pterocarpan

File:Pterocarpan.png 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.[https://www.nlm.nih.gov/cgi/mesh/2003/MB_cgi?term=PTEROCARPANS Pterocarpans on the National Library of Medicine – Medical Subject Headings]

2'-hydroxyisoflavone reductase is the enzyme responsible for the conversion in Cicer arietinum{{cite journal | last1=Tiemann | first1=Karin | last2=Hinderer | first2=Walter | last3=Barz | first3=Wolfgang | title=Isolation of NADPH:isoflavone oxidoreductase, a new enzyme of Pterocarpan phytoalexin biosynthesis in cell suspension cultures of Cicer arietinum | journal=FEBS Letters | publisher=Wiley | volume=213 | issue=2 | date=1987-03-23 | issn=0014-5793 | doi=10.1016/0014-5793(87)81515-6 | pages=324–328| doi-access=free }} and glyceollin synthase for the production of glyceollins, phytoalexins in soybean.{{cite journal | author = Welle R, Grisebach H | year = 1988 | title = Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers | journal = Arch. Biochem. Biophys. | volume = 263 | pages = 191–8 | pmid = 3369863 | doi = 10.1016/0003-9861(88)90627-3 | issue = 1 }}

Known compounds

File:Medicarpin structure.svg chemical structure]]

File:Phaseolin structure.svg – a prenylated pterocarpan – chemical structure]]

File:Glyceollin III.svg – a prenylated pterocarpan – chemical structure]]

Bitucarpin A and B, isolated from the aerial parts of Mediterranean plants Bituminaria morisiana and Bituminaria bituminosa{{cite journal | last1=Pistelli | first1=Luisa | last2=Noccioli | first2=Cecilia | last3=Appendino | first3=Giovanni | last4=Bianchi | first4=Federica | last5=Sterner | first5=Olov | last6=Ballero | first6=Mauro | title=Pterocarpans from Bituminaria morisiana and Bituminaria bituminosa | journal=Phytochemistry | publisher=Elsevier BV | volume=64 | issue=2 | year=2003 | issn=0031-9422 | doi=10.1016/s0031-9422(03)00190-0 | pages=595–598| pmid=12943781 }}
Erybraedin A and B, isolated from the stems of Erythrina subumbrans{{cite journal | last1=Rukachaisirikul | first1=Thitima | last2=Innok | first2=Phongsak | last3=Aroonrerk | first3=Nuntana | last4=Boonamnuaylap | first4=Woraluk | last5=Limrangsun | first5=Saranya | last6=Boonyon | first6=Chanakan | last7=Woonjina | first7=Umpawan | last8=Suksamrarn | first8=Apichart | title=Antibacterial Pterocarpans from Erythrina subumbrans | journal=Journal of Ethnopharmacology | publisher=Elsevier BV | volume=110 | issue=1 | year=2007 | issn=0378-8741 | doi=10.1016/j.jep.2006.09.022 | pages=171–175| pmid=17055201 }} and C, isolated from the leaves of Bituminaria morisiana[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]
Erythrabyssin II, erystagallin A, erythrabissin-1, and erycristagallin isolated from the stems of Erythrina subumbrans
Glycinol, glyceollidin I and II, glyceollins (glyceollin I, II, III and IV), found in the soybean (Glycine max){{cite journal | last1=Zimmermann | first1=M. Carla | last2=Tilghman | first2=Syreeta L. | last3=Boué | first3=Stephen M. | last4=Salvo | first4=Virgilio A. | last5=Elliott | first5=Steven | last6=Williams | first6=K. Y. | last7=Skripnikova | first7=Elena V. | last8=Ashe | first8=Hasina | last9=Payton-Stewart | first9=Florastina | last10=Vanhoy-Rhodes | first10=Lyndsay | last11=Fonseca | first11=Juan Pablo | last12=Corbitt | first12=Cynthia | last13=Collins-Burow | first13=Bridgette M. | last14=Howell | first14=Melanie H. | last15=Lacey | first15=Michelle | last16=Shih | first16=Betty Y. | last17=Carter-Wientjes | first17=Carol | last18=Cleveland | first18=Thomas E. | last19=McLachlan | first19=John A. | last20=Wiese | first20=Thomas E. | last21=Beckman | first21=Barbara S. | last22=Burow | first22=Matthew E. |display-authors=5| title=Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy | journal=Journal of Pharmacology and Experimental Therapeutics | publisher=American Society for Pharmacology & Experimental Therapeutics (ASPET) | volume=332 | issue=1 | date=2009-10-01 | issn=0022-3565 | doi=10.1124/jpet.109.160382 | pages=35–45| pmid=19797619 | pmc=2802480 }}{{Cite journal |last1=Cotrim |first1=Gustavo dos Santos |last2=Silva |first2=Deivid Metzker da |last3=Graça |first3=José Perez da |last4=Oliveira Junior |first4=Adilson de |last5=Castro |first5=Cesar de |last6=Zocolo |first6=Guilherme Julião |last7=Lannes |first7=Lucíola Santos |last8=Hoffmann-Campo |first8=Clara Beatriz |title=Glycine max (L.) Merr. (Soybean) metabolome responses to potassium availability |url=https://www.sciencedirect.com/science/article/pii/S0031942222003880 |journal=Phytochemistry |year=2023 |language=en |volume=205 |pages=113472 |doi=10.1016/j.phytochem.2022.113472 |pmid=36270412 |s2cid=253027906 |issn=0031-9422|url-access=subscription }}
Glycyrrhizol A, isolated from the root of the Chinese licorice plant (Glycyrrhiza uralensis)
Maackiain, isolated from the roots of Maackia amurensis subsp. Buergeri{{cite journal | last1=Matsuura | first1=Nobuyasu | last2=Nakai | first2=Rie | last3=Iinuma | first3=Munekazu | last4=Tanaka | first4=Toshiyuki | last5=Inoue | first5=Kenichro | title=A prenylated flavanone from roots of Maackia amurensis subsp. Buergeri | journal=Phytochemistry | publisher=Elsevier BV | volume=36 | issue=1 | year=1994 | issn=0031-9422 | doi=10.1016/s0031-9422(00)97051-1 | pages=255–256}}
Medicarpin, found in Medicago truncatula
Morisianine, isolated from the seeds of Bituminaria morisiana{{cite journal | last1=Leonti | first1=Marco | last2=Casu | first2=Laura | last3=Gertsch | first3=Jürg | last4=Bonsignore | first4=Leonardo | last5=Floris | first5=Costantino | last6=Casu | first6=Mariano | last7=Cottiglia | first7=Filippo | title=A pterocarpan from the seeds of Bituminaria morisiana | journal=Journal of Natural Medicines | publisher=Springer Science and Business Media LLC | volume=64 | issue=3 | date=2010-03-18 | issn=1340-3443 | doi=10.1007/s11418-010-0408-7 | pages=354–357| pmid=20238177 | s2cid=19190934 | url=https://boris.unibe.ch/2441/ }}
Orientanol A, isolated from the wood of Erythrina orientalis{{cite journal | last1=Tanaka | first1=Hitoshi | last2=Tanaka | first2=Toshihiro | last3=Etoh | first3=Hideo | title=A pterocarpan from Erythrina orientalis | journal=Phytochemistry | publisher=Elsevier BV | volume=45 | issue=1 | year=1997 | issn=0031-9422 | doi=10.1016/s0031-9422(96)00841-2 | pages=205–207}}
Phaseolin, found in French bean seeds{{cite journal | last1=Blagrove | first1=R. J. | last2=Colman | first2=P. M. | last3=Lilley | first3=G. G. | last4=Van Donkelaar | first4=A. | last5=Suzuki | first5=E. | title=Physicochemical and structural studies of phaseolin from French bean seed | journal=Plant Foods for Human Nutrition | publisher=Springer Science and Business Media LLC | volume=33 | issue=2–3 | year=1983 | issn=0921-9668 | doi=10.1007/bf01091313 | pages=227–229}}
Pisatin, found in Pisum sativum{{cite journal | last1=PERRIN | first1=DAWN R. | last2=BOTTOMLEY | first2=W. | title=Pisatin: an Antifungal Substance from Pisum sativum L. | journal=Nature | publisher=Springer Science and Business Media LLC | volume=191 | issue=4783 | year=1961 | issn=0028-0836 | doi=10.1038/191076a0 | pages=76–77| pmid=13734533 | s2cid=433477 }}
Striatine, isolated from aerial parts of Mundulea striata{{cite journal | last1=Manjary | first1=Frédéric | last2=Petitjean | first2=Alain | last3=Conan | first3=Jean-Yves | last4=Thérèse Martin | first4=Marie | last5=Frappier | first5=François | last6=Rasoanaivo | first6=Philippe | last7=Ratsimamanga-Urverg | first7=Suzanne | title=A prenylated pterocarpan from Mundulea striata | journal=Phytochemistry | publisher=Elsevier BV | volume=33 | issue=2 | year=1993 | issn=0031-9422 | doi=10.1016/0031-9422(93)85554-5 | pages=515–517}}
Trifolirhizin, found in Sophora flavescens

References

External links

[http://metacyc.org/META/new-image?type=PATHWAY&object=PWY-2229 Superpathway of pterocarpan biosynthesis (via formononetin) on metacyc.org]
[http://ctdbase.org/detail.go?type=chem&acc=D036343 Pterocarpans on the Comparative Toxicogenomics Database]

*Pterocarpans