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An Improved Synthesis of Apigenin and Luteolin
Corresponding Author(s) : B. Hari Babu
Asian Journal of Chemistry,
Vol. 28 No. 5 (2016): Vol 28 Issue 5
Abstract
Apigenin and luteolin are the antioxidant flavonoids found in foods such as parsley, artichoke, basil and celery. Both of these compounds have shown the ability to protect cells against cancer and also to inhibit DNA oxidative damage. These flavonoids are part of many nutraceutical formulations available in the market. There is a need for the development of cost effective methodologies to produce them in large quantities. The synthetic process developed for both these compounds is general and can be applied for other flavonoids also. An industrially applicable high pure product, cost effective synthesis and general synthetic method has been developed and presented.
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- T. Hirano, K. Oka and M. Akiba, Res. Commun. Chem. Pathol. Pharmacol., 64, 69 (1989).
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- K. Yamasaki, R. Hishiki, E. Kato and J. Kawabata, ACS Med. Chem. Lett., 2, 17 (2011); doi:10.1021/ml100171x.
- Y.F. Tong, S. Chen, Y.H. Cheng and S. Wu, Chin. Chem. Lett., 18, 407 (2007); doi:10.1016/j.cclet.2007.01.049.
References
T. Hirano, K. Oka and M. Akiba, Res. Commun. Chem. Pathol. Pharmacol., 64, 69 (1989).
G.G.J.M. Kuiper, J.G. Lemmen, B. Carlsson, J.C. Corton, H. Safe, T. van der Saag, B. van der Burg and J.-A. Gustafsson, Endocrinology, 139, 4252 (1998); doi:10.1210/endo.139.10.6216.
I.-K. Wang, S.-Y. Lin-Shiau and J.-K. Lin, Eur. J. Cancer, 35, 1517 (1999); doi:10.1016/S0959-8049(99)00168-9.
J. Mann, Secondary Metabolism, Oxford University Press, U.K., edn 2, pp. 279-280 (1992).
A. Ulubelen, M. Miski, P. Neuman and T.J. Mabry, J. Nat. Prod., 42, 261 (1979); doi:10.1021/np50003a002.
K. Shimoi, H. Okada, M. Furugori, T. Goda, S. Takase, M. Suzuki, Y. Hara, H. Yamamoto and N. Kinae, FEBS Lett., 438, 220 (1998); doi:10.1016/S0014-5793(98)01304-0.
M. López-Lázaro, Mini Rev. Med. Chem., 9, 31 (2009); doi:10.2174/138955709787001712.
T. Takahashi, M. Kobori, H. Shinmoto and T. Tsushida, Biosci. Biotechnol. Biochem., 62, 2199 (1998); doi:10.1271/bbb.62.2199.
S. Kawaii, Y. Tomono, E. Katase, K. Ogawa and M. Yano, Anticancer Res., 19, 1261 (1999).
F. Yin, E. Giuliano and J. van Herle, Thyroid, 9, 369 (1999); doi:10.1089/thy.1999.9.369.
J. Wang, R.-G. Zhou, T. Wu, T. Yang, Q.-X. Qin, L. Li, B. Yang and J. Yang, J. Chem. Res., 36, 121 (2012); doi:10.3184/174751912X13285269293913.
W.A. Hutchins and T.S. Wheeler, J. Chem. Soc., 91 (1939); doi:10.1039/jr9390000091.
J. Kim, P. Kwang-Su, L. Chaewoon and C. Youhoon, Bull. Korean Chem. Soc., 28, 2527 (2007); doi:10.5012/bkcs.2007.28.12.2527.
J. Menezes, S. Manjrekar, V. Pai, E. Patre and G. Tilve, Indian J. Chem., 48B, 1311 (2009).
R. Robinson and K. Venkataraman, J. Chem. Soc., 129, 2344 (1926); doi:10.1039/jr9262902344.
C. Gulati, R. Seth and K. Venkataraman, Org. Synth. Coll., 2, 522 (1943); 15, 70 (1935).
K. Ahluwalia, P. Bhagat, R. Aggarwal and R. Chandra, Intermediates for Organic Synthesis, I.K International Pvt. Ltd., India (2005).
A. Rambabu, M. Krishnamurthy, B. Haribabu and G.V. Subbaraju, Optimized Synthesis of 4',5,7-trimethoxy Apigenin, International Conference on Pure and Applied Chemistry (ICPAC-2014), Mauritius, 23-27 June 2014.
K. Yamasaki, R. Hishiki, E. Kato and J. Kawabata, ACS Med. Chem. Lett., 2, 17 (2011); doi:10.1021/ml100171x.
Y.F. Tong, S. Chen, Y.H. Cheng and S. Wu, Chin. Chem. Lett., 18, 407 (2007); doi:10.1016/j.cclet.2007.01.049.