GARDINERIN, A BIOLOGICALLY ACTIVE ACETOGENIN FROM THE SRI LANKAN GONIOTHALAMUS GARDINERI HOOK. F. AND THOMSON

Authors

  • Aruna J. Weerasinghe University of Peradeniya
  • Anura Wickramasinghe Department of Chemistry, University of Peradeniya, Peradeniya, Sri Lanka
  • Gavin Carr University of Peradeniya
  • David Williams University of Peradeniya
  • Raymond Andersen University of Peradeniya
  • Veranja Karunaratne University of Peradeniya

Keywords:

Gardinerin, New acetogenin, Goniothalamus gardineri, Annonaceae, Antioxidant activity, Cytotoxicity, Mosquitolarvicidal activity

Abstract

Objective: The study was undertaken to isolate biologically active compounds from Goniothalamus gardineri, a plant endemic to Sri Lanka.

Methods: Roots and flowers of Goniothalamus gardineri were extracted into dichloromethane and methanol. A new acetogenin, gardinerin isolated by column chromatography of the dichloromethane extract was structurally characterized using NMR and Mass spectroscopies. It was found to be mosquito larvicidal (against 2nd instar larvae of Aedes aegypti), cytotoxic (in the brine shrimp assay) and antioxidant (DPPH assay).

Results: Gardinerin exhibited potent mosquitolarvicidal activity (LC50 = 0.0744±0.37 ppm.), cytotoxicity (LC50 = 1.5±0.37 ppm) and antioxidant activity (IC50 =10.02±0.01 ppm). The same extract furnished (5R)-goniothalamin. The hexane extract of the flowers of G. gardineri yielded poriferesterol and stigmast-4, 22-dien-3-one.

Conclusion: The endemic plant G. gardineri has yielded an acetogenin possessing highly potent antioxidant, cytotoxic and mosquitolarvicidal activity.

 

Downloads

Download data is not yet available.

References

Orange A, Wolseley P, Karunaratne V, Bombuwela K. Two leprarioid lichens new to Sri Lanka. Bibl Lichenol 2001;78:327-33.

Jayalal RGU, Wolseley PA, Gueidan C, Aptroot A, Wijesundara DSA, Karunaratne V. Anzia mahaeliyensis and Anzia flavotenuis, two new species from Sri Lanka. Lichenol 2012;44:381-9.

Bandara BMR, Fernando IHS, Hewage CM, Karunaratne V, Adikaram NKB, Wijesundara DSA. Antifungal activity of some medicinal plants of Sri Lanka. J Natl Sci Counc Sri Lanka 1989;17:1-13.

Bandara BMR, Hewage CM, Jayammane L, Karunaratne V, Bandara KANP, Adikaram NKB, et al. Biological activity of some steam distillates from leaves of ten species of Rutaceous plants. J Natl Sci Counc Sri Lanka 1990;18:71.

Hewage CM, Bandara KANP, Karunaratne V, Bandara BMR, Wijesundara DSA. Insecticidal activity of some medicinal plants of Sri Lanka. J Natl Sci Counc Sri Lanka 1997;25:141-50.

Hewage CM, Bandara BMR, Karunaratne V, Wannigama GP, Pinto MRM, Wijesundara DSA. Antibacterial activity of some medicinal plants of Sri Lanka. J Natl Sci Counc Sri Lanka 1998;26:27–34.

Bandara BMR, Cortez D, Jayasinghe L, Karunaratne V, Wannigama GP, Sotheeswaran S. Aphorphine alkaloids from Litsea gardineri and Actinodaphne speciosa. Planta Med 1989;55:393.

Bandara BMR, Jayasinghe L, Karunaratne V, Wannigama GP, Bokel M, Kraus W. Isolation of pheanthine from Cyclea burmanai. Planta Med 1990;56:245.

Gunatilaka AAL, Dhanabalasingham B, Karunaratne V, Kikuchi T, Tezuka Y. Studies on terpenoids and steroids. Part 27. Structure of a D: A-Friedo-oleanane Triterpenoid from Salacia reticulata and revision of the structure of kokoonol, kokzeylanol series of triterpenoids. Tetrahedron 1993;49:10397.

Tezuka Y, Kikuchi T, Dhanabalasingham B, Karunaratne V, Gunatilaka AAL. Studies on terpenoids and steroids, 25. Complete 1H-and 13C-Nmr spectral assignments of salaciquinone, a New 7-Oxo-quinonemethide Dinortri-terpenoid. J Nat Prod 1994;57:270–6.

Kathirgamanathar S, Ratnasooriya WD, Baekstrom P, Andersen RJ, Karunaratne V. Chemistry and bioactivity of physciaceae lichens pyxine consocians and Heterodermia leucomelos. Pharm Biol 2006;44:217-20.

Thadhani VM, Choudhary MI, Ali S, Omar I, Siddique H, Karunaratne V. Antioxidant activity of some lichen metabolites. Nat Prod Res 2011;25:1827-37.

Thadhani VM, Choudhary MI, Khan S, Karunaratne V. Antimicrobial and toxicological activities of some depsides and depsidones. J Natl Sci Foundation 2012;40:43-8.

Karunaratne V, Hoveyda HR, Orvig C. General method for the synthesis of trishydroxamic acids. Tetrahedron Lett 1992;33:1827-30.

Kumar V, Karunaratne V, Meegalle MRSK. 1-[2′,4′-Dihydroxy-3′,5′-di-(3″-methylbut-2″-enyl)-6′-methoxy] phenylethanone from Acronychia pedunculata root bark. Phytochem 1989;28: 1278–9.

Ratnayake Bandara BM, Hewage CM, Karunaratne V, Adikaram NKB. Methyl ester of para-coumaric acid: antifungal principle of the rhizome of Costus speciosus. Planta Med 1988;54:477-8.

Yu D-Q. Recent works on anti-tumor constituents from Annonaceae plants in china. Pure Appl Chem 1999;71:1119-22.

Piers E, Karunaratne V. Conjugate addition of lithium phenylthio-and Cyano-[2-(4-chlorobut-l-enyl) cuprate to cyclic enones. An efficient methylenecylcopentane annulation process. J Chem Soc Chem Commun 1983;17:935-6.

Piers E, Karunaratne V. Methylenecyclopentane annulation: a synthesis of the sesquiterpenoid (±)-Pentalenene. J Chem Soc Chem Commun 1984;15:959-60.

Saunders RMK. The genus Goniothalamus (Annonaceae) in Sumatra. Bot J Linn Soc 2002;139:225-54.

Dassanayake MD. A revised handbook to the flora of ceylon. Oxford and IBH Publishing Co. Pvt. Ltd., New Delhi; 1996. p. 131-2.

Ahmad FB, Tukol WA, Omar S, Sharif AM. 5-Acetyl goniothalamin, a styryl dihydropyrone from Goniothalamus uvaroides. Phytochem 1999;30:2430-1.

Colegate SM, Din LB, Latiff A, Mat Salleh K, Samsudin MW, Skelton BW, et al. (+)-Isoaltholactone: a furanopyrone isolated from Goniothalamus species. Phytochem 1990;29:1701-4.

Oberlis NH, Chang CJ, McLaughlin JL. Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells. J Med Chem 1997;40:2102-6.

Mootoo BS, Ali A, Khan A, Reynolds WF, McLean S. Three novel monotetra hydrofuran annonaceous acetogenins from annona montana. J Nat Prod 2000;63:807–11.

Huneck S, Yoshimura I. Identification of lichen substances, Springer, Berlin; 1996. p. 394.

Slatkin DJ, Knapp JE, Schiff Jr JL. Steroids of cannabis sativa root. Phytochem 1975;14:580–1.

Bandara KA, Jacobsson U, Kumar V, Molleyres L-P. Insecticidal piperidine alkaloid from Microcos paniculata stem bark. Phytochem 2000;54:29-32.

Mayer BN, Ferrigni NR, Putnam JE, Jacobsen LB, Nichols DE, Mclaughlin JL. Brine shrimp: a convenient bioassay for active plant constituents. Planta Med 1982;45:31-4.

Hoye TR, Zhuang ZP. Validation of the 1H NMR chemical shift method for determination of stereochemistry in the Bistetrahydrofuranyl moiety of Uvaricin-related acetogenins from annonaceae: rilliniastatin 1 (and Asimicin). J Org Chem 1998;53:5578-80.

Jiang Z, Chen Y, Chen RR, Yu D-Q. Mono-tetrahydrofuran ring acetogenins from Goniothalamus donnaiensis. Phytochem 1997;46:327-31.

Published

01-09-2015

How to Cite

Weerasinghe, A. J., A. Wickramasinghe, G. Carr, D. Williams, R. Andersen, and V. Karunaratne. “GARDINERIN, A BIOLOGICALLY ACTIVE ACETOGENIN FROM THE SRI LANKAN GONIOTHALAMUS GARDINERI HOOK. F. AND THOMSON”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 7, no. 9, Sept. 2015, pp. 459-61, https://journals.innovareacademics.in/index.php/ijpps/article/view/7174.

Issue

Section

Original Article(s)