Torreyanic acid

Torreyanic acid
Clinical data
ATC code
  • none
Identifiers
  • (2E,2'E)-4,4'-[(1aR,5R,5aS,7aS,8aR,10aS,11aS)-2,7,9,11-tetraoxo-5,13-dipentyl-1a,2,5a,6,7,8a,9,10-octahydro-10,6-(epoxymethano)bis[1]benzoxireno[3,4-d:3',4'-g]isochromene-7a,11a(5H,11H)-diyl]bis(2-met hylbut-2-enoic acid)
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC38H44O12
Molar mass692.758 g·mol−1
3D model (JSmol)
  • CCCCC[C@@H]1[C@H]2C3C(OC([C@@]24C(=CO1)C(=O)[C@H]5[C@@](C4=O)(O5)C/C=C(\C)/C(=O)O)C6=C3C(=O)[C@@]7([C@H](C6=O)O7)C/C=C(\C)/C(=O)O)CCCCC
  • InChI=1S/C38H44O12/c1-5-7-9-11-21-23-24-25(28(40)32-36(49-32,29(24)41)15-13-18(3)33(42)43)30(48-21)38-20(17-47-22(26(23)38)12-10-8-6-2)27(39)31-37(50-31,35(38)46)16-14-19(4)34(44)45/h13-14,17,21-23,26,30-32H,5-12,15-16H2,1-4H3,(H,42,43)(H,44,45)/b18-13+,19-14+/t21?,22-,23?,26+,30?,31+,32+,36-,37+,38-/m1/s1 ☒N
  • Key:DQBVXDMPCDAQGS-YOWCJFHESA-N ☒N
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Torreyanic acid is a dimeric quinone first isolated and by Lee et al. in 1996 from an endophyte, Pestalotiopsis microspora. This endophyte is likely the cause of the decline of Florida torreya (Torreya taxifolia), an endangered species that is related to the taxol-producing Taxus brevifolia.[1] The natural product was found to be cytotoxic against 25 different human cancer cell lines with an average IC50 value of 9.4 μg/mL, ranging from 3.5 (NEC) to 45 (A549) μg/mL.[1][2] Torreyanic acid was found to be 5-10 times more potent in cell lines sensitive to protein kinase C (PKC) agonists, 12-o-tetradecanoyl phorbol-13-acetate (TPA), and was shown to cause cell death via apoptosis.[3] Torreyanic acid also promoted G1 arrest of G0 synchronized cells at 1-5 μg/mL levels, depending on the cell line.[1] It has been proposed that the eukaryotic translation initiation factor EIF-4a is a potential biochemical target for the natural compound.[3]

  1. ^ a b c Lee JC, Strobel GA, Lobkovsky E, Clardy J (1996). "Torreyanic Acid: A Selectively Cytotoxic Quinone Dimer from the Endophytic Fungus Pestalotiopsis microspora". The Journal of Organic Chemistry. 61 (10): 3232–3233. doi:10.1021/jo960471x.
  2. ^ Mehta G, Pan SC (October 2004). "Total synthesis of the novel, biologically active epoxyquinone dimer (+/-)-torreyanic acid: a biomimetic approach". Organic Letters. 6 (22): 3985–8. doi:10.1021/ol0483551. PMID 15496080.
  3. ^ a b Li C, Johnson RP, Porco JA (April 2003). "Total synthesis of the quinone epoxide dimer (+)-torreyanic acid: application of a biomimetic oxidation/electrocyclization/Diels-Alder dimerization cascade". Journal of the American Chemical Society. 125 (17): 5095–106. doi:10.1021/ja021396c. PMID 12708860.