Pterocarpan
Pterocarpansare derivatives ofisoflavonoidsfound in the familyFabaceae.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]
2'-hydroxyisoflavone reductaseis the enzyme responsible for the conversion inCicer arietinum[2]andglyceollin synthasefor the production ofglyceollins,phytoalexinsinsoybean.[3]
Known compounds
[edit]
- Bitucarpin AandB,isolated from the aerial parts of Mediterranean plantsBituminaria morisianaandBituminaria bituminosa[4]
- Erybraedin AandB,isolated from the stems ofErythrina subumbrans[5]andC,isolated from the leaves ofBituminaria morisiana[6]
- Erythrabyssin II,erystagallin A,erythrabissin-1,anderycristagallinisolated from the stems ofErythrina subumbrans[5]
- Glycinol,glyceollidin IandII,glyceollins(glyceollin I,II,IIIandIV), found in thesoybean(Glycine max)[7][8]
- Glycyrrhizol A,isolated from the root of the Chinese licorice plant (Glycyrrhiza uralensis)
- Maackiain,isolated from the roots ofMaackia amurensis subsp. Buergeri[9]
- Medicarpin,found inMedicago truncatula
- Morisianine,isolated from the seeds ofBituminaria morisiana[10]
- Orientanol A,isolated from the wood ofErythrina orientalis[11]
- Phaseolin,found inFrench beanseeds[12]
- Pisatin,found inPisum sativum[13]
- Striatine,isolated from aerial parts ofMundulea striata[14]
- Trifolirhizin,found inSophora flavescens
References
[edit]- ^Pterocarpans on the National Library of Medicine – Medical Subject Headings
- ^Tiemann, Karin; Hinderer, Walter; Barz, Wolfgang (23 March 1987)."Isolation of NADPH:isoflavone oxidoreductase, a new enzyme of Pterocarpan phytoalexin biosynthesis in cell suspension cultures of Cicer arietinum".FEBS Letters.213(2). Wiley: 324–328.doi:10.1016/0014-5793(87)81515-6.ISSN0014-5793.
- ^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.PMID3369863.
- ^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.ISSN0031-9422.PMID12943781.
- ^abRukachaisirikul, 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.ISSN0378-8741.PMID17055201.
- ^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
- ^Zimmermann, M. Carla; Tilghman, Syreeta L.; Boué, Stephen M.; Salvo, Virgilio A.; Elliott, Steven; et al. (1 October 2009)."Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy".Journal of Pharmacology and Experimental Therapeutics.332(1). American Society for Pharmacology & Experimental Therapeutics (ASPET): 35–45.doi:10.1124/jpet.109.160382.ISSN0022-3565.PMC2802480.PMID19797619.
- ^Cotrim, Gustavo dos Santos; Silva, Deivid Metzker da; Graça, José Perez da; Oliveira Junior, Adilson de; Castro, Cesar de; Zocolo, Guilherme Julião; Lannes, Lucíola Santos; Hoffmann-Campo, Clara Beatriz (2023)."Glycine max (L.) Merr. (Soybean) metabolome responses to potassium availability".Phytochemistry.205:113472.doi:10.1016/j.phytochem.2022.113472.ISSN0031-9422.PMID36270412.S2CID253027906.
- ^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.ISSN0031-9422.
- ^Leonti, Marco; Casu, Laura; Gertsch, Jürg; Bonsignore, Leonardo; Floris, Costantino; Casu, Mariano; Cottiglia, Filippo (18 March 2010)."A pterocarpan from the seeds of Bituminaria morisiana".Journal of Natural Medicines.64(3). Springer Science and Business Media LLC: 354–357.doi:10.1007/s11418-010-0408-7.ISSN1340-3443.PMID20238177.S2CID19190934.
- ^Tanaka, Hitoshi; Tanaka, Toshihiro; Etoh, Hideo (1997). "A pterocarpan from Erythrina orientalis".Phytochemistry.45(1). Elsevier BV: 205–207.doi:10.1016/s0031-9422(96)00841-2.ISSN0031-9422.
- ^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.ISSN0921-9668.
- ^PERRIN, DAWN R.; BOTTOMLEY, W. (1961). "Pisatin: an Antifungal Substance from Pisum sativum L.".Nature.191(4783). Springer Science and Business Media LLC: 76–77.doi:10.1038/191076a0.ISSN0028-0836.PMID13734533.S2CID433477.
- ^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.ISSN0031-9422.