Pterocarpan

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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. Pterocarpan.png
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.

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]

Contents

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]

Known compounds

Medicarpin chemical structure Medicarpin structure.svg
Medicarpin chemical structure
Phaseolin - a prenylated pterocarpan - chemical structure Phaseolin structure.svg
Phaseolin – a prenylated pterocarpan – chemical structure
Glyceollin III - a prenylated pterocarpan - chemical structure Glyceollin III.svg
Glyceollin III – a prenylated pterocarpan – chemical structure

References

  1. ↑ Pterocarpans on the National Library of Medicine – Medical Subject Headings
  2. ↑ 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 . ISSN   0014-5793.
  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. doi:10.1016/0003-9861(88)90627-3. PMID   3369863.
  4. ↑ 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.
  5. 1 2 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.
  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. ↑ 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. ISSN   0022-3565. PMC   2802480 . PMID   19797619.
  8. ↑ 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. ISSN   0031-9422. PMID   36270412. S2CID   253027906.
  9. ↑ 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.
  10. ↑ 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. ISSN   1340-3443. PMID   20238177. S2CID   19190934.
  11. ↑ 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. ISSN   0031-9422.
  12. ↑ 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.
  13. ↑ 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. ISSN   0028-0836. PMID   13734533. S2CID   433477.
  14. ↑ 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.
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