Osthole (1) as a natural product, has the potent anti-osteoporosis activity. In the present paper, a scaled-up biotransformation of 1 by Mucor spinosus AS 3.3450 was carried out for improving its activities and water-solubility. Nine metabolites were obtained in the biotransformation process of 1, and their structures were elucidated as 4′-hydroxyl-osthole (2), osthenol (3), osthenol-7-O-β-D-glucoside (4), 5′-hydroxyl- osthole (5), 5′-hydroxyl-2′,3′-dihydro-osthole (6), 2′,3′-dihydroxyl-osthole (7), 2′-ketone-3′-hydroxyl- osthole (8), 2′-acetoxy-3′-hydroxy-osthole (9) and 2′-hydroxyl-isoothole (10), on the basis of extensive spectral data including NMR-2D and MS spectroscopy. Among them, metabolites 6 and 8 were new. The hydroxylation, dehydrogenation, demethylation and glycosylation reactions of 1 by M. spinosus AS 3.3450 were reported in the present study. And anti-osteoporosis activities of all products were also evaluated by using MC3T3-E1 cells.

biotransformation, Mucor spinosus, anti-osteoporosis, Cunninghamella elegans, osthole

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14
7	bDGlcp	100.8	73.3	77.1	69.6	76.7	60.6
	Subst	160.1	112.8	144.5	117.4	126.7	111.5	157.8	113.4	152.1	21.6	121.3	131.4	17.7	25.4


1H NMR data:
missing...

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(C)=CCc1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)ccc2ccc(=O)oc12

392.404 g/mol (C₂₀H₂₄O₈)