Pachydictyols B and C: New diterpenes from dictyota dichotoma hudson

Ghada S.E. Abou-El-Wafa, Mohamed Shaaban, Khaled A. Shaaban, Mohamed E.E. El-Naggar, Armin Maier, Heinz H. Fiebig, Hartmut Laatsch

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

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[4.3.0.1(1,7)] decan-5-one (7), N-(4-bromo-n-butyl)-pipe ridin-2-one (8) and tert-hexadecanethiol. Structures 1-6 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.

Original languageEnglish
Pages (from-to)3109-3123
Number of pages15
JournalMarine Drugs
Volume11
Issue number9
DOIs
StatePublished - Sep 2013

Keywords

  • Bioactivity
  • Dictyota dichotoma
  • Diterpenes
  • Marine brown alga
  • Pachydictyols

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Pharmacology, Toxicology and Pharmaceutics (miscellaneous)

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