Dicerandrol C

Dicerandrol C
Names
	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
Identifiers
CAS Number	361445-55-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:65766;
ChEMBL	ChEMBL507894;
ChemSpider	10213918;
PubChem CID	11093875;
CompTox Dashboard (EPA)	DTXSID401336290 ;
	InChI 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 Key: KYQPTDIMYDSMHS-ACMZUNAXSA-N;
	SMILES 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;
Properties
Chemical formula	C38H38O16
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). Infobox references

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]

References

^ "KNApSAcK Metabolite Information - C00039011". www.knapsackfamily.com.
^ 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.
^ 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.
^ 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.

[1] "KNApSAcK Metabolite Information - C00039011". www.knapsackfamily.com.

[Wagenaar2001-2] 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.

[Ganapathy2017-3] 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.

[Frank2015-4] 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.

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