New Sesquiterpene Hydroquinones from Marine Brown Alga Dictyopteris undulata

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New Sesquiterpene Hydroquinones from Marine Brown Alga Dictyopteris undulata

Author Affiliations

¹Department of Chemistry and Biochemistry, California State University San Marcos, San Marcos, 92096, CA, USA

Res.J.chem.sci., Volume 2, Issue (9), Pages 9-13, September,18 (2012)

Abstract

One new sesquiterpene hydroquinone, together with four known sesquiterpene hydroquinones and one hydrocarbon have been isolated from the bioassay-guided fractionation of the CH₂Cl₂ extract of the marine brown alga Dictyopteris undulata (zonarioides). The structural elucidation is based on the analysis of spectroscopic data. This is the first report of isolation of 6 from this alga.

References

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Sun H.H., McEnroe FAcetoxycrenulide, a new bicyclic cyclopropanediterpenoid from the brown seaweed Org. Chem., 48, 1903–1906 (1983)
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Siamopoulou P., Bimplakis A., Iliopoulou D., Vagias C., Cos P., Berghe D.V. and Roussis V., Diterpenes from the brown algae Dictyota dichotoma and Dictyota linearis, Phytochemistry, 65, 2025–2030 (2004)
Fenical W. and Sims J.J.Fungitoxic Hydroquinones from the Brown Seaweed Dictyopteris zonarioides,J. Org. Chem.(1973)
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Cimino G, Stefano SD, Fenical W, Minale L, Sims JJ. Experientia, 31, 1250-1251 (1975)
Ochi M., Kotsuki H., Muraka Kstructure of Yahazunol, a New SeqiterpeneHydroquinone from the Brown Seaweed undulata, Bull. Chem. Soc. Jap 52(2), 629-630 (1979)
Fenical W., Sims J.J., Wing R.M., Radlick Pa sesquiterpene from the brown seaweedzonarioide,Phytochemistry, 11, 1161-1164 (1972)
Kajiwara T., Hatanaka A., Tanaka Y., Kawai TM., Tsuneya T. and Fujimura T., Volatile constituents from marine brown algae of Japanese DictyopterisPhytochemistry, 28, 636-639 (1989)
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Suzuki M., Kowata N., Kurosawa E., Kobayashi H Tanaka I., Chemistry Lett., 228, 2187-2190 (1981)
Segawa M., Yamano K. and Shrahama H., A germacrane-sesquiterpene from the brown alga Dictyopteris 974 (1990)
Koenig G.M. and Wright A.D.183 (1995)
Boland W. and Mueller D.G.,310 (1987)
Yamada K., Ojika M. and Tan H. 1634 (1980)
Moore R.E., Pettus J.A.J. and39, 2201-2207 (1974)
Pasadas G.A., Alcaide I.V., Rios JVicario I.M. and Camacho quantification of the hydrocarbonssubcutaneous fresh fat of Iberian pig by offcombination of high performance liquid chromatography and gas chromatography,J. Chromatogr.A(2006)

[ref1] Faulkner D.J., Marine natural products19, 1–48 (2002)

[ref2] Amico V., Oriente G., Piattelli MFattorusso E., Magno S. andon the dolabellane skeleton from Tetrahedron,36, 1409–1414 (1980)

[ref3] Sun H.H., McEnroe FAcetoxycrenulide, a new bicyclic cyclopropanediterpenoid from the brown seaweed Org. Chem., 48, 1903–1906 (1983)

[ref4] Ishitsuka M.O., Kusumi T. andxenicane and norxenicane lactones from the brown alga Dictyota dichotoma,J. Org. Chem.5.Siamopoulou P., Bimplakis ACos P., Berghe D.V. and Roussis V.brown algae Dictyota dichotoma and Dictyata linearis,Phytochemistry,65, 2025–2030 (2004)

[ref5] Siamopoulou P., Bimplakis A., Iliopoulou D., Vagias C., Cos P., Berghe D.V. and Roussis V., Diterpenes from the brown algae Dictyota dichotoma and Dictyota linearis, Phytochemistry, 65, 2025–2030 (2004)

[ref6] Fenical W. and Sims J.J.Fungitoxic Hydroquinones from the Brown Seaweed Dictyopteris zonarioides,J. Org. Chem.(1973)

[ref7] Fenical W. and Mcconnel O.isochromazonarol, new chromanolsseaweed Dictyopteris undulate Experientia, 31, 1004-1005 (1975)

[ref8] Cimino G, Stefano SD, Fenical W, Minale L, Sims JJ. Experientia, 31, 1250-1251 (1975)

[ref9] Ochi M., Kotsuki H., Muraka Kstructure of Yahazunol, a New SeqiterpeneHydroquinone from the Brown Seaweed undulata, Bull. Chem. Soc. Jap 52(2), 629-630 (1979)

[ref10] Fenical W., Sims J.J., Wing R.M., Radlick Pa sesquiterpene from the brown seaweedzonarioide,Phytochemistry, 11, 1161-1164 (1972)

[ref11] Kajiwara T., Hatanaka A., Tanaka Y., Kawai TM., Tsuneya T. and Fujimura T., Volatile constituents from marine brown algae of Japanese DictyopterisPhytochemistry, 28, 636-639 (1989)

[ref12] Suzuki M.,Kawai T., Ishhara Volatile constituents from marine brown algae of Japanese Dictyopteris, Kurosawa E., Bulletin of the 2368(1981)

[ref13] Suzuki M., Kowata N., Kurosawa E., Kobayashi H Tanaka I., Chemistry Lett., 228, 2187-2190 (1981)

[ref14] Segawa M., Yamano K. and Shrahama H., A germacrane-sesquiterpene from the brown alga Dictyopteris 974 (1990)

[ref15] Koenig G.M. and Wright A.D.183 (1995)

[ref16] Boland W. and Mueller D.G.,310 (1987)

[ref17] Yamada K., Ojika M. and Tan H. 1634 (1980)

[ref18] Moore R.E., Pettus J.A.J. and39, 2201-2207 (1974)

[ref19] Pasadas G.A., Alcaide I.V., Rios JVicario I.M. and Camacho quantification of the hydrocarbonssubcutaneous fresh fat of Iberian pig by offcombination of high performance liquid chromatography and gas chromatography,J. Chromatogr.A(2006)