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{{Refimprove|date=December 2009}}
{{Chembox
{{Chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 361726608
| verifiedrevid = 361726608
| ImageFile = pinosylvin.png
| ImageFile = Pinosylvin.svg
| ImageSize = 200px
| ImageSize =
| IUPACName = 5-[(''E'')-2-Phenylethenyl]benzene-1,3-diol
| PIN = 5-[(1''E'')-2-Phenylethen-1-yl]benzene-1,3-diol
| OtherNames = (''E'')-3,5-Stilbenediol<br>''trans''-3,5-Dihydroxystilbene
| OtherNames = (''E'')-3,5-Stilbenediol<br>''trans''-3,5-Dihydroxystilbene
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 102-61-4
| CASNo = 22139-77-1
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem = 5280457
| UNII = 881R434AIB
⚫
| PubChem = 5280457
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 101506
| ChEMBL = 101506
| SMILES = C1=CC=C(C=C1)\C=C\C2=CC(=CC(=C2)O)O
| SMILES = C1=CC=C(C=C1)\C=C\C2=CC(=CC(=C2)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444110
| InChI = 1/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+
| InChIKey = YCVPRTHEGLPYPB-VOTSOKGWBH
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = YCVPRTHEGLPYPB-VOTSOKGWSA-N
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=14 | H=12 | O=2
| Formula = C<sub>14</sub>H<sub>12</sub>O<sub>2</sub>
| MolarMass = 212.244 g/mol
| Appearance = white solid
| Density =
| ExactMass = 212.08373 u
| MeltingPtC = 153 to 155
| Appearance =
| Density =
| MeltingPt_notes =
| BoilingPt =
| MeltingPt = 153–155&nbsp;°C
| BoilingPt =
| Solubility =
| Solubility =
⚫
}}
⚫
| Section3 = {{Chembox Hazards
⚫
| MainHazards =
⚫
| FlashPt =
| Autoignition =
}}
}}
⚫
|Section3={{Chembox Hazards
⚫
| MainHazards =
⚫
| FlashPt =
| AutoignitionPt =
⚫
}}
}}
}}


'''Pinosylvin''' is an [[organic compound]] with the formula C<sub>6</sub>H<sub>5</sub>CH=CHC<sub>6</sub>H<sub>3</sub>(OH)<sub>2</sub>. A white solid, it is related to [[trans-stilbene]], but with two [[hydroxy group]]s on one of the phenyl substituents. It is very soluble in many organic solvents, such as [[acetone]].<ref>{{Cite book|title=CRC Handbook of Chemistry and Physics, 95th Edition|last=M.|first=Haynes, William|date=2014|publisher=CRC Press|isbn=9781482208689|edition= 95th |location=Hoboken|pages=458|chapter=3|oclc=908078665}}</ref>
'''Pinosylvin''' is a pre-infectious [[stilbenoid]] toxin (i.e. synthesized prior to infection), contrary to [[phytoalexin]]s which are synthesized during infection. It is present in the [[heartwood]] of ''[[Pinaceae]]''.<ref>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}}</ref> It is a fungitoxin protecting the wood from fungal infection.<ref>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}}</ref> It is also found in ''[[Gnetum cleistostachyum]]''.<ref>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, {{INIST|15332136}}</ref>


==Occurrence==
⚫
Injected in rats, pinosylvin shows a rapid [[glucuronidation]] and a poor [[bioavailability]].<ref>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}}</ref>
Pinosylvin is produced in plants in response to fungal infections, [[ozone]]-induced stress, and physical damage for example.<ref name=":0">{{Cite journal|last1=Hovelstad|first1=Hanne|last2=Leirset|first2=Ingebjorg|last3=Oyaas|first3=Karin|last4=Fiksdahl|first4=Anne|date=2006-01-31|title=Screening analyses of pinosylvin stilbenes, resin acids and lignans in Norwegian conifers|journal=Molecules (Basel, Switzerland)|volume=11|issue=1|pages=103–114|issn=1420-3049|pmid=17962750|doi=10.3390/11010103|citeseerx=10.1.1.599.4403|pmc=6148674 |doi-access=free }}</ref> It is a fungitoxin protecting the wood from fungal infection.<ref>{{Cite journal|last1=Lee|first1=S. K.|last2=Lee|first2=H. J.|last3=Min|first3=H. Y.|last4=Park|first4=E. J.|last5=Lee|first5=K. M.|last6=Ahn|first6=Y. H.|last7=Cho|first7=Y. J.|last8=Pyee|first8=J. H.|date=March 2005|title=Antibacterial and antifungal activity of pinosylvin, a constituent of pine|journal=Fitoterapia|volume=76|issue=2|pages=258–260|doi=10.1016/j.fitote.2004.12.004|issn=0367-326X|pmid=15752644}}</ref> It is present in the [[heartwood]] of ''[[Pinaceae]]''<ref name=":0" /> and also found in ''[[Gnetum cleistostachyum]]''.<ref>{{Cite journal|last1=Yao|first1=Chun-Suo|last2=Lin|first2=Mao|last3=Liu|first3=Xin|last4=Wang|first4=Ying-Hong|date=April 2005|title=Stilbene derivatives from Gnetum cleistostachyum|journal=Journal of Asian Natural Products Research|volume=7|issue=2|pages=131–137|doi=10.1080/10286020310001625102|issn=1028-6020|pmid=15621615}}</ref>

⚫
Injected in rats, pinosylvin undergoes rapid [[glucuronidation]] and a poor [[bioavailability]].<ref>{{Cite journal|last1=Roupe|first1=Kathryn A.|last2=Yáñez|first2=Jaime A.|last3=Teng|first3=Xiao Wei|last4=Davies|first4=Neal M.|date=November 2006|title=Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats|journal=The Journal of Pharmacy and Pharmacology|volume=58|issue=11|pages=1443–1450|doi=10.1211/jpp.58.11.0004|issn=0022-3573|pmid=17132206|doi-access=free}}</ref>


== Biosynthesis ==
== Biosynthesis ==
[[Pinosylvin synthase]] is an enzyme that catalyzes the chemical reaction 3 [[malonyl-CoA]] + [[cinnamoyl-CoA]] → 4 [[Coenzyme A|CoA]] + pinosylvin + 4 CO<sub>2</sub>
[[Pinosylvin synthase]], an [[enzyme]], catalyzes the biosynthesis of pinosylvin from [[malonyl-CoA]] and [[cinnamoyl-CoA]]:
:3 malonyl-S-CoA + cinnamoyl-S-CoA → 4 CoA-SH + pinosylvin + 4 CO<sub>2</sub>

This biosynthesis is noteworthy because plant biosyntheses employing cinnamic acid as a starting point are rare compared to the more common use of [[p-Coumaric acid|''p''-coumaric acid]]. Two other compounds produced from [[cinnamic acid]] are anigorufone and [[curcumin]].<ref>{{Cite journal|last1=Schmitt|first1=B.|last2=Hölscher|first2=D.|last3=Schneider|first3=B.|date=February 2000|title=Variability of Phenylpropanoid PBiosynthesis of Phenylphenalenones in ''Anigozanthos preissii''|journal=Phytochemistry|volume=53|issue=3|pages=331–337|issn=0031-9422|pmid=10703053|doi=10.1016/s0031-9422(99)00544-0}}</ref><ref>{{Cite journal|last1=Kita|first1=Tomoko|last2=Imai|first2=Shinsuke|last3=Sawada|first3=Hiroshi|last4=Kumagai|first4=Hidehiko|last5=Seto|first5=Haruo|date=July 2008|title=The Biosynthetic Pathway of Curcuminoid in Turmeric (''Curcuma longa'') as Revealed by <sup>13</sup>C-Labeled Precursors|journal=Bioscience, Biotechnology, and Biochemistry|volume=72|issue=7|pages=1789–1798|doi=10.1271/bbb.80075|issn=1347-6947|pmid=18603793|doi-access=free}}</ref>


== References ==
== References ==
{{Reflist}}
{{Reflist}}


{{Stilbenes}}
<!--== See also ==
-->

{{Stilbenoids}}


[[Category:Stilbenoids]]
[[Category:Stilbenoids]]


{{Natural-phenol-stub}}

[[fa:پینوسیلوین]]

Latest revision as of 00:09, 3 December 2023

Pinosylvin
Names
Preferred IUPAC name
5-[(1E)-2-Phenylethen-1-yl]benzene-1,3-diol
Other names
(E)-3,5-Stilbenediol
trans-3,5-Dihydroxystilbene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.208.695 Edit this at Wikidata
UNII
  • 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+ ☒N
    Key: YCVPRTHEGLPYPB-VOTSOKGWSA-N ☒N
  • InChI=1/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-VOTSOKGWBH
  • C1=CC=C(C=C1)\C=C\C2=CC(=CC(=C2)O)O
Properties
C14H12O2
Molar mass 212.248 g·mol−1
Appearance white solid
Melting point 153 to 155 °C (307 to 311 °F; 426 to 428 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Pinosylvin is an organic compound with the formula C6H5CH=CHC6H3(OH)2. A white solid, it is related to trans-stilbene, but with two hydroxy groups on one of the phenyl substituents. It is very soluble in many organic solvents, such as acetone.[1]

Occurrence

[edit]

Pinosylvin is produced in plants in response to fungal infections, ozone-induced stress, and physical damage for example.[2] It is a fungitoxin protecting the wood from fungal infection.[3] It is present in the heartwood of Pinaceae[2] and also found in Gnetum cleistostachyum.[4]

Injected in rats, pinosylvin undergoes rapid glucuronidation and a poor bioavailability.[5]

Biosynthesis

[edit]

Pinosylvin synthase, an enzyme, catalyzes the biosynthesis of pinosylvin from malonyl-CoA and cinnamoyl-CoA:

3 malonyl-S-CoA + cinnamoyl-S-CoA → 4 CoA-SH + pinosylvin + 4 CO2

This biosynthesis is noteworthy because plant biosyntheses employing cinnamic acid as a starting point are rare compared to the more common use of p-coumaric acid. Two other compounds produced from cinnamic acid are anigorufone and curcumin.[6][7]

References

[edit]
  1. ^ M., Haynes, William (2014). "3". CRC Handbook of Chemistry and Physics, 95th Edition (95th ed.). Hoboken: CRC Press. p. 458. ISBN 9781482208689. OCLC 908078665.{{cite book}}: CS1 maint: multiple names: authors list (link)
  2. ^ a b Hovelstad, Hanne; Leirset, Ingebjorg; Oyaas, Karin; Fiksdahl, Anne (2006-01-31). "Screening analyses of pinosylvin stilbenes, resin acids and lignans in Norwegian conifers". Molecules (Basel, Switzerland). 11 (1): 103–114. CiteSeerX 10.1.1.599.4403. doi:10.3390/11010103. ISSN 1420-3049. PMC 6148674. PMID 17962750.
  3. ^ Lee, S. K.; Lee, H. J.; Min, H. Y.; Park, E. J.; Lee, K. M.; Ahn, Y. H.; Cho, Y. J.; Pyee, J. H. (March 2005). "Antibacterial and antifungal activity of pinosylvin, a constituent of pine". Fitoterapia. 76 (2): 258–260. doi:10.1016/j.fitote.2004.12.004. ISSN 0367-326X. PMID 15752644.
  4. ^ Yao, Chun-Suo; Lin, Mao; Liu, Xin; Wang, Ying-Hong (April 2005). "Stilbene derivatives from Gnetum cleistostachyum". Journal of Asian Natural Products Research. 7 (2): 131–137. doi:10.1080/10286020310001625102. ISSN 1028-6020. PMID 15621615.
  5. ^ Roupe, Kathryn A.; Yáñez, Jaime A.; Teng, Xiao Wei; Davies, Neal M. (November 2006). "Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats". The Journal of Pharmacy and Pharmacology. 58 (11): 1443–1450. doi:10.1211/jpp.58.11.0004. ISSN 0022-3573. PMID 17132206.
  6. ^ Schmitt, B.; Hölscher, D.; Schneider, B. (February 2000). "Variability of Phenylpropanoid PBiosynthesis of Phenylphenalenones in Anigozanthos preissii". Phytochemistry. 53 (3): 331–337. doi:10.1016/s0031-9422(99)00544-0. ISSN 0031-9422. PMID 10703053.
  7. ^ Kita, Tomoko; Imai, Shinsuke; Sawada, Hiroshi; Kumagai, Hidehiko; Seto, Haruo (July 2008). "The Biosynthetic Pathway of Curcuminoid in Turmeric (Curcuma longa) as Revealed by 13C-Labeled Precursors". Bioscience, Biotechnology, and Biochemistry. 72 (7): 1789–1798. doi:10.1271/bbb.80075. ISSN 1347-6947. PMID 18603793.
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