Phytochemical investigation and isolation of new compounds from the stems of Tinospora cordifolia Miers

Document Type: Original Article

Authors

1 Phytochemistry Research Laboratory, Faculty of Pharmacy, Jamia Hamdard, New Delhi- 110062, India

2 College of Pharmacy, Jazan University, Jazan, Saudi Arabia

3 1-F/O PHARMACY, DEPT OF PHARMACOGNOSY, JAMIA HAMDARD UNIVERSITY, NEW DELHI 2-Phytochemistry Research Laboratory, Faculty of Pharmacy, Jamia Hamdard, New Delhi- 110062, India

Abstract

Tinospora cordifolia (Willd.) Miers, (Menispermaceae), a glabrous, deciduous and trailing plant found in tropical India, China, Sri Lanka, Bangladesh and Myanmar. It is used to treat anemia, debility, diabetes, diarrhea, dysentery, dyspepsia, fevers, jaundice, rheumatism, urinary and skin diseases and snake bites. Its air-dried stem powder was exhaustively extracted with methanol. The concentrated methanolic extract was adsorbed on silica gel (60-120 mesh) for the preparation of a slurry. The dried slurry was chromatographed over silica gel column packed in petroleum ether. The column was eluted with petroleum ether, chloroform and methanol successively in order of increasing polarity to isolate a variety of new chemical constituents characterized as trans-cinnamoyl 2-n-hexanyl-7-methoxynaphthyl amide (2), trans-cinnamoyl 2-n- pentanyl- 6,7- dimethoxynaphthyl amide (3), trans-cinnamoyl 2-n-octanyl-7-methoxynaphthyl amide (4), β-D-arabinosyl-O-geranilan-10′-oate (5), 4,5,7-trimethoxy-2-naphthol-2-O-α-L- arabinofuranosyl-(2′→1′′)-O-α-L-arabinopyranosyl-2′′-O-pentane (6), 5,7-dimethoxy-2-naphthol-2-O-α-L-arabinopyranosyl-(2′→1′′)-α-L- arabinopyranosyl-2′′-O-decane (7) and 5-hydroxy-4''-methoxy-7- flavanoxy- (7→7'''')- β-O-labdan-1-en-3''''α,19''''-olide-18''''-oic acid (tinolabdenyl flavanone) (8) along with cetyl alcohol (1). The structures of all the isolated phytoconstituents have been established on the basis of spectral data analysis and chemical reactions.

Graphical Abstract

Phytochemical investigation and isolation of new compounds from the stems of Tinospora cordifolia Miers

Keywords

Main Subjects


Abiramasundari, G., Gowda, C.M.M., Pampapathi, G., Praveen, S., Shivamurugan, S., Vijaykumar, M., Devi, A., Sreepriya, M., 2017. Ethnomedicine based evaluation of osteoprotective properties of Tinospora cordifolia on in vitro and in vivo model systems. Biomed. Pharmacother. 87, 342-354.

Ahmad F., Ali M., Alam P., 2010. New phytoconstituents from the stem bark of Tinospora cordifolia Miers. Nat. Prod. Res. 24(10), 926-934.

Anonymous, 1976. The Wealth of India, a Dictionary of Indian Raw Materials and Industrial Products. Vol. 10, National Institute of Science Communication and Information Resources, CSIR, New Delhi. p. 251.

Anonymous, 2007. Unani Pharmacopoeia of India, Central Council for Research in Unani Medicine, Department of AYUSH, Ministry of Health & Family Welfare, Government of India. Vol. 1, Part 1, p. 30.

Bhatt, R.K., Hanuman, J.B., Sabata, B.K., 1988. A new clerodane derivative from Tinospora cordifolia. Phytochemistry. 27, 1212-1216.

Bhatt, R.K., Sabata, B.K., 1989. Furanoid diterpene glucoside from Tinospora cordifolia. Phytochemistry, 28, 2419-9422.

Biswas, P., Saha, A., Maity, L.N., 2015. Antistress activity of Tinospora cordifolia with application of yoga. Int. J. Ayurvedic Med. 6, 220-224.

Chopra, R.N., 1982. Chopra's Indigenous Drugs of India. 2nd Ed. Calcutta, India, Academic Publishers, 426-428.

Gangan, V.D., Pradhan, P., Sipahimalani, A.T., Banerji, A., 1994. Cordifolisides A, B, C: Norditerpene furan glycosides from Tinospora cordifolia. Phytochemistry. 37, 781-786.

Gangan, V.D., Pradhan, P., Sipahimalani, A.T., Banerji, A., 1995. Norditerpene furan glycosides from Tinospora cordifolia. Phytochemistry. 39, 1139-1142.

Gangan, V.D., Pradhan, P., Sipahimalani, A.T., Banerji, A., 1996. Palmatosides C, F: Diterpene furan glucosides from Tinospora cordifolia- Structural elucidation by 2D NMR spectroscopy. Indian J. Chem. Sec B. 35, 630-634.

Gangan, V.D., Pradhan, P., Sipahimalani, A.T., Bhave, V.G., Patil, K.A., 1997. N--Feruloyltyramine from Tinospora cordifolia. Indian J. Chem. Sec B. 36, 837-849.

Ghosal, S., Vishwakarma, R.A., 1997. Tinocordiside a new rearranged cadinane sesquiterpene glycoside from Tinospora cardifolia. J. Nat. Prod. 60, 839-841.

Hanuman, J.B., Bhatt, R.K., Sabata, B.K., 1986. A diterpenoid furano-lactone from Tinospora cordifolia. Phytochemistry. 25, 1677-1680.

Hanuman, J.B., Bhatt, R.K., Sabata, B.K., 1988. A clerodane furano-diterpene from Tinospora cordifolia. J. Nat. Prod. 51, 197-201.

Khan, M.A., Gray, A.I., Waterman, P.G., 1989. Tinosporaside, an 18-norclerodane glucoside from Tinospora cordifolia. Phytochemistry. 28, 273-275.

Kirtikar, K.R., Basu, B.D., 1975. Indian medicinal plants (2nd Ed., pp. 75-80), Dehradun, India, M/S Bishen Singh & Mahendra Pal Singh.

Maurya, R., Handa, S.S., 1998. Tinocordifolin, a sesquiterpene from Tinospora cordifolia. Phytochemistry. 49, 1343-1346.

Maurya, R., Manhas, L.R., Gupta, P., Mishra, P.K., Singh, G., Yadav, P.P., 2004. Amritosides A, B, C and D: clerodane furano diterpene glucosides from Tinospora cordifolia. Phytochemistry. 65(14), 2051-2055.

Maurya, R., Wazir, V., Tyagi, A., Kapil, R.S. 1996. Cordifoliosides A and B, two new phenylpropene disaccharides from Tinospora cordifolia possessing immunostimulant activity. Nat. Prod. Lett. 8, 7-10.

Maurya, R., Wazir, V., Tyagi, A., Kapil, R.S., 1995. Clerodane diterpenoids from Tinospora cordifolia. Phytochemistry. 38, 559-561.

Pathak, A.K., Agarwal, P.K., Jain, D.C., Sharma, R.P., Howarth, O.W., 1995. NMR studies of 20β-hydroxyecdysone, a steroid isolated from Tinospora cordifolia. Indian J Chem. Sec. B. 34, 674-676.

Pradhan, P., Gangan, V.D., Sipahimalani, A.T., Banerji, A., 1997. Two phytoecdysones from Tinospora cordifolia: Structural assignments by 2D NMR spectroscopy. Indian J. Chem. Sec. B. 36, 958-562.

Quattrocchi, U., 2012. CRC World Dictionary of Medicinal and Poisonous Plants: Common Names, Scientific Names, Eponyms, Synonyms and Etymology. CRC Press, Boca Raton, Florida, p. 3743.

Rong, Q., Xu, M., Dong, Q., Zhang, Y.L., Li, Y.L., Ye, G., Zhao, L., 2016. In vitro and in vivo bactericidal activity of Tinospora sagittata (Oliv.) Gagnep. var. craveniana (S.Y.Hu) Lo and its main effective component, palmatine, against porcine Helicobacter pylori. BMC Complement. Altern. Med. 16, 8.

Sachdeva, H., Sehgal, R., Kaur, S., 2014. Tinospora cordifolia as a protective and immunomodulatory agent in combination with cisplatin against murine visceral leishmaniasis. Exp. Parasitol. 137, 53-65.

Sarma, D.N.K., Khosa, R.L., Sahai, M., 1995. Isolation of Jatrorrhizine from Tinospora cordifolia Roots. Planta Med., 61, 98-99.

Sarma, D.N.K., Padma, P., Khosa, R.L., 1998. Constituents of Tinospora cordifolia root. Fitoterapia. 69, 541-542.

Shah, P.A., Shah, G.B., 2015. Uricosuric activity of Tinospora cordifolia. Bangladesh J. Pharmacol. 10, 884-890.

Sharma, B., Dabur, R., 2016. Protective Effects of Tinospora cordifolia on hepatic and gastrointestinal toxicity induced by chronic and moderate alcoholism. Alcohol Alcohol. 51, 1-10.

Singh, B., Sharma, P., Kumar, A., Chadha, P., Kaur, R., Kaur, A., 2016. Antioxidant and in vivo genoprotective effects of phenolic compounds identified from an endophytic Cladosporium velox and their relationship with its host plant Tinospora cordifolia. J. Ethnopharmacol. 194, 450-456.

Singh, D., Chaudhuri, P.K., 2017. Chemistry and pharmacology of Tinospora cordifolia. Nat. Prod. Commun. 12, 299-308.

Singh, D.P., Awasthi, H., Luqman, S., Singh, S., Mani, D., 2015. Hepatoprotective effect of a polyherbal extract containing Andrographis paniculata, Tinospora cordifolia and Solanum nigrum against paracetamol induced hepatotoxicity. Pharmacogn. Mag. 11, S375-S379.

Singh, S.S., Pandey, S.C., Srivastava, S., Gupta, V.S.B., Patro, B., Ghosh, A.C., 2003. Chemistryand medicinal properties ofTinospora cordifolia (guduchi).Indian J. Pharmacol. 35, 83-91.

Sinha, K., Mishra, N.P., Singh, J., Khanuja, S.P.S., 2004.Tinospora cordifolia(Guduchi), a reservoir plant for therapeutic applications: A review. Indian J. Tradit. Know. 3(3), 257-270.

Sipahimalani, A.T., Noerr, H., Wagner, H., 1994. Phenylpropanoid glycosides and tetrahydrofuranlignan glycosides from the adaptogenic plant drugs Tinospora cordifolia and Drypetes roxburghii. Planta Med. 60, 596-597.

Swaminathan, K., Sinha, U.C., Bhatt, R.K., Sabata, B.K., Tavale, S.S., 1989. Structure of tinosporide, a diterpenoid furanolactone from Tinospora cordifolia Miers. Acta Crystallogr. C. 45, 134-136.

Wazir, V., Maurya, R., Kapil, R.S. 1995. Cordioside, a clerodane furano diterpene glucoside from Tinospora cordifolia. Phytochemistry. 38, 447-449.