Pterocarpan

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Class of chemical compounds

title: "Pterocarpan" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["pterocarpans"] description: "Class of chemical compounds" topic_path: "general/pterocarpans" source: "https://en.wikipedia.org/wiki/Pterocarpan" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Class of chemical compounds ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/b/b5/Pterocarpan.png" caption="2''H''-chromene]] moiety (dotted green circle). The systematic name for it is 6''H''-[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.

2'-hydroxyisoflavone reductase is the enzyme responsible for the conversion in Cicer arietinum and glyceollin synthase for the production of glyceollins, phytoalexins in soybean.

Known compounds

::figure[src="https://upload.wikimedia.org/wikipedia/commons/d/d6/Medicarpin_structure.svg" caption="[[Medicarpin]] chemical structure"] ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/4/4f/Phaseolin_structure.svg" caption="Phaseolin]] – a prenylated pterocarpan – chemical structure"] ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/c/c4/Glyceollin_III.svg" caption="[[Glyceollin III]] – a prenylated pterocarpan – chemical structure"] ::

References

References

  1. [https://meshb.nlm.nih.gov/#/record/ui?name=PTEROCARPANS Pterocarpans on the National Library of Medicine – Medical Subject Headings]
  2. (1987-03-23). "Isolation of NADPH:isoflavone oxidoreductase, a new enzyme of Pterocarpan phytoalexin biosynthesis in cell suspension cultures of Cicer arietinum". Wiley.
  3. Welle R, Grisebach H. (1988). "Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers". Arch. Biochem. Biophys..
  4. (2003). "Pterocarpans from Bituminaria morisiana and Bituminaria bituminosa". Elsevier BV.
  5. (2007). "Antibacterial Pterocarpans from Erythrina subumbrans". Elsevier BV.
  6. [http://epub.uni-regensburg.de/17223/ 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. (2009-10-01). "Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy". American Society for Pharmacology & Experimental Therapeutics (ASPET).
  8. (2023). "Glycine max (L.) Merr. (Soybean) metabolome responses to potassium availability". Phytochemistry.
  9. (1994). "A prenylated flavanone from roots of Maackia amurensis subsp. Buergeri". Elsevier BV.
  10. (2010-03-18). "A pterocarpan from the seeds of Bituminaria morisiana". Springer Science and Business Media LLC.
  11. (1997). "A pterocarpan from Erythrina orientalis". Elsevier BV.
  12. (1983). "Physicochemical and structural studies of phaseolin from French bean seed". Springer Science and Business Media LLC.
  13. (1961). "Pisatin: an Antifungal Substance from Pisum sativum L.". Springer Science and Business Media LLC.
  14. (1993). "A prenylated pterocarpan from Mundulea striata". Elsevier BV.

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pterocarpans