Terpestacin

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

Terpestacin
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
  • 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).
Infobox references

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]

References
  1. 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.
  • Grigoriev PA, Schlegel B, Schmidtke M, Gräfe U (September 2002). "Alteration of membrane polarization by (−)-terpestacin, a biologically active fungal metabolite". Die Pharmazie. 57 (9): 653–4. PMID 12369460.
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