Pinosilvina

 
Pinosilvina
Nombre IUPAC
5-[(E)-2-Phenylethenyl]benzene-1,3-diol
General
Otros nombres (E)-3,5-Stilbenediol
trans-3,5-Dihydroxystilbene
Fórmula estructural Imagen de la estructura
Fórmula molecular C14H12O2
Identificadores
Número CAS 102-61-4[1]​
ChEBI 17323
ChEMBL 101506
ChemSpider 4444110
PubChem 5280457
UNII 881R434AIB
C1=CC=C(C=C1)\C=C\C2=CC(=CC(=C2)O)O
InChI=1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+
Key: YCVPRTHEGLPYPB-VOTSOKGWSA-N
Propiedades físicas
Masa molar 212.244 g/mol g/mol
Punto de fusión 153 °C (426 K)
Valores en el SI y en condiciones estándar
(25 ℃ y 1 atm), salvo que se indique lo contrario.
[editar datos en Wikidata]

Pinosilvina es una toxina pre-infecciosa estilbenoide (es decir, sintetizado antes de la infección), lo contrario de la fitoalexinas que se sintetizan durante la infección. Está presente en el duramen de Pinaceae.[2]​ Es una fungitoxina que protege la madera de la infección por hongos.[3]​ También se encuentra en Gnetum cleistostachyum.[4]​

Inyectado en ratas, la pinosilvina muestra una rápida glucuronidación y una pobre biodisponibilidad.[5]​

Biosíntesis

Pinosilvina sintasa es una enzima que cataliza la reacción química 3 de malonil-CoA + cinamoil-CoA → 4 CoA + pinosilvina + 4 CO2

Esta biosíntesis es notable porque en la biosíntesis de plantas se emplea ácido cinámico como punto de partida que es raro en comparación con el uso más común de ácido p-cumárico. Sólo unos pocos compuestos identificados, como anigorufona y la curcumina, utilizan ácido cinámico como su molécula de inicio.[6]​[7]​

Referencias

  1. ↑ Número CAS
  2. ↑ Screening Analyses of Pinosylvin Stilbenes, Resin Acids and Lignans in Norwegian Conifers. Hanne Hovelstad, Ingebjorg Leirset, Karin Oyaas and Anne Fiksdahl, Molecules, 2006, 11(1), pages 103-114, doi 10.3390/11010103
  3. ↑ Antibacterial and antifungal activity of pinosylvin, a constituent of pine. S.K. Lee, H.J. Lee, H.Y. Min, E.J. Park, K.M. Lee, Y.H. Ahn, Y.J. Cho and J.H. Pyee, Fitoterapia, Volume 76, Issue 2, March 2005, Pages 258–260, doi 10.1016/j.fitote.2004.12.004
  4. ↑ Stilbenes from Gnetum cleistostachyum. Yao Chun-Suo, Lin Mao, LIiu Xin and Wang Ying-Hong, Huaxue xuebao, 2003, volume 61, no 8, pages 1331-1334,
  5. ↑ Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. Kathryn A. Roupe, Jaime A. Yáñez, Xiao Wei Teng and Neal M. Davies, Journal of Pharmacy and Pharmacology, November 2006, Volume 58, Issue 11, pages 1443–1450, doi 10.1211/jpp.58.11.0004
  6. ↑ Schmitt, Bettina; Hölscher, Dirk; Schneider, Bernd (2000). «Variability of phenylpropanoid precursors in the biosynthesis of phenylphenalenones in Anigozanthos preissii». Phytochemistry 53 (3): 331-7. PMID 10703053. doi:10.1016/S0031-9422(99)00544-0. 
  7. ↑ Kita, Tomoko; Imai, Shinsuke; Sawada, Hiroshi; Kumagai, Hidehiko; Seto, Haruo (2008). «The Biosynthetic Pathway of Curcuminoid in Turmeric (Curcuma longa) as Revealed by 13C-Labeled Precursors». Bioscience, Biotechnology, and Biochemistry 72 (7): 1789. doi:10.1271/bbb.80075. 

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