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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/02 08:41:58」(JST)

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Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. Phorbol was first isolated in 1934 as the hydrolysis product of croton oil, which is derived from the seeds of the purging croton, Croton tiglium.^[2]^[3]^[4]^[5]^[6] The structure of phorbol was determined in 1967.^[7]^[8] It is very soluble in most polar organic solvents, as well as in water.

Various esters of phorbol have important biological properties, the most notable of which is the capacity to act as tumor promoters through activation of protein kinase C.^[9] They mimic diacylglycerols, glycerol derivatives in which two hydroxyl groups have reacted with fatty acids to form esters. The most common phorbol ester is 12-O-tetradecanoylphorbol-13-acetate (TPA), also called phorbol-12-myristate-13-acetate (PMA), which is used as a biomedical research tool in models of carcinogenesis. TPA, together with ionomycin, can also be used to stimulate T-cell activation, proliferation, and cytokine production, and is used in protocols for intracellular staining of these cytokines.^[10]

References

^ Merck Index, 11th Edition, 7306
^ Flaschenträger B, v. Wolffersdorff R (1934). "Über den Giftstoff des Crotonöles. 1. Die Säuren des Crotonöles". Helvetica Chimica Acta 17 (1): 1444–1452. doi:10.1002/hlca.193401701179.
^ Flaschenträger B, Wigner G (1942). "Über den Giftstoff des Crotonöles. V. Die Gewinnung von Crotonharz, Dünnem Öl und Phorbol aus dem Crotonöl durch Alkoholyse". Helvetica Chimica Acta 25 (3): 569–581. doi:10.1002/hlca.19420250315.
^ Kauffmann T, Neumann H, Lenhardt K (1959). "Zur Konstitution des Phorbols, I. Über die reduzierende Gruppe des Phorbols". Chemische Berichte 92 (8): 1715–1726. doi:10.1002/cber.19590920802.
^ Kauffmann T, Eisinger A, Jasching W, Lenhardt K (1959). "Zur Konstitution des Phorbols, I. Über die reduzierende Gruppe des Phorbols". Chemische Berichte 92 (8): 1727–1738. doi:10.1002/cber.19590920803.
^ Tseng S-S, van Duuren BL, Solomon JJ (1977). "Synthesis of 4aα-Phorbol 9-Myristate 9a-Acetate and Related Esters". J. Org. Chem. 42 (33): 3645–3649. doi:10.1021/jo00443a002.
^ 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 Croton tiglium L". Tetrahedron Letters 8 (33): 3165–3170. doi:10.1016/S0040-4039(01)89890-7.
^ 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". Chem. Commun. (London) 1967 (14): 716–717. doi:10.1039/C19670000716.
^ Blumberg PM (1988). "Protein Kinase C as the Receptor for the Phorbol Ester Tumor Promoters: Sixth Rhoads Memorial Award Lecture" (pdf). Cancer Res. 48 (1): 1–8. PMID 3275491.
^ "Flow Cytometry Intracellular Staining Guide". eBioscience, Inc. Retrieved 2011-09-25.

External links

Phorbols at the US National Library of Medicine Medical Subject Headings (MeSH)

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English Journal

Erk-Creb pathway suppresses glutathione-S-transferase pi expression under basal and oxidative stress conditions in zebrafish embryos.

Hrubik J1, Glisic B1, Fa S1, Pogrmic-Majkic K1, Andric N2.
Toxicology letters.Toxicol Lett.2016 Jan 5;240(1):81-92. doi: 10.1016/j.toxlet.2015.10.013. Epub 2015 Oct 19.
Transcriptional activation of phase II enzymes including glutathione-S-transferase pi class (Gst Pi) is important for redox regulation and defense from xenobiotics. The role of extracellular signal-regulated kinase (Erk) and protein kinase B (Akt) in regulation of Gst Pi expression has been describe
PMID 26494252

Ankyrin exposure induced by activated protein kinase C plays a potential role in erythrophagocytosis.

Tang F1, Ren Y1, Wang R1, Lei X1, Deng X1, Zhao Y1, Chen D1, Wang X2.
Biochimica et biophysica acta.Biochim Biophys Acta.2016 Jan;1860(1 Pt A):120-8. doi: 10.1016/j.bbagen.2015.10.017. Epub 2015 Oct 22.
BACKGROUND: In physiological and pathological conditions activated protein kinace C (PKC) has been observed in the erythrocytes. Externalization of ankyrin followed by Arg-Gly-Asp (RGD)/integrin recognition also triggers erythrophagocytosis. In the present study, to test whether activated PKC is ass
PMID 26498044

Regulation of Extrasynaptic GABAA α4 Receptors by Ethanol-Induced Protein Kinase A, but Not Protein Kinase C Activation in Cultured Rat Cerebral Cortical Neurons.

Carlson SL1, Bohnsack JP1, Patel V1, Morrow AL2.
The Journal of pharmacology and experimental therapeutics.J Pharmacol Exp Ther.2016 Jan;356(1):148-56. doi: 10.1124/jpet.115.228056. Epub 2015 Oct 19.
Ethanol produces changes in GABAA receptor trafficking and function that contribute to ethanol dependence symptomatology. Extrasynaptic γ-aminobutyric acid A receptors (GABAA-R) mediate inhibitory tonic current and are of particular interest because they are potentiated by physiologically relevant
PMID 26483396

Japanese Journal

血管内皮前駆細胞から分泌される可溶性CD93分子

池脇信直,園田徹,土井宏太郎 [他]
九州保健福祉大学研究紀要 (16), 121-128, 2015-03
NAID 40020406612

ジャトロファの利活用のためのホルボール・エステルの毒性およびリスク管理の検討

加藤順子,武市祥司
日本リスク研究学会誌 24(4), 221-230, 2015
… This plant is known to be toxic when consumed and known to contain antinutrients/toxins such as trypsin inhibitor and phorbol esters (PE). …
NAID 130005061914

Antiarrhythmic Peptide AAP10 Prevents Arrhythmias Induced by Protein Kinase C Activation in Rabbit Left Ventricular Wedges

, ,
International Heart Journal advpub(0), 2015
… As the mechanisms underlying PKC activation induced arrhythmias are not yet fully verified, we investigated the role of gap junctions in arrhythmias induced by PKC activation.Arterially-perfused rabbit left ventricular preparations were randomly assigned to perfusion with phorbol ester (PMA) or in combination with AAP10. …
NAID 130004941347

Related Pictures

★リンクテーブル★

リンク元	「ホルボール」「フォルボール」
拡張検索	「phorbol myristate acetate」「phorbol 12-myristate 13-acetate」「tetradecanoylphorbol acetate」「phorbol myristateacetate」

「ホルボール」

Phorbol^[1]
Names
	IUPAC name 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one
Identifiers
CAS Number	17673-25-5
ChemSpider	390610
Jmol interactive 3D	Image
PubChem	442070
	InChI 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 Key: QGVLYPPODPLXMB-UBTYZVCOSA-N ; 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 Key: QGVLYPPODPLXMB-UBTYZVCOBR ;
	SMILES OCC1=C[C@]([C@@](C(C)4C)([H])[C@]4(O)[C@H](O)[C@H]2C)([H])[C@]2(O)[C@@](C=C(C)C3=O)([H])[C@@]3(O)C1 ;
Properties
Chemical formula	C20H28O6
Molar mass	364.44 g/mol
Melting point	250 to 251 °C (482 to 484 °F; 523 to 524 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references