Candibrin A A furanocoumarin dimer from |
Candibrin A |
Paper |
Doi, M., Nakamori, T., Shibano, M., Taniguchi, M. Wang, N-.H. and Baba, K. (2004).
Acta Cryst. C60, o833-o835. Candibirin A, a furanocoumarin dimer isolated from Heracleum candicans WALL.
Copyright © International Union of Crystallography
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ABSTRACT: Candibirin A (I), a new furanocoumarin dimer, was isolated from Heracleum candicans WALL. 1H NMR and MS spectra indicated that (I) was a dimer of heraclenin or heraclenol, but the linkage structure and its chirality have been unknown. The dioxane linkage having (R,R)-configurations was elucidated from dimethylsulfoxide-solvated crystals. Therefore, it was supported that (I) was a dimerization product from heraclenin by reaction of epoxy group. Moreover, the dimethylformamide solution gave the different crystal form. Its folded structure was different from the extended structure of the former, but the puckering of dioxane linkage were very similar to each other. This showed that the rotation of ether bonds, which was a linker between furanocoumarin and dioxane moieties, caused the conformational flexibility of (I). |
DMSO form One of two DMSO molecules are disordered to two sites. Inset shows the disrodering state. |
DMF form The DMF molecule is sandwiched in between two furanocoumarin rings. |
DMSO form Formula C32H28O10,2(C2H6OS) Mr 728.8 System orthorhombic Space group P212121 a 10.903(2) b 13.068(2) c 24.400(4) β 90.0 V 3476.5(11) Z 4 T, K 200.0(2) Dx 1.392 F(0 0 0) 1536 Wavelength 0.7107 μ 0.218 NREF (obs) 30564 Rint 0.0255 NREF (used) 7659 θmax 27.1 Flack param. 0.04(6) for 3379 Friedels R 0.0370 wR 0.0951 (Δ/σ)max 0.003 Fraction θmax 0.999 Δρmax 0.397 Δρmin -0.191 PDB coord. kde3dmf.pdbThe absolute structure was determined from anomalous dispersion effects from the sulfur atoms of dimethylsulfoxide (DMSO). |
DMF form Formula C32H28O10,C3H7NO Mr 645.6 System monoclinic Space group P21 a 8.2000(7) b 16.213(1) c 11.671(1) β 97.244(1) V 1539.2(2) Z 2 T, K 200.0(2) Dx 1.393 F(0 0 0) 680 Wavelength 0.7107 μ 0.104 NREF (obs) 13520 Rint 0.0174 NREF (used) 3516 θ max 27.1 R 0.0419 wR 0.1144 (Δ/σ)max < 0.001 Fraction θmax 0.998 Δρmax 0.666 Δρmin -0.376 PDB coord. kde3dmso.pdb |