Dicerandrol C

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Dicerandrol C
Preferred IUPAC name
(5R,5′R,6R,6′R,10aR,10′aR)-10a,10′a-Bis[(acetyloxy)methyl]-1,1′,8,8′-tetrahydroxy-6,6′-dimethyl-9,9′-dioxo-5,5′,7,7′,9,9′,10a,10′a-octahydro-6H,6′H-[2,2′-bixanthene]-5,5′-diyl diacetate
3D model (JSmol)
  • InChI=1S/C38H38O16/c1-15-11-23(43)29-33(47)27-25(53-37(29,13-49-17(3)39)35(15)51-19(5)41)9-7-21(31(27)45)22-8-10-26-28(32(22)46)34(48)30-24(44)12-16(2)36(52-20(6)42)38(30,54-26)14-50-18(4)40/h7-10,15-16,35-36,45-48H,11-14H2,1-6H3/t15-,16-,35-,36-,37+,38+/m1/s1
  • CC1CC(=O)C2=C(C3=C(C=CC(=C3O)C4=C(C5=C(C=C4)OC6(C(C(CC(=O)C6=C5O)C)OC(=O)C)COC(=O)C)O)OC2(C1OC(=O)C)COC(=O)C)O
Molar mass 750.70 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dicerandrol C is a natural product. It is a less toxic isomer of phomoxanthone A (PXA) and phomoxanthone B (PXB), all three of which are members of the class of phomoxanthone compounds. The phomoxanthones are named after the fungus Phomopsis, from which they were first isolated, and after their xanthonoid structure. Chemically, they are dimers of two tetrahydroxanthones that are covalently linked to each other. Dicerandrol C itself is a homodimer of two identical diacetylated tetrahydroxanthones. The position of the link between the two tetrahydroxanthones is the only structural difference between dicerandrol C and its isomers PXA and PXB: In PXA, the two xanthonoid monomers are symmetrically linked at C-4,4’, while in PXB, they are asymmetrically linked at C-2,4’, and in dicerandrol C, they are symmetrically linked at C-2,2’.[2][3][4]


  1. ^ "KNApSAcK Metabolite Information - C00039011". www.knapsackfamily.com.
  2. ^ Wagenaar, Melissa M; Clardy, Jon (2001). "Dicerandrols, New Antibiotic and Cytotoxic Dimers Produced by the Fungus Phomopsis longicolla Isolated from an Endangered Mint". Journal of Natural Products. 64 (8): 1006–9. doi:10.1021/np010020u. PMID 11520215.
  3. ^ Ganapathy, Dhandapani; Reiner, Johannes R; Valdomir, Guillermo; Senthilkumar, Soundararasu; Tietze, Lutz F (2017). "Enantioselective Total Synthesis and Structure Confirmation of the Natural Dimeric Tetrahydroxanthenone Dicerandrol C". Chemistry - A European Journal. 23 (10): 2299–2302. doi:10.1002/chem.201700020. PMID 28120501.
  4. ^ Frank, M; Niemann, H; Böhler, P; Stork, B; Wesselborg, S; Lin, W; Proksch, P (2015). "Phomoxanthone A--From Mangrove Forests to Anticancer Therapy". Current Medicinal Chemistry. 22 (30): 3523–32. doi:10.2174/0929867322666150716115300. PMID 26179997.