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| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 361726608
| verifiedrevid = 361726608
| ImageFile = pinosylvin.png
| ImageFile = Pinosylvin.svg
| ImageSize =
| ImageSize =
| PIN = 5-[(1''E'')-2-Phenylethen-1-yl]benzene-1,3-diol
| PIN = 5-[(1''E'')-2-Phenylethen-1-yl]benzene-1,3-diol
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|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=14 | H=12 | O=2
| C=14 | H=12 | O=2
| Appearance =
| Appearance = white solid
| Density =
| Density =
| MeltingPtC = 153 to 155
| MeltingPtC = 153 to 155
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⚫
'''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 that is synthetized in plants during fungal infections, [[ozone]] induced stress and physical damage for example.<ref name=":0">{{Cite journal|last=Hovelstad|first=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}}</ref> It is a fungitoxin protecting the wood from fungal infection.<ref>{{Cite journal|last=Lee|first=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|last=Yao|first=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>


==Occurrence==
⚫
Injected in rats, pinosylvin shows a rapid [[glucuronidation]] and a poor [[bioavailability]].<ref>{{Cite journal|last=Roupe|first=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}}</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>
⚫
Pinosylvin is solid and needle-like. It is very soluble on [[acetone]], [[benzene]] and [[chloroform]].<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>


== Biosynthesis ==
== Biosynthesis ==
[[Pinosylvin synthase]] is an enzyme that catalyzes the chemical reaction
[[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>
⚫
3 [[malonyl-CoA]] + [[cinnamoyl-CoA]] → 4 [[Coenzyme A|CoA]] + pinosylvin + 4 [[CO2|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. Only a few identified compounds, such as [[anigorufone]] and [[curcumin]], use [[cinnamic acid]] as their start molecule.<ref>{{Cite journal|last=Schmitt|first=B.|last2=Hölscher|first2=D.|last3=Schneider|first3=B.|date=February 2000|title=Variability of phenylpropanoid precursors in the biosynthesis 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|last=Kita|first=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 13C-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 ==

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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