Bioassay-directed chromatographic separation of the ethyl acetate extract of the whole plant of Psittacanthus cucullaris afforded a new phenolic xyloside, ellagic acid-4-O-β-xyloside-3,3',4'-trimethyl ether (1) together with four known compounds, ellagic acid-4-O-β-xyloside-3,3'-dimethyl ether (2), gallic acid, β-sitosterol, and β-sitosterol β-D-glucoside. The structure of the new compound was determined by spectroscopic methods. Like other β-D-xylosides, compounds 1 and 2 stimulated the formation of glycosaminoglycan chains when fed to the cultured Chinese hamster ovary cells.

Psittacanthus cucullaris, phenolic xyloside, glycoside primer

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14
4	bDXylp	100.8	72.0	75.1	68.3	65.8
3	Me	60.6
3'	Me	60.3
4'	Me	55.7
	Subst	112.6	140.9	140.1	153.3	111.0	111.5	157.3	111.70	140.2	139.9	150.6	106.5	111.4	157.2

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COc1cc2c(=O)oc3c(OC)c(O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)cc4c(=O)oc(c1OC)c2c34

476.39 g/mol (C₂₂H₂₀O₁₂)

Bioassay-directed chromatographic separation of the ethyl acetate extract of the whole plant of Psittacanthus cucullaris afforded a new phenolic xyloside, ellagic acid-4-O-β-xyloside-3,3',4'-trimethyl ether (1) together with four known compounds, ellagic acid-4-O-β-xyloside-3,3'-dimethyl ether (2), gallic acid, β-sitosterol, and β-sitosterol β-D-glucoside. The structure of the new compound was determined by spectroscopic methods. Like other β-D-xylosides, compounds 1 and 2 stimulated the formation of glycosaminoglycan chains when fed to the cultured Chinese hamster ovary cells.

Psittacanthus cucullaris, phenolic xyloside, glycoside primer

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COc1cc2c(=O)oc3c(O)c(O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)cc4c(=O)oc(c1OC)c2c34

462.363 g/mol (C₂₁H₁₈O₁₂)

Bioassay-directed chromatographic separation of the ethyl acetate extract of the whole plant of Psittacanthus cucullaris afforded a new phenolic xyloside, ellagic acid-4-O-β-xyloside-3,3',4'-trimethyl ether (1) together with four known compounds, ellagic acid-4-O-β-xyloside-3,3'-dimethyl ether (2), gallic acid, β-sitosterol, and β-sitosterol β-D-glucoside. The structure of the new compound was determined by spectroscopic methods. Like other β-D-xylosides, compounds 1 and 2 stimulated the formation of glycosaminoglycan chains when fed to the cultured Chinese hamster ovary cells.

Psittacanthus cucullaris, phenolic xyloside, glycoside primer

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC[C@H](CC[C@H](C)[C@@H]1CC[C@@H]2[C@@H]3CC=C4C[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C

576.859 g/mol (C₃₅H₆₀O₆)