Secondary Metabolites from the leaves and stems of Leonotis nepetifolia (Lamiaceae)

doi.org/10.26538/tjnpr/v2i6.7

Authors

  • Yomica Powder-George Department of Chemistry, The University of the West Indies, St. Augustine, Trinidad and Tobago.

Keywords:

Leonotis nepetifolia,, Shandilay,, Lamiaceae,, Isolation,, Structure elucidation,, Trinidad

Abstract

Leonotis nepetifolia (L.) R. Br. (Lamiaceae), commonly known as ‘Shandilay’, is well-known and widely used in Trinidadian ethnomedicine as well as in different countries for the treatment of various ailments. Biological activities for the plant and many phytoconstituents have been reported; however, the plant species located in Trinidad is yet to be investigated for its chemical
constituents. This study was conducted to investigate the secondary metabolites that may be responsible for the observed traditional medicinal uses of the plant. A phytochemical investigation of the chloroform and 1-butanol fractions of the crude methanol extract of the leaves and stems from L. nepetifolia resulted in the isolation of 7 compounds which were identified as Stigmasterol3-O-β-D-glucoside (1), trans-caffeic acid (2), trans-p-coumaric acid (3), Apigenin-7-O-β-Dglucoside (4), Uridine (5), Luteolin-7-O-β-D-glucoside (6) and Adenosine (7). Isolation of the seven compounds was performed by a combination of silica gel column chromatography and size exclusion column chromatography on Sephadex® LH-20. The chemical structures of these compounds were determined by comprehensive analyses of their 1H and 13C NMR, COSY, HSQC, and HMBC spectroscopic data, and HREIMS mass spectrometric data, as well as comparison of spectral data with that reported in the literature. To the best of the author’s knowledge, this is the
first report on the isolation of compounds 1–7 from L. nepetifolia, compounds 1-3 and 5 from the genus Leonotis and compound 7 from the Lamiaceae family. These reported bioactive constituents might be responsible for some of the observed biological activities of the plant Leonotis nepetifolia.

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References

Dhawan NG, Khan AS, Srivastava P. A general appraisal of Leonotis nepetifolia (L) R. Br: an essential medicinal plant. Bull Env Pharmacol Life Sci. 2013; 2(8):118-121.

Veerabadran U, Venkatraman A, Souprayane A, Narayanasamy M, Perumal D, Elumalai S, Sivalingam S, Devaraj V, Perumal A. Evaluation of antioxidant potential of leaves of Leonotis nepetifolia and its inhibitory effect on MCF7 and Hep2 cancer cell lines. Asian Pac J Trop Dis.

; 3(2):103-110.

Ueda F, Iizuka K, Tago K, Narukawa Y, Kiuchi F, Kasahara T, Tamura H, Funakoshi-Tago M. Nepetaefuran and leonotinin isolated from Leonotis nepetaefolia R. Br. potently inhibit the LPS signaling pathway by suppressing

the transactivation of NF-κB. Int Immunopharmacol. 2015; 28(2):967-976.

Imran S, Suradkar SS, Koche DK. Phytochemical analysis of Leonotis nepetifolia (L) R. BR. A wild medicinal plant of Lamiaceae. Biosci Discov. 2012; 3(2):196-197.

Takeda T, Narukawa Y, Hada N. Studies on the constituents of Leonotis nepetaefolia. Chem Pharm Bull. 1999; 47(2):284-286.

Clement YN, Baksh-Comeau YS, Seaforth CE. An ethnobotanical survey of medicinal plants in Trinidad. J Ethnobiol Ethnomed. 2015; 11(1):67.

Clement YN, Morton-Gittens J, Basdeo L, Blades A, Francis MJ, Gomes N, Janjua M, Singh A. Perceived efficacy of herbal remedies by users accessing primary healthcare in Trinidad. BMC Complement Altern Med. 2007; 7(1):4.

Lans C. Ethnomedicines used in Trinidad and Tobago for reproductive problems. J Ethnobiol Ethnomed. 2007; 3(1):13.

Clement YN, Williams AF, Aranda D, Chase R, Watson N, Mohammed R, Stubbs O, Williamson D. Medicinal herb use among asthmatic patients attending a specialty care facility in Trinidad. BMC Complement Altern Med. 2005; 5(1):3.

Mahabir D, Gulliford MC. Use of medicinal plants for diabetes in Trinidad and Tobago. Rev Panam Salud Pública. 1997; 1(3):174-179.

Li J, Fronczek FR, Ferreira D, Burandt Jr CL, Setola V, Roth BL, Zjawiony JK. Bis-spirolabdane Diterpenoids from Leonotis nepetaefolia. J Nat Prod. 2012; 75(4):728-734.

Bagby MO, Smith Jr CR, Wolff IA. Laballenic Acid. A New Allenic Acid from Leonotis nepetaefolia Seed Oil1. J Org Chem. 1965; 30(12):4227-4229.

Purushothaman KK, Vasanth S, Connolly JD, Labbé C. 4, 6, 7-Trimethoxy-5-methylchromen-2-one, a new coumarin from Leonotis nepetaefolia. J Chem Soc Perkin Trans 1. 1976; (23):2594-2595.

Williams AF, Clement YN, Nayak SB, Rao AV. Leonotis nepetifolia Protects against Acetaminophen-Induced Hepatotoxicity: Histological Studies and the Role of Antioxidant Enzymes. Nat Prod Chem Res. 2016; 4(222):2.

Parra-Delgado H, García Ruiz G, Nieto Camacho A, Martínez-Vázquez M. Anti-inflammatory activity of some extracts and isolates from Leonotis nepetaefolia on TPAinduced edema model. Rev Soc Quím Méx. 2004; 48(4):293-295.

Oliveira DM, Melo FG, Balogun SO, Flach A, de Souza EC, de Souza GP, Rocha ID, da Costa LA, Soares IM, da Silva LI, Ascêncio SD. Antibacterial mode of action of the hydroethanolic extract of Leonotis nepetifolia (L.) R. Br. involves bacterial membrane perturbations. J

Ethnopharmacol. 2015; 172:356-363.

Oliveira AP, Guimarães AL, Pacheco AG, Araújo CS, Oliveira Júnior RG, Lavor ÉM, Silva MG, Araújo EC, Mendes RL, Rolim LA, Costa MP. Phytochemical study on antimicrobial and cytotoxic activity of specimens of Leonotis nepetifolia LR (Br). Quím Nova. 2016; 39(1):32-37.

Ayanwuyi LO, Kwanashie HO, Hussaini IM, Yaro AH. Preliminary studies on the behavioural effects of the methanol extract of Leonotis nepetifolia Linn stem in mice. Afr J Tradit Complement Altern Med. 2016; 13(4):15-21.

Ridhay A, Noor A, Soekamto NH, Harlim T, van Altena I. A stigmasterol glycoside from the root wood of Melochia Umbellata (Houtt) Stapf var. degrabrata K. Indones J Chem. 2012; 12(1):100-103.

Jeong CH, Jeong HR, Choi GN, Kim DO, Lee UK, Heo HJ. Neuroprotective and anti-oxidant effects of caffeic acid isolated from Erigeron annuus leaf. Chin Med. 2011; 6(1):25.

Ashour A, Amer M, Marzouk A, Shimizu K, Kondo R, ElSharkawy S. Corncobs as a potential source of functional chemicals. Molecules. 2013; 18(11):13823-13830.22. Yassa N, Saeidnia S, Pirouzi R, Akbaripour M, Shafiee A. Three phenolic glycosides and immunological properties of Achillea millefolium from Iran, population of Golestan. Daru. 2007; 15(1):49-52.

Pouchert CJ. Aldrich Library of 13C and 1H FT-NMR Spectra; Aldrich Chemical: Milwaukee, WI; 1995. Vol. III, 370-371 p.

Chiruvella KK, Mohammed A, Dampuri G, Ghanta RG, Raghavan SC. Phytochemical and antimicrobial studies of methyl angolensate and luteolin-7-O-glucoside isolated from callus cultures of Soymida febrifuga. Int. J Biomed Sci: IJBS. 2007; 3(4):269.

Ciuffreda P, Casati S, Manzocchi A. Complete 1H and 13C NMR spectral assignment of α‐ and β‐adenosine, 2′‐deoxyadenosine and their acetate derivatives. Magn Reson Chem. 2007; 45(9):781-784.

Wink M. Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochem. 2003; 64(1):3-19.

Sampaio BL, Edrada-Ebel R, Da Costa FB. Effect of the environment on the secondary metabolic profile of Tithonia diversifolia: a model for environmental metabolomics of plants. Sci Rep. 2016; 6:29265.

Tang R, Chen K, Cosentino M, Lee KH. Apigenin-7-O-β-Dglucopyranoside, an anti-HIV principle from Kummerowia striata. Bioorg Med Chem Lett. 1994; 4(3): 455-458.

Luceri C, Giannini L, Lodovici M, Antonucci E, Abbate R, Masini E, Dolara P. p-Coumaric acid, a common dietary phenol, inhibits platelet activity in vitro and in vivo. Br J Nutr. 2007; 97(3):458-463.

Chutvirasakul B. Stability-Indicating Method to Determine Bioactive Nucleosides in Crude Drugs, Extracts, and products from Cordyceps Sinensis and Cordyceps Militaris. Thai J Pharm Sci. 2017; 41(2):52-60

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Published

2018-06-01

How to Cite

Powder-George, Y. (2018). Secondary Metabolites from the leaves and stems of Leonotis nepetifolia (Lamiaceae): doi.org/10.26538/tjnpr/v2i6.7. Tropical Journal of Natural Product Research (TJNPR), 2(6), 293–296. Retrieved from https://tjnpr.org/index.php/home/article/view/610