Andrastin A

Andrastin A
Names
IUPAC name
(3S,5R,8S,9R,10S,13R,14R)-methyl 3-acetoxy-10-formyl-4,4,8,12,13,16-hexamethyl-15,17-dioxo-2,3,4,5,6,7,8,9,10,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-14-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C28H38O7/c1-15-13-19-25(6,28(23(33)34-8)22(32)16(2)21(31)26(15,28)7)11-9-18-24(4,5)20(35-17(3)30)10-12-27(18,19)14-29/h13-14,16,18-20H,9-12H2,1-8H3/t16?,18-,19-,20+,25+,26+,27+,28-/m1/s1
    Key: GRBXNADBNJGZRK-GJEDHNSHSA-N
  • CC1C([C@]2(C)C(C)=C[C@]3([H])[C@@](CC[C@@]4([H])[C@@]3(C=O)CC[C@H](OC(C)=O)C4(C)C)(C)[C@]2(C(OC)=O)C1=O)=O
Properties
C28H38O7
Molar mass 486.605 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Andrastin A is a farnesyltransferase inhibitor isolate of Penicillium species including Penicillium albocoremium[1] and Penicillium roqueforti.[2] It has been produced bio-synthetically by porting the relevant gene sequence into Aspergillus oryzae.[3]

  1. ^ Overy DP, Larsen TO, Dalsgaard PW, Frydenvang K, Phipps R, Munro MH, Christophersen C (2005). "Andrastin A and barceloneic acid metabolites, protein farnesyl transferase inhibitors from Penicillium albocoremium: chemotaxonomic significance and pathological implications". Mycol Res. 109 (Pt 11): 1243–1249. doi:10.1017/S0953756205003734. PMID 16279417.
  2. ^ Nielsen KF, Dalsgaard PW, Smedsgaard J, Larsen TO (April 2005). "Andrastins A-D, Penicillium roqueforti Metabolites consistently produced in blue-mold-ripened cheese". J. Agric. Food Chem. 53 (8): 2908–13. doi:10.1021/jf047983u. PMID 15826038.
  3. ^ Matsuda, Yudai; Awakawa, Takayoshi; Abe, Ikuro (September 2013). "Reconstituted biosynthesis of fungal meroterpenoid andrastin A". Tetrahedron. 69 (38): 8199–8204. doi:10.1016/j.tet.2013.07.029.