Characterization of tyrosinase inhibitors in the twigs of Cudrania tricuspidata and their structure-activity relationship study.

The twigs of Cudrania tricuspidata were found to show strong tyrosinase inhibitory activity, and further detailed component analysis resulted in the isolation of a new flavanol glucoside, (2S,3S)-2,3-trans-dihydromorin-7-O-β-d-glucoside (1), plus twenty-seven known compounds (2-28). Their structures were elucidated on the basis of ESI-MS and NMR spectral data. Among the isolated compounds, trans-dihydromorin (8), oxyresveratrol (9), and steppogenin (12) were found to exhibit significant tyrosinase inhibition activities. Moreover, the structure-activity relationship of these isolated compounds was also discussed.

[1]  K. Park,et al.  Xanthones from Cudrania Tricuspidata displaying potent α-glucosidase inhibition , 2007 .

[2]  T. Hwang,et al.  Anthraquinones from Polygonum cuspidatum as tyrosinase inhibitors for dermal use , 2008, Phytotherapy research : PTR.

[3]  Alfred M. Mayer,et al.  Polyphenol oxidases in plants. Recent progress , 1986 .

[4]  G. Thyagarajan,et al.  New prenylated isoflavones and a prenylated dihydroflavonol from Millettia pachycarpa , 1980 .

[5]  M. Miyazawa,et al.  Inhibitory compound of tyrosinase activity from the sprout of Polygonum hydropiper L. (Benitade). , 2007, Biological & pharmaceutical bulletin.

[6]  Te-Sheng Chang,et al.  An Updated Review of Tyrosinase Inhibitors , 2009, International journal of molecular sciences.

[7]  M. Hattori,et al.  Effects on anti-lipid peroxidation of Cudrania cochinchinensis var. gerontogea. , 1994, Journal of ethnopharmacology.

[8]  Antioxidant and cytotoxic activities of xanthones from Cudrania tricuspidata. , 2005, Bioorganic & medicinal chemistry letters.

[9]  K. Park,et al.  Selective ABTS Radical-Scavenging Activity of Prenylated Flavonoids from Cudrania tricuspidata , 2006, Bioscience, biotechnology, and biochemistry.

[10]  C. Ito,et al.  A Novel Depsidone and Some New Xanthones from Garcinia species , 1997 .

[11]  S. Ross,et al.  Flavonoids from Maclura tinctoria. , 1999, Phytochemistry.

[12]  Zong-Ping Zheng,et al.  Water-soluble constituents of Cudrania tricuspidata (Carr.) Bur. , 2006 .

[13]  Paul B Taylor,et al.  A new dimeric dihydrochalcone and a new prenylated flavone from the bud covers of Artocarpus altilis: potent inhibitors of cathepsin K. , 2002, Journal of natural products.

[14]  F. Scheinmann,et al.  Studies in the xanthone series—VI: Claisen rearrangements, selective demethylations and synthesis of dihydroisojacareubin and alvaxanthone trimethyl ether☆☆☆★ , 1965 .

[15]  Dimitrios Tsimogiannis,et al.  Free radical scavenging and antioxidant activity of 5,7,3′,4′-hydroxy-substituted flavonoids , 2004 .

[16]  Mingfu Wang,et al.  Tyrosinase inhibitors from paper mulberry (Broussonetia papyrifera) , 2008 .

[17]  Qin Zhu,et al.  Tyrosinase inhibitory constituents from the roots of Morus nigra: a structure-activity relationship study. , 2010, Journal of agricultural and food chemistry.

[18]  Toshio Fukai,et al.  Antifungal agents from the roots of Cudrania cochinchinensis against Candida, Cryptococcus, and Aspergillus species. , 2003, Journal of natural products.

[19]  E. Wollenweber,et al.  Exudate flavonoids of Inula viscosa , 1991 .

[20]  C. Ito,et al.  A Novel Depsidone and Some New Xanthones from Garcinia Species. , 1998 .

[21]  H. Uyama,et al.  Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future , 2005, Cellular and Molecular Life Sciences CMLS.

[22]  P. Eklund,et al.  Antioxidant activity of knotwood extractives and phenolic compounds of selected tree species. , 2003, Journal of agricultural and food chemistry.

[23]  Byong Won Lee,et al.  Anti-atherosclerotic and anti-inflammatory activities of catecholic xanthones and flavonoids isolated from Cudrania tricuspidata. , 2006, Bioorganic & medicinal chemistry letters.

[24]  S. Sarker,et al.  Pyranoisoflavones from Rinorea welwitschii. , 2000, Fitoterapia.

[25]  T. Nomura,et al.  Structures of four new isoprenylated xanthones, cudraxanthones h,i,j, and k1,2. , 1990, Planta medica.

[26]  Qin Zhu,et al.  Phenolic tyrosinase inhibitors from the stems of Cudrania cochinchinensis. , 2011, Food & function.

[27]  T. Pan,et al.  Three New Prenylflavones from Artocarpus altilis , 1993 .

[28]  N. Nakamura,et al.  Prenylated flavonoids from Moghania philippinensis. , 2003, Phytochemistry.

[29]  D. Ferreira,et al.  Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. , 2005, Phytochemistry.

[30]  Y. Boo,et al.  Flavonoids, taxifolin and luteolin attenuate cellular melanogenesis despite increasing tyrosinase protein levels , 2008, Phytotherapy research : PTR.

[31]  Mingfu Wang,et al.  Isolation of tyrosinase inhibitors from Artocarpus heterophyllus and use of its extract as antibrowning agent. , 2008, Molecular nutrition & food research.

[32]  T. Kumazawa,et al.  Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-beta-D-glucopyranosides. , 2006, Carbohydrate research.

[33]  D. Tobin,et al.  Melanin pigmentation in mammalian skin and its hormonal regulation. , 2004, Physiological reviews.

[34]  S. McCormick,et al.  Flavonoids of Wyethia angustifolia and W. helenioides , 1986 .

[35]  F. Richard-Forget,et al.  Inhibition of endive (Cichorium endivia L.) polyphenoloxidase by a Carica papaya latex preparation , 2001 .