Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae . It is a group of compounds which can be described as benzo-pyrano-furano-benzenes (i.e. 6H -[1]benzofuro[3,2-c]chromene skeleton) which can be formed by coupling of the B ring to the 4-one position.[1]
Pterocarpan chemical structure. It consists of a 1-benzofuran moiety (dotted blue circle) fused to a 2H -chromene moiety (dotted green circle). The systematic name for it is 6H -[1]benzofuro[3,2-c]chromene. The new numbering of the resulting moiety is shown with red numbers.
2'-hydroxyisoflavone reductase is the enzyme responsible for the conversion in Cicer arietinum [2] and glyceollin synthase for the production of glyceollins , phytoalexins in soybean .[3]
Medicarpin chemical structure
Phaseolin – a prenylated pterocarpan – chemical structure
Glyceollin III – a prenylated pterocarpan – chemical structure
Bitucarpin A and B , isolated from the aerial parts of Mediterranean plants Bituminaria morisiana and Bituminaria bituminosa [4]
Erybraedin A and B , isolated from the stems of Erythrina subumbrans [5] and C , isolated from the leaves of Bituminaria morisiana [6]
Erythrabyssin II , erystagallin A , erythrabissin-1 , and erycristagallin isolated from the stems of Erythrina subumbrans [5]
Glycinol , glyceollidin I and II , glyceollins (glyceollin I , II , III and IV ), found in the soybean (Glycine max )[7] [8]
Glycyrrhizol A , isolated from the root of the Chinese licorice plant (Glycyrrhiza uralensis )
Maackiain , isolated from the roots of Maackia amurensis subsp. Buergeri [9]
Medicarpin , found in Medicago truncatula
Morisianine , isolated from the seeds of Bituminaria morisiana [10]
Orientanol A , isolated from the wood of Erythrina orientalis [11]
Phaseolin , found in French bean seeds[12]
Pisatin , found in Pisum sativum [13]
Striatine , isolated from aerial parts of Mundulea striata [14]
Trifolirhizin , found in Sophora flavescens
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. doi :10.1016/0003-9861(88)90627-3 . PMID 3369863 .
Pistelli, Luisa; Noccioli, Cecilia; Appendino, Giovanni; Bianchi, Federica; Sterner, Olov; Ballero, Mauro (2003). "Pterocarpans from Bituminaria morisiana and Bituminaria bituminosa". Phytochemistry . 64 (2). Elsevier BV: 595–598. doi :10.1016/s0031-9422(03)00190-0 . ISSN 0031-9422 . PMID 12943781 .
Rukachaisirikul, Thitima; Innok, Phongsak; Aroonrerk, Nuntana; Boonamnuaylap, Woraluk; Limrangsun, Saranya; Boonyon, Chanakan; Woonjina, Umpawan; Suksamrarn, Apichart (2007). "Antibacterial Pterocarpans from Erythrina subumbrans". Journal of Ethnopharmacology . 110 (1). Elsevier BV: 171–175. doi :10.1016/j.jep.2006.09.022 . ISSN 0378-8741 . PMID 17055201 .
Matsuura, Nobuyasu; Nakai, Rie; Iinuma, Munekazu; Tanaka, Toshiyuki; Inoue, Kenichro (1994). "A prenylated flavanone from roots of Maackia amurensis subsp. Buergeri". Phytochemistry . 36 (1). Elsevier BV: 255–256. doi :10.1016/s0031-9422(00)97051-1 . ISSN 0031-9422 .
Blagrove, R. J.; Colman, P. M.; Lilley, G. G.; Van Donkelaar, A.; Suzuki, E. (1983). "Physicochemical and structural studies of phaseolin from French bean seed". Plant Foods for Human Nutrition . 33 (2–3). Springer Science and Business Media LLC: 227–229. doi :10.1007/bf01091313 . ISSN 0921-9668 .
Manjary, Frédéric; Petitjean, Alain; Conan, Jean-Yves; Thérèse Martin, Marie; Frappier, François; Rasoanaivo, Philippe; Ratsimamanga-Urverg, Suzanne (1993). "A prenylated pterocarpan from Mundulea striata". Phytochemistry . 33 (2). Elsevier BV: 515–517. doi :10.1016/0031-9422(93)85554-5 . ISSN 0031-9422 .