Medicinal Chemistry of Alternative Therapeutics: Novelty and Hopes with Genus Ammannia

Author(s): Harish C. Upadhyay* .

Journal Name: Current Topics in Medicinal Chemistry

Volume 19 , Issue 10 , 2019

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Abstract:

The plants have formed the basis of folklore remedy since the beginning of human civilization. The cumulative human endeavor and experience over a period of thousands of years developed into well to organize traditional medicine systems viz. Ayurvedic, Unani, Chinese amongst others. Across the world, traditional medicine is either the mainstay of health care or serves as a complement to modern drugs. In view of worldwide use of traditional medicines, World Health Organization launched ‘WHO-Traditional Medicine Strategy 2014-2023’ for the development of strong policies regarding knowledge-base, safety, quality-control and effectiveness of traditional/alternative therapeutics for national health systems. Besides their use in traditional medicine, plants have always been a good source of modern drug/pharmacologically active molecules. More than half of the modern pharmaceuticals are either plant isolates or their derivatives. The plant-based drugs are not only effective, but have better compatibility with human biological systems because of more biologically relevant chemistry, hence lesser side effects. Some of the species of genus Ammannia (Lythraceae) have been reported for their magical medicinal values. Many herbal formulations containing Ammannia spp. have been patented for treatment of serious diseases/disorders like cancer, spinal disease, human female infertility, chronic tonsillitis, pelvic inflammatory disease, treatment of bladder stones, urinary tract infections, dermatitis etc. The uses of Ammannia spp. in traditional medicine have been further verified by the biological activities of their extracts as well as isolation of bioactive phytomolecules. The current review provides details about Ammannia spp.; its use in folklore remedy, herbal formulations, biological activities of extracts, isolation of bioactive phytomolecules and SAR study of semi-synthetic derivatives to analyze the possibility of new drug molecules of plant origin.

Keywords: Ammannia, Folklore, SAR, Tetralone, Anti-tubercular, Anti-cancer, Anti-diabetic, Bioenhancer.

[1]
Samuelsson, G. Drugs of natural origin: A textbook of pharmacognosy.In: Swedish Pharmaceutical Press, 5th ed; Stockholm. , 2004.
[2]
Cragg, G.M.; Newman, D.J.; Snader, K.M. Natural products in drug discovery and development. J. Nat. Prod., 1997, 60(1), 52-60.
[http://dx.doi.org/10.1021/np9604893] [PMID: 9014353]
[3]
Newman, D.J.; Cragg, G.M.; Snader, K.M. The influence of natural products upon drug discovery. Nat. Prod. Rep., 2000, 17(3), 215-234.
[http://dx.doi.org/10.1039/a902202c] [PMID: 10888010]
[4]
WHO-Traditional medicine. (Available at: https://www.afro. who.int/health-topics/traditional-medicine
[5]
WHO traditional medicine strategy: 2014-2023.(Available at: www.who.int/medicines/publications/traditional/trm_strategy14_23/en/
[6]
Sheng-Ji, P. Ethnobotanical approaches of traditional medicine studies: some experiences from Asia. Pharm. Biol., 2001, 39(Suppl. 1), 74-79.
[PMID: 21554174]
[7]
Tucakov, J. Healing with plants – phytotherapy. Beograd. Culture (Que.), 1971, 180-190.
[8]
Chopra, A.; Doiphode, V.V. Ayurvedic medicine. Core concept, therapeutic principles, and current relevance. Med. Clin. North Am., 2002, 86(1), 75-89. vii. [http://dx.doi.org/10.1016/S0025-7125(03)00073-7] [PMID: 11795092]
[9]
Hostettmann, K.; Marston, A.; Maillard, M.; Hamburger, M., Eds.; Phytochemistry of plants used in traditional medicine. In: Natural Product Letters. Clarendon Press; Oxford,1995. [https://doi.org/10.1080/10575639608043582]
[10]
Clark, A.M. Natural products as a resource for new drugs. Pharm. Res., 1996, 13(8), 1133-1144.
[http://dx.doi.org/10.1023/A:1016091631721] [PMID: 8865302]
[11]
Shu, Y.Z. Recent natural products based drug development: A pharmaceutical industry perspective. J. Nat. Prod., 1998, 61(8), 1053-1071.
[http://dx.doi.org/10.1021/np9800102] [PMID: 9722499]
[12]
Balunas, M.J.; Kinghorn, A.D. Drug discovery from medicinal plants. Life Sci., 2005, 78(5), 431-441.
[http://dx.doi.org/10.1016/j.lfs.2005.09.012] [PMID: 16198377]
[13]
Harvey, A.L. Natural products in drug discovery. Drug Discov. Today, 2008, 13(19-20), 894-901.
[http://dx.doi.org/10.1016/j.drudis.2008.07.004] [PMID: 18691670]
[14]
Wainwright, M. Miracle cure: The story of penicillin and the golden age of antibiotics. In: Blackwell; Blackwell: Oxford, UK, 1990.
[15]
Newman, D.J.; Cragg, G.M.; Snader, K.M. Natural products as sources of new drugs over the period 1981-2002. J. Nat. Prod., 2003, 66(7), 1022-1037.
[http://dx.doi.org/10.1021/np030096l] [PMID: 12880330]
[16]
Newman, D.J.; Cragg, G.M. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod., 2012, 75(3), 311-335.
[http://dx.doi.org/10.1021/np200906s] [PMID: 22316239]
[17]
Dias, D.A.; Urban, S.; Roessner, U. A historical overview of natural products in drug discovery. Metabolites, 2012, 2(2), 303-336.
[http://dx.doi.org/10.3390/metabo2020303] [PMID: 24957513]
[18]
Thomford, N.E.; Senthebane, D.A.; Rowe, A.; Munro, D.; Seele, P.; Maroyi, A.; Dzobo, K. Natural products for drug discovery in the 21st century: Innovations for novel drug discovery. Int. J. Mol. Sci., 2018, 19(6), 1578.
[http://dx.doi.org/10.3390/ijms19061578] [PMID: 29799486]
[19]
Randhawa, G.K.; Kullar, J.S. Rajkumar, Bioenhancers from mother nature and their applicability in modern medicine. Int. J. Appl. Basic Med. Res., 2011, 1(1), 5-10.
[http://dx.doi.org/10.4103/2229-516X.81972] [PMID: 23776764]
[20]
Upadhyay, H.C.; Dwivedi, G.R.; Darokar, M.P.; Chaturvedi, V.; Srivastava, S.K. Bioenhancing and antimycobacterial agents from Ammannia multiflora. Planta Med., 2012, 78(1), 79-81.
[http://dx.doi.org/10.1055/s-0031-1280256] [PMID: 21969115]
[21]
Cronquist, A. An integrated system of classification of flowering plants. In: Brittonia Columbia University Press; New York, 1981., Volume 34 Issue 2, pp. 268-270.
[22]
Graham, S.A. A revision of ammannia (Lythraceae) in the western hemisphere. J. Arnold Arbor., 1985, 66, 395-420.
[http://dx.doi.org/10.5962/bhl.part.13185]
[23]
Hooker, J.D. Genera Plantarum. L. Reeve & Co., 1879, Vol 1, 57-102.
[24]
Bentham, G.; Hooker, J.D. Lythraceae. Genera Plantarum. L. Reeve & Co., 1867, 1, 773-785.
[25]
Chakravarty, A.K. Weed flora of paddy fields of West Bengal. Indian Agric., 1957, 1, 19-20.
[26]
Hooker, J.D. Flora of British India. Nature, 1874, Vol 12, 3-5.
[27]
Blatter, E.; Hallberg, F. A revision of the Indian species of Rotala and Ammannia. J. Bombay Nat. Hist. Soc., 1918, 25, 701-722.
[28]
Singh, S.C.; Khanuja, S.P.S. Lucknow flora: The plant wealth of the region. CIMAP publication.,India, 170.2006 , pp. ii+522p.
[29]
Ammannia multiflora (Roxb.) In: Flora of Pakistan. (Available at: http://www.efloras.org/florataxon.aspx?flora_id=5&taxon_id=200014626).
[30]
Burkil, I.H. Dictionary of the economic plants of the Malay Peninsula. In:Ministry of Agriculture and co-operatives, 2nd ed; Ministry of Agriculture and Co-operatives: Kuala Lumpur, Malaysia, 1966, Vol. 1, p. 2444.
[31]
Nadkarni, K.M. Indian Materia Medica. In: Popular Prakashan Pvt. Ltd; Bombay, India, 1976, Vol. 11, pp. 91-92.
[32]
Chopra, R.N.; Nayer, S.L.; Chopra, I.C. Glossary of Indian Medicinal Plants. Council of Scientific & Industrial Research, New Delhi, India, 1956, p p. 15.
[33]
Dymock, W.; Warden, C.J.H.; Hooper, D. Pharmacographia Indica (reprinted by Institute of health and Tibbi research). Hamdard Foundation press.,.1972, XV (1-12), 173.
[34]
Perry, M. Medicinal plants of East and South Asia attributed properties and uses; M.I.T. press: Cambridge, England, 1980, p. 249.
[35]
Sabins, S.D.; Bedi, S.J. Ethnobotanical studies in Dadra-Nagar Haveli and Daman. Indian J. For., 1983, 61, 65-69.
[36]
Sahu, T.R. Less known uses of weeds as medicinal plants. Anc. Sci. Life, 1984, 3(4), 245-249.
[PMID: 22557414]
[37]
Mukerjee, T.; Bhalla, N.; Singh, G.; Jain, H.C. Herbal medicines for kidney stones. Indian Drugs, 1984, 21, 224-228.
[38]
Joshi, P. Herbal drugs in guinea worm disease by the tribes of Southern Rajasthan (India). Int. J. Pharmacogn., 1991, 29, 33-38.
[http://dx.doi.org/10.3109/13880209109082846]
[39]
Prasad, K.V.; Bharathi, K.; Srinivasan, K.K. Evaluation of Ammannia baccifera Linn. for antiurolithic activity in albino rats. Indian J. Exp. Biol., 1994, 32(5), 311-313.
[PMID: 7927522]
[40]
Sivarayan, V.V.; Balachandran, I. Ayurvedic drugs and their plant sources. Oxford & IBH publishing Co. Pvt. Ltd; Delhi, India, 1994, pp. 358-359.
[41]
Khare, C.P. Indian Medicinal Plants: An Illustrated dictionary; Springer-Verlag Publishers, 2007, pp. 42-43.
[42]
Kirtikhar, K.R.; Basu, B.D. Indian Medicinal Plants: Part 11; Lalit Mohan Publication: Allahabad, India, 1918, pp. 61-62.
[43]
Katewa, S.S.; Galav, P.K. Traditional herbal medicines from Shekhawati region of Rajasthan. Indian J. Tradit. Knowl., 2005, 4, 237-245.
[44]
Jeeva, S.; Kiruba, S.; Mishra, B.P.; Venugopal, N.; Dhas, S.S.M. Weeds of Kanyakumari district and their value in rural life. Indian J. Tradit. Knowl., 2006, 5, 501-509.
[45]
Cao, J. Traditional Chinese medicine preparation (oral administration) for treating urethritis. Chinese Patent 101954011A., June 01, 2011.
[46]
Wu, H.; Wu, J. A Chinese medicinal liquid for the treatment of abscess, sore, and itching. Chinese Patent 101524449A. 2009.
[47]
Meng, G. Chinese medicinal composition for treatment of spinal disease. Chinese patent 101417003A, April 11, 2009.
[48]
Huang, M.; Yin, H.; Zhang, X. A Chinese medicinal composition for the treatment of female infertility. Chinese Patent 1110585A. 1995.
[49]
Zhang, H. Medicine for treating gastroenteritic diseases. Chinese Patent 1398606A, 2003.
[50]
Zhang, L. Medicament for treating gastrointestinal diseases. Chinese Patent 1965910A, 2007.
[51]
Wang, S. A Chinese medicinal combination for the treatment of fracture. Chinese Patent 1686213A, 2005.
[52]
Liao, X. A Chinese medicinal composition for treating liver cancer, intestinal cancer and gastric cancer. Chinese Patent 1582997A, 2005.
[53]
Sheng, Q. Preparation for treating chronic endometritis and preparation method thereof. Chinese Patent 105434868A, 2016.
[54]
Zheng, Z.; Han, D.; Xu, G. Chinese and western medicinal disinfection solution with good microbicidal effect for clinical laboratory, and preparation method thereof. Chinese Patent 107913327A, 2018.
[55]
Liu, C. A traditional Chinese medicine composition for treating chronic tonsillitis due to lung and stomach heat excess. Chinese Patent 105250453A. 2016.
[56]
Liu, C. Chinese medicine ointment for treating bedsore and its preparation method. Chinese Patent 105213641A, 2016.
[57]
Li, X. Traditional Chinese medicine powder for the treatment of burn and its preparation method. Chinese Patent 105148065A, 2015.
[58]
Tiwari, N.L. Carctol. Indian Patent 007DE00421A, 2008.
[59]
He, S. External patch for treating otitis media. Chinese Patent 105963623A, 2016.
[60]
Du, M. A composition for treating old ankle sprain traditional Chinese medicine. Chinese Patent 105943748A. 2016.
[61]
Lv, H. Traditional Chinese medicine for treatment of uremia detoxification preparations. Chinese Patent 106880665A, 2017.
[62]
Chen, L. For treating meniere disease of pharmaceutical composition. Chinese Patent 105943716A, 2016.
[63]
Guan, X.; Qiu, R.; Qiu, Y.; Ju, J.; Zhou, L. Pharmaceutical for treating urethritis and preparation method thereof. Chinese Patent 105920340A, 2016.
[64]
Wang, C. Treating thyroid nodules of pharmaceutical composition and preparation method thereof. Chinese Patent 105816553A, 2016.
[65]
Xue, W.; Li, K.; Liang, S.; Li, A.; Yan, Y.; Lv, X. Traditional Chinese medicine for treating acute simple appendicitis and its preparation method. Chinese Patent 105641216A, 2016.
[66]
Gong, C. Chinese medicine for treatment of bladder stones. Chinese Patent 104922526A, 2015.
[67]
Liu, H. A kind of dermatitis repair cream and preparation method thereof. Chinese Patent 108619029A, 2018.
[68]
Zhang, Y. A new Chinese medicine preparation for treating synovitis and preparation method there of. Chinese Patent 106963901A, 2017.
[69]
Wang, Y. A drug for treatment of viral myocarditis. Chinese Patent 105770221A, 2016.
[70]
Wang, J.; Sun, X.; Li, Y. Chinese medicinal composition for treating infective vaginitis and preparation method thereof. Chinese Patent 105412915A, 2016.
[71]
Wang, L. A Chinese medicinal composition for treating pelvic inflammatory disease. Chinese Patent 105056035A, 2015.
[72]
Sun, T. Drug for treating urinary tract infections and preparation method thereof Chinese Patent 104645045A, 2015.
[73]
Liu, H. Dermatitis cream of plant formulation and preparation method thereof. Chinese Patent 108434049A, 2018.
[74]
Uddin, S.J.; Grice, I.D.; Tiralongo, E. Cytotoxic effects of bangladeshi medicinal plant extracts. Evid. Based Complement. Alternat. Med., 2011, 2011578092.
[http://dx.doi.org/10.1093/ecam/nep111] [PMID: 19706693]
[75]
Loganayaki, N.; Manian, S. Antitumor activity of the methanolic extract of Ammannia baccifera L. against Dalton’s ascites lymphoma induced ascitic and solid tumors in mice. J. Ethnopharmacol., 2012, 142(1), 305-309.
[http://dx.doi.org/10.1016/j.jep.2012.05.008] [PMID: 22613234]
[76]
Joanofarc, J.; Sangeeta, J.; Jayakumari, S.; Kumar, S.S.; Gopinadh, B.; Sam, S.K.G. Antipyretic and diuretic activity of Ammania baccifera. Nat. Prod. Sci., 2003, 9, 180-182.
[77]
Simonsen, H.T.; Nordskjold, J.B.; Smitt, U.W.; Nyman, U.; Palpu, P.; Joshi, P.; Varughese, G. In vitro screening of Indian medicinal plants for antiplasmodial activity. J. Ethnopharmacol., 2001, 74(2), 195-204.
[http://dx.doi.org/10.1016/S0378-8741(00)00369-X] [PMID: 11167038]
[78]
Upadhyay, H.C.; Sisodia, B.S.; Agrawal, J.; Pal, A.; Darokar, M.P.; Srivastava, S.K. Antimalarial potential of extracts and isolated compounds from four species of genus Ammannia. Med. Chem. Res., 2014, 23, 870-876.
[http://dx.doi.org/10.1007/s00044-013-0682-5]
[79]
Parekh, J.; Chanda, S. Antibacterial and phytochemical studies on twelve species of Indian medicinal plants. Afr. J. Biomed. Res., 2007, 10, 175-181.
[80]
Dash, S.; Das, C.; Sahoo, D.C.; Sahoo, A.C.; Nayak, D. Preliminary phytochemical studies and antimicrobial activity of leaf of Ammannia baccifera (Linn.). Pharmacologyonline, 2008, 3, 129-132.
[81]
Dhanapal, R.; Kavimani, S.; Matha, V.S.B.; Gupta, M.; Basu, S.K. Antisteroidogenic activity of ethanol extract of Ammania baccifera (L.) whole plant in female albino mice ovaries. Iranian J. Pharmacol. Therapeutics, 2005, 4, 43-45.
[82]
Rajasekaran, A.; Vellaichamy, S.; Darlinquine, S. Evaluation of wound healing activity of Ammannia baccifera and Blepharis maderaspatensis leaf extracts on rats. Rev. Bras. Farmacogn., 2012, 22, 418-427.
[http://dx.doi.org/10.1590/S0102-695X2011005000207]
[83]
Loganayaki, N.; Siddhuraju, P.; Manian, S. Antioxidant, anti-inflammatory and anti-nociceptive effects of Ammannia baccifera L. (Lythracceae), a folklore medicinal plant. J. Ethnopharmacol., 2012, 140(2), 230-233.
[http://dx.doi.org/10.1016/j.jep.2012.01.001] [PMID: 22285520]
[84]
Thakkar, S.M.; Deshmukh, V.K.; Saoji, A.N.; Duragkar, N.J. Chemical examination of Ammannia baccifera Linn. (Lythraceae). J. Indian Chem. Soc., 1986, 63, 619-620.
[85]
Deeseenthum, S.; Tip-pyang, S.; Wattanasirmkit, K.; Phuwapraisirisan, P. Toxic metabolites from Ammannia baccifera. Asian Coordinating Group for Chemistry, 2000, 12, 47-50.
[86]
Upadhyay, H.C.; Thakur, J.P.; Saikia, D.; Srivastava, S.K. Anti-tubercular agents from Ammannia baccifera (Linn.). Med. Chem. Res., 2013, 22, 16-21.
[http://dx.doi.org/10.1007/s00044-012-9998-9]
[87]
Balraj, P.; Nagarajan, S. Flavonol glycosides from three members of the Lythraceae. J. Nat. Prod., 1981, 44, 660-661.
[http://dx.doi.org/10.1021/np50018a004]
[88]
Graham, S.A.; Timmermann, B.N.; Mabry, T.J. Flavonoid glycosides in Ammannia coccinea (Lythraceae). J. Nat. Prod., 1980, 43, 644-645.
[http://dx.doi.org/10.1021/np50011a021]
[89]
Gohar, A.A.; Maatooq, G.T.; Mrawan, E.M.; Zaki, A.A.; Takaya, Y. Two oleananes from Ammannia auriculata Willd. Nat. Prod. Res., 2012, 26(14), 1328-1333.
[http://dx.doi.org/10.1080/14786419.2011.582841] [PMID: 21790491]
[90]
Nawwar, M.A.; Youb, N.A.; El-Raey, M.A.; Zaghloul, S.S.; Hashem, A.M.; Mostafa, E.S.; Eldahshan, O.; Werner, V.; Becker, A.; Haertel, B.; Lindequist, U.; Linscheid, M.W. Polyphenols in Ammania auriculata: structures, antioxidative activity and cytotoxicity. Pharmazie, 2014, 69(11), 860-864.
[PMID: 25985585]
[91]
Nawwar, M.; Ayoub, N.; El-Raey, M.; Zaghloul, S.; Hashem, A.; Mostafa, E.; Eldahshan, O.; Lindequist, U.; Linscheid, M.W. Acylated flavonol diglucosides from Ammania auriculata. Z. Natforsch. C J. Biosci., 2015, 70(1-2), 39-43.
[http://dx.doi.org/10.1515/znc-2014-4165] [PMID: 25854842]
[92]
Upadhyay, H.C.; Verma, R.K.; Srivastava, S.K. Quantitative determination of bioactive 4-hydroxy-α-tetralone, tetralone-4-O-β-D-glucopyranoside and ellagic acid in Ammannia baccifera (Linn.) by reversed-phase high-performance liquid chromatography. J. Chromatogr. Sci., 2013, 51(1), 21-25.
[http://dx.doi.org/10.1093/chromsci/bms099] [PMID: 22700790]
[93]
Upadhyay, H.C.; Verma, R.K.; Srivastava, S.K. A validated LC method for separation and determination of tetralone-4-O-β-D-glucopyranoside and 4-hydroxy-α-tetralone in Ammannia multiflora. Chromatogr. Res. Int., 2012, 2012, 1-4.
[http://dx.doi.org/10.1155/2012/162302]
[94]
Upadhyay, H.C.; Verma, R.K.; Srivastava, S.K. A simple and reliable method for the determination of tetralone-4-O-β-D-glucopyranoside and 4-hydroxy-α-tetralone in three species of Ammannia by reversed-phase HPLC. Curr. Res. Med. Aromat. Plants, 2013, 35(3-4), 136-141.
[95]
Lin, W.Y.; Peng, C.F.; Tsai, I.L.; Chen, J.J.; Cheng, M.J.; Chen, I.S. Antitubercular constituents from the roots of Engelhardia roxburghiana. Planta Med., 2005, 71(2), 171-175.
[http://dx.doi.org/10.1055/s-2005-837786] [PMID: 15729627]
[96]
Upadhyay, H.C.; Jaiswal, N.; Tamrakar, A.K.; Srivastava, A.K.; Gupta, N.; Srivastava, S.K. Antihyperglycemic agents from Ammannia multiflora. Nat. Prod. Commun., 2012, 7(7), 899-900.
[http://dx.doi.org/10.1177/1934578X1200700724] [PMID: 22908576]
[97]
An, T.Y.; Hu, L.H.; Chen, R.M.; Chen, Z.L.; Li, J.; Shen, Q. Anti-diabetes agents-I: tetralone derivative from Juglans regia. Chin. Chem. Lett., 2003, 14(5), 489-490.
[98]
Chan-Bacab, M.J.; Peña-Rodríguez, L.M. Plant natural products with leishmanicidal activity. Nat. Prod. Rep., 2001, 18(6), 674-688.
[http://dx.doi.org/10.1039/b100455g] [PMID: 11820764]
[99]
Fournet, A.; Barrios, A.A.; Muñoz, V.; Hocquemiller, R.; Roblot, F.; Cavé, A. Antileishmanial activity of a tetralone isolated from Ampelocera edentula, a Bolivian plant used as a treatment for cutaneous leishmaniasis. Planta Med., 1994, 60(1), 8-12.
[http://dx.doi.org/10.1055/s-2006-959397] [PMID: 8134421]
[100]
Dwivedi, G.R.; Singh, A.; Upadhyay, H.C.; Pati, S.; Singh, D.P. Determination of drug resistance mechanism(s) of clinical isolates of P. aeruginosa and phytoextract as drug resistance reversal agent. EC Microbiology, 2017, 13(1), 35-41.
[101]
Dwivedi, G.R.; Upadhyay, H.C.; Yadav, D.K.; Singh, V.; Srivastava, S.K.; Khan, F.; Darmwal, N.S.; Darokar, M.P. 4-Hydroxy-α-tetralone and its derivative as drug resistance reversal agents in multi drug resistant Escherichia coli. Chem. Biol. Drug Des., 2014, 83(4), 482-492.
[http://dx.doi.org/10.1111/cbdd.12263] [PMID: 24267788]


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VOLUME: 19
ISSUE: 10
Year: 2019
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DOI: 10.2174/1568026619666190412101047
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