ABSTRACT
Fusarins G1/G2 (1/2) and G3/G4 (3/4), two sets of interesting examples of diastereoisomers with substantially identical NMR data, were discovered from natural products. The reason was discussed and the generally applicable determinant conditions were proposed. The minimum interval for stereoclusters to be entirely segregated was also discussed.
ABSTRACT
Three new isocoumarin derivatives, mucorisocoumarins A-C (1-3, resp.), together with seven known compounds, 4-10, were isolated from the cold-adapted fungal strain Mucor sp. (No.â XJ07027-5). The structures of the new compounds were identified by detailed IR, MS, and 1D- and 2D-NMR analyses. It was noteworthy that compounds 1, 2, 4, and 5 were successfully resolved by chiral HPLC, indicating that 1-7 should exist as enantiomers. In an embryonic developmental toxicity assay using a zebrafish model, compound 3 produced developmental abnormalities in the zebrafish embryos. This is the first report of isocoumarins with developmental toxicity to zebrafish embryos.
Subject(s)
Embryo, Nonmammalian/abnormalities , Embryo, Nonmammalian/drug effects , Isocoumarins/chemistry , Isocoumarins/toxicity , Mucor/chemistry , Zebrafish/embryology , Acclimatization , Animals , Cold Temperature , Embryo, Nonmammalian/embryology , Embryonic Development/drug effects , Isocoumarins/isolation & purification , Mucor/physiologyABSTRACT
Two new naphthaline glucosides, 2-hydroxy-3-methoxy-8-methyl-1-O-ß-d-glucopyranosylnaphthaline (1) and 1-hydroxy-3-methoxy-8-methyl-2-O-ß-d-glucopyranosylnaphthaline (2), together with one new isocoumarin glucoside, 3-(3,3-dichloro-2-hydroxylpropyl)-6-methoxy-8-O-ß-d-glucopyranosyl-1H-isochromen-1-one (3), were isolated from a cold-adapted fungal strain Mucor sp. (No. XJ07027-5). Their structures were characterized by detailed analyses of IR, MS, 1D- and 2D-NMR spectra. Among them, 2 showed moderate cytotoxic activity against five tumor cells (A-549, HL-60, MCF-7, SMMC-7721, and SW480).
