Structure Database (LMSD)

Common Name
Pinosylvin
Systematic Name
Synonyms
LM ID
LMPK13090001
Formula
C14H12O2
Exact Mass
Calculate m/z
212.08373
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Aromatic polyketides [PK13]
Diphenyl ethers, biphenyls, dibenzyls and stilbenes [PK1309]

Biological Context

Pinosylvin is a stilbene originally isolated from pine heartwood that has diverse biological activities.1,2,3,4,5,6 It activates sirtuin 1 (SIRT1) and induces glucose uptake in isolated rat L6 skeletal muscle myotubes.2 Pinosylvin reduces radial growth in a panel of 28 plant pathogenic fungi when used at a concentration of 100 μg/ml.3 It reduces expression of matrix metalloproteinase-2 (MMP-2), MMP-9, and membrane type 1-MMP in and inhibits migration of HT-1080 cells.4 Pinosylvin (10 mg/kg, i.p.) reduces the number of tumor nodules and lung tumor weight in a CT26 mouse xenograft model of metastatic colon cancer. It decreases hind paw volume and myeloperoxidase (MPO) activity in a rat model of adjuvant-induced arthritis.5 Pinosylvin also exhibits plant antifeedant activity against L. americanus (snowshoe hares).6

This information has been provided by Cayman Chemical

References

1. Alvarez-Novoa, J.C., Erdtman, H., and Lindstedt, G. Constituents of pine heartwood. XIX. The heartwood of Pinus pinea, Pinus pinaster, Pinus halepensis, and Pinus nigra. Acta Chem. Scand. 4(3), 444-447 (1950).
2. Modi, S., Yaluri, N., Kokkola, T., et al. Plant-derived compounds strigolactone GR24 and pinosylvin activate SIRT1 and enhance glucose uptake in rat skeletal muscle cells. Sci. Rep. 7(1), 17606 (2017).
3. Seppänen, S.K., Syrjälä, L., von Weissenberg, K., et al. Antifungal activity of stilbenes in in vitro bioassays and in transgenic Populus expressing a gene encoding pinosylvin synthase. Plant Cell. Rep. 22(8), 584-593 (2004).
4. Park, E.-J., Park, H.-J., Chung, H.-J., et al. Antimetastatic activity of pinosylvin, a natural stilbenoid, is associated with the suppression of matrix metalloproteinases. J. Nutr. Biochem. 23(8), 946-952 (2012).
5. Mačičková, T., Drábiková, K., Nosál', R., et al. In vivo effect of pinosylvin and pterostilbene in the animal model of adjuvant arthritis. Neuro. Endocrinol. Lett. 31(Suppl 2), 91-95 (2013).
6. Sullivan, T.P., Crump, D.R., Wieser, H., et al. Influence of the plant antifeedant, pinosylvin, on suppression of feeding by snowshoe hares. J. Chem. Ecol. 18(7), 1151-1164 (1992).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Pinus sylvestris (#3349)
Pinopsida (#58019)
Antibacterial and antifungal activity of pinosylvin, a constituent of pine.,
Fitoterapia, 2005
Pubmed ID: 15752644

String Representations

InChiKey (Click to copy)
YCVPRTHEGLPYPB-VOTSOKGWSA-N
InChi (Click to copy)
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+
SMILES (Click to copy)
C1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1

Other Databases

Wikipedia
Pinosylvin
KEGG ID
C01745
CHEBI ID
17323
PubChem CID
5280457
Cayman ID
27612

Calculated Physicochemical Properties

Heavy Atoms 16
Rings 2
Aromatic Rings 2
Rotatable Bonds 2
Van der Waals Molecular Volume 203.34
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 3.27
Molar Refractivity 65.14

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Created at
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Updated at
5th Feb 2022
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