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Diterpenes from the latex of Euphorbia nivulia
Biochemical Systematics and Ecology 31 (2003) 447–449 www.elsevier.com/locate/biochemsyseco
Diterpenes from the latex of Euphorbia nivulia V. Ravikanth, V.L. Niranjan Reddy, A. Vijender Reddy, P.V. Diwan, Y. Venkateswarlu ∗ Natural Product Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India Received 9 August 2001; accepted 27 June 2002
Keywords: Euphorbia nivulia; Euphorbiaceae; Diterpenes
1. Subject and source Euphorbia nivulia Buch.-Ham. (Euphorbiaceae) is a small tree which grows in the state of Andhra Pradesh, India. The latex of E. nivulia was collected from Bhadrachalam Forest, Andhra Pradesh in December 1999. The plant was identified by Professor M. Prabhakar, Plant Anatomy and Taxonomy Laboratory, Department of Botany, Osmania University, Hyderabad. A voucher specimen of the same is deposited in the Osmania University Herbarium (HY) with AC No. 001662. 2. Previous work Several cycloartane triterpenes derivatives have been reported from this plant (Satynarayana et al., 1991, 1992; Rao et al., 1986). 3. Present study The latex (1.5 kg) was dried in a vacuum oven at 35 °C and the thus obtained powder of E. nivulia was extracted with methanol (3×1 litre) at room temperature. ∗
Corresponding author. Tel.: +91-40-7193167; fax: +91-40-7173757. E-mail address: [email protected] (Y. Venkateswarlu).
0305-1978/03/$ - see front matter 2002 Elsevier Science Ltd. All rights reserved. doi:10.1016/S0305-1978(02)00174-6
448
V. Ravikanth et al. / Biochemical Systematics and Ecology 31 (2003) 447–449
The combined extract was concentrated and obtained crude gummy substance (18 g) subjected to column chromatography over silica gel to afford three ingol diterpenes 3,12-O-diacetyl-7-O-angeloyl-8-methoxyingol 1 (2.5 g), 3,7,12-O-triacetyl-8-O-benzoylingol 2 (110 mg) and 7-O-angeloyl-8-methoxy-12-O-acetylingol 3 (30 mg). The physical and spectral (IR, 1H, 13C and MS) properties of these compounds were found to be identical to those reported earlier (Lin and Kinghorn, 1983; Connolly et al., 1984). This is the first of the isolation of these compounds from E. nivulia. The 13CNMR data of compound 1, not hitherto reported earlier, is given here.
13
C Data of compound 1: (CDCl3, 50 MHz): 31.4 (C-1), 29.4 (C-2), 76.6 (C-3), 73.4 (C-4), 116.9 (C-5), 138.4 (C-6), 74.0 (C-7), 78.6 (C-8), 27.31(C-9), 19.3 (C10), 30.5 (C-11), 71.0 (C-12), 42.9 (C-13), 207.5 (C-14), 71.04 (C-15), 16.47 (C16), 17.6 (C-17), 29.2 (C-18), 16.9 (C-19), 13.29 (C-20), 170.6 (3-CO-CH3), 20.9 (3-CO-CH3), 170.3 (12-CO-CH3), 20.3 (12-CO-CH3), 56.3 (OMe), 166.6 (C-1⬘), 127.6 (C-2⬘), 138.4 (C-3⬘), 15.7 (C-4⬘), 20.4 (C-5⬘).
4. Chemotaxonomic significance These ingol diterpenes (1), (2) and (3) may be useful as taxonomic markers of this plant. This plant seems to be a rich source when compared to those reported in other plants (Lin and Kinghorn, 1983; Connolly et al., 1984; Opferkuch and Hecker, 1973; Abo and Evans, 1981).
Acknowledgements We are grateful to the director, IICT and Dr. J.S. Yadav for their encouragement. V.R., V.L.N.R. and A.V.R. are thankful to C.S.I.R and U.G.C. for fellowships.
V. Ravikanth et al. / Biochemical Systematics and Ecology 31 (2003) 447–449
449
References Abo, K.A., Evans, F.J., 1981. Planta Med. 43, 392. Connolly, J.D., Fakunle, C.O., Rycroft, D.S., 1984. Tetrahedron Lett. 25 (34), 3773. Lin, L-J., Kinghorn, A.D., 1983. Phytochemistry 22 (12), 2795. Opferkuch, H.J., Hecker, E., 1973. Tetrahedron Lett., 3611. Rao, L.K., Ramaraj, K.S., Nath, R.A., Rao, S.R.P.V.T., Sundararamaiah, T., 1986. Phytochemistry 25 (1), 277. Satyanarayana, V., Krupadanam, G.L.D., Srimannarayana, G., 1991. Ind. J. Chem. Sect. B 30, 989. Satyanarayana, V., Krupadanam, G.L.D., Srimannarayana, G., 1992. Fitoterapia 63, 82.
Diterpenes from the latex of Euphorbia nivulia V. Ravikanth, V.L. Niranjan Reddy, A. Vijender Reddy, P.V. Diwan, Y. Venkateswarlu ∗ Natural Product Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India Received 9 August 2001; accepted 27 June 2002
Keywords: Euphorbia nivulia; Euphorbiaceae; Diterpenes
1. Subject and source Euphorbia nivulia Buch.-Ham. (Euphorbiaceae) is a small tree which grows in the state of Andhra Pradesh, India. The latex of E. nivulia was collected from Bhadrachalam Forest, Andhra Pradesh in December 1999. The plant was identified by Professor M. Prabhakar, Plant Anatomy and Taxonomy Laboratory, Department of Botany, Osmania University, Hyderabad. A voucher specimen of the same is deposited in the Osmania University Herbarium (HY) with AC No. 001662. 2. Previous work Several cycloartane triterpenes derivatives have been reported from this plant (Satynarayana et al., 1991, 1992; Rao et al., 1986). 3. Present study The latex (1.5 kg) was dried in a vacuum oven at 35 °C and the thus obtained powder of E. nivulia was extracted with methanol (3×1 litre) at room temperature. ∗
Corresponding author. Tel.: +91-40-7193167; fax: +91-40-7173757. E-mail address: [email protected] (Y. Venkateswarlu).
0305-1978/03/$ - see front matter 2002 Elsevier Science Ltd. All rights reserved. doi:10.1016/S0305-1978(02)00174-6
448
V. Ravikanth et al. / Biochemical Systematics and Ecology 31 (2003) 447–449
The combined extract was concentrated and obtained crude gummy substance (18 g) subjected to column chromatography over silica gel to afford three ingol diterpenes 3,12-O-diacetyl-7-O-angeloyl-8-methoxyingol 1 (2.5 g), 3,7,12-O-triacetyl-8-O-benzoylingol 2 (110 mg) and 7-O-angeloyl-8-methoxy-12-O-acetylingol 3 (30 mg). The physical and spectral (IR, 1H, 13C and MS) properties of these compounds were found to be identical to those reported earlier (Lin and Kinghorn, 1983; Connolly et al., 1984). This is the first of the isolation of these compounds from E. nivulia. The 13CNMR data of compound 1, not hitherto reported earlier, is given here.
13
C Data of compound 1: (CDCl3, 50 MHz): 31.4 (C-1), 29.4 (C-2), 76.6 (C-3), 73.4 (C-4), 116.9 (C-5), 138.4 (C-6), 74.0 (C-7), 78.6 (C-8), 27.31(C-9), 19.3 (C10), 30.5 (C-11), 71.0 (C-12), 42.9 (C-13), 207.5 (C-14), 71.04 (C-15), 16.47 (C16), 17.6 (C-17), 29.2 (C-18), 16.9 (C-19), 13.29 (C-20), 170.6 (3-CO-CH3), 20.9 (3-CO-CH3), 170.3 (12-CO-CH3), 20.3 (12-CO-CH3), 56.3 (OMe), 166.6 (C-1⬘), 127.6 (C-2⬘), 138.4 (C-3⬘), 15.7 (C-4⬘), 20.4 (C-5⬘).
4. Chemotaxonomic significance These ingol diterpenes (1), (2) and (3) may be useful as taxonomic markers of this plant. This plant seems to be a rich source when compared to those reported in other plants (Lin and Kinghorn, 1983; Connolly et al., 1984; Opferkuch and Hecker, 1973; Abo and Evans, 1981).
Acknowledgements We are grateful to the director, IICT and Dr. J.S. Yadav for their encouragement. V.R., V.L.N.R. and A.V.R. are thankful to C.S.I.R and U.G.C. for fellowships.
V. Ravikanth et al. / Biochemical Systematics and Ecology 31 (2003) 447–449
449
References Abo, K.A., Evans, F.J., 1981. Planta Med. 43, 392. Connolly, J.D., Fakunle, C.O., Rycroft, D.S., 1984. Tetrahedron Lett. 25 (34), 3773. Lin, L-J., Kinghorn, A.D., 1983. Phytochemistry 22 (12), 2795. Opferkuch, H.J., Hecker, E., 1973. Tetrahedron Lett., 3611. Rao, L.K., Ramaraj, K.S., Nath, R.A., Rao, S.R.P.V.T., Sundararamaiah, T., 1986. Phytochemistry 25 (1), 277. Satyanarayana, V., Krupadanam, G.L.D., Srimannarayana, G., 1991. Ind. J. Chem. Sect. B 30, 989. Satyanarayana, V., Krupadanam, G.L.D., Srimannarayana, G., 1992. Fitoterapia 63, 82.