ハイパフォリン
| Hyperforin | |
|---|---|
 | |
 | |
| (1R,5S,7R,8S) -4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl) -8-(4-methylpent-3-enyl) -1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione | |
| Identification information | |
| CAS registration number | 11,079-53-1 |
| It is an address number on a day | J15.315J |
| |
| Characteristic | |
| Chemical formula | C35H52O4 |
| Molar mass | 536.78 g/mol |
| I can put a case, the data without the special mention for normal temperature (25 degrees Celsius), the ordinary pressure (100 kPa). | |
ヒペルホリン (hyperforin) or ハイパフォリン is one of the chief ingredients included in the extract of セイヨウオトギリ (Saint Jones Wirt) with a kind of prenylated phloroglucinol.
Table of contents
Pharmacologic action
It is thought that ハイパフォリン is a main active ingredient of the antidepressant action of the extract of セイヨウオトギリ [1]. ハイパフォリン is shown to obstruct the uptake of neurotransmitters such as serotonin, dopamine, noradrenaline, gamma-aminobutyric acid (GABA), the glutaminic acid [2]. ハイパフォリン is specialized as an activator of ion channel TRPC6 controlling nerve axonal germination. Because the uptake of sodium in nerve cells and the calcium ion is caused by activation of TRPC6, the neurotransmitter uptake inhibition action of ハイパフォリン is explained [3]. It is thought that ハイパフォリン has the action to derive enzyme cytochrome P450 (CYP3A4 and CYP2C9) by binding to the pregnane X receptor (PXR) [4].
History
Was elucidated by the study group of the シェムヤキン creature organic chemistry research institute (former Soviet Union science academy of Moscow), and the structure of ハイパフォリン was announced in 1975 [5]; [6]. In 2010, the total synthesis of the enantiomer of ハイパフォリン is reported by Masakatsu Shibazaki and others [7].
Footnote
- ^ Newall, Carol A.; Joanne Barnes; Anderson, Linda R. (2002). Herbal medicines: a guide for healthcare professionals. London: Pharmaceutical Press. ISBN 0-85369-474-5.
- ^ Chatterjee SS, Bhattacharya SK, Wonnemann M, Singer A, Müller WE (1998). "Hyperforin as a possible antidepressant component of hypericum extracts." Life Sci. 63 (6): 499–510. doi: 10.1016/S0024-3205(98) 00299-9. PMID 9718074.
- ^ Leuner K, Kazanski V, Müller M, et al (December 2007). "Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels." The FASEB journal: official publication of the Federation of American Societies for Experimental Biology 21 (14): 4101–11. doi: 10.1096/fj.07-8110com. PMID 17666455.
- ^ Moore LB, Goodwin B, Jones SA, et al (June 2000). "St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor". Proceedings of the National Academy of Sciences of the United States of America 97 (13): 7500–2. doi: 10.1073/pnas.130155097. PMC 16574. It is . PMID 10852961
- ^ Bystrov NS, Gupta ShR, Dobrynin VN, Kolosov MN, Chernov BK (January 1976). "Structure of the antibiotic hyperforin" (Russian). Doklady Akademii nauk SSSR 226 (1): 88–90. PMID 1248360.
- ^ Bystrov NS, Chernov BK, Dobrynin VN, Kolosov MN (1975). "The structure of hyperforin." Tetrahedron Letters 16 (32): 2791-2794. doi: 10.1016/S0040-4039(00) 75,241-5.
- ^ Shimizu Y, Shi SL, Usuda H, Kanai M, Shibasaki M (2010). "Catalytic asymmetric total synthesis of ent-hyperforin." Angew. Chem. Int. Ed. Engl. 49 (6): 1103-1106. doi: 10.1002/anie.200906678. PMID 20063336.
Allied item
This article is taken from the Japanese Wikipedia ハイパフォリン
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