Chemical components and tyrosinase inhibitors from the twigs of Artocarpus heterophyllus

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 15, 2009, Pages 6649-6655

  Zheng, Zong Ping ^a   Chen, Sibao ^b   Wang, Shiyun ^b   Wang, Xia Chang ^c   Cheng, Ka Wing ^a   Wu, Jia Jun ^a   Yang, Dajiang ^b   Wang, Mingfu ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b State Key Laboratory of Chinese Medicine and Molecular Pharmacology   (China)

^c CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Artocarpus heterophyllus; Chemical constituents; Phenolic compounds; Twigs; Tyrosinase inhibitors

Indexed keywords

FUNGAL PROTEIN; MONOPHENOL MONOOXYGENASE; PEPTIDE; PLANT EXTRACT;

AGARICALES; ARTICLE; BARK; BREADFRUIT; CHEMISTRY; DRUG ANTAGONISM; ENZYMOLOGY; PLANT ROOT;

AGARICALES; ARTOCARPUS; FUNGAL PROTEINS; MONOPHENOL MONOOXYGENASE; PEPTIDES; PLANT BARK; PLANT EXTRACTS; PLANT ROOTS;

ARTOCARPUS ALTILIS; ARTOCARPUS HETEROPHYLLUS; BASIDIOMYCOTA;

EID: 68249108904     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9014685     Document Type: Article

References (29)

1. Mayer, A. M. Polyphenol oxidases in plants: recent progress. Phytochemistry 1987, 26, 11-20.
2. Raper. H. S. The anaerobic oxidases. Physiol. Rev. 1928, 8, 245-282.
3. Kobayashi, T.; Vieira, W. D.; Potterf, B.; Sakai, C.; Imokawa. G. Modulation of melanogenic protein expression during the switch from eu- to phenomelanogenesis. J. Cell Sci. 1995, 108, 2301-2309.
4. Olivares. C.; Jimenez-Cervantes, C.; Lozano. J. A.; Solano, F.; Garcia-Borron, J. C. The 5,6-dihydroxyindole-2-carboxylic acid (DHICA) oxidase activity of human tyrosinase, Biochem J. 2001, 354, 131-139.
5. Mayer. M. A.; Harel, E. Review: polyphenoloxidases in plants. Phytochemistry 1979, 18, 193-215.
6. Rigal, D.; Cerny, M.; Richard-Forget, F.; Varoquaux, P. Polyphenoloxidase by a Carica papaya latex preparation, Int. J. Food Sci. Technol. 2001, 36, 677-684.
7. Ahvenainen, R. New approaches in improving the shelf-life of minimally processed fruits and vegetables. Trends Food Sci. Technol 1996, 7, 179-187.
8. Sapers. G. M. Browning of food: control by sulfites, antioxidants and other means. Food Technol. 1993, 47, 75-84.
9. Li, H.; Cheng, K. W.; Cho, C. H.; He, Z.; Wang, M. Oxyresveratrol as an antibrowning agent for cloudy apple juices and fresh-cut apples. J. Agric. Food Chem. 2007, 55, 2604-2610.
10. Zheng, Z. P.; Cheng, K. W.; To, J. T. K.; Li, H.; Wang, M. Isolation of tyrosinase inhibitors from Artoearpus heterophyllus and use of its extract as anti-browning agent. Mol. Nutr. Food Res. 2008, 12, 1530-1538.
11. Vanni. A.; Gastaldi, D.; Giunata. G. Kinetic investigations on the double enzymatic activity of the tyrosinase mushroom. Ann. Chim. 1990, 80, 35-60.
12. Soekamto. N. H.; Achmad. S. A.; Ghisalberti, E. L.; Hakim, E. H.; Syah, Y. M. Artoindonesianins X and Y, two isoprenylated 2-arylbenzofurans, from Artoearpus fretessi (Moraceae). Phytochemistry 2003, 64, 831-834.
13. Fukai, T.; Pei, Y. H.; Xu, C. Q.; Wu, L. J.; Chen, Y. J. Components of the root bark of Morus cathayana. 1. Structures of five new isoprenylated flavonoids, sanggenols A-E and a diprenyl-2-arylbenzofuran, mulberrofuran V. Heterocvcles 1996, 43, 425-436.
14. Kijjoa, A.; Cidade, H. M.; Pinto, M. M. M.; Gonzalez, M. J. T. G.; Anantachoke. C.; Gedris. T. E.; Heaz. W. Prenylflavonoids from Artocarpus elasticus, Phytochemistry 1996, 43, 691-694.
15. Chung, M. I. ; Lu, C. M.; Huang, P. L.; Lin, C. N. Prenylflavonoids of Artoearpus heterophyllus. Phytochemistry 1995, 40, 1279-1282.
16. Wenkert, E.; Gottlieb, H. E. Carbon-13 nuclear magnetic resonance spectroscopy of flavonoid and isoflavonoid compounds. Phytochemistry 1977 16, 1811-1816.
17. Champavier, Y.; Comte, G.; Vercauteren, J.; Allais, D. P.; Chulia, A. J. Norterpenoid and sesquiterpenoid glucosides from Juniperus phynicea and Galega officinalis. Phytochemistry 1999, 50, 12191223.
18. Nilsson, M.; Duarte, I. F.; Almeida, C.; Delgadillo, I.; Goodfelllow, B. J.; Gil, A. M.; Morris, G. A. High-resolution NMR and diffusionordered spectroscopy of port wine. J. Agric. Food Chem. 2004, 52, 3736-3743.
19. Wu, Z. J.; Ouyang, M. A.; Wang, S. B. Two new phenolic watersoluble constituents from branch bark of Davidiu involucrata. Nat. Prod. Res. 2008, 22, 483-488.
20. Lin, C. N.; Lu, C. M.; Huang. P. L. Flavonoids from Artoearpus heterophyllus. Phytochemistry 1995, 39, 1447-1451.
21. Kuo, P. C.; Chiu, C. C.; Shi, L. S.; Li, C. Y.; Wu, S. J.; Damu, A. G.; Wu, P. L.; Kuoh, C. S.; Wu, T. S. Non-alkaloidal constituents from the stem of Ficus septica. J. Chin. Chem. Soc. 2002, 49, 113-116.
22. Hano, Y.; Matsumoto, Y.; Shinohara, K.; Sun, J.; Nomura, T. Cudraflavones C and D, two new prenylflavones from the root bark of Cudraniu ricuspidala (Carr.) Bur. Heteroeycles 1990, 31, 1339-1344.
23. Basnet, P.; Kadota, S.; Terashima, S.; Shimizu, M.; Namba, T. Two new 2-arylbenzofuran derivatives from hypoglycemic activity-bearing fractions of Moras insignis. Chem. Pharm. Bull. 1993, 41, 12381243.
24. Syah, Y. M.; Hakim, E. H.; Makmur, L.; Kurdi, V. A.; Ghisaiberti, E. L.; Aimi, N.; Achmad, S. A. Prenylated 2-arylbenzofurans from two species of Artoearpus. Nat. Prod. Commum. 2006, 1, 549552.
25. Wang, Y. H.; Hou, A. J.; Chen, L.; Chen, D.; Chen, D. F.; Sun, H. D.; Zhao, Q. S.; Bastow, K. F.; Nakanish, Y.; Wang, X. H.; Lee, K. H. New isoprenylated flavones. artochamins A-E, and cytotoxic principles from Artocarpus chama. J. Nat. Prod. 2004, 67, 757-761.
26. Kajiyana, K.; Demizu, S.; Hiraga, Y.; Kinoshita, K.; Koyama, K.; Takahashi, K.; Tamura, Y.; Okada, K.; Kinoshita, T. New prenylflavones and dibenzoylmethane from Glycyrrhiza inflata. J. Nat. Prod. 1992, 55, 1197-1203.
27. Aida, M.; Shinomiya, K.; Hano, Y.; Normura, T. Artonins J, K, and L, three new isoprenylated flavones from the root bark oí Artoearpus heterophyllus Lamk. Heterocycles 1993, 36, 575-583.
28. 13C NMR of flavonolignans from Hydnocarpus wightiana. Phytochemistry 1979, 18, 506-508.
29. Nagahata, T. Artocarpin derivative or artocarpin-like compound, and hair growth/restoration composition, skin-whitening cosmetic composition, pharmaceutical as anti-cancer, antiphlogistic/analgesic, antipyretic or antiallergic agent and pharmaceutical for treatment of pigmented skin lesion each comprising the same. PCT Int. Appl. WO2008020490, 2008.