A phenethyl bromo ester from Citharexylum fruticosum

S. Ganapaty, D.V. Rao, S.T. Pannakal

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A new compound, (2S)-p-hydroxyphenethyl 2-bromo-2-methyldodeconate (1) and 7,3′-dimethoxy-5,4′-dihydroxy flavone, together with lupeol and stigmasterol were isolated from the stem bark of Citharexylum fruticosum (Verbenaceae). The structures of the compounds were established on the basis of the interpretation of NMR (1H, 13C, COSY and HMBC) spectra, as well as low and high-resolution mass spectrometric data. In this paper, we report on the structure elucidation of 1.
Original languageEnglish
Pages (from-to)399-402
Number of pages4
JournalNatural Product Communications
Volume5
Issue number3
Publication statusPublished - 2010
Externally publishedYes

Fingerprint

flavone
Verbenaceae
Stigmasterol
lupeol
stigmasterol
flavones
Esters
bark
esters
stems
(2S)-p-hydroxyphenethyl 2-bromo-2-methyldodeconate
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy

Cite this

Ganapaty, S., Rao, D. V., & Pannakal, S. T. (2010). A phenethyl bromo ester from Citharexylum fruticosum. Natural Product Communications, 5(3), 399-402.
Ganapaty, S. ; Rao, D.V. ; Pannakal, S.T. / A phenethyl bromo ester from Citharexylum fruticosum. In: Natural Product Communications. 2010 ; Vol. 5, No. 3. pp. 399-402.
@article{02bb9f458af147f184f781c9f890344d,
title = "A phenethyl bromo ester from Citharexylum fruticosum",
abstract = "A new compound, (2S)-p-hydroxyphenethyl 2-bromo-2-methyldodeconate (1) and 7,3′-dimethoxy-5,4′-dihydroxy flavone, together with lupeol and stigmasterol were isolated from the stem bark of Citharexylum fruticosum (Verbenaceae). The structures of the compounds were established on the basis of the interpretation of NMR (1H, 13C, COSY and HMBC) spectra, as well as low and high-resolution mass spectrometric data. In this paper, we report on the structure elucidation of 1.",
author = "S. Ganapaty and D.V. Rao and S.T. Pannakal",
note = "Export Date: 10 November 2017 Correspondence Address: Ganapaty, S.; Pharmacognosy and Phytochemistry Division, University College of Pharmaceutical Sciences, Andhra University, Visakhapatnam-530 003, Andhra Pradesh, India; email: ganapatyseru@gmail.com Chemicals/CAS: lupeol, 545-47-1; stigmasterol, 83-48-7; (2S)-p-hydroxyphenethyl 2-bromo-2-methyldodeconate; Laurates; Plant Extracts; Solvents References: Grible, G., Naturally occurring organohalogen compounds: A comprehensive review (1996) Progress in the Chemistry of Organic Natural Products, 63, pp. 24-36. , Hertz W, Kirby GW, Moore RE, Steglich W, Tamm C. (Eds.), Springer Verlag, Vienna and New York; Mu, H.L., Wesen, C., Sundin, P., Halogenated fatty acids. Formation and occurrence in lipids (1997) Trac-trends in Analytical Chemistry, 16, pp. 266-274; Fusetani, N., Sugano, M., Matsunaga, S., Hashimoto, K., H,K-ATPase inhibitors from the marine sponge Siphnochalina truncata Absolute configuration of siphonodiol and two related metabolites (1987) Tetrahedron Letters, 28, pp. 4311-4312; Brantley, S.E., Molinski, T.F., Preston, C.M., Delong, E.F., Brominated acetylenic fatty acids from Xestospongia sp., a marine sponge bacteria association (1995) Tetrahedron, 51, pp. 7667-7672; Carballeira, N.M., Sostre, A., Stefanov, K., Popov, S., Kujumigiev, A., Dimitrova-Konaklieva, S., Tosteson, C.G., Tosteson, T.R., The fatty acid composition of a Vibrio alginolyticus associated with the alga Cladophora coelothrix. Identification of the novel 9- methyl-10- hexanedecenoic acid (1997) Lipids, 32, pp. 1271-1275; Van Soest, R.W.M., Fusetani, N., Andersen, R.J., (1998) Sponge Sciences: Multidisciplinary Perspectives, pp. 3-30. , Watanabe Y, Fusetani N, (Eds), Springer-Verlag, Tokyo; Lerch, M.L., Harper, M.K., Faulkner, J.D., Brominated polyacetylenes from the Philippines sponge Diplastrella sp (2003) Journal of Natural Products, 66, pp. 667-670; Mac Millan, J.B., Molinski, T.F., Majusculoic acid, a brominated cyclopropyl fatty acid from a marine cyanobacterial mat assemblage (2005) Journal of Natural Products, 68, pp. 604-606; Quinn, R.J., Tucker, D., Further acetylenic acids from the marine sponge Xestospongia testudinaria (1991) Journal of Natural Products, 54, pp. 290-294; Ichiba, T., Scheuer, P.J., Kellyborges, M., Sponge-derived polyunsaturated C16 di- and tribromocarboxylic acids (1994) Helvetica Chimica Acta, 76, pp. 2814-2816; Bourguet-Kondracki, M.L., Rakotoarisoa, M.T., Martin, M.T., Guyot, M., Bioactive bromopolyacetylenes from the marine sponge Xestospongia testudinaria (1992) Tetrahedron Letters, 33, pp. 225-226; Patil, A.D., Kokke, W.C., Cochran, S., Francis, T.A., Tomszek, T., Westley, J.W., Brominated polyacetylenic acids from the marine sponge Xestospongia muta: Inhibitors of HIV protease (1992) Journal of Natural Products, 55, pp. 1170-1177; Fusetani, N., Li, H., Tamura, K., Matsunaga, S., Antifungal brominated C18 acetylenic acids from the marine sponge, Petrosia volcano Hoshino (1993) Tetrahedron, 49, pp. 1203-1210; Rezanka, T., Dembitsky, V., Brominated fatty acids from lichen Acorospora gobiensis (1999) Phytochemistry, 50 (1), pp. 97-99. , DOI 10.1016/S0031-9422(98)00499-3, PII S0031942298004993; Rezanka, T., Dembitsky, V., Novel brominated lipidic compounds from lichens of Central Asia (1999) Phytochemistry, 51, pp. 963-968; Rezanka, T., Dembitsky, V., Bromoallenic lipid compounds from the lichens of Central Asia (2001) Phytochemistry, 56, pp. 869-874; Ganapaty, S., Venkata Rao, Chemical exsamination of the leaves of Citharexylum fruticosum var. subserratum (1983) Fitoterapia, pp. 13-15; Ganapaty, S., Heni, J., Venkata Rao, D., Rimpler, H., Iridoid glucosides from the leaves of Citharexylum fruticosum (1988) Planta Medica, pp. 42-43; Subramaniam, M., Purushotham, K.K., Sarada, A., Connolly, J.D., A new flavone 6-glucoside from Citharexylum subserratum (1976) Phytochemistry, 15, p. 838; Yang, Y.-P., Cheng, M.-J., Teng, C.-M., Chang, Y.-L., Tsai, I.-L., Chen, I.-S., Chemical and anti-platelet constituents from Formosan Zanthoxylum simulans (2002) Phytochemistry, 61 (5), pp. 567-572. , DOI 10.1016/S0031-9422(02)00268-6, PII S0031942202002686; Szafranek, B.M., Synak, E.E., Cuticular waxes from potato (Solanum tuberosum) leaves (2006) Phytochemistry, 67 (1), pp. 80-90. , DOI 10.1016/j.phytochem.2005.10.012, PII S0031942205005212; Gulz, P.G., Marner, F.J., Esters of benzyl alcohol and 2-phenylethanol-1 in epicuticular waxes from Jojoba leaves (1986) Zeitschrift fuer Naturforschung C, 41, pp. 673-676; Rezanka, T., Dembitsky, V.M., Polyhalogenated homosesquiterpenic fatty acids from Plocamium cartilagineurn (2001) Phytochemistry, 57 (4), pp. 607-611. , DOI 10.1016/S0031-9422(01)00086-3, PII S0031942201000863; Crews, P., Kho-Wiseman, E., Cartilagineal. An unusual monoterpene aldehyde from a marine alga (1974) Journal of Organic Chemistry, 39, pp. 3303-3304; Mynderse, J.S., Faulkner, D.J., Polyhalogenated monoterpenes from the red alga Plocamium cartilagineum (1975) Tetrahedron, 31, pp. 1963-1967; D{\'i}az-Marrero, A.R., Dorta, E., Cueto, M., Rovirosa, J., San-Martin, A., Darias, J., Supporting the NMR-based empirical rules to determine the stereochemistry and halogen regiochemistry of vicinal vinyl dihalides. Naturally occurring monoterpenes as chemical models (2004) Tetrahedron, 60, pp. 5049-5052; Jetter, R., Riederer, M., Cuticular waxes from the leaves and fruit capsules of eight Papaveraceae species (1996) Canadian Journal of Botany, 74 (3), pp. 419-430; Steinbauer, M.J., Schiestl, F.P., Davies, N.W., Monoterpenes and epicuticular waxes help female autumn gum moth differentiate between waxy and glossy Eucalyptus and leaves of different ages (2004) Journal of Chemical Ecology, 30, pp. 1117-1142; Anjaneyulu, A.S.R., Madhusudhana, R.A., Kameswara, R.V., Ramachandra, R.L., Pelter, A., Ward, R.S., The isolation and structure of 6″-bromo-isoarboreol - The first bromine containing lignan (1975) Tetrahedron Letters, 52, pp. 4697-4700",
year = "2010",
language = "English",
volume = "5",
pages = "399--402",
journal = "Natural Product Communications",
issn = "1934-578X",
publisher = "Natural Product Communications",
number = "3",

}

Ganapaty, S, Rao, DV & Pannakal, ST 2010, 'A phenethyl bromo ester from Citharexylum fruticosum', Natural Product Communications, vol. 5, no. 3, pp. 399-402.

A phenethyl bromo ester from Citharexylum fruticosum. / Ganapaty, S.; Rao, D.V.; Pannakal, S.T.

In: Natural Product Communications, Vol. 5, No. 3, 2010, p. 399-402.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A phenethyl bromo ester from Citharexylum fruticosum

AU - Ganapaty, S.

AU - Rao, D.V.

AU - Pannakal, S.T.

N1 - Export Date: 10 November 2017 Correspondence Address: Ganapaty, S.; Pharmacognosy and Phytochemistry Division, University College of Pharmaceutical Sciences, Andhra University, Visakhapatnam-530 003, Andhra Pradesh, India; email: ganapatyseru@gmail.com Chemicals/CAS: lupeol, 545-47-1; stigmasterol, 83-48-7; (2S)-p-hydroxyphenethyl 2-bromo-2-methyldodeconate; Laurates; Plant Extracts; Solvents References: Grible, G., Naturally occurring organohalogen compounds: A comprehensive review (1996) Progress in the Chemistry of Organic Natural Products, 63, pp. 24-36. , Hertz W, Kirby GW, Moore RE, Steglich W, Tamm C. (Eds.), Springer Verlag, Vienna and New York; Mu, H.L., Wesen, C., Sundin, P., Halogenated fatty acids. Formation and occurrence in lipids (1997) Trac-trends in Analytical Chemistry, 16, pp. 266-274; Fusetani, N., Sugano, M., Matsunaga, S., Hashimoto, K., H,K-ATPase inhibitors from the marine sponge Siphnochalina truncata Absolute configuration of siphonodiol and two related metabolites (1987) Tetrahedron Letters, 28, pp. 4311-4312; Brantley, S.E., Molinski, T.F., Preston, C.M., Delong, E.F., Brominated acetylenic fatty acids from Xestospongia sp., a marine sponge bacteria association (1995) Tetrahedron, 51, pp. 7667-7672; Carballeira, N.M., Sostre, A., Stefanov, K., Popov, S., Kujumigiev, A., Dimitrova-Konaklieva, S., Tosteson, C.G., Tosteson, T.R., The fatty acid composition of a Vibrio alginolyticus associated with the alga Cladophora coelothrix. Identification of the novel 9- methyl-10- hexanedecenoic acid (1997) Lipids, 32, pp. 1271-1275; Van Soest, R.W.M., Fusetani, N., Andersen, R.J., (1998) Sponge Sciences: Multidisciplinary Perspectives, pp. 3-30. , Watanabe Y, Fusetani N, (Eds), Springer-Verlag, Tokyo; Lerch, M.L., Harper, M.K., Faulkner, J.D., Brominated polyacetylenes from the Philippines sponge Diplastrella sp (2003) Journal of Natural Products, 66, pp. 667-670; Mac Millan, J.B., Molinski, T.F., Majusculoic acid, a brominated cyclopropyl fatty acid from a marine cyanobacterial mat assemblage (2005) Journal of Natural Products, 68, pp. 604-606; Quinn, R.J., Tucker, D., Further acetylenic acids from the marine sponge Xestospongia testudinaria (1991) Journal of Natural Products, 54, pp. 290-294; Ichiba, T., Scheuer, P.J., Kellyborges, M., Sponge-derived polyunsaturated C16 di- and tribromocarboxylic acids (1994) Helvetica Chimica Acta, 76, pp. 2814-2816; Bourguet-Kondracki, M.L., Rakotoarisoa, M.T., Martin, M.T., Guyot, M., Bioactive bromopolyacetylenes from the marine sponge Xestospongia testudinaria (1992) Tetrahedron Letters, 33, pp. 225-226; Patil, A.D., Kokke, W.C., Cochran, S., Francis, T.A., Tomszek, T., Westley, J.W., Brominated polyacetylenic acids from the marine sponge Xestospongia muta: Inhibitors of HIV protease (1992) Journal of Natural Products, 55, pp. 1170-1177; Fusetani, N., Li, H., Tamura, K., Matsunaga, S., Antifungal brominated C18 acetylenic acids from the marine sponge, Petrosia volcano Hoshino (1993) Tetrahedron, 49, pp. 1203-1210; Rezanka, T., Dembitsky, V., Brominated fatty acids from lichen Acorospora gobiensis (1999) Phytochemistry, 50 (1), pp. 97-99. , DOI 10.1016/S0031-9422(98)00499-3, PII S0031942298004993; Rezanka, T., Dembitsky, V., Novel brominated lipidic compounds from lichens of Central Asia (1999) Phytochemistry, 51, pp. 963-968; Rezanka, T., Dembitsky, V., Bromoallenic lipid compounds from the lichens of Central Asia (2001) Phytochemistry, 56, pp. 869-874; Ganapaty, S., Venkata Rao, Chemical exsamination of the leaves of Citharexylum fruticosum var. subserratum (1983) Fitoterapia, pp. 13-15; Ganapaty, S., Heni, J., Venkata Rao, D., Rimpler, H., Iridoid glucosides from the leaves of Citharexylum fruticosum (1988) Planta Medica, pp. 42-43; Subramaniam, M., Purushotham, K.K., Sarada, A., Connolly, J.D., A new flavone 6-glucoside from Citharexylum subserratum (1976) Phytochemistry, 15, p. 838; Yang, Y.-P., Cheng, M.-J., Teng, C.-M., Chang, Y.-L., Tsai, I.-L., Chen, I.-S., Chemical and anti-platelet constituents from Formosan Zanthoxylum simulans (2002) Phytochemistry, 61 (5), pp. 567-572. , DOI 10.1016/S0031-9422(02)00268-6, PII S0031942202002686; Szafranek, B.M., Synak, E.E., Cuticular waxes from potato (Solanum tuberosum) leaves (2006) Phytochemistry, 67 (1), pp. 80-90. , DOI 10.1016/j.phytochem.2005.10.012, PII S0031942205005212; Gulz, P.G., Marner, F.J., Esters of benzyl alcohol and 2-phenylethanol-1 in epicuticular waxes from Jojoba leaves (1986) Zeitschrift fuer Naturforschung C, 41, pp. 673-676; Rezanka, T., Dembitsky, V.M., Polyhalogenated homosesquiterpenic fatty acids from Plocamium cartilagineurn (2001) Phytochemistry, 57 (4), pp. 607-611. , DOI 10.1016/S0031-9422(01)00086-3, PII S0031942201000863; Crews, P., Kho-Wiseman, E., Cartilagineal. An unusual monoterpene aldehyde from a marine alga (1974) Journal of Organic Chemistry, 39, pp. 3303-3304; Mynderse, J.S., Faulkner, D.J., Polyhalogenated monoterpenes from the red alga Plocamium cartilagineum (1975) Tetrahedron, 31, pp. 1963-1967; Díaz-Marrero, A.R., Dorta, E., Cueto, M., Rovirosa, J., San-Martin, A., Darias, J., Supporting the NMR-based empirical rules to determine the stereochemistry and halogen regiochemistry of vicinal vinyl dihalides. Naturally occurring monoterpenes as chemical models (2004) Tetrahedron, 60, pp. 5049-5052; Jetter, R., Riederer, M., Cuticular waxes from the leaves and fruit capsules of eight Papaveraceae species (1996) Canadian Journal of Botany, 74 (3), pp. 419-430; Steinbauer, M.J., Schiestl, F.P., Davies, N.W., Monoterpenes and epicuticular waxes help female autumn gum moth differentiate between waxy and glossy Eucalyptus and leaves of different ages (2004) Journal of Chemical Ecology, 30, pp. 1117-1142; Anjaneyulu, A.S.R., Madhusudhana, R.A., Kameswara, R.V., Ramachandra, R.L., Pelter, A., Ward, R.S., The isolation and structure of 6″-bromo-isoarboreol - The first bromine containing lignan (1975) Tetrahedron Letters, 52, pp. 4697-4700

PY - 2010

Y1 - 2010

N2 - A new compound, (2S)-p-hydroxyphenethyl 2-bromo-2-methyldodeconate (1) and 7,3′-dimethoxy-5,4′-dihydroxy flavone, together with lupeol and stigmasterol were isolated from the stem bark of Citharexylum fruticosum (Verbenaceae). The structures of the compounds were established on the basis of the interpretation of NMR (1H, 13C, COSY and HMBC) spectra, as well as low and high-resolution mass spectrometric data. In this paper, we report on the structure elucidation of 1.

AB - A new compound, (2S)-p-hydroxyphenethyl 2-bromo-2-methyldodeconate (1) and 7,3′-dimethoxy-5,4′-dihydroxy flavone, together with lupeol and stigmasterol were isolated from the stem bark of Citharexylum fruticosum (Verbenaceae). The structures of the compounds were established on the basis of the interpretation of NMR (1H, 13C, COSY and HMBC) spectra, as well as low and high-resolution mass spectrometric data. In this paper, we report on the structure elucidation of 1.

M3 - Article

VL - 5

SP - 399

EP - 402

JO - Natural Product Communications

JF - Natural Product Communications

SN - 1934-578X

IS - 3

ER -

Ganapaty S, Rao DV, Pannakal ST. A phenethyl bromo ester from Citharexylum fruticosum. Natural Product Communications. 2010;5(3):399-402.