Terpestacin

Last updated
Terpestacin
Terpestacin.svg
Names
Preferred IUPAC name
(3aR,5E,7S,10E,14E,16aS)-2,7-Dihydroxy-3-[(2S)-1-hydroxypropan-2-yl]-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydrocyclopenta[15]annulen-1(3aH)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C25H38O4/c1-16-7-6-8-17(2)13-14-25(5)20(11-10-18(3)21(27)12-9-16)22(19(4)15-26)23(28)24(25)29/h7,10,13,19-21,26-28H,6,8-9,11-12,14-15H2,1-5H3/b16-7+,17-13+,18-10+/t19-,20-,21+,25+/m1/s1
    Key: UTGBBPSEQPITLF-IXRUDUFRSA-N
  • InChI=1/C25H38O4/c1-16-7-6-8-17(2)13-14-25(5)20(11-10-18(3)21(27)12-9-16)22(19(4)15-26)23(28)24(25)29/h7,10,13,19-21,26-28H,6,8-9,11-12,14-15H2,1-5H3/b16-7+,17-13+,18-10+/t19-,20-,21+,25+/m1/s1
    Key: UTGBBPSEQPITLF-IXRUDUFRBX
  • C/C/1=C\CC/C(=C/C[C@]2([C@H](C/C=C(/[C@H](CC1)O)\C)C(=C(C2=O)O)[C@H](C)CO)C)/C
Properties
C25H38O4
Molar mass 402.575 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Terpestacin is a fungal metabolite first isolated from Arthrinium . [1]

In preliminary research, it has been studied for its potential anti-HIV [1] and anti-cancer potential. [2] [3]

A laboratory synthesis of terpestacin has been reported. [4]

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References

  1. 1 2 Iimura, Seiji; Oka, Masahisa; Narita, Yukio; Konishi, Masataka; Kakisawa, Hiroshi; Gao, Qi; Oki, Toshikazu (1993). "Terpestacin, a novel syncytium formation inhibitor, isolated from Arthrinium species". Tetrahedron Letters. 34 (3): 493–496. doi:10.1016/0040-4039(93)85110-I.
  2. Jung HJ, Shim JS, Lee J, Song YM, Park KC, Choi SH, Kim ND, Yoon JH, Mungai PT, Schumacker PT, Kwon HJ (April 2010). "Terpestacin inhibits tumor angiogenesis by targeting UQCRB of mitochondrial complex III and suppressing hypoxia-induced reactive oxygen species production and cellular oxygen sensing". J Biol Chem. 285 (15): 11584–95. doi: 10.1074/jbc.M109.087809 . PMC   2857036 . PMID   20145250.
  3. Park KC, Choi SH (December 2013). "Effects of endostatin and a new drug terpestacin against human neuroblastoma xenograft and cell lines". Pediatric Surgery International. 29 (12): 1327–40. doi:10.1007/s00383-013-3398-1. PMID   24072200. S2CID   13088535.
  4. Chan, Johann; Jamison, Timothy F. (September 2003). "Synthesis of (−)-Terpestacin via Catalytic, Stereoselective Fragment Coupling: Siccanol Is Terpestacin, Not 11- -Terpestacin" (PDF). Journal of the American Chemical Society. 125 (38): 11514–11515. doi:10.1021/ja0373925. PMID   13129351.