounds from immature avocado fruit peel / N.K.B. Adikaram, D.F. Ewing, A.M. Karunaratne et al. // Phytochemistry. - 1992. - Vol. 31. - P. 93-96.
- Allen E.H., Thomas C.A. Time course of safynol accumulation in resistant and susceptible safflower infected with Phytophthora drechsleri // Physiol. Plant Pathol. 1971. Vol.1. P. 235-240.
- Allen E.H., Thomas C.A. Trans-trans-3,11-tridecadiene-5,7,9-triyne-1,2-diol, an antifungal polyacetylene from diseased safflower (Carthamus tinctorius) // Phytochemistry. 1971. Vol.10. P.1579-1582.
- Ayer W.A., Craw P.A. Metabolites of the fairy ring fungus, Marasmius oreades. Part 2 Norsesquiterpenes, further sesquiterpenes, and agrocybin // Can. J. Chem. 1989. Vol. 67. P. 1371-1380.
- Bohlmann F. Naturally-occurring acetylenes, in Lam, J. et al., Eds., Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds (NOARC), Bioactive Molecules. - Elsevier, Amsterdam, 1988. - Vol. 7 - P. 1-19.
- Bohlmann F., Burkhardt T., Zdero C. // Naturally Occurring Acetylenes. London, 1973. 547 p.
- Christensen L.P. Biological activities of naturally occurring acetylenes and related compounds from higher plants // Recent Res. Devel. Phytochem. - 1998. - Vol. 2. - P. 227-257.
- Christensen L.P., Brandt K. Acetylenes and psoralens. - Wiley-Blackwell: Oxford, UK, 2006. - P. 147-163.
- Christensen L.P., Jakobsen H.B. Polyacetylenes: Distribution in higher plants, pharmacological effects and analysis // Chromatographic Science Series. 2008. Vol. 99. P. 757-816.
- Christensen L.P., Jensen M., Kidmose U. Simultaneous determination of ginsenosides and polyacetylenes in American ginseng root (Panax quinquefolium L) by high-performance liquid chromatography // J. Agric. Food Chem. 2006. Vol.54. P. 8995-9003.
- Christensen L.P. Biological activities of naturally occurring acetylenes and related compounds from higher plants // Rec. Res. Dev. Phytochem. - 1998. - Vol.2. - P. 227-257.
- De Wit P.J.G.M., Kodde E. Induction of polyacetylenic phytoalexins in Lycopersicon esculentum after inoculation with Cladosporium fulvum (syn. Fulvia fulva) // Physiologica Plant Pathology. 1981. Vol.18. P. 143-148.
- Dembitsky V.M. Anticancer activity of natural and synthetic acetylenic lipids // Lipids. - 2006. - Vol.41, N.10. - P. 883-924.
- Ebel J. Phytoalexin synthesis: the biochemical analysis of the induction process // Ann. Rev. Phytopathol. - 1986. - Vol.24. - P. 235-264.
- Occurrence of falcarinol and falcarindiol in tomato plants after infection with Verticillium albo-atrum and charcterization of four phytoalexins by capillary gas chromatography-mass spectrometry / D.M. Elgersma, A.C.M. Weijman, H.J. Roeymans et al. // Phytopathol. Z. - 1984. - Vol. 109. - P. 237-240.
- Inhibition of 15-hydroxyprostaglandin dehydrogenase activity in rabbit gastric antral mucosa by panxynol isolated from oriental medicines / Y. Fujimoto, S. Sakuma, S. Komatsu et al. // J. Pharm. Pharmacol. - 1998. - Vol.50. - P. 1075-1078.
- Multiple modes of insecticidal action of three classes of polyacetylene derivatives from Rudbeckia hirta / G. Guillet, B.J.R. Philogène, J. O’Meara et al. // Phytochemistry. - 1997. - Vol. 46. - P. 495-498.
- Hansen L., Boll P.M. Polyacetylenes in Araliaceae: their chemistry, biosynthesis and biological significance // Phytochemistry. 1986. Vol.25. P. 285-293.
- Harding V.K., Heale J.B. The accumulation of inhibitory compounds in the induced resistance response of carrot slices to Botrytis cinerea // Physiol. Plant Pathol. 1981. Vol.18. P. 7-15.
- Imoto S., Ohta Y. Elicitation of diacetylenic compounds in suspension cultured cells of eggplant // Plant Physiol. 1988. Vol.86. P. 176-181.
- Isolation of dehydrofalcarinol as a seed germination inhibitor from Artemisia capillaris roots / T.Ishizu, T.Ohsaki, N.Tanaka et al. // Bull. Fukuoka Univ. Ed. - 1999. - Vol.48. - P. 6772.
- Antimycobacterial polyynes of Deveil’s Club (Oplopanax horridus), a North American naitive medicinal plant / M.Kobaisy, Z.Abramowski, L.Lermer et al. // Journal of Natural Products. - 1997. - Vol. 60, N 11. - P.1210-1213.
- Dihydromatricaria ester: acetylenic acid secreted by soldier beetle / J. Meinwald, Y.C.Meinwald, A.M. Chalmers et al. // Science. - 1968. - Vol. 160. - P. 890-892.
- Minto R.E., Blacklock B.J. Biosynthesis and Function of Polyacetylenes and Allied Natural Products // Prog. Lipid Res. 2008. Vol. 47, Is.4. P. 233-306.
- Nawar H.F., Kuti J.O. Wyerone acid phytoalexin synthesis and peroxidase activity as markers for resistance of broad beans to chocolate spot disease // J. Phytopathol. 2003. Vol.151. P. 564-570.
- Cytotoxic and insecticidal constituents of the unripe fruit of Persea Americana / N.H. Oberlies, L.L. Rogers, J.M. Martin et al. // J. Nat. Prod. - 1998. - Vol. 61. - P. 781-785.
- Stevens K.L. Allelopathic polyacetylenes from Centaurea repens (Russian knapweed) // J. Chem. Ecol. - 1986. - Vol.12. - P.1205-1211.
- Tietjen K.G., Matern U. Induction and suppression of phytoalexin biosynthesis in cultured cells of safflower, Carthamus tinctorius L. by metabolites of Alternaria carthami Chowdhury // Arch. Biochem. Biophys. 1984. Vol. 229. P.136-144.
- Yano K., Ishizu T. Capillen, a seed germination inhibitor from Artemisia capillaris roots // Phytochemistry. 1994. Vol. 37, N 3. P. 689-690.
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