RSS-Feed abonnieren
DOI: 10.1055/s-2005-871277
Antimitotic Properties of Pterocarpans Isolated from Platymiscium floribundum on Sea Urchin Eggs
Publikationsverlauf
Received: September 3, 2004
Accepted: January 10, 2005
Publikationsdatum:
18. Juli 2005 (online)
![](https://www.thieme-connect.de/media/plantamedica/200507/lookinside/thumbnails/10.1055-s-2005-871277-1.jpg)
Abstract
This study reports the antimitotic effects on sea urchin eggs of five known pterocarpans: (+)-3,10-dihydroxy-9-methoxypterocarpan, (+)-3,9-dimethoxypterocarpan [(+)-homopterocarpin], (+)-2,3,9-trimethoxypterocarpan, (+)-3,4-dihydroxy-9-methoxypterocarpan [(+)-vesticarpan] and (+)-3-hydroxy-9-methoxypterocarpan [(+)-medicarpin], isolated from the trunk of Platymiscium floribundum, a native tree from Brazil. All tested compounds showed strong activity in this assay, with 2,3,9-trimethoxypterocarpan being the most active (log IC50 of -8.10 ± 0.02; -7.91 ± 0.01; -7.97 ± 0.02 M for first and third cleavages, and blastulae stages, respectively). These data suggest that the 2-methoxy substituent can be an important pharmacophoric unit.
References
-
1 Dewick P M. Isoflavonoids. In: Harborne JB, editor
The Flavonoids, Advances in Research Since 1980 . Chapman & Hall London; 1994: pp 125-209 - 2 Engler T A, Lynch K O, Reddy J P, Gregory G S. Synthetic pterocarpans with anti-HIV activity. Bioorg Med Chem Lett. 1993; 3 1229-32
- 3 Silva A JM, Coelho A L, Simas A BC, Moraes R AM, Pinheiro D A, Fernandes F FA, Arruda E Z, Costa P RR, Melo P A. Synthesis and pharmacological evaluation of prenylated and benzylated pterocarpans against snake venom. Bioorg Med Chem Lett. 2004; 14 431-5
- 4 Birt D F, Hendrich S, Wang W. Dietary agents in cancer prevention: flavonoids and isoflavonoids. Phamacol Therap. 2001; 90 157-77
-
5 Jacobs R S, Wilson L. Fertilized sea urchin egg as a model for detecting cell division inhibitors. In: Aszalor A, editor
Modern analysis of antibiotics . Marcel Dekker, Inc New York; 1981: pp 481-93 - 6 Costa-Lotufo L V, Silveira E R, Barros M CP, Lima M AS, Moraes M EA, Moraes M O. Antiproliferative effects of abietane diterpenes from Aegiphila lhotzkyana . Planta Med. 2004; 70 180-2
-
7 Fusetani N. Marine metabolites which inhibit development of echinoderm embryos. In: Scheuer, PJ, editor
Biorganic Marine Chemistry . Springer-Verlag Berlin; 1987: pp 61-92 -
8 Brandhorst B P. Informational content of the echinoderm egg. In: Browder, LW, editor
Developmental Biology a Comprehensive Synthesis. Oogenesis . Plenum Press New York; 1985: pp 525-76 -
9 Chabner B A, Ryan D P, Paz-Ares L, Garcia-Chabonero R, Calabresi P. Antineoplastic agents. In: Hardman JG and Limbird LE, editor
Goodman & Gilman’s The Pharmacological Basis of Therapeutics, . McGraw-Hill New York; 2001: pp 1389-459 - 10 Sconzo G, Romancino D, Fasulo G, Cascino D, Giudice G. Effect of doxorubicin and phenytoin on sea urchin development. Pharmazie. 1995; 50 616-9
- 11 Jacobs R S, White S, Wilson L. Selective compounds derived from marine organisms: effects on cell division in fertilized sea urchin eggs. Fed Proc. 1981; 40 26-9
- 12 Ducki S, Forrest R, Hadfield J A, Kendall A, Lawrence N J, McGown A T, Rennison D. Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg Med Chem Lett. 1998; 8 1051-6
- 13 Middleton E, Kandaswami C, Theoharides T C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol Rev. 2000; 52 673-751
- 14 Costa-Lotufo L V, Jimenez P C, Wilke D V, Leal L KAM, Cunha G MA, Silveira E R, Canuto K M, Viana G SB, Moraes M EA, Moraes M O, Pessoa C. Antiproliferative effects of several compounds isolated from Amburana cearensis A.C. Smith. Z Naturforsch Teil C. 2003; 58 675-80
- 15 Kurosawa K, Ollis W D, Redman B T, Sutherland I O, Gottlieb O R. Vestitol and Vesticarpan, isoflavonoids from Machaerium vestitum . Phytochemistry. 1978; 17 1413-5
- 16 McMurry T BH, Martin E, Donnely D MX, Thompson J C. 3-Hydroxy-9-methoxy- and 3-methoxy-9-hydroxypterocarpans. Phytochemistry. 1972; 11 3283-6
- 17 Pueppke S G, VanEtten H D. Identification of three new pterocarpans (6a,11a-dihydro-6H-benzofuro[3,2-c][1]benzopyrans) from Pisum sativum infected with Fusarium solani f. sp. pisi . J Chem Soc Perkin Trans I 1975: 946-8
- 18 Ingham L J. Fungal modification of pterocarpan phytoalexins from Melilotus alba and Trifolium pratense . Phytochemistry. 1976; 15 1489-95
- 19 Letchier M R, Shirley M I. Phenolic compounds from the heartwood of Dalbergia nitidula . Phytochemistry. 1976; 15 354-5
- 20 Jimenez P C, Fortier S C, Lotufo T MC, Pessoa C, Moraes M EA, Moraes M O, Costa-Lotufo L V. Biological activity in extracts of ascidians (Tunicata, Ascidiacea) from the northeastern Brazilian coast. J Exp Mar Biol Ecol. 2003; 287 93-101
Letícia Veras Costa-Lotufo
Departamento de Fisiologia e Farmacologia,
Universidade Federal do Ceará
Rua Cel Nunes de Melo 1127
Caixa Postal-3157
60430-270 Fortaleza
Ceará
Brasil
Telefon: +55-85-4009-8255
Fax: +55-85-4009-8333
eMail: lvcosta@secrel.com.br