Triterpenic and acyl glycosides from the leaves of Centella asiatica (L.) Urban
محورهای موضوعی : Pharmacognosy
1 - Department of Biochemistry, School of Chemical and Life Sciences, Jamia Hamdard, New Delhi-110 062, India
2 - Phytochemistry Research Laboratory, School of Pharmaceutical Sciences and Research, Jamia Hamdard, New Delhi-110 062, India
کلید واژه: isolation, Acyl glucosides, Leaves, <i>Centella asiatica</i> (L.), Triterpenic glycosides, Structure elucidation,
چکیده مقاله :
Centella asiatica (L.) Urban (Apiaceae) is a small perennial, prostrate herb indigenous to India, south-eastern Asia, United States and Africa. It is used to treat anxiety, asthma, blood circulation, cancer, colds, cough, elephantiasis, epilepsy, fevers, gastrointestinal problems, hepatic, skin and urinary tract diseases, hydrocele, hypertension, hysteria, insomnia, rheumatism, scleroderma, strangury, ulcers and wounds. Plants have an enormous potential for the management and treatment of different kind of illness. The active constituents of this plant induce the healing and regeneration of the lost tissue by multiple mechanisms. Plants gives us phytomedicines and these phytomedicines are not only cheap and affordable but are also safe as hyper sensitive reactions are rarely encountered with the use of these agents. The presence of various life-sustaining constituents in plants has urged scientist to examine these plants with a view to determine potential wound healing properties Phytochemical investigation of a methanolic extract of the leaves resulted in the isolation of five new compounds characterized as urs-12-en-3β-ol-28-oic acid-3-O-β-D-glucopyranosyl-2′- arachidate (ursolic acid glucosidic arachidate (1), urs-12-en-3β-ol-28-oic acid 3-O-β-D-xylopyranosyl-(2′→1′′)-O-β-D- xylopyranoside (ursolic acid 3-O-β-D-dixyloside (3), n-dodecanoyl-O-β-D-glucopyranosyl-(6′→1′′)-O-β-D-glucopyranosyl-(6′′→1′′′)-O-β-D-glucopyranosyl-6′′′→1′′′′)- O-β-D-glucopyranoside (lauroyl tetraglucoside (5), n-octanoyl-O-β-D-glucopyranosyl-(6a→1b)-O-β-D-glucopyranosyl-(6b→1c)-O-β-D-glucopyranosyl-(6c→1d)-O-β-D-glucopyranosyl-(6d→1e)–O-β-D-gluco- pyranoside (caproyl pentaglucoside (6) and ursan-3β-ol-28-al-3-O-α-L-arabinopyranosyl-(2a→1b)-O-α-L-arabinopyranosyl-(2b→1c)-O-α-L-arabinopyranosyl-(2c→1d)-O-α-L-glucopyranosyl-(2d→1e)-O-α-L-glucopyranosyl-(2e→1f)-O-α-L-glucopyranoside (ursolic aldehyde 3-O-α-L-hexaglycoside (7) along with two known phytoconstituents identified as n-decanoyl-O-β-D-glucopyranosyl- (6′→1′′)-O-β-D- glucopyranoside (n-capryl diglucoside (2) and glyceryl 1-decanoyl –2- phosphate (4), The structures of these phytoconstituents have been elucidated on the basis of spectral analysis and chemical reactions.
Aizad, S., Mohd Khairiri, N., Yahaya, B.H., Zubairi, S.I., 2017. A novel anti-proliferative activity (EC50) of pegaga (Centella asiatica) extract through in vitro 3-D culture microenvironment. J. Teknol. 79(2), 1-10.
Ali, M., 2001. Techniques in Terpenoid Identification. Birla Publications, New Delhi, India.
Azis, H.A., Taher, M., Ahmed, A.S., Sulaiman, W.M.A.W., Susanti, D., Chowdhury, S.R., Zakaria, Z.A., 2017. In vitro and In vivo wound healing studies of methanolic fraction of Centella asiatica extract. S. Afr. J. Bot. 108, 163-174.
Aziz, Z.A., Davey. M.R., Power, J.B., Anthony, P., Smith. R.M., Lowe, K.C., 2007. Production of asiaticoside and madecassoside in Centella asiatica in vitro and in vivo. Biol. Plant. 51(1), 34-42.
Brinkhaus, B.，Lindner, M.，Schuppan, D., 2000. Chemical，pharmacological and clinical profile of the East Asian medical plant Centella asiatica. Phytomedicine 7(5), 427-448.
Chong, N.J., Aziz, Z., 2011. A systematic review on the chemical constituents of Centella asiatica. Res. J. Pharm. Biol. Chem. Sci. 2(3), 445-459.
Chopra, R.N., Nayar. S.L., Chopra. I.C., 1986. Glossary of Indian Medicinal Plants (Including the Supplement) New Delhi. Council of Scientific and Industrial Research, New Delhi, India.
Fitrianda, E., Sukandar, E.Y., Elfahmi, Adnyana, I.K., 2017. Antidiabetic activity of extract, fractions, and asiaticoside compound isolated from Centella asiatica Linn. Leaves in alloxan-induced diabetic mice. Asian J. Pharm. Clin. Res. 10(10), 268-272.
Gohil, K.J., Patel, J.A., Gajjar, A.K., 2010. Pharmacological review on Centella asiatica: A potential herbal cure-all. Indian J. Pharm. Sci. 72(5), 546-556.
Hashim, P., Sidek, H., Helan, M.H.M., Sabery, A., Palanisamy. U.D., Ilham, M., 2011. Triterpene composition and bioactivities of Centella asiatica. Molecules 16, 1310-1322.
Idris, F.N., Nadzir, M.M., 2017. Antimicrobial activity of Centella asiatica on Aspergillus niger and Bacillus subtilis, in: Klemes, J.J., Liew, P.Y., Ho, W.S., Lim, J.S. (Eds.), Chemical Engineering Transactions. Italian Association of Chemical Engineering - AIDIC, pp. 1381-1386.
James, J.T., Dubery, I.A., 2009. Pentacyclic triterpenoids from the medicinal herb, Centella asiatica (L.) Urban. Molecules 14, 3922-3941.
Jiang, Z.Y.，Zhang, X.M.，Zhou, J., 2005. New triterpenoid glycosides from Centella asiatica．Helv. Chim. Acta. 88(2), 297-303.
Khan, M.A., Ali, M., Alam, P., 2010. Phytochemical investigation of the fruit peels of Citrus reticulata Blanco, Nat. Prod. Res. 24(7), 610-620.
Kuroda, M., Mimaki, Y., Harada, H., Sakagami, H., Sashida, Y., 2001. Five new triterpene glycosides from Centella asiatica. Nat. Med. 55(3), 134-138.
Machado, R.R.P., Dutra, R.C., Pittella, F., Raposo, N.R.B., Lesche, B., Duarte, R.S., Soares, G.L.G., Kaplan, M.A.C., 2015. Screening antimycobacterial activity of Baccharis dracunculifolia, Centella asiatica, Lantana camara and Pterodon emarginatus. Rev. Bras. Plantas Med. 17(4), 891-899.
Machado, R.R.P., Dutra, R.C., Pittella, F., Raposo, N.R.B., Lesche, B., Duarte, R.S., Soares, G.L.G., Kaplan, M.A.C., 2015. Screening antimycobacterial activity of Baccharis dracunculifolia, Centella asiatica, Lantana camara and Pterodon emarginatus. Rev. Bras. Plantas Med. 17(4), 891-899.
Mahato, S.B., Kundu, A.P., 1994. 13C NMR spectra of pentacyclic compounds-A complication and some salient features. Phytochemistry 37, 1517-1575.
Matsuda, H.，Morikawa, T.，Ueda, H., Yoshikawa M., 2001a. Medicinal foodstuffs．XXVI．Inhibitors of aldose reductase and new triterpene and its oligoglycoside，centellasapogenol A and centellasaponin A，from Centella asiatica （Gotu Kola). Heterocycles 55(8), 1499-1504.
Matsuda, H.， Morikawa, T.，Ueda, H.，Yoshikawa, M., 2001b. Medicinal foodstuffs. XXVII．Saponin constituents of gotu kola (2): structures of new ursane and oleanane type triterpene oligoglycosides，centellasaponins B，C,and D from Centella asiatica cultivated in Sri Lanka．Chem. Pharm. Bull. 49(10), 1368-1371.
Nataraj, J., Manivasagam, T., Justin Thenmozhi, A., Essa, M.M., 2017. Neurotrophic effect of asiatic acid, a triterpene of Centella asiatica against chronic 1-methyl 4-phenyl 1, 2, 3, 6-tetrahydropyridine hydrochloride/probenecid mouse model of Parkinson’s disease: The role of MAPK, PI3K-Akt-GSK3β and mTOR signalling pathways. Neurochem. Res. 42(5), 1354-1365.
Oyedeji, O.A.，Afolayan, A.J., 2005. Chemical composition and antibacterial activity of the essential oil of Centella asiatica growing in South Africa. PharmBiol. 43(3), 249-252.
Panathula, C.S., Mahadev, M.D., Naidu, C.V., 2014. Phytochemical investigation and in vitro antimicrobial activity of Centella asiatica (L.) Urban. A potent antijaundice medicinal plant. Int. J. Phytomedicine 6(2), 195-200.
Park, J.H., Choi, J.Y., Son, D.J., Park, E.K., Song, M.J., Hellström, M., Hong, J.T., 2017. Anti-inflammatory effect of titrated extract of Centella asiatica in phthalic anhydride-induced allergic dermatitis animal model. Int. J. Mol. Sci. 18(4).
Qin, L.P.，Ding, R.X.，Zhang, W.D., 1998. Essential oil from Centella asiatica and its antidepressant activity. Di Er Jun Yi Da Xue Xue Bao. 19(2), 186-187.
Quattrocchi, U., 2012. CRC World Dictionary of Medicinal and Poisonous Plants: Common Names, Scientific Names, Eponyms, Synonyms and Etymology. CRC Press, Boca Raton, Florida.
Shukla, Y.N.，Srivastava, R.，Tripathi, A.K.，Prajapati V., 2000. Characterization of an ursane triterpenoid from Centella asiatica with growth inhibitory activity against Spilarctia obliqua．Pharm. Biol. 38(4), 262-267.
Siddiqui, B.S., Aslam, H., Ali, S.T., Khan, S., Begum, S., 2007. Chemical constituents of Centella asiatica. J. Asian Nat. Prod. Res. 9(4), 407-414.
Singh, S., Gautam, A., Sharma, A., Batra, A., 2010. Centella asiatica (L.): A plant with immense medicinal potential but threatened. Int. J. Pharm. Sci. Rev. Res. 4(2), 9-17.
Sultan, R.A., Mahmood, S.B.Z., Azhar, I., Ahmed, S.W., Mahmood, Z.A., 2014. Biological activities assessment of Centella asiatica (Linn.). J. Herbs Spices Med. Plants 20(3), 319-327.
Wijeweera, P., Arnason, J.T., Koszycki, D., Merali, Z., 2006. Evaluation of anxiolytic properties of Gotukola-(Centella asiatica) extracts and asiaticoside in rat behavioral models. Phytomedicine, 13(9-10), 668-676.
Zainol, M.K.，Abd-Hamid, A.，Yusof, S.，Muse, R., 2003. Antioxidative activity and total phenolic compounds of leaf，root and petiole of four accessions of Centella asiatica （L）Urban．Food Chem. 81(4), 575-581.
Zheng, C.J., Qin, L.P., 2007. Chemical components of Centella asiatica and their bioactivities. J. Chin. Integr. Med. 5(3), 348-351.
Zheng, H.M., Choi, M.J., Kim, J.M., Cha, K.H., Lee, K.W., Park, Y.H., Hong, S.S., Lee, D.H., 2016. Centella asiatica leaf extract protects against indomethacin-induced gastric mucosal injury in rats. J. Med. Food 19(1), 38-46.
