New Coumarins from Pterocaulon polystachyum

Abstract

Aerial parts of Pterocaulon polystachyum from Chaco province, Argentina, afforded the known coumarins ayapin, isoscopoletin, prenyletin, prenyletin methyl ether, virgatenol, obtusinin, 5-methoxy-6,7-methylenedioxycoumarin, 5-(3,3-dimethylallyloxy)-6,7-methylenedioxycoumarin, 5-(2′,3′-dihydroxy-3-methylbutanoxy)-6,7-methylenedioxycoumarin, haplopinol methyl ether, 6-(1,1-dimethyl-2-propenyl)-7-hydroxycoumarin and demethylnieshoutin; the last two are new as natural products while the five new coumarins from the collection were isovirgatenol, 3′-deoxyobtusinin, 6-methoxy-7-(2′-hydroxyethoxy)-coumarin, 5-(2′-hydroxyethoxy)-6,7-methylenedioxycoumarin and a substance tentatively identified as 5-hydroxy-6,7-methylenedioxy-8-(3,3-dimethylallyl)-coumarin.

References

• 1 Cabrera A L, Ragonese A M. Revision de genero Pterocaulon (Compositae). Darwiniana 1978; 185 - 257, as cited in Anderberg, AA. Taxonomy and phylogeny of the tribe Plucheae.  Plant Systematics and Ecology. 1991;  176 145-77
• 2 Cabrera A L, Burkart A E. Flora Illustrada de Entre Rios (Argentina), Parte VI. Coleccion Cientifica del INTA Buenos Aires; 1974: 290-301
• 3 Martinez Crovetto R. Instituto Miguel Lillo Miscelánea; 1981: No 69
• 4 Palacios R S, Rojo A A, Coussio J D, de Kimpe N, Debenedetti S L. 6,7-Dioxygenated and 5,6,7-trioxygenated coumarins from Pterocaulon polystachium .  Planta Medica. 1999;  65 294-5
• 5 Debenedetti S L, Nadinic E L, Coussio J D, de Kimpe N, Boeykens M. Two 6,7-dioxygenated coumarins from Pterocaulon virgatum .  Phytochemistry. 1998;  48 707-10
• 6 Matkarinov A D, Batirov E K, Malikov V M, Seitmuratov E. Obtusinin, a new coumarin from Haplophyllum obtusifolium .  Khimia Prirodnikh Soedinenii 1980; 16 : 328 - 30; Chemical Abstracts. 1980;  93 164316d
• 7 Ahluwalia V K, Khanna M, Singh R P. Synthesis of obtusinin and 7-(3′-hydroxymethylbut-2′-enyloxy)-6-methoxy-2H-1-benzopyran-2-one.  Monatshefte für Chemie. 1982;  113 197-200
• 8 Mulholland D A, Taylor D AH. Limonoid extractives from the genera Capuronianthus, Neobegua and Quivisianthe .  Phytochemistry. 1988;  27 1741-3
• 9 Debenedetti S L, Palacios P S, Nadinic E L, Coussio J D, de Kimpe N, Boeykens M, Feneau-Dupont J ., DeClerq J -P. 5-(3-Methyl-2-butenyloxy)-6,7-methylenedioxycoumarin, a 5,6,7-trioxygenated coumarin from Pterocaulon virgatum .  Journal of Natural Products. 1994;  57 1539-42
• 10 Cardona L, García B, Pedro J R, Pérez J. A coumarin-hemiterpene ether from Carduus tenuiflorus .  Phytochemistry. 1992;  31 3989-91
• 11 Matkarinov A D, Batirov E K, Malikov V M, Seitmuratov E. Coumarins of Haplophyllum obtusifolium .  Khimia Prirodnikh Soedinenii 1980; 16 : 565 - 7; Chemical Abstracts. 1980;  93 200982d
• 12 Debenedetti S L, de Kimpe N, Boeykens M, Coussio J D, Kesteleyn B. Structural revision of four coumarins from Pterocaulon species.  Phytochemistry. 1997;  45 1515-7
• 13 Ballantyne M M, McCabe P N, Murray R DH. Claisen rearrangements - II. Syntheses of six natural coumarins.  Tetrahedron. 1971;  27 871-7
• 14 Gonzalez A G, Lopez Dorta H, Medina Medina M C. Sintesis de cumarinas. IV. Productos de transposición de la 7-(3,3′-dimetilaliloxy)-cumarina.  Anales de Química. 1983;  79 471-3
• 15 Sharma R B, Raj K, Kapil R S. Biosynthesis of chalepin in Ruta graveolens .  Indian Journal of Chemistry. 1998;  37B 247-51
• 16 Pistelli L, Bertol A, Bilia A R, Morelli I. Minor constituents from Bupleurum fruticosum roots.  Phytochemistry. 1996;  41 1579-82
• 17 Magalhães A F, Frighetto R TG. Synthesis of 7-(2,3-epoxy-3-methyl-butyloxy)-5,6-methylenedioxycoumarin and derivatives.  Química Nova 1983; 6 : 165; Chemical Abstracts. 1984;  100 120726W