Kinetic Studies on the Hydrogenation of Curcuminoids Isolated from Curcuma Longa by LC/MS

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Kinetic Studies on the Hydrogenation of Curcuminoids Isolated from Curcuma Longa by LC/MS

Author Affiliations

¹R and D Centre, Aurea Biolabs (P) Ltd, Cochin, INDIA

Res.J.chem.sci., Volume 5, Issue (4), Pages 33-36, April,18 (2015)

Abstract

In the present study, we investigated the catalytic palladium hydrogenation of curcuminoids, the major constituent isolated from Turmeric root (Curcuma longa) at various time intervals and monitored by LC/MS. The study revealed that the most of the curcuminoids hydrogenated within two hours period and gave the corresponding tetra, hexa and octa-hydrocurcuminoids at different ratio except bisdemethoxycurcumin, which gave only hexa-hydrogenated derivative. Even though, Palladium-carbon catalyst does not favour the reduction of carbonyl group, due to the presence of the conjugated double bonds hydrogenation occurred.

References

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Soni Himesh, Patel Sita Sharan, Mishra K., Nayak Govind and Singhai A.K., Qualitative and quantitative profile of curcumin from ethanolic extract of Curcuma longa,IRJP2,, 180-184 (2011)
Benny Antony, Merina Benny and Rao S.B., Enhancing the absorption of curcuminoids, Journal of Spices India, 23-26 (2005)
Roughley P. J. and Whiting D. A., Experiments in the biosynthesis of curcumin, J. Chem. Soc., Perkin Trans. 1, 20, 2379–2388 (1973)
Carl Wagner E., Pamela Marshall A., Thomas Cahill M. and Zeynab Mohamed, Visually following the hydrogenation of curcumin to tetrahydrocurcumin in a natural product experiment that enhances student understanding of NMR spectroscopy, J. Chem. Educ., 90, 930933 (2013)
Poorichaya Somparn, Chada Phisalaphong, Somjai Nakornchal, Supeenun Unchern and Noppawan Phumala Morales, Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives, Biol. Pharm. Bull.,30(1), 74-78 (2007)
Toshihiko Osawa, Yasunori Sugiyama, Masanori Inayoshi and Shunro Kawakishi, Antioxidative activity of tetrahydrocurcuminoids, Biosci. Biotech. Biochem., 59 (9), 1609-1612 (1995)
Kunihiko Okada, Chantima Wangpoengtrakul, Tomoyuki Tanaka, Shinya Toyokuni, Koji Uchida and Toshihiko Osawa, Curcumin and especially tetrahydrocurcumin ameliorate oxidative stress-induced renal injury in mice,J. Nutr., 131(8)2090-2095 (2001)
Leelavinothan Pari and Rosalin Amali D., Protective role of tetrahydrocurcumin (THC) an active principle of turmeric on chloroquine induced hepatotoxicity in rats, J Pharm Pharmaceut Sci.,8(1), 115-123 (2005)
Rong-Jyh Lin, Chung-Yi Chenc, Li-Yu Chunga and Chuan-Min Yen, Larvicidal activities of ginger (Zingiber officinale) against Angiostrongylus cantonensis, Acta Tropica, 115, 69–76 (2010)
Khanitta Srimuangwong, Chainarong Tocharus, Pornphrom Yoysungnoen Chintana, Apichart Suksamrarn and Jiraporn Tocharus, Hexahydrocurcumin enhances inhibitory effect of 5-fluorouracil on HT-29 human colon cancer cells, World J Gastroenterol, 18(19), 2383-2389 (2012)
Revathy S., Elumalai S., Merina Benny Antony, Isolation, Purification and identification of curcuminoids from Turmeric (Curcuma longa L.) by Column Chromatography, Journal of Experimental Sciences,2(7), 21-25 (2011)

[ref1] Julie S. Jurenka Anti-inflammatory properties of curcumin, a major constituent of Curcuma longa: A review of pre-clinical and clinical research,Alternative Medicine Review, 14(2), 141-153 (2009)

[ref2] Soni Himesh, Patel Sita Sharan, Mishra K., Nayak Govind and Singhai A.K., Qualitative and quantitative profile of curcumin from ethanolic extract of Curcuma longa,IRJP2,, 180-184 (2011)

[ref3] Benny Antony, Merina Benny and Rao S.B., Enhancing the absorption of curcuminoids, Journal of Spices India, 23-26 (2005)

[ref4] Roughley P. J. and Whiting D. A., Experiments in the biosynthesis of curcumin, J. Chem. Soc., Perkin Trans. 1, 20, 2379–2388 (1973)

[ref5] Carl Wagner E., Pamela Marshall A., Thomas Cahill M. and Zeynab Mohamed, Visually following the hydrogenation of curcumin to tetrahydrocurcumin in a natural product experiment that enhances student understanding of NMR spectroscopy, J. Chem. Educ., 90, 930933 (2013)

[ref6] Poorichaya Somparn, Chada Phisalaphong, Somjai Nakornchal, Supeenun Unchern and Noppawan Phumala Morales, Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives, Biol. Pharm. Bull.,30(1), 74-78 (2007)

[ref7] Toshihiko Osawa, Yasunori Sugiyama, Masanori Inayoshi and Shunro Kawakishi, Antioxidative activity of tetrahydrocurcuminoids, Biosci. Biotech. Biochem., 59 (9), 1609-1612 (1995)

[ref8] Kunihiko Okada, Chantima Wangpoengtrakul, Tomoyuki Tanaka, Shinya Toyokuni, Koji Uchida and Toshihiko Osawa, Curcumin and especially tetrahydrocurcumin ameliorate oxidative stress-induced renal injury in mice,J. Nutr., 131(8)2090-2095 (2001)

[ref9] Leelavinothan Pari and Rosalin Amali D., Protective role of tetrahydrocurcumin (THC) an active principle of turmeric on chloroquine induced hepatotoxicity in rats, J Pharm Pharmaceut Sci.,8(1), 115-123 (2005)

[ref10] Rong-Jyh Lin, Chung-Yi Chenc, Li-Yu Chunga and Chuan-Min Yen, Larvicidal activities of ginger (Zingiber officinale) against Angiostrongylus cantonensis, Acta Tropica, 115, 69–76 (2010)

[ref11] Khanitta Srimuangwong, Chainarong Tocharus, Pornphrom Yoysungnoen Chintana, Apichart Suksamrarn and Jiraporn Tocharus, Hexahydrocurcumin enhances inhibitory effect of 5-fluorouracil on HT-29 human colon cancer cells, World J Gastroenterol, 18(19), 2383-2389 (2012)

[ref12] Revathy S., Elumalai S., Merina Benny Antony, Isolation, Purification and identification of curcuminoids from Turmeric (Curcuma longa L.) by Column Chromatography, Journal of Experimental Sciences,2(7), 21-25 (2011)