A New Isorhamnetin Glycoside and Other Phenolic Compounds from Callianthemum taipaicum

A new flavonol glycoside together with five known phenolic compounds were isolated from the whole herb of Callianthemum taipaicum.The compounds were identified as isorhamnetin-3-O-α-L-arabinoside-7-O-β-D-glucoside (1), isorhamnetin-3-O-β-D-glucoside (2), dibutyl phthalate (3), (+)-1-hydroxylpinoresinol-4'-β-D-glucoside (4), pinoresinol-4'-O-β-D-glucoside (5) and 2-phenylethyl-β-primeveroside (6). Compound 1 was identified as a new flavonol glycoside. The compound 6 was isolated for the first time as natural product. All compounds were isolated for the first time from the Callianthemum genus. Furthermore, the 2D-NMR data of the four known compounds 2–5 are given for the first time in this paper. All the structures were identified on the basis of detailed spectral analysis. The compounds 1 and 4 exhibited certain antifungal activity.

[1]  Bing-rui Liu,et al.  Four new fluorenone alkaloids and one new dihydroazafluoranthene alkaloid from Caulophyllum robustum Maxim. , 2011, Fitoterapia.

[2]  D. Passarella,et al.  New flavonol glycosides from Aconitum burnatii Gáyer and Aconitum variegatum L. , 2010, Fitoterapia.

[3]  Shang-Tzen Chang,et al.  Effects of alkyl chain length of gallates on their antifungal property and potency as an environmentally benign preservative against wood-decay fungi. , 2009 .

[4]  Da-yuan Zhu,et al.  Flavonoid Glycosides from Ranunculus chinensis Bge. , 2007 .

[5]  Y. Kuo,et al.  Inhibitory activity against tobacco mosaic virus (TMV) replication of pinoresinol and syringaresinol lignans and their glycosides from the root of Rhus javanica var. roxburghiana. , 2007, Journal of agricultural and food chemistry.

[6]  C. O. Delang.  The role of medicinal plants in the provision of health care in Lao PDR , 2007 .

[7]  A. Robertson,et al.  Scope and mechanistic insights into the use of tetradecyl(trihexyl)phosphonium bistriflimide: a remarkably selective ionic liquid solvent for substitution reactions. , 2006, Chemistry.

[8]  Marcy J. Balunas,et al.  Drug discovery from medicinal plants. , 2005, Life sciences.

[9]  K. Sakata,et al.  Efficient Synthesis of β‐Primeverosides as Aroma Precursors by Transglycosylation of β‐Diglycosidase from Penicillium multicolor , 2005 .

[10]  D. Choi,et al.  Flavonol glycosides from the leaves of Eucommia ulmoides O. with glycation inhibitory activity. , 2004, Journal of ethnopharmacology.

[11]  A. Krumbein,et al.  Structural investigations of flavonol glycosides from sea buckthorn (Hippophaë rhamnoides) pomace by NMR spectroscopy and HPLC-ESI-MS(n). , 2004, Journal of agricultural and food chemistry.

[12]  G. Samuelsson.  Drugs of natural origin : a textbook of pharmacognosy , 1999 .

[13]  G. Cordell.  Changing strategies in natural products chemistry , 1995 .

[14]  G. Samuelsson.  Drugs Of Natural Origin , 1992 .

[15]  F. Simone,et al.  Flavonol glycosides from Eupatorium tinifolium , 1990 .

[16]  R. Oshima,et al.  Resolution of the enantiomers of aldoses by liquid chromatography of diastereoisomeric 1-(N-acetyl-α-methylbenzylamino)-1-deoxyalditol acetates , 1982 .

[17]  T. Mabry,et al.  Isorhamnetin 3-O-glucoside 7-O-arabinoside from Eschscholzia mexicana , 1973 .

[18]  W. Hui,et al.  An examination of the euphorbiaceae of Hong Kong. VI. Isolation and structure of glochidonol, a new triterpene ketol from Glochidion wrightii Benth. , 1968, Journal of the Chemical Society. Perkin transactions 1.