Planta Med 2012; 78(1): 79-81
DOI: 10.1055/s-0031-1280256
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Bioenhancing and Antimycobacterial Agents from Ammannia multiflora

Harish C. Upadhyay1 , Gaurav R. Dwivedi2 , Mahendra P. Darokar2 , Vinita Chaturvedi3 , Santosh K. Srivastava1
  • 1Analytical Chemistry Division, Central Institute of Medicinal and Aromatic Plants, P. O. CIMAP, Lucknow, India
  • 2Molecular and Bioprospection Division, Central Institute of Medicinal and Aromatic Plants, P. O. CIMAP, Lucknow, India
  • 3Drug Target Discovery and Development Division, Central Drug Research Institute, Lucknow, India
Further Information

Publication History

received May 9, 2011 revised August 26, 2011

accepted August 30, 2011

Publication Date:
27 September 2011 (online)

Abstract

The methanolic extract of Ammannia multiflora (Lythraceae) showed significant bioenhancing activity with the antibiotic nalidixic acid. Bioassay-guided fractionation of MeOH extract resulted in the isolation of a novel compound, 2,5-bis-(3,3′-hydroxyaryl)tetrahydrofuran, named as ammaniol (5), along with 9 other known compounds (1–4, 6–10). Furthermore, compound 4-hydroxy-α-tetralone (1) was converted into five semisynthetic acyl derivatives, 1A1E, which were evaluated along with compounds 1, 5, 6, 9, and 10 for their bioenhancing activity in combination with nalidixic acid against the two strains, CA8000 and DH5α, of Escherichia coli. The results showed that the methanolic extract of A. multiflora and compounds 1 and 9 possessed significant bioenhancing activity and reduced the dose of nalidixic acid fourfold while compounds 5, 6, 10 and semisynthetic derivatives 1A1E reduced the dose of nalidixic acid twofold. Compound 5 was also tested for antimycobacterial activity against Mycobacterium H37Rv and was found to show moderate activity (MIC 25 µg/mL) against this pathogen.

Supporting Information

References

  • 1 Stermitz F R, Lorenz P, Tawara J N, Zenewicz L A, Lewis K. Synergy in a medicinal plant: antimicrobial action of berberine potentiated by 5-azpo-methoxyhydrocarpin, a multidrug pump inhibitor.  Proc Natl Acad Sci USA. 2000;  97 1433-1437
  • 2 Huang M, Yin H, Zhang X. A Chinese medicinal composition for the treatment of female infertility. Chin Patent 1110585 1995
  • 3 Zhang L. A Chinese medicinal composition for treating gastroenteropathy. Chin Patent 1965910 2007
  • 4 Joanofarc J, Sangeeta J, Jayakumari S, Kumar S, Sadish, Gopinadh B, Kishore G S S. Antipyretic and diuretic activity of Ammania baccifera.  Nat Prod Sci. 2003;  9 180-182
  • 5 Dash S, Das C, Sahoo D C, Sahoo A C, Nayak D. Preliminary phytochemical studies and antimicrobial activity of leaf of Ammannia baccifera (Linn.).  Pharmacology. 2008;  3 129-132
  • 6 Uddin S J, Grice I D, Tiralongo E. Cytotoxic effects of Bangladeshi medicinal plant extracts.  Evid Based Compl Alt Med. advance online publication 2011;  Article ID 578092, DOI: 10.1093/ecam/nep111
  • 7 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 Therapeut. 2005;  4 43-45
  • 8 Singh S C, Khanuja S P S. Lucknow flora: The plant wealth of the region. Lucknow: CIMAP; 2006: 170
  • 9 Balraj P, Nagarajan S. Flavonol glycosides from three members of the Lythraceae.  J Nat Prod. 1981;  44 660-661
  • 10 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;  74 195-204
  • 11 Khanuja S P S, Arya J S, Srivastava S K, Shasany A K, Santhakumar T R, Darokar M P, Kumar S. Antibiotic pharmaceutical composition with lysergol as bio-enhancer and method of treatment. PCT WO 03080059, US Patent 20030181425, IN Patent 233906 2003
  • 12 Khanuja S P S, Arya J S, Tiruppadiripulivur R S K, Saikia D, Kaur H, Singh M, Gupta S C, Shasany A K, Darokar M P, Srivastava S K, Gupta M M, Verma S C, Pal A. Novel nitrite glycosides useful as a bio-enhancer of drugs and nutrients process of its isolation from Moringa oleifera . US Patent 6858588 2005
  • 13 Khanuja S P S, Srivastava S, Kumar T R S, Gupta M M, Tripathy A K, Singh M, Bahl J R, Lal R K, Darokar M P, Shasany A K, Kumar S. Bioactive hexane fraction from Vetiveria zizanioides . US Patent 6676974 2004
  • 14 Hernandez A, Pascual C, Valverde S. Neo-olivil, a new lignan from Thymus longiflorus.  Phytochemistry. 1981;  20 180-182
  • 15 Schottner M, Reiner J, Tayman F S K. (+)-Neo-olivil from roots of Urtica dioica.  Phytochemistry. 1997;  46 1107-1109
  • 16 Rahman M M A, Dewick P M, Jackson D E, Lucas J A. Lignans from Forsythia intermedia.  Phytochemistry. 1990;  29 1971-1980
  • 17 Calis I, Gazar H A, Piacente S, Pizza C. Secondary metabolites from roots of Astragalus zahlbruckneri.  J Nat Prod. 2001;  64 1179-1182
  • 18 Saxena M, Faridi U, Mishra R, Gupta M M, Darokar M P, Srivastava S K, Singh D, Luqman S, Khanuja S P S. Cytotoxic agents from Terminalia arjuna.  Planta Med. 2007;  73 1486-1490
  • 19 Petersdorf R G, Sherris J C. Methods and significance of in vitro testing of bacterial sensitivity to drugs.  Am J Med. 1965;  39 766-779
  • 20 Jorgensson J H, Turnigde D J, Washington J A. Antibacterial susceptibility tests: dilution and disc diffusion methods. In: Murray P R, editor Manual of clinical microbiology. 7th ed. Washington, DC: American Society of Microbiology; 1995
  • 21 Performance standards for antimicrobial susceptibility testing: ninth informational supplement. Vol. 19. Wayne: National Committee for Clinical Laboratory Standards (NCCLS); 1999: 21
  • 22 Kumar S. Properties of adenyl cyclase and cyclic adenosine 3′,5′-monophosphate receptor protein deficient mutants of Escherichia coli.  J Bacteriol. 1976;  125 545-555
  • 23 McClachy J K. Susceptibility testing of mycobacteria.  Lab Med. 1978;  9 47-52

Santosh K. Srivastava

Analytical Chemistry Department
Central Institute of Medicinal and Aromatic Plants

P. O. CIMAP

Lucknow 226015

India

Phone: +91 52 22 35 96 23

Fax: +91 52 22 34 26 66

Email: santoshkumar_1955@yahoo.com

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