Pterocarpano

Pterocarpanos son derivados de isoflavonoides que se encuentran en la familia Fabaceae. Es un grupo de compuestos que puede ser descrito como benzo-pirano-furano-bencenos (es decir, 6H-[1]benzofuro[3,2-c] cromeno esqueleto) que se puede formar por acoplamiento del anillo B a la 4 posición.^[1]

2'-reductasa hydroxyisoflavone es la enzima responsable de la conversión en Cicer arietinum^[2] y glyceollin sintasa para la producción de glyceollinas, fitoalexinas en la soja.^[3]

Compuestos conocidos[editar]

Bitucarpin A y B, aislado de las partes aéreas de las plantas mediterráneas Bituminaria morisiana y Bituminaria bituminosa^[4]
Erybraedin A y B, aislado de los tallos de Erythrina subumbrans^[5] y C, aislado de las hojas de Bituminaria morisiana^[6]
Erythrabyssin II, erystagallin A, erythrabissin-1, y erycristagallin aislado de los tallos de Erythrina subumbrans^[5]
Glycinol, glyceollidin I y II, glyceollins (glyceollin I, II, III y IV), que se encuentra en la soja (Glycine max)^[7]
Glycyrrhizol A, aislado de la raíz de la planta de regaliz chino (Glycyrrhiza uralensis)
Maackiain, aislado de la raíz de Maackia amurensis subsp. Buergeri^[8]
Medicarpin, que se encuentra en Medicago truncatula
Morisianine, aislados de las semillas de Bituminaria morisiana^[9]
Orientanol A, aislada de la madera de Erythrina orientalis^[10]
Phaseolin, que se encuentra en las semillas de frijol francés^[11]
Pisatin, que se encuentra en Pisum sativum^[12]
Striatine, aislado de las partes aéreas de Mundulea striata^[13]
Trifolirhizin, que se encuentra en Sophora flavescens

Referencias[editar]

↑ Pterocarpans on the National Library of Medicine - Medical Subject Headings
↑ Isolation of NADPH:isoflavone oxidoreductase, a new enzyme of Pterocarpan phytoalexin biosynthesis in cell suspension cultures of Cicer arietinum. Karin Tiemann, Walter Hinderer and Wolfgang Barz, FEBS Letters, Volume 213, Issue 2, 23 March 1987, Pages 324-328, doi 10.1016/0014-5793(87)81515-6
↑ Welle R, Grisebach H (1988). «Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers». Arch. Biochem. Biophys. 263 (1): 191-8. PMID 3369863. doi:10.1016/0003-9861(88)90627-3.
↑ Pterocarpans from Bituminaria morisiana and Bituminaria bituminosa. Dedicated to the memory of Professor Jeffrey B. Harborne. Luisa Pistelli, Cecilia Noccioli, Giovanni Appendino, Federica Bianchi, Olov Sterner and Mauro Ballero, Phytochemistry, Volume 64, Issue 2, September 2003, Pages 595-598, doi 10.1016/S0031-9422(03)00190-0
↑ ^a ^b Antibacterial Pterocarpans from Erythrina subumbrans. Thitima Rukachaisirikul, Phongsak Innok, Nuntana Aroonrerk, Woraluk Boonamnuaylap, Saranya Limrangsun, Chanakan Boonyon, Umpawan Woonjina and Apichart Suksamrarn, Journal of Ethnopharmacology, Volume 110, Issue 1, 1 March 2007, Pages 171-175, doi 10.1016/j.jep.2006.09.022
↑ New cytotoxic prenylated isoflavonoids from Bituminaria morisiana. Cottiglia Filippo, Casu Laura, Bonsignore Leonardo, Casu Mariano, Floris Costantino, Leonti Marco, Gertsch Juerg and Heilmann Jörg, Planta medica 71 (3) (2005), pp. 254-260
↑ Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy. M. Carla Zimmermann, Syreeta L. Tilghman, Stephen M. Boué, Virgilio A. Salvo, Steven Elliott, K. Y. Williams, Elena V. Skripnikova, Hasina Ashe, Florastina Payton-Stewart, Lyndsay Vanhoy-Rhodes, Juan Pablo Fonseca, Cynthia Corbitt, Bridgette M. Collins-Burow, Melanie H. Howell, Michelle Lacey, Betty Y. Shih, Carol Carter-Wientjes, Thomas E. Cleveland, John A. McLachlan, Thomas E. Wiese, Barbara S. Beckman and Matthew E. Burow, JPET January 2010 vol. 332 no. 1, doi 10.1124/jpet.109.160382
↑ A prenylated flavanone from roots of Maackia amurensis subsp. Buergeri. Nobuyasu Matsuura, Rie Nakai, Munekazu Iinuma, Toshiyuki Tanaka and Kenichro Inoue, Phytochemistry, Volume 36, Issue 1, May 1994, Pages 255-256, doi 10.1016/S0031-9422(00)97051-1
↑ A pterocarpan from the seeds of Bituminaria morisiana. Marco Leonti, Laura Casu, Jurg Gertsch, Leonardo Bonsignore, Costantino Floris, Mariano Casu and Filippo Cottiglia, J Nat Med (2010) 64:354–357, doi 10.1007/s11418-010-0408-7
↑ A pterocarpan from Erythrina orientalis. Hitoshi Tanaka, Toshihiro Tanaka and Hideo Etoh, Phytochemistry, Volume 45, Issue 1, May 1997, Pages 205-207, doi 10.1016/S0031-9422(96)00841-2
↑ Physicochemical and structural studies of phaseolin from French bean seed. R. J. Blagrove, P. M. Colman, G. G. Lilley, A. Van Donkelaar and E. Suzuki, Plant Foods For Human Nutrition (formerly Qualitas Plantarum), Volume 33, Numbers 2-3, 227-229, doi 10.1007/BF01091313
↑ Pisatin: an Antifungal Substance from Pisum sativum L. Dawn R. Perrin and W. Bottomley, Nature 191, 76 - 77 (1 July 1961), doi 10.1038/191076a0
↑ A prenylated pterocarpan from Mundulea striata. Frédéric Manjary, Alain Petitjean, Jean-Yves Conan, Marie Thérèse Martin, François Frappier, Philippe Rasoanaivo and Suzanne Ratsimamanga-Urverg, Phytochemistry, Volume 33, Issue 2, 13 May 1993, Pages 515-517, doi 10.1016/0031-9422(93)85554-5

Enlaces externos[editar]

Datos: Q7256727
Multimedia: Pterocarpans / Q7256727

[1] Pterocarpans on the National Library of Medicine - Medical Subject Headings

[2] Isolation of NADPH:isoflavone oxidoreductase, a new enzyme of Pterocarpan phytoalexin biosynthesis in cell suspension cultures of Cicer arietinum. Karin Tiemann, Walter Hinderer and Wolfgang Barz, FEBS Letters, Volume 213, Issue 2, 23 March 1987, Pages 324-328, doi 10.1016/0014-5793(87)81515-6

[3] Welle R, Grisebach H (1988). «Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers». Arch. Biochem. Biophys. 263 (1): 191-8. PMID 3369863. doi:10.1016/0003-9861(88)90627-3.

[4] Pterocarpans from Bituminaria morisiana and Bituminaria bituminosa. Dedicated to the memory of Professor Jeffrey B. Harborne. Luisa Pistelli, Cecilia Noccioli, Giovanni Appendino, Federica Bianchi, Olov Sterner and Mauro Ballero, Phytochemistry, Volume 64, Issue 2, September 2003, Pages 595-598, doi 10.1016/S0031-9422(03)00190-0

[Rukachaisirikul-5] Antibacterial Pterocarpans from Erythrina subumbrans. Thitima Rukachaisirikul, Phongsak Innok, Nuntana Aroonrerk, Woraluk Boonamnuaylap, Saranya Limrangsun, Chanakan Boonyon, Umpawan Woonjina and Apichart Suksamrarn, Journal of Ethnopharmacology, Volume 110, Issue 1, 1 March 2007, Pages 171-175, doi 10.1016/j.jep.2006.09.022

[6] New cytotoxic prenylated isoflavonoids from Bituminaria morisiana. Cottiglia Filippo, Casu Laura, Bonsignore Leonardo, Casu Mariano, Floris Costantino, Leonti Marco, Gertsch Juerg and Heilmann Jörg, Planta medica 71 (3) (2005), pp. 254-260

[7] Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy. M. Carla Zimmermann, Syreeta L. Tilghman, Stephen M. Boué, Virgilio A. Salvo, Steven Elliott, K. Y. Williams, Elena V. Skripnikova, Hasina Ashe, Florastina Payton-Stewart, Lyndsay Vanhoy-Rhodes, Juan Pablo Fonseca, Cynthia Corbitt, Bridgette M. Collins-Burow, Melanie H. Howell, Michelle Lacey, Betty Y. Shih, Carol Carter-Wientjes, Thomas E. Cleveland, John A. McLachlan, Thomas E. Wiese, Barbara S. Beckman and Matthew E. Burow, JPET January 2010 vol. 332 no. 1, doi 10.1124/jpet.109.160382

[8] A prenylated flavanone from roots of Maackia amurensis subsp. Buergeri. Nobuyasu Matsuura, Rie Nakai, Munekazu Iinuma, Toshiyuki Tanaka and Kenichro Inoue, Phytochemistry, Volume 36, Issue 1, May 1994, Pages 255-256, doi 10.1016/S0031-9422(00)97051-1

[9] A pterocarpan from the seeds of Bituminaria morisiana. Marco Leonti, Laura Casu, Jurg Gertsch, Leonardo Bonsignore, Costantino Floris, Mariano Casu and Filippo Cottiglia, J Nat Med (2010) 64:354–357, doi 10.1007/s11418-010-0408-7

[10] A pterocarpan from Erythrina orientalis. Hitoshi Tanaka, Toshihiro Tanaka and Hideo Etoh, Phytochemistry, Volume 45, Issue 1, May 1997, Pages 205-207, doi 10.1016/S0031-9422(96)00841-2

[11] Physicochemical and structural studies of phaseolin from French bean seed. R. J. Blagrove, P. M. Colman, G. G. Lilley, A. Van Donkelaar and E. Suzuki, Plant Foods For Human Nutrition (formerly Qualitas Plantarum), Volume 33, Numbers 2-3, 227-229, doi 10.1007/BF01091313

[12] Pisatin: an Antifungal Substance from Pisum sativum L. Dawn R. Perrin and W. Bottomley, Nature 191, 76 - 77 (1 July 1961), doi 10.1038/191076a0

[13] A prenylated pterocarpan from Mundulea striata. Frédéric Manjary, Alain Petitjean, Jean-Yves Conan, Marie Thérèse Martin, François Frappier, Philippe Rasoanaivo and Suzanne Ratsimamanga-Urverg, Phytochemistry, Volume 33, Issue 2, 13 May 1993, Pages 515-517, doi 10.1016/0031-9422(93)85554-5

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