Bioassay/RIA-directed HPLC purification of a MeOH extract of the seeds of Xerophyllum tenax yielded 20-hydroxyecdysone and 20-hydroxyecdysone 2-β-D-glucopyranoside. the latter being a novel natural product. The structures were elucidated primarily on the basis of 1D and 2D NMR spectroscopic evidence. The ecdysteroid agonist activity of these isolates was determined on the B-11 tumorous blood cell line of Drosophila melanogaster. ED50 values for 20-hydroxyecdysone and 20-hydroxyecdysone 2-β-D-glucopyranoside were found to be 8.0x10(-9) M and 1.3x10(-4) M, respectively. The significance of the presence of ecdysteroid conjugates in plants is discussed.

chemotaxonomy, Drosophila melanogaster, steroid, Liliaceae, seeds, Xerophyllum tenax, Melanthiaceae, ecdysteroid, bioassay

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2	bDGlcp	101.7	75.4	78.7	71.6	78.6	62.7
	Subst


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2	bDGlcp	5.02	4.05	4.32	4.25	4.00	4.36-4.54
	Subst


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2	bDGlcp	101.7/5.02	75.4/4.05	78.7/4.32	71.6/4.25	78.6/4.00	62.7/4.36-4.54
	Subst

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(C)(O)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)C4C[C@@H](O)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C[C@]4(C)C3CC[C@]12C

642.783 g/mol (C₃₃H₅₄O₁₂)