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Mar. Drugs 2013, 11(9), 3109-3123;

Pachydictyols B and C: New Diterpenes from Dictyota dichotoma Hudson

Department of Botany, Faculty of Science, Mansoura University, Algomhuria St. 60, El-Mansoura 35516, Egypt
Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany
Chemistry of Natural Compounds Department, Division of Pharmaceutical Industries, National Research Centre, El-Behoos St. 33, Dokki-Cairo 12622, Egypt
Oncotest GmbH, Am Flughafen 12-14, D-79108 Freiburg, Germany
These authors contributed equally to this work.
Deceased on 9 December 2011.
Author to whom correspondence should be addressed.
Received: 19 June 2013 / Revised: 12 August 2013 / Accepted: 12 August 2013 / Published: 22 August 2013
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Two new diterpenoids, pachydictyol B (1a/1b) and C (2), were isolated from the dichloromethane extract of the marine brown alga, Dictyota dichotoma, collected from the Red Sea coast of Egypt, along with the known metabolites, pachydictyol A (3a), dictyol E (4), cis-africanan-1α-ol (5a), fucosterol (6), tetrahydrothiophen-1,1-dioxide and poly-β-hydroxybutyric acid. GC-MS analysis of the nonpolar fractions also indicated the presence of β-bourbonene and nonanal, along with three hydrocarbons and five fatty acids or their simple derivatives, respectively. GC-MS analysis of the unsaponifiable algal petroleum ether extract revealed the presence of a further eight compounds, among them 2,2,6,7-tetramethyl-10-oxatricyclo[,7)]decan-5-one (7), N-(4-bromo-n-butyl)-pipe ridin-2-one (8) and tert-hexadecanethiol. Structures 16 were assigned by 1D and 2D NMR, mass spectra (EI, CI, HREI and HRESI) and by comparison with data from related structures. The crude algal extract was potently active against the breast carcinoma tumor cell line, MCF7 (IC50 = 0.6 µg mL−1); pachydictyol B (1a) and dictyol E (4) showed weak antimicrobial properties, and the other compounds were inactive. Pachydictyols B (1a) and C (2) demonstrated a weak and unselective cytotoxicity against twelve human tumor cell lines with a mean IC50 of >30.0 µM. View Full-Text
Keywords: marine brown alga; Dictyota dichotoma; pachydictyols; diterpenes; bioactivity marine brown alga; Dictyota dichotoma; pachydictyols; diterpenes; bioactivity

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Abou-El-Wafa, G.S.E.; Shaaban, M.; Shaaban, K.A.; El-Naggar, M.E.E.; Maier, A.; Fiebig, H.H.; Laatsch, H. Pachydictyols B and C: New Diterpenes from Dictyota dichotoma Hudson. Mar. Drugs 2013, 11, 3109-3123.

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