Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Terpenoids and Its Commercial Utility from Neem: The Nature's Own Pharmacy: A Review
Corresponding Author(s) : A.S. Sathish Kumar
Asian Journal of Chemistry,
Vol. 26 No. 16 (2014): Vol 26 Issue 16
Abstract
Plant derived bio products have become integral part of world health care system which not only include botanical drugs but also agro chemicals, cosmetics, nutraceuticals, flavors and fragrances and so on. The World Bank estimates that global trade in plant derived products will grow at average 10-12 % per year and will reach whooping USD 123 billion by 2020. Inevitably this brought attention to our sthala vriksha or sacred tree neem (Azadirachta indica) considered as store house of high value products with vast array of biological activities like insecticidal, spermicidal, anticancer, hypoglycemic, antiulcer, antiinflammatory, and many more. However due to inherent complexities in scalability which includes consistent supply chain and difficulty in synthesizing bioactive metabolites using established chemical routes and seasonal variation in bio-efficacy with change in plant chemistry, place, age etc. makes large scale production of most of them is impossible. Hence there is need for a paradigm shift in combining traditional approaches with more sophisticated biotechnological methods to produce these products in heterologous system, thereby enabling a consistent scale-up at a commercial level. This article reviews the terpenoids reported in neem so far, their proposed biosynthetic pathways and potential avenues for expressing them in microbial cell factories.
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- P.M. Murali, K. Nalini and S. Lakshimisubramaniam, Tree Science Conference, New Delhi, pp. 46 (1998).
- T.R. Govindachari, Curr. Sci., 63, 117 (1992).
- P. Sharma, L. Tomar and M.B.V. Bachwani, Int. Res. J. Pharmacy, 2, 97 (2011).
- H.S. Puri, Neem, The Divine Tree, Azadirachta indica, Harwood Academic Publications, Amsterdam, The Netherlands, pp. 90 (1999).
- A. Tomar, Neem: An Introduction; In: Neem: A Treatise, I.K. International Publishing House Pvt Ltd., New Delhi, Ch. 1, pp. 3-19 (2009).
- A. Tomar, Neem in Health and Cosmetics; In Neem: A Treatise, I.K. International Publishing House Pvt Ltd., New Delhi, Ch. 31, pp. 461-485. (2009).
- B.S. Siddiqui, S.T. Ali and S.K. Ali, Chemical Wealth of Azadirachta indica (Neem); In: Neem: A A Treatise, I.K. International Publishing House Pvt Ltd., New Delhi, Ch 13,pp. 171 (2009).
- N. Saxena and Y. Kumar, Chemistry of Azadirachtin and other Bioactive Isoprenoids from Neem (Azadirachta indica A. Juss); In: Neem: A Treatise, I.K. International Publishing House Pvt Ltd., New Delhi, Ch 14, pp. 208 (2009).
- B.S. Siddiqui, M. Rasheed, F. Ilyas, T. Gulzar, R.M. Tariq and S.N.H. Naqvi, Z. Naturforsch., 59c, 104 (2004).
- A.H. Wafaa, Hassan Amer, Nefisa, M.A., EL-Shayeb, J. Appl. Sci. Res., 3, 1050 (2007).
- I. Ara, B.S. Siddiqui, S. Faizi and S. Siddiqui, Phytochemistry, 28, 1177 (1989); doi:10.1016/0031-9422(89)80204-3.
- Rasheed, Ph.D. Dissertation, Studies on the Chemical Constituents of Azadirachta indica A. Juss (Neem), University of Karachi, Pakistan (2002).
- S. Siddiqui, B.S. Siddiqui and S. Faizi, Planta Med., 51, 478 (1985); doi:10.1055/s-2007-969567.
- S. Siddiqui, S. Faizi, B.S. Siddiqui and Ghiasuddin, J. Nat. Prod., 55, 303 (1992); doi:10.1021/np50081a005.
- B.S. Siddiqui, F. Afshan, T. Gulzar, R. Sultana, S.N.-H. Naqvi and R.M. Tariq, Chem. Pharm. Bull. (Tokyo), 51, 415 (2003); doi:10.1248/cpb.51.415.
- B.S. Siddiqui and M. Rasheed, Helv. Chim. Acta, 84, 1962 (2001); doi:10.1002/1522-2675(20010711)84:7<1962::AID-HLCA1962>3.0.CO;2-V.
- S. Siddiqui, T. Mahmood, B.S. Siddiqui and S. Faizi, Heterocycles, 26, 1827 (1987); doi:10.3987/R-1987-07-1827.
- T.R. Govindachari, B. Suresh, G. Gopalakrishnan, B. Banumathy and S. Masilamani, Phytoparasitica, 26, 109 (1998); doi:10.1007/BF02980677.
- S.M. Lee, J.L. Olsen, M.P. Schweizer and J.A. Klocke, Phytochemistry, 27, 2773 (1988); doi:10.1016/0031-9422(88)80661-7.
- D. Lavie, M.K. Jain and S.R. Shpan-Gabrielith, Chem. Commun., 910 (1967); doi:10.1039/c19670000910.
- C.R. Narayanan, R.V. Pachapurkar, B.M. Sawant and M.S. Wadia, Indian J. Chem., 7, 187 (1969).
- A. Akhila, G. Adam, K. Rani, J. Schmidt and B. Schneider, Fortschr. Chem. Org. Naturst., 78, 147 (1999); doi:10.1007/978-3-7091-6394-8.
- G.E. Veitch, A. Boyer and S.V. Ley, Angew. Chem., 47, 9402 (2008); doi:10.1002/anie.200802675.
- C. Devakumar and R. Kumar, Curr. Sci., 95, 573 (2008).
- S.R. Rojatkar, V.S. Bhat, M.M. Kulkarni, V.S. Joshi and B.A. Nagasampagi, Phytochemistry, 28, 203 (1989); doi:10.1016/0031-9422(89)85038-1.
- I. Ara, B.S. Siddiqui, S. Faizi and S. Siddiqui, Phytochemistry, 27, 1801 (1988); doi:10.1016/0031-9422(88)80447-3.
- B.S. Siddiqui, F. Afshan and S. Faizi, Tetrahedron, 57, 10281 (2001); doi:10.1016/S0040-4020(01)01027-4.
- M. Bokel, R. Cramer, H. Gutzeit, S. Reeb and W. Kraus, Tetrahedron, 46, 775 (1990); doi:10.1016/S0040-4020(01)81360-0.
- W.A. Helmy, H.I. Abd-Alla, H. Amer and M.M. El-Safty, Australian J. Basic Appl. Sci., 1, 801 (2007).
- K. Muffler, D. Leipold, M.-C. Scheller, C. Haas, J. Steingroewer, T. Bley, H.E. Neuhaus, M.A. Mirata, J. Schrader and R. Ulber, Process Biochem., 46, 1 (2011); doi:10.1016/j.procbio.2010.07.015.
- K. Biswas, I. Chattopadhyay, R.K. Banerjee and U. Bandyopadhyay, Curr. Sci., 82, 1336 (2002).
- J. Jauch, Angew. Chem., 47, 34 (2008); doi:10.1002/anie.200703814.
- M.B. Isman, Phytoparasitica, 25, 339 (1997); doi:10.1007/BF02981099.
- N.M. Krishnan, S. Pattnaik, P. Jain, P. Gaur, R. Choudhary, S. Vaidyanathan, S. Deepak, A.K. Hariharan, P.G. Krishna, J. Nair, L. Varghese, N.K. Valivarthi, K. Dhas, K. Ramaswamy and B. Panda, BMC Genomics, 13, 464 (2012); doi:10.1186/1471-2164-13-464.
- K. Rani and A. Akhila, Nat. Prod. Lett., 4, 179 (1994); doi:10.1080/10575639408043902.
- P.M. Dewick, Medicinal Natural Products: A Biosynthetic Approach, John Wiley & Sons, New York, edn 2 (2002).
- E.M. Davis and R. Croteau, Curr. Topics Chem., 209, 53 (2000); doi:10.1007/3-540-48146-X_2.
- P.K. Ajikumar, K. Tyo, S. Carlsen, O. Mucha, T.H. Phon and G. Stephanopoulos, Mol. Pharm., 5, 167 (2008); doi:10.1021/mp700151b.
- J.D. Newman and J. Chappell, Crit. Rev. Biochem. Mol. Biol., 34, 95 (1999); doi:10.1080/10409239991209228.
- J. Kirby and J.D. Keasling, Annu. Rev. Plant Biol., 60, 335 (2009); doi:10.1146/annurev.arplant.043008.091955.
References
P.M. Murali, K. Nalini and S. Lakshimisubramaniam, Tree Science Conference, New Delhi, pp. 46 (1998).
T.R. Govindachari, Curr. Sci., 63, 117 (1992).
P. Sharma, L. Tomar and M.B.V. Bachwani, Int. Res. J. Pharmacy, 2, 97 (2011).
H.S. Puri, Neem, The Divine Tree, Azadirachta indica, Harwood Academic Publications, Amsterdam, The Netherlands, pp. 90 (1999).
A. Tomar, Neem: An Introduction; In: Neem: A Treatise, I.K. International Publishing House Pvt Ltd., New Delhi, Ch. 1, pp. 3-19 (2009).
A. Tomar, Neem in Health and Cosmetics; In Neem: A Treatise, I.K. International Publishing House Pvt Ltd., New Delhi, Ch. 31, pp. 461-485. (2009).
B.S. Siddiqui, S.T. Ali and S.K. Ali, Chemical Wealth of Azadirachta indica (Neem); In: Neem: A A Treatise, I.K. International Publishing House Pvt Ltd., New Delhi, Ch 13,pp. 171 (2009).
N. Saxena and Y. Kumar, Chemistry of Azadirachtin and other Bioactive Isoprenoids from Neem (Azadirachta indica A. Juss); In: Neem: A Treatise, I.K. International Publishing House Pvt Ltd., New Delhi, Ch 14, pp. 208 (2009).
B.S. Siddiqui, M. Rasheed, F. Ilyas, T. Gulzar, R.M. Tariq and S.N.H. Naqvi, Z. Naturforsch., 59c, 104 (2004).
A.H. Wafaa, Hassan Amer, Nefisa, M.A., EL-Shayeb, J. Appl. Sci. Res., 3, 1050 (2007).
I. Ara, B.S. Siddiqui, S. Faizi and S. Siddiqui, Phytochemistry, 28, 1177 (1989); doi:10.1016/0031-9422(89)80204-3.
Rasheed, Ph.D. Dissertation, Studies on the Chemical Constituents of Azadirachta indica A. Juss (Neem), University of Karachi, Pakistan (2002).
S. Siddiqui, B.S. Siddiqui and S. Faizi, Planta Med., 51, 478 (1985); doi:10.1055/s-2007-969567.
S. Siddiqui, S. Faizi, B.S. Siddiqui and Ghiasuddin, J. Nat. Prod., 55, 303 (1992); doi:10.1021/np50081a005.
B.S. Siddiqui, F. Afshan, T. Gulzar, R. Sultana, S.N.-H. Naqvi and R.M. Tariq, Chem. Pharm. Bull. (Tokyo), 51, 415 (2003); doi:10.1248/cpb.51.415.
B.S. Siddiqui and M. Rasheed, Helv. Chim. Acta, 84, 1962 (2001); doi:10.1002/1522-2675(20010711)84:7<1962::AID-HLCA1962>3.0.CO;2-V.
S. Siddiqui, T. Mahmood, B.S. Siddiqui and S. Faizi, Heterocycles, 26, 1827 (1987); doi:10.3987/R-1987-07-1827.
T.R. Govindachari, B. Suresh, G. Gopalakrishnan, B. Banumathy and S. Masilamani, Phytoparasitica, 26, 109 (1998); doi:10.1007/BF02980677.
S.M. Lee, J.L. Olsen, M.P. Schweizer and J.A. Klocke, Phytochemistry, 27, 2773 (1988); doi:10.1016/0031-9422(88)80661-7.
D. Lavie, M.K. Jain and S.R. Shpan-Gabrielith, Chem. Commun., 910 (1967); doi:10.1039/c19670000910.
C.R. Narayanan, R.V. Pachapurkar, B.M. Sawant and M.S. Wadia, Indian J. Chem., 7, 187 (1969).
A. Akhila, G. Adam, K. Rani, J. Schmidt and B. Schneider, Fortschr. Chem. Org. Naturst., 78, 147 (1999); doi:10.1007/978-3-7091-6394-8.
G.E. Veitch, A. Boyer and S.V. Ley, Angew. Chem., 47, 9402 (2008); doi:10.1002/anie.200802675.
C. Devakumar and R. Kumar, Curr. Sci., 95, 573 (2008).
S.R. Rojatkar, V.S. Bhat, M.M. Kulkarni, V.S. Joshi and B.A. Nagasampagi, Phytochemistry, 28, 203 (1989); doi:10.1016/0031-9422(89)85038-1.
I. Ara, B.S. Siddiqui, S. Faizi and S. Siddiqui, Phytochemistry, 27, 1801 (1988); doi:10.1016/0031-9422(88)80447-3.
B.S. Siddiqui, F. Afshan and S. Faizi, Tetrahedron, 57, 10281 (2001); doi:10.1016/S0040-4020(01)01027-4.
M. Bokel, R. Cramer, H. Gutzeit, S. Reeb and W. Kraus, Tetrahedron, 46, 775 (1990); doi:10.1016/S0040-4020(01)81360-0.
W.A. Helmy, H.I. Abd-Alla, H. Amer and M.M. El-Safty, Australian J. Basic Appl. Sci., 1, 801 (2007).
K. Muffler, D. Leipold, M.-C. Scheller, C. Haas, J. Steingroewer, T. Bley, H.E. Neuhaus, M.A. Mirata, J. Schrader and R. Ulber, Process Biochem., 46, 1 (2011); doi:10.1016/j.procbio.2010.07.015.
K. Biswas, I. Chattopadhyay, R.K. Banerjee and U. Bandyopadhyay, Curr. Sci., 82, 1336 (2002).
J. Jauch, Angew. Chem., 47, 34 (2008); doi:10.1002/anie.200703814.
M.B. Isman, Phytoparasitica, 25, 339 (1997); doi:10.1007/BF02981099.
N.M. Krishnan, S. Pattnaik, P. Jain, P. Gaur, R. Choudhary, S. Vaidyanathan, S. Deepak, A.K. Hariharan, P.G. Krishna, J. Nair, L. Varghese, N.K. Valivarthi, K. Dhas, K. Ramaswamy and B. Panda, BMC Genomics, 13, 464 (2012); doi:10.1186/1471-2164-13-464.
K. Rani and A. Akhila, Nat. Prod. Lett., 4, 179 (1994); doi:10.1080/10575639408043902.
P.M. Dewick, Medicinal Natural Products: A Biosynthetic Approach, John Wiley & Sons, New York, edn 2 (2002).
E.M. Davis and R. Croteau, Curr. Topics Chem., 209, 53 (2000); doi:10.1007/3-540-48146-X_2.
P.K. Ajikumar, K. Tyo, S. Carlsen, O. Mucha, T.H. Phon and G. Stephanopoulos, Mol. Pharm., 5, 167 (2008); doi:10.1021/mp700151b.
J.D. Newman and J. Chappell, Crit. Rev. Biochem. Mol. Biol., 34, 95 (1999); doi:10.1080/10409239991209228.
J. Kirby and J.D. Keasling, Annu. Rev. Plant Biol., 60, 335 (2009); doi:10.1146/annurev.arplant.043008.091955.