Ergosterol peroxide

Ergosterol peroxide (5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol) is a steroid derivative. It has been isolated from a variety of fungi, yeast, lichens and sponges,[1][2][3][4][5] and has been reported to exhibit immunosuppressive,[6] anti-inflammatory,[7] antiviral,[8] trypanocidal [9] and antitumor activities in vitro.[10][11]

Ergosterol peroxide
Ball-and-stick model of ergosterol peroxide
Names
IUPAC name
(3S,5S,8S,9R,10R,13R,14R,17R)-10,13-dimethyl-17-[(1R,2E,4R)-1,4,5-trimethylhex-2-en-1-yl]-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1
  • O[C@@H]2C[C@]\13OO[C@]4(/C=C/1)[C@@H]([C@]3(CC2)C)CC[C@]5(C)[C@@H]([C@@H](/C=C/[C@H](C)C(C)C)C)CC[C@@H]45
Properties
C28H44O3
Molar mass 428.647
Density 1.08g/cm3
Boiling point 499.7 °C (931.5 °F; 772.8 K) at 760mmHg
Hazards
Flash point 256 °C (493 °F; 529 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Lobo AM, Abreu PM, Prabhakar S, Godhino LS, Jones R, Rzepa HS, Williams DJ (1988). "Triterpenoids of the fungus Pisolithus tinctorius". Phytochemistry. 27 (11): 3569–74. Bibcode:1988PChem..27.3569L. doi:10.1016/0031-9422(88)80770-2.
  2. Jimenez C, Quinoa E, Rignera R, Vilalta R, Quintella JM (1989). "The dietary origin of epidioxy steroids in Actinia equina. A carbon14 incorporation experiment". Journal of Natural Products. 52 (3): 619–22. doi:10.1021/np50063a023.
  3. Kahols K, Kangas L, Hiltunen R (1989). "Ergosterol peroxide, an active compound from Inonotus radiatus". Planta Medica. 55 (4): 389–90. doi:10.1055/s-2006-962036. PMID 2813575.
  4. Tchouankeu JC, Nyasse B, Tsamo E, Sondengam B, Morin C (1992). "An ergostane derivative from the bark of Entandrophragma utile". Phytochemistry. 31 (2): 704–705. Bibcode:1992PChem..31..704T. doi:10.1016/0031-9422(92)90067-Z.
  5. Fujimoto H, Nakayama Y, Yamazaki M (1994). "Isolation and characterization of immunosuppressive components of three mushrooms, Pisolithus tinctorius, Microporus flabelliformis and Lenzites betulina". Chem. Pharm. Bull. 42 (3): 694–97. doi:10.1248/cpb.42.694. PMID 8004718.
  6. Yasukawa K, Akihisa T, Kanno H, Kaminaga T, Izumida M, Sakoh T, Tamura T, Takido M (1996). "Inhibitory effects of sterols isolated from Chlorella vulgaris on 12-O-tetradecanoylphorbol-13-acetate-induced inflammation and tumor promotion in mouse skin". Biological and Pharmaceutical Bulletin. 19 (4): 573–576. doi:10.1248/bpb.19.573. PMID 8860961.
  7. Lindequist U, Lesnau A, Teuscher E, Pilgrim H (1989). "Antiviral activity of ergosterol peroxide". Pharmazie. 44 (8): 579–80. PMID 2594833.
  8. Nakanishi T, Murata H, Inatomi Y, Inada A, Murata J, Lang FA, Yamasaki K, Nakano M, Kawahata T, Mori H, Otake T (1998). "Screening of anti-HIV-1 activity of North American plants. Anti-HIV-1 activities of plant extracts, and active components of Lethalia vulpina (L.) Hue". Journal of Natural Medicines. 52: 521–26.
  9. Ramos-Ligonio, Angel; López-Monteon, Aracely; Trigos, Ángel (2012-06-01). "Trypanocidal Activity of Ergosterol Peroxide from Pleurotus ostreatus". Phytotherapy Research. 26 (6): 938–943. doi:10.1002/ptr.3653. ISSN 1099-1573. PMID 22083593. S2CID 1858275.
  10. Bok JW, Lermer L, Chilton J, Klingeman HG, Towers NG (1999). "Antitumor sterols from the mycelia of Cordyceps sinensis". Phytochemistry. 51 (7): 891–98. Bibcode:1999PChem..51..891B. CiteSeerX 10.1.1.565.2857. doi:10.1016/S0031-9422(99)00128-4. PMID 10423860.
  11. Nam KS, Jo YS, Kim YH, Hyun JW, Kim HW (2001). "Cytotoxic activities of acetoxyscirpenediol and ergosterol peroxide from Paecilomyces tenuipes". Life Sciences. 69 (2): 229–37. doi:10.1016/s0024-3205(01)01125-0. PMID 11441913. S2CID 8970168.
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