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Group of chemical compounds
Chemical structure of 12-O-tetradecanoylphorbol-13-acetate , a phorbol ester
Phorbol esters are a class of chemical compounds found in a variety of plants, particularly in the families Euphorbiaceae and Thymelaeaceae .[ 1] [ 2] Chemically, they are ester derivatives of the tetracyclic diterpenoid phorbol .
Biological activity
Protein kinase C (PKC) is a phorbol ester receptor.[ 2] [ 3] Phorbol esters can stimulate PKC in a similar way to diglycerides .[ 2] [ 3]
Phorbol esters are known for their ability to promote tumors .[ 2] In particular, 12-O-tetradecanoylphorbol-13-acetate (TPA) is used as a biomedical research tool in models of carcinogenesis .[ 4] [ 5]
Plants that contain phorbol esters are often poisonous .[ 5]
References
^ Goel, G; Makkar, H. P.; Francis, G; Becker, K (2007). "Phorbol esters: Structure, biological activity, and toxicity in animals". International Journal of Toxicology . 26 (4): 279–88. CiteSeerX 10.1.1.320.6537 . doi :10.1080/10915810701464641 . PMID 17661218 . S2CID 11550625 .
^ a b c d Evans, Gerald A.; Farrar, William L. (1998-01-01), "Phorbol Esters" , in Delves, Peter J. (ed.), Encyclopedia of Immunology (Second Edition) , Oxford: Elsevier, pp. 1940–1942, doi :10.1006/rwei.1999.0488 , ISBN 978-0-12-226765-9 , retrieved 2020-11-26
^ a b Weimer, R.; Richmond, J. (2015-01-01), "Munc13 and Associated Molecules☆" , Reference Module in Biomedical Sciences , Elsevier, doi :10.1016/b978-0-12-801238-3.04674-2 , ISBN 978-0-12-801238-3 , retrieved 2020-11-26
^ Emerit, Ingrid; Cerutti, Peter A. (1981). "Tumour promoter phorbol-12-myristate-13-acetate induces chromosomal damage via indirect action". Nature . 293 (5828): 144–6. Bibcode :1981Natur.293..144E . doi :10.1038/293144a0 . PMID 7266668 . S2CID 45253610 .
^ a b Abdel-Fatta Rizk (1990). Poisonous Plant Contamination of Edible Plants . CRC Press. pp. 43–44. ISBN 9780849363696 .
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14 -prostaglandin J2
α-Sanshool (ginger , Sichuan and melegueta peppers )
Acrolein
Allicin (garlic )
Allyl isothiocyanate (mustard , radish , horseradish , wasabi )
AM404
ASP-7663
Bradykinin
Cannabichromene (cannabis )
Cannabidiol (cannabis )
Cannabigerol (cannabis )
Cinnamaldehyde (cinnamon )
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (cumin )
Curcumin (turmeric )
Dehydroligustilide (celery )
Diallyl disulfide
Dicentrine (Lindera spp.)
Farnesyl thiosalicylic acid
Formalin
Gingerols (ginger )
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
Ligustilide (celery , Angelica acutiloba )
Linalool (Sichuan pepper , thyme )
Methylglyoxal
Methyl salicylate (wintergreen )
N-Methylmaleimide
Nicotine (tobacco )
Oleocanthal (olive oil )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (Dorrigo pepper )
Shogaols (ginger , Sichuan and melegueta peppers )
Tear gases
Tetrahydrocannabinol (cannabis )
Tetrahydrocannabiorcol
Thiopropanal S-oxide (onion )
Umbellulone (Umbellularia californica )
WIN 55,212-2
Blockers
TRPC
TRPM
TRPML
TRPP
TRPV
Activators
2-APB
5',6'-EET
9-HODE
9-oxoODE
12S-HETE
12S-HpETE
13-HODE
13-oxoODE
20-HETE
α-Sanshool (ginger , Sichuan and melegueta peppers )
Allicin (garlic )
AM404
Anandamide
Bisandrographolide (Andrographis paniculata )
Camphor (camphor laurel , rosemary , camphorweed , African blue basil , camphor basil )
Cannabidiol (cannabis )
Cannabidivarin (cannabis )
Capsaicin (chili pepper )
Carvacrol (oregano , thyme , pepperwort , wild bergamot , others)
DHEA
Diacyl glycerol
Dihydrocapsaicin (chili pepper )
Estradiol
Eugenol (basil , clove )
Evodiamine (Euodia ruticarpa )
Gingerols (ginger )
GSK1016790A
Heat
Hepoxilin A3
Hepoxilin B3
Homocapsaicin (chili pepper )
Homodihydrocapsaicin (chili pepper )
Incensole (incense )
Lysophosphatidic acid
Low pH (acidic conditions)
Menthol (mint )
N-Arachidonoyl dopamine
N-Oleoyldopamine
N-Oleoylethanolamide
Nonivamide (PAVA) (PAVA spray )
Nordihydrocapsaicin (chili pepper )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
Phenylacetylrinvanil
Phorbol esters (e.g., 4α-PDD )
Piperine (black pepper , long pepper )
Polygodial (Dorrigo pepper )
Probenecid
Protons
RhTx
Rutamarin (Ruta graveolens )
Resiniferatoxin (RTX) (Euphorbia resinifera /pooissonii )
Shogaols (ginger , Sichuan and melegueta peppers )
Tetrahydrocannabivarin (cannabis )
Thymol (thyme , oregano )
Tinyatoxin (Euphorbia resinifera /pooissonii )
Tramadol
Vanillin (vanilla )
Zucapsaicin
Blockers