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A 2-methylene-β-alanine methyl ester derivative from the soft coral Sinularia dissecta
Biochemical Systematics and Ecology 27 (1999) 661 } 662
Short Communication
A 2-methylene-b-alanine methyl ester derivative from the soft coral Sinularia dissecta P. Ramesh , N. Srinivasa Reddy , T. Prabakar Rao , J. Venkateswara Rao, Y. Venkateswarlu * Natural Product Laboratory, Organic Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India Toxicology Laboratory, Biology Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India Received 23 September 1998; received in revised form 23 November 1998; accepted 24 November 1998
Keywords: Sinularia dissecta; 2-Methylene-b-alanine methyl ester; Sesquiterpene; Toxicity
1. Subject and source In continuation of our search for biologically active molecules from marine organisms (Venkateswarlu et al., 1994; Reddy et al., 1993), we have investigated the soft coral Sinularia dissecta collected from Mandapam Coast (N 173, E 833) at a depth of 20 ft by skin diving, during October 1997. A voucher specimen (IIC-233) was deposited at the Museum of the National Institute of Oceanography, Goa, India. 2. Previous work The genus Sinularia has yielded several types of compounds (Faulkner, 1998) mainly cembrane derived diterpenes (Iguchi et al., 1996), sesquiterpenes (Kashman et al., 1980) and polyhydroxy steroids (Jagodzinska et al., 1985). 3. Present study The 1 : 1 dichloromethane : methanol extract of the soft coral Sinularia dissecta was subjected to gel "ltration chromatography (Sephadex LH-20, 1 : 1 CH Cl : CH OH) *Corresponding author. Tel.: 0091 40 7170512; fax: 0091 40 7173757; e-mail: root@cslict. ren.nic.in IICT Communication No. 4150 0305-1978/99/$ - see front matter 1999 Elsevier Science Ltd. All rights reserved. PII: S0 30 5 - 19 7 8( 9 8 )00 1 29 -X
662
P. Ramesh et al./Biochemical Systematics and Ecology 27 (1999) 661}662
followed by silica gel chromatography to a!ord 4,5-seco-african-4,5-dione (1) and a homogeneous mixture of a-keto-2-methylene-b-alanine methyl esters (2). Compounds 1 and 2 were characterized by comparing their physical and spectral data with those reported in the literature (Catalan et al., 1992; Yunker and Schener, 1978).
Compound 1 was previously isolated from the plant ¸ippia integrifolia (Catalan et al., 1992) however, this is the "rst time it has been isolated from a marine source. Compound 2 was identi"ed as an a-keto fatty acid amide of 2-methylene-b-alanine methyl ester which was previously isolated from an unidenti"ed sponge (Yunker and Schener, 1978). But this is the "rst time it has been isolated from the soft coral Sinularia dissecta and di!ers from the other amide compounds (spermine derivatives), which are used as anti-cancer agents (Hashimoto et al., 1990). We report C NMR spectral data for compound 2 here as previous authors have not done so. Compound 2 exhibited mild activity against brine shrimp assay having LC 175.14$5.91 ppm. C NMR of compound 2 (CDCl , 50 MHz) : d 198.5 (s, C-2'), 165.8 (s, C-1), 159.9 (s, C-1'), 135.8 (s, C-2), 127.2 (t, C-4), 51.9 (q, -OMe), 40.3 (t, C-3), 36.7 (t, -CH -), 31.9 (t, -CH -), 29.6 (t, -CH -), 29.5 (t, -CH -), 29.3 (t, -CH -), 29.1 (t, -CH -), 23.2 (t, -CH -), 22.7 (t, -CH -) and 14.1 (q, CH ). Acknowledgements The authors are thankful to the Department of Ocean Development for "nancial assistance, NSR to CSIR, and PR to UGC (New Delhi) for providing fellowships. References Catalan, C. A. N., De Fenik, I. J. S., De Arriazu, P. J., Kokke, W. C. M. C., 1992. Phytochemistry 31, 4025. Faulkner, D. J., 1998. Natural Product Reports 15, 113. Hashimoto, T., Fuseya, N., Takahashi, K., Nohara, C., 1990. Jpn. Kokai ¹okkyo Koho Jp 63, 307, 849 (patent). Iguchi, K., Kajiyama, K., Miyauka, H., Yamada, Y., 1996. J. Org. Chem. 61, 5998. Jagodzinska, B. M., Trimmer, J. S., Fenical, W., Djerassi, C., 1985. J. Org. Chem. 50, 1435. Kashman, Y., Bodner, M., Finer-Moore, Janet, S., Clardy, J., 1980. Experientia 36, 891. Reddy, M. V. R., Lakshman, S., Rama Rao, A. V., Venkateswarlu, Y., Rao, J. V., 1993. J. Nat. Prod. 56, 970. Venkateswarlu, Y., Biabani, M. A. F., Reddy, M. V. R., Rao, T. P., Kunwar, A. C., Faulkner, D. J., 1994. ¹etrahedron ¸ett. 35, 2249. Yunker, M. B., Schener, P. G., 1978. ¹etrahedron ¸ett. 47, 4651.
Short Communication
A 2-methylene-b-alanine methyl ester derivative from the soft coral Sinularia dissecta P. Ramesh , N. Srinivasa Reddy , T. Prabakar Rao , J. Venkateswara Rao, Y. Venkateswarlu * Natural Product Laboratory, Organic Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India Toxicology Laboratory, Biology Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India Received 23 September 1998; received in revised form 23 November 1998; accepted 24 November 1998
Keywords: Sinularia dissecta; 2-Methylene-b-alanine methyl ester; Sesquiterpene; Toxicity
1. Subject and source In continuation of our search for biologically active molecules from marine organisms (Venkateswarlu et al., 1994; Reddy et al., 1993), we have investigated the soft coral Sinularia dissecta collected from Mandapam Coast (N 173, E 833) at a depth of 20 ft by skin diving, during October 1997. A voucher specimen (IIC-233) was deposited at the Museum of the National Institute of Oceanography, Goa, India. 2. Previous work The genus Sinularia has yielded several types of compounds (Faulkner, 1998) mainly cembrane derived diterpenes (Iguchi et al., 1996), sesquiterpenes (Kashman et al., 1980) and polyhydroxy steroids (Jagodzinska et al., 1985). 3. Present study The 1 : 1 dichloromethane : methanol extract of the soft coral Sinularia dissecta was subjected to gel "ltration chromatography (Sephadex LH-20, 1 : 1 CH Cl : CH OH) *Corresponding author. Tel.: 0091 40 7170512; fax: 0091 40 7173757; e-mail: root@cslict. ren.nic.in IICT Communication No. 4150 0305-1978/99/$ - see front matter 1999 Elsevier Science Ltd. All rights reserved. PII: S0 30 5 - 19 7 8( 9 8 )00 1 29 -X
662
P. Ramesh et al./Biochemical Systematics and Ecology 27 (1999) 661}662
followed by silica gel chromatography to a!ord 4,5-seco-african-4,5-dione (1) and a homogeneous mixture of a-keto-2-methylene-b-alanine methyl esters (2). Compounds 1 and 2 were characterized by comparing their physical and spectral data with those reported in the literature (Catalan et al., 1992; Yunker and Schener, 1978).
Compound 1 was previously isolated from the plant ¸ippia integrifolia (Catalan et al., 1992) however, this is the "rst time it has been isolated from a marine source. Compound 2 was identi"ed as an a-keto fatty acid amide of 2-methylene-b-alanine methyl ester which was previously isolated from an unidenti"ed sponge (Yunker and Schener, 1978). But this is the "rst time it has been isolated from the soft coral Sinularia dissecta and di!ers from the other amide compounds (spermine derivatives), which are used as anti-cancer agents (Hashimoto et al., 1990). We report C NMR spectral data for compound 2 here as previous authors have not done so. Compound 2 exhibited mild activity against brine shrimp assay having LC 175.14$5.91 ppm. C NMR of compound 2 (CDCl , 50 MHz) : d 198.5 (s, C-2'), 165.8 (s, C-1), 159.9 (s, C-1'), 135.8 (s, C-2), 127.2 (t, C-4), 51.9 (q, -OMe), 40.3 (t, C-3), 36.7 (t, -CH -), 31.9 (t, -CH -), 29.6 (t, -CH -), 29.5 (t, -CH -), 29.3 (t, -CH -), 29.1 (t, -CH -), 23.2 (t, -CH -), 22.7 (t, -CH -) and 14.1 (q, CH ). Acknowledgements The authors are thankful to the Department of Ocean Development for "nancial assistance, NSR to CSIR, and PR to UGC (New Delhi) for providing fellowships. References Catalan, C. A. N., De Fenik, I. J. S., De Arriazu, P. J., Kokke, W. C. M. C., 1992. Phytochemistry 31, 4025. Faulkner, D. J., 1998. Natural Product Reports 15, 113. Hashimoto, T., Fuseya, N., Takahashi, K., Nohara, C., 1990. Jpn. Kokai ¹okkyo Koho Jp 63, 307, 849 (patent). Iguchi, K., Kajiyama, K., Miyauka, H., Yamada, Y., 1996. J. Org. Chem. 61, 5998. Jagodzinska, B. M., Trimmer, J. S., Fenical, W., Djerassi, C., 1985. J. Org. Chem. 50, 1435. Kashman, Y., Bodner, M., Finer-Moore, Janet, S., Clardy, J., 1980. Experientia 36, 891. Reddy, M. V. R., Lakshman, S., Rama Rao, A. V., Venkateswarlu, Y., Rao, J. V., 1993. J. Nat. Prod. 56, 970. Venkateswarlu, Y., Biabani, M. A. F., Reddy, M. V. R., Rao, T. P., Kunwar, A. C., Faulkner, D. J., 1994. ¹etrahedron ¸ett. 35, 2249. Yunker, M. B., Schener, P. G., 1978. ¹etrahedron ¸ett. 47, 4651.