WordNet

formed by reaction between an acid and an alcohol with elimination of water

PrepTutorEJDIC

エステル(酸とアルコールから水を分離してできる化合物の総称)

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/08/27 21:00:08」(JST)

wiki en

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. PMA, 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 4a.alpha.-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, Szczepanski Ch v, 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) (14): 716. doi:10.1039/C19670000716.
^ Blumberg PM (1988). "Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture". Cancer Res. 48 (1): 1–8. PMID 3275491.
^ "Flow Cytometry Intracellular Staining Guide". eBioscience, Inc. http://www.ebioscience.com/resources/best-protocols/flow-cytometry/flow-cytometry-intracellular-staining-quick-guide.htm. Retrieved 2011-09-25.

External links

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

Wikimedia Commons has media related to: Phorbols

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. リポ蛋白の分類、代謝、およびアテローム性動脈硬化症における役割 lipoprotein classification metabolism and role in atherosclerosis
2. 原発性免疫不全症の診断のためのフローサイトメトリー flow cytometry for the diagnosis of primary immunodeficiencies
3. HDLコレステロール：異常値の臨床的側面 hdl cholesterol clinical aspects of abnormal values
4. 神経筋接合部に作用する毒素の概要 overview of neuromuscular junction toxins
5. リポ蛋白および止血因子に対する運動の影響 effects of exercise on lipoproteins and hemostatic factors

English Journal

PKD1 is downregulated in non-small cell lung cancer and mediates the feedback inhibition of mTORC1-S6K1 axis in response to phorbol ester.

Ni Y1, Wang L1, Zhang J1, Pang Z1, Liu Q2, Du J3.
The international journal of biochemistry & cell biology.Int J Biochem Cell Biol.2015 Mar;60:34-42. doi: 10.1016/j.biocel.2014.12.018. Epub 2015 Jan 9.
Protein kinase D1 (PKD1) is increasingly implicated in multiple biological and molecular events that regulate the proliferation or invasiveness in several cancers. However, little is known about the expression and functions of PKD1 in non-small cell lung cancer (NSCLC). In the present study, 34 pair
PMID 25578563

Bryostatin-1 causes radiosensitization of BMG-1 malignant glioma cells through differential activation of protein kinase-Cδ not evident in the non-malignant AA8 fibroblasts.

Dagur RS1, Hambarde S, Chandna S.
Molecular and cellular biochemistry.Mol Cell Biochem.2015 Mar;401(1-2):49-59. doi: 10.1007/s11010-014-2291-0. Epub 2014 Dec 4.
Bryostatin-1 (bryo-1), a non-phorbol ester, is known to sensitize mammalian cells against certain chemotherapeutic drugs. We assessed its ability to modify radiation response of mammalian cells using Chinese hamster fibroblasts AA8 cells and human malignant glioma BMG-1 cells. In the malignant gliom
PMID 25472878

T lymphocytes possess the machinery for 5-HT synthesis, storage, degradation and release.

Chen Y1, Leon-Ponte M, Pingle SC, O'Connell PJ, Ahern GP.
Acta physiologica (Oxford, England).Acta Physiol (Oxf).2015 Feb 14. doi: 10.1111/apha.12470. [Epub ahead of print]
AIM: Although activated T lymphocytes express tryptophan hydroxylase 1 and produce 5-HT, the metabolic fate and cellular handling of this 5-HT is unclear. Here we investigated key proteins in T cells linked to 5-HT metabolism and storage, and compare differences in 5-HT synthesis and metabolism betw
PMID 25683571

Japanese Journal

ジャトロファ(Jatropha curcas L.)油粕の化学組成,in vitro乾物消化率,発生ガス総量およびメタン発生量

田川伸一,呂仁龍,堀口健一,吉田宣夫,高橋敏能,市原昭一,菱沼真一
日本草地学会誌 59(2), 120-123, 2013-07-15
… Since it could not be studied in this research, it is important to consider means of reducing phorbol ester content in future. …
NAID 110009624851

Artificial Analogs of Naturally Occurring Tumor Promoters as Biochemical Tools and Therapeutic Leads

NAKAGAWA Yu
Bioscience, biotechnology, and biochemistry 76(7), 1262-1274, 2012-07-23
… Phorbol esters, teleocidins, and aplysiatoxins are typical examples of naturally occurring tumor promoters. … This review focuses on artificial analogs of phorbol esters, teleocidins, and aplysiatoxins, and discusses their potential as biochemical tools and therapeutic leads. …
NAID 10030981582

Characterization of the casbene synthase homolog from Jatropha (Jatropha curcas L.)

Nakano Yoshimi,Ohtani Misato,Polsri Wipada [他],USAMI Toru,SAMBONGI Kazuo,DEMURA Taku
Plant biotechnology 29(2), 185-189, 2012-06-25
… Since phorbol esters (PEs) are the major contributor to toxicity, a better understanding of PE biosynthesis is expected to elucidate an effective strategy for the utilization of Jatropha plants. … CS has been hypothesized to catalyze the first step of phorbol biosynthesis. …
NAID 10030804406

Related Pictures

★リンクテーブル★

「phorbol」

Phorbol
	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
Jmol-3D images	Image 1
	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
Molecular formula	C20H28O6
Molar mass	364.44 g/mol
Melting point	250–251 °C
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

ホルボール、フォルボール

[0] Merck Index, 11th Edition, 7306

[Flaschentr.C3.A4ger_1934-1] 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.

[Flaschentr.C3.A4ger_1942-2] 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_1959a-3] 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_1959B-4] 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_1977-5] Tseng S-S, Van Duuren BL, Solomon JJ (1977). "Synthesis of 4a.alpha.-phorbol 9-myristate 9a-acetate and related esters". J. Org. Chem. 42 (33): 3645–3649. doi:10.1021/jo00443a002.

[Hecker_1967-6] Hecker E, Bartsch H, Bresch H, Gschwendt M, Härle B, Kreibich G, Kubinyi H, Schairer HU, Szczepanski Ch v, 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_1967-7] 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) (14): 716. doi:10.1039/C19670000716.

[pmid3275491-8] Blumberg PM (1988). "Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture". Cancer Res. 48 (1): 1–8. PMID 3275491.

[urlFlow_Cytometry_Intracellular_Staining_Guide-9] "Flow Cytometry Intracellular Staining Guide". eBioscience, Inc. http://www.ebioscience.com/resources/best-protocols/flow-cytometry/flow-cytometry-intracellular-staining-quick-guide.htm. Retrieved 2011-09-25.

匿名

検索

案内

案内

phorbol ester