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624:, and activate the kinase. Diacylglycerol is degraded quickly by the body, allowing PKC to be reversibly activated. When phorbol esters bind to the receptor, they are not degraded as efficiently by the body, leading to constitutively active PK. PKC is involved in a number of important cell signaling pathways. Thus, phorbol ester exposure can show a wide range of results.
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from which phorbol was initially isolated. Its seeds and oil have been used for hundreds of years in traditional medicine, generally as a purgative, and the seeds were mentioned in
Chinese herbal texts 2000 years ago. The purgative effects of the oil are largely attributed to the high percentage of
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Because of their mechanism of action, phorbol esters can be used to study tumor proliferation and pain response. TPA is most commonly used in the laboratory to induce a cellular response. For example, TPA can be used to measure response to pain and test compounds that may mitigate the inflammatory
640:
pathway. Thus, exposure to phorbol products can induce an inflammatory response in tissues. Symptoms can include edema and pain, especially to the skin and mucous membranes. While phorbol itself does not have irritant activity, nearly all phorbol esters are highly irritant, with a wide range of
635:
The main results of phorbol exposure are tumor promotion and inflammatory response. Although phorbol is not a carcinogen itself, it greatly enhances the action of other substances and promotes tumor proliferation. PKC is a key component in biological pathways controlling cell growth and
636:
differentiation. When phorbol esters bind to PKC, cell proliferation pathways are activated. This effect greatly promotes tumors when the cells are exposed to even a sub-carcinogenic amount of a substance. PKC is also involved in activation of inflammation pathways such as the
1531:
Medeiros, Rodrigo; Otuki, Michel F; Avellar, Maria
Christina W; Calixto, João (March 2007). "Mechanisms underlying the inhibitory actions of the pentacyclic triterpene α-amyrin in the mouse skin inflammation induced by phorbol ester 12-O-tetradecanoylphorbol-13-acetate".
591:, as well as in water. In the manchineel, this leads to an additional exposure risk during rain, where liquid splashing from an undamaged tree may also be injurious. Contact with the tree or consumption of its fruit can lead to symptoms such as severe pain and swelling.
679:
that can be evaluated for anti-cancer activity. Previously, the difficulty with synthesizing phorbol had been creating C–C bonds, especially in the six-membered ring at the top of the molecule. This synthesis starts from
619:
Phorbol derivatives work primarily by interacting with protein kinase C (PKC), although they can interact with other phospholipid membrane receptors. The esters bind to PKC in a similar way to its natural ligand,
924:
Hecker E; Bartsch H; Bresch H; Gschwendt M; Härle B; Kreibich G; Kubinyi H; Schairer HU; v. Szczepanski C; Thielmann HW (1967). "Structure and
Stereochemistry of the Tetracyclic Diterpene Phorbol from
655:) of phorbol esters for male mice was found to be about 27 mg/kg, with the mice showing hemorrhage and congestion of pulmonary blood vessels, as well as lesions throughout the body.
479:
343:
InChI=1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18-,19-,20-/m1/s1
353:
InChI=1/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18-,19-,20-/m1/s1
1098:
Adolf, W; Hecker, E (1984). "On the active principles of the spurge family. X. Skin irritants, cocarcingoens, and cryptic carcinogens from the latex of the manchineel tree".
1477:
Wender, Paul A.; Kogen, Hiroshi; Lee, Hee Yoon; Munger, John D.; Wilhelm, Robert S.; Williams, Peter D. (1989). "Studies on tumor promoters. 8. The synthesis of phorbol".
725:
anti-cancer, antiviral, and antibacterial activities. The phorbol derivatives in croton oil are used in folk medicine, with purported purgative, counter-irritant, or
958:
Pettersen RC, Ferguson G, Crombie L, Games ML, Pointer DJ (1967). "The
Structure and Stereochemistry of Phorbol, Diterpene Parent of Co-carcinogens of Croton Oil".
709:, can also be used to stimulate T-cell activation, proliferation, and cytokine production, and is used in protocols for intracellular staining of these cytokines.
796:
Flaschenträger B, Wigner G (1942). "Über den
Giftstoff des Crotonöles. V. Die Gewinnung von Crotonharz, Dünnem Öl und Phorbol aus dem Crotonöl durch Alkoholyse".
369:
1393:
Li, Cai-Yan; Devappa, Rakshit K; Liu, Jian-Xin; Lv, Jian-Min; Makkar, HPS; Becker, K (February 2010). "Toxicity of
Jatropha curcas phorbol esters in mice".
32:
1028:
Wang, Xiao-Yang; Liu, Li-Ping; Qin, Guo-Wei; Kang, Ting-Guo (2015). "Tigliane
Diterpenoids from the Euphorbiaceae and Thymelaeaceae Families".
671:
phorbol was developed in 2015. While this synthesis will not replace natural isolation products, it will enable researchers to create phorbol
1760:
548:
856:
Kauffmann T, Eisinger A, Jasching W, Lenhardt K (1959). "Zur
Konstitution des Phorbols, I. Über die reduzierende Gruppe des Phorbols".
705:
response. TPA and other phorbol esters can also be used to induce tumor formation and to study mechanism of action. TPA, together with
1063:
Beutler, John A.; Alvarado, Ada
Belinda; McCloud, Thomas G. (1989). "Distribution of phorbol ester bioactivity in the euphorbiaceae".
555:(TPA), also called phorbol-12-myristate-13-acetate (PMA), which is used as a biomedical research tool in contexts such as models of
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Soluble in DMSO (25mg/ml), 100% ethanol (25mg/ml), acetone, ether or dimethyl formamide; almost insoluble in aqueous buffers.
826:
Kauffmann T, Neumann H, Lenhardt K (1959). "Zur
Konstitution des Phorbols, I. Über die reduzierende Gruppe des Phorbols".
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seeds in 1934. The structure of the compound was determined in 1967, and a total synthesis was described in 2015.
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Zhang, Xiao-Long; Wang, Lun; Li, Fu; Yu, Kai; Wang, Ming-Kui (2013). "Cytotoxic Phorbol Esters of Croton tiglium".
886:
Tseng SS, van Duuren BL, Solomon JJ (1977). "Synthesis of 4aα-Phorbol 9-Myristate 9a-Acetate and Related Esters".
1504:
Wender, Paul A.; Rice, Kenneth D.; Schnute, Mark E. (1997). "The First Formal Asymmetric Synthesis of Phorbol".
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Flaschenträger B; v. Wolffersdorff R (1934). "Über den Giftstoff des Crotonöles. 1. Die Säuren des Crotonöles".
42:
Help add sources such as review articles, monographs, or textbooks. Please also establish the relevance for any
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987:"Protein Kinase C as the Receptor for the Phorbol Ester Tumor Promoters: Sixth Rhoads Memorial Award Lecture"
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Blue, Lauren M; Sailing, Christopher; DeNapoles, Christopher; Fondots, Jordan; Johnson, Edward S (2011).
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131:)-4a,7b,9,9a-Tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5
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have important biological properties, the most notable of which is the capacity to act as
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Crystal structure of phorbol-13-acetate bound to the C1B domain of protein kinase C delta
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families. Phorbol is the active constituent of the highly toxic New World tropical
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Goel, Gunjan; Makkar, Harinder P.S.; Francis, George; Becker, Klaus (July 2007).
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Goel, Gunjan; Makkar, Harinder P.S.; Francis, George; Becker, Klaus (July 2007).
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Pal, Prince Kumar; Nandi, Manmath Kumar; Singh, Narendra Kumar (Jan–Mar 2014).
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Overview of the complete synthesis of (+)-phorbol starting with (+)-3-carene
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1561:"Detoxification of Croton tiglium L. seeds by Ayurvedic process of Śodhana"
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Phorbol is a natural product found in many plants, especially those of the
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cited. Unsourced or poorly sourced material may be challenged and removed.
1616:"Phorbol Esters: Structure, Biological Activity, and Toxicity in Animals"
1328:"Phorbol Esters: Structure, Biological Activity, and Toxicity in Animals"
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1674:"The Story of PKC: A Discovery Marked by Unexpected Twists and Turns"
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Kawamura, Shuhei; Chu, Hang; Felding, Jakob; Baran, Phil S. (2016).
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Except where otherwise noted, data are given for materials in their
1430:"NF-κB activation by protein kinase C isoforms and B-cell function"
1184:"Manchineel Dermatitis in North American Students in the Caribbean"
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684:, and uses a series of 19 steps to eventually create (+)-phorbol.
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Moscat, Jorge; Diaz-Meco, María T; Rennert, Paul (January 2003).
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phorbol esters contained in the oil. Phorbol was isolated from
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to form esters. The most common and potent phorbol ester is
527:. The structure of phorbol was determined in 1967. Various
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250 to 251 °C (482 to 484 °F; 523 to 524 K)
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OCC1=C((C(C)4C)()4(O)(O)2C)()2(O)(C=C(C)C3=O)()3(O)C1
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675:for use in research, especially creating phorbol
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1265:"Nineteen-step total synthesis of (+)-phorbol"
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513:. Phorbol was first isolated in 1934 as the
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1506:Journal of the American Chemical Society
1479:Journal of the American Chemical Society
1133:Strickland, Nicola H (August 12, 2000).
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641:half-maximal inhibitory concentration (
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713:Possible and purported medicinal uses
346:Key: QGVLYPPODPLXMB-UBTYZVCOSA-N
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1620:International Journal of Toxicology
1332:International Journal of Toxicology
1135:"Eating a manchineel "beach apple""
648:) values. The median lethal dose (
356:Key: QGVLYPPODPLXMB-UBTYZVCOBR
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1201:10.1111/j.1708-8305.2011.00568.x
553:-tetradecanoylphorbol-13-acetate
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460:(at 25 °C , 100 kPa).
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1672:Kikkawa, Ushio (June 2019) .
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583:. It is very soluble in most
37:secondary or tertiary sources
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1395:Food and Chemical Toxicology
501:is a natural, plant-derived
135:-cyclopropabenzoazulen-5-one
1761:Protein kinase C activators
1225:Journal of Natural Products
700:Uses in biomedical research
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1188:Journal of Travel Medicine
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1446:10.1038/sj.embor.embor704
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870:10.1002/cber.19590920803
840:10.1002/cber.19590920802
810:10.1002/hlca.19420250315
505:. It is a member of the
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1565:Ancient Science of Life
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798:Helvetica Chimica Acta
768:Helvetica Chimica Acta
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985:Blumberg PM (1988).
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581:Hippomane mancinella
95:Preferred IUPAC name
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1289:10.1038/nature17153
1281:2016Natur.532...90K
1112:10.1021/np50033a015
930:Tetrahedron Letters
900:10.1021/jo00443a002
615:Mechanism of action
602:, is the source of
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717:The phorbol ester
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1042:10.1021/cr200397n
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