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Ergosterol peroxide

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Ergosterol peroxide
Ball-and-stick model of ergosterol peroxide
Names
IUPAC name (3S,5S,8S,9R,10R,13R,14R,17R)-10,13-dimethyl-17--1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopentaphenanthren-3-ol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • O2C\13OO4(/C=C/1)(3(CC2)C)CC5(C)((/C=C/(C)C(C)C)C)CC45
Properties
Chemical formula C28H44O3
Molar mass 428.647
Density 1.08g/cm
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 , 100 kPa). Infobox references
Chemical compound

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, and has been reported to exhibit immunosuppressive, anti-inflammatory, antiviral, trypanocidal and antitumor activities in vitro.

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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