Hybrid flavan-chalcones, aromatase and lipoxygenase inhibitors, from Desmos cochinchinensis

Phytochemistry

Volumn 72, Issue 16, 2011, Pages 2062-2067

  Bajgai, Santi Prasad ^a   Prachyawarakorn, Vilailak ^b   Mahidol, Chulabhorn ^a,b,c   Ruchirawat, Somsak ^a,b,c   Kittakoop, Prasat ^a,b  

^a Research and Innovation   (Thailand)

^b CHULABHORN RESEARCH INSTITUTE   (Thailand)

^c MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Annonaceae; Antioxidant activity; Aromatase inhibitor; Cancer chemoprevention; Chalcone; Cytotoxic activity; Desmos cochinchinensis; Flavan; Lipoxygenase inhibitor

Indexed keywords

AROMATASE INHIBITOR; CHALCONE DERIVATIVE; DESMOSFLAVAN A; DESMOSFLAVAN B; FLAVONOID; LIPOXYGENASE INHIBITOR;

ANNONACEAE; ARTICLE; CHEMISTRY; HUMAN; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; TUMOR CELL LINE;

ANNONACEAE; AROMATASE INHIBITORS; CELL LINE, TUMOR; CHALCONES; FLAVONOIDS; HUMANS; LIPOXYGENASE INHIBITORS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

ANNONACEAE; DESMOS COCHINCHINENSIS;

EID: 80052960367     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.07.002     Document Type: Article

References (50)

1. S. Ahmad, D.A. Israf, N.H. Lajis, K. Shaari, H. Mohamed, A.A. Wahab, K.T. Ariffin, W.Y. Hoo, N.A. Aziz, A.A. Kadir, M.R. Sulaiman, and M.N. Somchit Cardamonin, inhibits pro-inflammatory mediators in activated RAW 264.7 cells and whole blood Eur. J. Pharmacol. 538 2006 188 194
2. T. Akashi, N. Saito, H. Hirota, and S. Ayabe Anthocyanin-producing dandelion callus as a chalcone synthase source in recombinant polyketide reductase assay Phytochemistry 46 1997 283 287 (Pubitemid 27391139)
3. M.W. Barrett, W. Klyne, P.M. Scopes, A.C. Fletcher, L.J. Porter, and E. Haslam Plant proanthocyanidins. Part 6. Chiroptical studies. Part 95. Circular dichroism of procyanidins J. Chem. Soc. Perkin Trans 1 1979 2375 2377
4. C. Bheemasankara Rao, T. Namosiva Rao, and S. Suryaprakasam Cardamonin and alpinetin from the seeds of Amomum subulatum Planta Med. 29 1976 391 392
5. J.J. Botha, D.A. Young, D. Ferreira, and D.G. Roux Synthesis of condensed tannins. Part 1. Stereoselective and stereospecific syntheses of optically pure 4-arylflavan-3-ols, and assessment of their absolute stereochemistry at C-4 by means of circular dichroism J. Chem. Soc. Perkin Trans 1 1981 1213 1219
6. P.D. Bremner, and J.J. Meyer Pinocembrin chalcone: an antibacterial compound from Helichrysum trilineatum Planta Med. 64 1998 777 (Pubitemid 29021593)
7. C.M. Cao, Y. Peng, L.J. Xu, Y.J. Wang, J.S. Yang, and P.G. Xiao Two flavonoid dimers from Sarcandra hainanensis (PEI) Swamy et Bailey Chem. Pharm. Bull. 57 2009 743 746
8. J. Carmichael, W.G. DeGraff, A.F. Gazdar, J.D. Minna, and J.B. Mitchell Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of radiosensitivity Cancer Res. 47 1987 943 946 (Pubitemid 17027906)
9. A.B. Castrellon, and S. Gluck Chemoprevention of breast cancer Expert. Rev. Anticancer Ther. 8 2008 443 452 (Pubitemid 351836291)
10. G.N. Diaz Napal, M.C. Carpinella, and S.M. Palacios Antifeedant activity of ethanolic extract from Flourensia oolepis and isolation of pinocembrin as its active principle compound Bioresour. Technol. 100 2009 3669 3673
11. A. Doyle, and J.B. Griffiths Mammalian cell culture: essential techniques 1997 John Wiley & Sons Chichester, UK
12. C. Eckermann, G. Schroder, S. Eckermann, D. Strack, J. Schmidt, B. Schneider, and J. Schroder Stilbenecarboxylate biosynthesis: a new function in the family of chalcone synthase-related proteins Phytochemistry 62 2003 271 286 (Pubitemid 36168927)
13. C. Gerhauser, K. Klimo, E. Heiss, I. Neumann, A. Gamal-Eldeen, J. Knauft, G.Y. Liu, S. Sitthimonchai, and N. Frank Mechanism-based in vitro screening of potential cancer chemopreventive agents Mutat. Res. 523-524 2003 163 172 (Pubitemid 36293243)
14. M.M. Gleason, C.J. Rojas, K.S. Learn, M.H. Perrone, and G.E. Bilder Characterization and inhibition of 15-lipoxygenase in human monocytes: comparison with soybean 15-lipoxygenase Am. J. Physiol. 268 1995 C1301 C1307
15. F. Hanawa, T. Yamada, and T. Nakashima Phytoalexins from Pinus strobus bark infected with pinewood nematode, Bursaphelenchus xylophilus Phytochemistry 57 2001 223 228 (Pubitemid 32458380)
16. H. Howell, E. Malan, J.A. Steenkamp, E.V. Brandt, and J. Brand Identification of two novel promelacacinidin dimers from Acacia nigrescens J. Nat. Prod. 65 2002 769 771 (Pubitemid 34547433)
17. Iwahashi, H., 2008. Antioxidants, skin cosmetics, foods, and beverages containing Desmos extracts for beauty care. Japan, JP 2008291001.
18. T. Jaipetch, S. Kanghae, O. Pancharoen, V.A. Patrick, V. Reutrakul, P. Tuntiwachwuttikul, and A.H. White Constituents of Boesenbergia pandurata (syn. Kaempferia pandurata): isolation, crystal structure and synthesis of (±)-boesenbergin A Aust. J. Chem 35 1982 351 361
19. L.D. Juliawaty, M. Kitajima, H. Takayama, S.A. Achmad, and N. Aimi A 6-substituted-5,6-dihydro-2-pyrone from Cryptocarya strictifolia Phytochemistry 54 2000 989 993
20. M.M. Koganov, O.V. Dueva, and B.L. Tsorin Activities of plant-derived phenols in a fibroblast cell culture model J. Nat. Prod. 62 1999 481 483 (Pubitemid 29165229)
21. N.A. Koorbanally, M. Randrianarivelojosia, D.A. Mulholland, L.Q. van Ufford, and A.J. van den Berg Chalcones from the seed of Cedrelopsis grevei (Ptaeroxylaceae) Phytochemistry 62 2003 1225 1229 (Pubitemid 36383591)
22. N. Kumar, B. Singh, P. Bhandari, A.P. Gupta, S.K. Uniyal, and V.K. Kaul Biflavonoids from Lonicera japonica Phytochemistry 66 2005 2740 2744 (Pubitemid 41727660)
23. S.X. Liao, G.Y. Han, Y.R. Zhang, Q.T. Zheng, and C.H. He Studies on the chemical constituents of the root of Desmos cochinchinensis Lour Yao Xue Xue Bao 24 1989 110 113
24. Q. Liao, D.H. Shi, W. Zheng, X.J. Xu, and Y.H. Yu Antiproliferation of cardamonin is involved in mTOR on aortic smooth muscle cells in high fructose-induced insulin resistance rats Eur. J. Pharmacol. 641 2010 179 186
25. S.N. Lopez, M.G. Sierra, S.J. Gattuso, R.L. Furlan, and S.A. Zacchino An unusual homoisoflavanone and a structurally-related dihydrochalcone from Polygonum ferrugineum (Polygonaceae) Phytochemistry 67 2006 2152 2158 (Pubitemid 44344758)
26. R. Lukacin, S. Schreiner, K. Silber, and U. Matern Starter substrate specificities of wild-type and mutant polyketide synthases from Rutaceae Phytochemistry 66 2005 277 284 (Pubitemid 40169987)
27. X.M. Ma, Y. Liu, and Y.P. Shi Phenolic derivatives with free-radical-scavenging activities from Ixeridium gracile (DC.) Shih Chem. Biodivers. 4 2007 2172 2181 (Pubitemid 47527668)
28. C. Menna, F. Olivieri, A. Catalano, and A. Procopio Inhibition of the LOX pathways, alone or in association with COX-2 pathway, appears to be a promising field for detecting new molecular target and engineering new chemopreventive strategies on cancer Curr. Pharm. Des. 16 2010 725 733
29. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63 (Pubitemid 14203433)
30. M.A. Nelson Inhibition of lipoxygenase activity: implications for the treatment and chemoprevention of prostate cancer Cancer Biol. Ther. 6 2007 237 (Pubitemid 46641628)
31. N. Qais, M.M. Rahman, M.A. Rashid, H. Koshino, K. Nagasawa, and T. Nakata Antibacterial flavonoids from Desmos chinensis Fitoterapia 67 1996 554 555 (Pubitemid 27062255)
32. L.W. Rice Hormone prevention strategies for breast, endometrial and ovarian cancers Gynecol. Oncol. 118 2010 202 207
33. N. Saarinen, S.C. Joshi, M. Ahotupa, X. Li, J. Ammala, S. Makela, and R. Santti No evidence for the in vivo activity of aromatase-inhibiting flavonoids J. Steroid. Biochem. Mol. Biol. 78 2001 231 239 (Pubitemid 32953617)
34. H. Shimura, M. Matsuura, N. Takada, and Y. Koda An antifungal compound involved in symbiotic germination of Cypripedium macranthos var. Rebunense (Orchidaceae) Phytochemistry 68 2007 1442 1447 (Pubitemid 46659735)
35. D.M. Stresser, S.D. Turner, J. McNamara, P. Stocker, V.P. Miller, C.L. Crespi, and C.J. Patten A high-throughput screen to identify inhibitors of aromatase (CYP19) Anal. Biochem. 284 2000 427 430
36. N.J. Sun, D.K. Ho, J.M. Sneddon, R.E. Stephens, and J.M. Cassady New cytotoxic cycloartane triterpenoids from Desmos cochinchinensis (Annonaceae) Nat. Prod. Lett. 1 1992 109 115
37. N.J. Sun, D.K. Ho, X.E. Hu, J.M. Sneddon, R.E. Stephens, and J.M. Cassady New cytotoxic fatty acid from Desmos cochinchinensis (Annonaceae) Nat. Prod. Lett. 7 1995 35 41
38. M. Taniguchi, A. Fujiwara, and K. Baba Three flavonoids from Daphne odora Phytochemistry 45 1997 183 188 (Pubitemid 27175485)
39. M. Taniguchi, A. Fujiwara, K. Baba, and N.H. Wang Two biflavonoids from Daphne acutiloba Phytochemistry 49 1998 863 867 (Pubitemid 28445180)
40. E.C. Torres-Santos, D.L. Moreira, M.A. Kaplan, M.N. Meirelles, and B. Rossi-Bergmann Selective effect of 2′,6′-dihydroxy-4′- methoxychalcone isolated from Piper aduncum on Leishmania amazonensis Antimicrob. Agents Chemother. 43 1999 1234 1241 (Pubitemid 29214753)
41. P. Tuchinda, V. Reutrakul, P. Claeson, U. Pongprayoon, T. Sematong, T. Santisuk, and W.C. Taylor Anti-inflammatory cyclohexenyl chalcone derivatives in Boesenbergia pandurata Phytochemistry 59 2002 169 173 (Pubitemid 34123581)
42. J.A. van Meeuwen, S. Nijmeijer, T. Mutarapat, S. Ruchirawat, P.C. de Jong, A.H. Piersma, and M. van den Berg Aromatase inhibition by synthetic lactones and flavonoids in human placental microsomes and breast fibroblasts-a comparative study Toxicol. Appl. Pharmacol. 228 2008 269 276
43. N.C. Veitch, and R.J. Grayer Chalcones, dihydrochalcones, and aurones O.M. Andersen, K.R. Markham, Flavonoids: Chemistry, Biochemistry and Applications 2006 CRC Press, Taylor & Francis Group Boca Raton 1087
44. Z.T. Wang, C.W. Lau, F.L. Chan, X. Yao, Z.Y. Chen, Z.D. He, and Y. Huang Vasorelaxant effects of cardamonin and alpinetin from Alpinia henryi K Schum. J. Cardiovasc. Pharmacol. 37 2001 596 606 (Pubitemid 32377915)
45. C.A. Williams, J.B. Harborne, M. Newman, J. Greenham, and J. Eagles Chrysin and other leaf exudate flavonoids in the genus Pelargonium Phytochemistry 46 1997 1349 1353 (Pubitemid 28000402)
46. Y.X. Wu, and X. Fang Apigenin, chrysin, and luteolin selectively inhibit chymotrypsin-like and trypsin-like proteasome catalytic activities in tumor cells Planta Med. 76 2010 128 132
47. J. Wu, S. Liao, H. Liang, and S. Mao Desmosflavone: a new flavone from Desmos cochinchinensis Lour Chin. Chem. Lett. 5 1994 211 212
48. J.H. Wu, X.H. Wang, Y.H. Yi, and K.H. Lee Anti-AIDS agents 54, a potent anti-HIV chalcone and flavonoids from genus Desmos Bioorg. Med. Chem. Lett. 13 2003 1813 1815
49. K. Zhai, L. Hu, J. Chen, C.Y. Fu, and Q. Chen Chrysin induces hyperalgesia via the GABAA receptor in mice Planta Med. 74 2008 1229 1234
50. Zhang, S., Nao, H., Huang, O., Liang, Y., Liu, Y., 2008. Traditional Chinese medicine preparation for treating fungous skin diseases and its production. China, CN 101181559.