Bioactivity of compounds isolated from the leaves of the Lantana camara Linn plant

doi:10.5246/jcps.2019.05.035

Abstract

Abstract:

Two compounds with different bioactivitieswere isolated from the leaves of the Lantana camara Linn plant. Compound 1wastriterpenoid (Lantadene B)(22β-dimethylacroyloxy-3-oxoolean-12-en-28-oic-acid, C₃₅H₅₂O₅), which was isolatedfrom n-hexane fraction and obtained as white solid (amorphous). Compound 2was glycosideflavonoid (5-hydroxy-6,4′-dimethoxyflavon-7-O-glucopyranose, C₂₃H₂₄O₁₁), which was isolated from ethyl acetate and obtained as pale yellow solid (amorphous). Extraction was performed withmaceration method using methanol solvent. Subsequently, fractionation was carried out using n-hexane and ethyl acetate solvents. Isolation and purification of both fractions were conductedusing chromatography method. The structure of the isolated compounds was determined throughspectralanalyses of ultraviolet (UV), infrared (IR), and nuclear magnetic resonance (¹H NMR and ¹³C NMR), distortionless enhancement by polarization transfer (DEPT), heteronuclear multiple bond connectivity (HMBC), heteronuclear single quantum correlation (HSQC), and H-H COSY (¹H-¹H homonuclear correlatedspectroscopy). The cytotoxic activity of compound 1 was tested against MCF-7 breast cancer cellsin vitro using MTT assay (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide), showing very strong cytotoxic activity in inhibiting the growth of MCF-7 breast cancer cells, and the IC₅₀ value was 1.1336 µM. The antioxidant activity of compound 2 was tested using DPPH assay (1,1-diphenyl-2-picrylhydrazyl), showing strong activity in inhibiting free radicals, and its IC₅₀ value was 71.03 mg/L.

Key words: Lantana camara Linn, Lantadene B, Glycosides flavonoid, MCF-7 breast cell cancer, Cytotoxic, Antioxidant activity

CLC Number:

R284

Supporting:

Suryati, Elida Mardiah, Mai Efdi, Kartika MZ, Yuni Mala Sari. Bioactivity of compounds isolated from the leaves of the Lantana camara Linn plant[J]. Journal of Chinese Pharmaceutical Sciences, 2019, 28(5): 360-368.

References

[1] Caesar, P.; Kumar, A.J. Studies on Phytochemical Screening of Leaf Fraction of Lantana camara Linn. J. Pharm. Res. 2016, 10, 304-307.

[2] Alqahtani, A.; Hamid, K.; Kam, A.; Wong, K.H.; Abdelhak, Z.; Razmovski-Naumovski, V.; Chan, K.; Li, K.M.; Groundwater, P.W.; Li, G.Q. The pentacyclic triterpenoids in herbal medicines and their pharmacological activities in diabetes and diabetic complications. Curr. Med. Chem. 2013, 20, 908-931.

[3] Swamy, M.K.; Sinniah, U.R.; Akhtar, M.S. In vitro pharmacological activities and GC-MS analysis of different solvent extracts of lantana camara leaves collected from tropical region of malaysia. Evid. Based Complement. Alternat. Med. 2015, 2015, 506413.

[4] Suryati, A.; Santoni, K.; Aziz, M.Z.H. Antioxidant activity and total phenolic contentof ethyl acetate extract and fractions of Lantana camara L. leaf. Der Pharma. Chemica. 2016, 8, 92-96.

[5] Ediruslan, Y.; Manjang, Suryati, H.. Structure elucidation of brine shrimp toxic compound from Lantana camara L. leaves. J. Chem. Pharm. Res. 2015, 7, 250-255.

[6] Mariajancyrani.; Chandramohan.; Ravikumar. Terpenes and Antimicrobial Activity from Lantana Camara Leaves. Res. J. Recent Sci. 2014, 3, 52-55.

[7] Rajashekar, Y.; Vijay Kumar, H.; Ravindra, K.V.; Bakthavatsalam, N. Isolation and characterization of biofumigant from leaves of Lantana camara for control of stored grain insect pests. Ind. Crops Prod. 2013, 51, 224-228.

[8] Fatope, M.O.; Salihu, L.; Asante, S.K.; Takeda, Y. Larvicidal activity of extracts and triterpenoids from lantana camara. Pharm. Biol. 2002, 40, 564-567.

[9] Nascimento, A.M.; de Souza, L.M.; Baggio, C.H.; de P Werner, M.F.; Maria-Ferreira, D.; da Silva, L.M.; Sassaki, G.L.; Gorin, P.A.J.; Iacomini, M.; Cipriani, T.R. Gastroprotective effect and structure of a rhamnogalacturonan from Acmella oleracea. Phytochemistry. 2013, 85, 137-142.

[10] Kazmi, I.; Afzal, M.; Ali, B.; Damanhouri, Z.A.; Ahmaol, A.; Anwar, F. Anxiolytic potential of ursolic acid derivative: A stearoyl glucoside isolated from Lantana camara L. (Verbanaceae). Asian Pac. J. Trop. Med. 2013, 6, 433-437.

[11] Kalita, S.; Kumar, G.; Karthik, L.; Rao, K.V.B. In vitro antioxidant and DNA damage inhibition activity of aqueous extract of Lantana camara L. (Verbenaceae) leaves. Asian Pac. J. Trop. Biomed. 2012, 2, S1675-S1679.

[12] Abou El-Kassem, L.T.; Mohammed, R.S.; El Souda, S.S.; El-Anssary, A.A.; Hawas, U.W.; Mohmoud, K.; Farrag, A.R. Digalacturonide flavones from Egyptian Lantana camara flowers with in vitro antioxidant and in vivo hepatoprotective activities. Z. Naturforsch. C. 2012, 67, 381-390.

[13] Kalita, S.; Kumar, G.; Karthik, L.; Venkata, K.; Rao, B. Phytochemical Composition and In Vitro Hemolytic Activity of Lantana Camara L. (Verbenaceae) Leaves. Pharmacologyonline. 2011, 1, 59-67.

[14] Begum, S.; Zehra, S.Q.; Siddiqui, B.S.; Fayyaz, S.; Ramzan, M. Pentacyclic triterpenoids from the aerial parts of Lantana camara and their nematicidal activity. Chem. Biodivers. 2008, 5, 1856-1866.

[15] Sharma, P.; Bansal, M.; Singh, J.; Sharma, M. Lantadene A-induced apoptosis in human leukemia HL-60 cells. Indian J. Pharmacol. 2007, 39, 140.

[16] O’Neill, M.J.; Lewis, J.A.; Noble, H.M.; Holland, S.; Mansat, C.; Farthing, J.E.; Foster, G.; Noble, D.; Lane, S.J.; Sidebottom, P.J.; Lynn, S.M.; Hayes, M.V.; Dix, C.J. Isolation of translactone-containing triterpenes with thrombin inhibitory activities from the leaves of Lantana camara. J. Nat. Prod. 1998, 61, 1328-1331.

[17] Kartika, S.; Mai Efd, M.Z. A Triterpenoid from The Leaves of Tahi Ayam (Lantana camara Linn). Indonesian J. Fundamental. Applied Chem. 2018, 740.

[18] Abdjul, D.B.; Yamazaki, H.; Maarisit, W.; Rotinsulu, H.; Wewengkang, D.S.; Sumilat, D.A.; Kapojos, M.M.; Losung, F.; Ukai, K.; Namikoshi, M. Oleanane triterpenes with protein tyrosine phosphatase 1B inhibitory activity from aerial parts of Lantana camara collected in Indonesia and Japan. Phytochemistry. 2017, 144, 106-112.

[19] Nugroho, A.; Heryani, H.; Choi, J.S.; Park, H.J. Identification and quantification of flavonoids in Carica papaya leaf and peroxynitrite-scavenging activity. Asian Pac. J. Trop. Biomed. 2017, 7, 208-213.

[20] Saxena, D.J.S.M. Bioactive compound from leaves part of Lantana camara. World J. Pharmaceutical Res. 2014, 3, 693-697.