Our Phytochemical Research on Parthenium hysterophorous

Author(s): Biswanath Das*, Nayaki Salvanna, Rathod Aravind Kumar, Ratna Das

Journal Name: Mini-Reviews in Organic Chemistry

Volume 17 , Issue 7 , 2020

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Graphical Abstract:


Parthenium hysterophorus (Compositae), an obnoxious weed, was investigated thoroughly for its chemical constituents. We isolated a large number of pseudoguaianolides and other compounds. Many of the isolates are new natural products. Parthenin, the major pseudoguaianolide, was synthetically converted to its various analogues. Some of the constituents of the plant and of the prepared analogues were found to possess significant antibacterial and anticancer properties. Here, we review our phytochemical research on Parthenium hysterophorus informing of our work on the isolation, structure elucidation, synthetic modifications, and bioevaluation of its chemical constituents.

Keywords: Bioactivity, chemistry, natural constituents, Parthenium hysterophorus, phytochemical investigation, structure elucidation, synthetic conversion.

Herz, W.; Watanabe, H.; Miyazaki, M.; Kishida, Y. The structure of parthenin and ambrosin. J. Am. Chem. Soc., 1962, 84, 2601-2610.
(a)Rodríguez, E.; Dillon, M.O.; Mabry, T.J.; Mitchell, J.C.; Towers, G.H. Dermatologically active sesquiterpene lactones in trichomes of Parthenium hysterophorus L. (Compositae). Experientia, 1976, 32(2), 236-238.
[http://dx.doi.org/10.1007/BF01937785] [PMID: 1269624]
(b)Narasimhan, T.R.; Ananth, M.; Swamy, M.N.; Babu, M.R.; Mangala, A.; Rao, P.V. Toxicity of Parthenium hysterophorus L. to cattle and buffaloes. Experientia, 1977, 33(10), 1358-1359.
[http://dx.doi.org/10.1007/BF01920179] [PMID: 908415]
(a)Kanchan, S.D. Growth inhibitors from Parthenium hysterophorus Linn. Curr. Sci., 1975, 44, 358-359.
(b)Patil, T.M.; Hedge, B.A. Isolation and purification of sesquiterpene lactones from the leaves of Parthenium hysterophorus L - Its alleo-pathic and cytotoxic effects. Curr. Sci., 1988, 57, 1178-1181.
(a)Kupchan, S.M.; Eakin, M.A.; Thomas, A.M. Tumor inhibitors. 69. Structure-cytotoxicity relationships among the sesquiterpene lactones. J. Med. Chem., 1971, 14(12), 1147-1152.
[http://dx.doi.org/10.1021/jm00294a001] [PMID: 5116225]
(b)Mew, D.; Balza, F.; Towers, G.H.N.; Levy, J.G. Anti-tumor effects of the sesquiterpene lactone Parthenin. Planta Med., 1982, 45, 23-27.
Mukherjee, B.; Chatterjee, M. Antitumor activity of Parthenium hysterophorus and its effect in the modulation of biotransforming enzymes in transplanted murine leukemia. Planta Med., 1993, 59(6), 513-516.
[http://dx.doi.org/10.1055/s-2006-959750] [PMID: 8302949]
Das, B.; Das, R. Chemical investigation in Parthenium hysterophorus - An alleopathic plant. Allelopathy J., 1995, 2, 99-104.
Das, B.; Das, R. A new pseudoguaianolide from Parthenium hysterophorus. Ind. J. Heteroatom Chem., 1977, 7, 163-164.
Das, R.; Krishaniah, M.; Kumar, R.A.; Das, B. Two minor parthenin analogues from Parthenium hysterophorus. Ind. J. Hetero. Chem., 2007, 17, 7-10.
Das, B.; Jangili, P.; Srilatha, M.; Kashanna, J.; Das, R. Pseudoguaianolides from a collection of the flowers of Parthenium hysterophorus Linn (Composiate). J. Org. Biomol. Chem., 2013, 1, 195-200.
Venkataiah, B.; Ramesh, C.; Ravindranath, N.; Das, B. Charminarone, a seco-pseudoguaianolide from Parthenium hysterophorus. Phytochemistry, 2003, 63(4), 383-386.
[http://dx.doi.org/10.1016/S0031-9422(03)00147-X] [PMID: 12770584]
Ramesh, C.; Ravindranath, N.; Das, B.; Prabhakar, A.; Bharatam, J.; Ravikumar, K.; Kashinatham, A.; McMorris, T.C. Pseudoguaianolides from the flowers of Parthenium hysterophorus. Phytochemistry, 2003, 64(4), 841-844.
[http://dx.doi.org/10.1016/S0031-9422(03)00425-4] [PMID: 14559278]
Das, R.; Geethangili, M.; Majhi, A.; Das, B.; Rao, Y.K.; Tzeng, Y-M. A new highly oxygenated pseudoguaianolide from a collection of the flowers of Parthenium hysterophorus. Chem. Pharm. Bull. (Tokyo), 2005, 53(7), 861-862.
[http://dx.doi.org/10.1248/cpb.53.861] [PMID: 15997155]
Das, R.; Reddy, V.S.; Venkateswarlu, K.; Das, B. New anhydroparthenin analogues from Parthenium hysterophorus. Ind. J. Hetero. Chem., 2005, 14, 59-60.
Das, R.; Mahender, G.; Rao, Y.K.; Ramesh, C.; Venkateswarlu, K.; Ravikumar, K.; Geethangili, M.; Tzeng, Y-M. Pseudoguaianolide from the flowers of Parthenium hysterophorus. Helv. Chim. Acta, 2006, 89, 285-290.
Das, B.; Reddy, K.R.; Ravikanth, B.; Sharma, A.V.S.; Sridhar, B. The new pseudoguaianolides from the flowers of Parthenium hysterophorus. Helv. Chim. Acta, 2008, 91, 1137-1143.
Das, B.; Reddy, V.S.; Krishnaiah, M.; Sharma, A.V.S.; Ravi Kumar, K.; Rao, J.V.; Sridhar, V. Acetylated pseudoguaianolides from Parthenium hysterophorus and their cytotoxic activity. Phytochemistry, 2007, 68(15), 2029-2034.
[http://dx.doi.org/10.1016/j.phytochem.2007.05.002] [PMID: 17570445]
Das, B.; Das, R. Novel pseudoguaianolides from Parthenium hyste-rophorus: NMR detective investigation. Sci. Cult., 2008, 74, 55-58.
Das, R.; Srilatha, M.; Satyalakshmi, G.; Das, B. Perthoxynol, a new epoxy-sesquiterpenoids from Parthenium hysterophorus. Ind. J. Hetero. Chem., 2011, 20, 297-298.
Das, B.; Paramesh, J.; Srilatha, M.; Das, R. A new pseudoguaianolide from the flowers of Parthenium hysterophorus. Ind. J. Hetero. Chem., 2013, 22, 413-414.
Das, B.; Venkataiah, B.; Kashinatham, A. (+) Syringaresinol from Parthenium hysterophorus. Fitoterpia, 1999, 70, 101-102.
Das, B.; Venkataiah, B. Conversion of parthenin to anhydroparthenin using microwave irradiation. Synth. Commun., 1999, 29, 863-866.
Ramesh, C.; Harikrishna, K.; Murty, U.S.N.; Das, B. Analogues of parthenin and their antibacterial activity. ARKIVOC, 2003, ix, 126-132.
Das, B.; Satyalakshmi, G.; Bhunia, N.; Reddy, K.R.; Reddy, V.S.; Mahender, G. Chemical transformations of parthenin, a natural bioactive sesquiterpenoid. Nat. Prod. Commun., 2009, 4(1), 9-14.
[http://dx.doi.org/10.1177/1934578X0900400104] [PMID: 19370866]
Venkataiah, B.; Das Kashinatham, A.B. Investigation on Parthenium hysterophorus L and chemical and biochemical modifications of parthenin alleochemical. Allelopathy J., 1999, 6, 57-62.
Das, B.; Venkataiah, B.; Kashinatham, A. Chemical and biochemical modifications of parthenin. Tetrahedron, 1999, 55, 6585-6594.
Das, B.; Ramesh, C.; Ravindranath, N.; Mahender, G.; Holla, H. Synthesis of novel spiro-2-isoxazolenes derived from parthenin. Indian J. Chem., 2005, 44B, 2149-2151.
Pickman, A.K.; Schneider, E.F. Inhibitions of fungal growth by selected sesquiterpene lactones. Biochem. Syst. Ecol., 1993, 21, 307-314.
Hopper, M.; Kirby, G.C.; Kulkarni, M.M.; Kulkarni, S.N.; Nagasampagi, B.A.; O’Neill, M.J.; Phillipson, J.D.; Rojatkar, S.R.; Warthus, D.C. Antimalerial activity of parthenin and derivatives. Eur. J. Med. Chem., 1999, 25, 717-723.
Sharma, G.L.; Bhutani, K.K. Plant based antiamoebic drugs; Part II. Amoebicidal activity of parthenin isolated from Parthenium hysterophorus. Planta Med., 1988, 54(2), 120-122.
[http://dx.doi.org/10.1055/s-2006-962366] [PMID: 2900531]
Saeed, M.; Jacob, S.; Sandigo, L.P.; Sugimoto, Y.; Khalid, H.E.; Opatz, T.; Thines, E.; Efferth, T. Cytottoxicity of sesquiterpenes lactones neoambrosin and damsin from Ambrosa maritima against multidrug-resistant cancer cells. Front. Pharmacol., 2015, 6, Article 267.

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Article Details

Year: 2020
Published on: 08 October, 2020
Page: [843 - 854]
Pages: 12
DOI: 10.2174/1570193X17666191218092812
Price: $65

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