Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.035; wR factor = 0.089; data-to-parameter ratio = 10.0.In the title compound, C 24 H 25 N 5 O 4 , the stereogenic C atom bonded to three N atoms and one C atom has an S configuration and its directly bonded neighbour has an R configuration. An intramolecular N-HÁ Á ÁO hydrogen bond supports the near coplanarity of the two C 3 N 2 -five-membered rings [dihedral angle = 5.64 (10) ]. In the crystal, molecules are linked by N-HÁ Á ÁN hydrogen bonds, forming a C(8) chain propagating in [001]. The chains are connected by C-HÁ Á ÁO interactions, generating a three-dimensional network. The previous study [Nagel et al. (1974). Chem. Commun. pp. 1021-1022] did not establish the absolute structure and no atomic coordinates were published or deposited.
Related literatureFor the previous structure, see : Nagel et al. (1974). For background to oxaline and its properties, see: Steyn (1970); Koizumi et al. (2004). For puckering parameters, see : Cremer & Pople (1975).
ExperimentalCrystal data
In order to discover structurally new and bioactive compounds from marine life, we studied the secondary metabolites of the marine-derived fungi associated with a marine sponge (XS-3) from the Xisha islands. As a result, 4-O-methylcandidusin A (1), a new p-terphenyl alcohol, along with nine known analogs (2-10), were isolated and identified from the marine spongederived fungus Aspergillus candidus OUCMDZ-1051. The structures of these compounds were determined by analyzing spectroscopic data, especially 1D and 2D NMR. The new compound 1 selectively inhibited the growth of the MDA-MB-468, BT474 and A431 human cancer cell lines with the IC 50 values of 1.84, 6.05 and 0.98 μmol/L, respectively. Compound 1 also displayed a selective antimicrobial activity against Escherichia coli with an MIC value of 27.3 μmol/L. The results indicated 4-O-methylcandidusin A (1) as a potential lead in the new drug discovery for triple negative breast cancer, invasive ductal breast cancer and epidermoid cancer. The antimicrobial metabolites also evidenced a clue for chemical defense of sponges by their associated microorganisms.
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