5-脫氫表甾醇

化合物

5-脫氫表甾醇(英語:5-Dehydroepisterol,化學式C28H44O)是油菜素類固醇等物質生物合成過程中的中間產物[1],由C-5甾醇去飽和酶催化表甾醇生成[2],再通過7-脫氫膽固醇還原酶轉化為24-亞甲基膽固醇[3]

5-脫氫表甾醇
Ball-and-stick model of 5-dehydroepisterol
IUPAC名
(3S,10R,13R)-17-[(1R)-1,5-dimethyl-4-methylenehexyl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
別名 24-Methylcholesta-5,7,24(28)-trienol, ergosta-5,7,24(28)-trien-3β-ol, campesta-7,24(28)-dien-3β-ol
識別
CAS號 23582-83-4  checkY
PubChem 10894570
ChemSpider 9069833
SMILES
 
  • O[C@@H]4C/C3=C/C=C1\[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCC(=C)/C(C)C)C)[C@@]3(C)CC4
InChI
 
  • 1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1
InChIKey ZEPNVCGPJXYABB-LOIOQLKMBD
KEGG C15780
性質
化學式 C28H44O
莫耳質量 396.648 g·mol−1 g·mol⁻¹
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

表甾醇和5-脫氫表甾醇在利什曼原蟲Leishmania)中也有發現[4][5]

參考文獻

  1. ^ Tomomi Morikawa, Masaharu Mizutani, Nozomu Aoki, Bunta Watanabe, Hirohisa Saga, Shigeki Saito, Akira Oikawa, Hideyuki Suzuki, Nozomu Sakurai, Daisuke Shibata, Akira Wadano, Kanzo Sakata, Daisaku Ohta. Cytochrome P450 CYP710A Encodes the Sterol C-22 Desaturase in Arabidopsis and Tomato. The Plant Cell. 2006-04, 18 (4): 1008–1022 [2019-10-27]. ISSN 1040-4651. PMC 1425849 . PMID 16531502. doi:10.1105/tpc.105.036012 (英語). 
  2. ^ 位於KEGG途徑資料庫的反應R07491
  3. ^ 位於KEGG途徑資料庫的反應R07492
  4. ^ Goad LJ, Holz GG, Beach DH. Sterols of ketoconazole-inhibited Leishmania mexicana mexicana promastigotes. Mol Biochem Parasitol. June 1985, 15 (3): 257–79. PMID 4033689. doi:10.1016/0166-6851(85)90089-1. 
  5. ^ Rodrigues JC, Attias M, Rodriguez C, Urbina JA, Souza W. Ultrastructural and Biochemical Alterations Induced by 22,26-Azasterol, a Δ24(25)-Sterol Methyltransferase Inhibitor, on Promastigote and Amastigote Forms of Leishmania amazonensis. Antimicrob Agents Chemother. February 2002, 46 (2): 487–99. PMC 127026 . PMID 11796362. doi:10.1128/AAC.46.2.487-499.2002.