The structures and stereochemistry of cytotoxic sesquiterpene quinones from dactylospongia elegans

Jaime Rodríguez, Emilio Quiñoá, Ricardo Riguera, Barbara M. Peters, Leif M Abrell, Phillip Crews

Research output: Contribution to journalArticle

89 Citations (Scopus)

Abstract

The cytotoxicity of a crude extract from Dactylospongia elegans stimulated a search for the active constituents. The structures and absolute stereochemistry are elucidated for four new 9, 11,18, 19, and thirteen previously described compounds, 3, 4, 6a, 7, 8, 10, 12 - 17, 21. These compounds were isolated from collections of D. elegans obtained from three different Indo-Pacific regions, Fiji, Papua New Guinea, and Thailand. This species appears to elaborate a broader range of the mixed biogenesis sesquiterpene-hydroquinone (-quinone) metabolites in comparison to those of other sponges or seaweeds. Three compounds, 4, 9, and 13, were potent (IC50's were less than 1 μg/mL). The quinone ring appears to be essential for this in vitro activity.

Original languageEnglish (US)
Pages (from-to)6667-6680
Number of pages14
JournalTetrahedron
Volume48
Issue number32
DOIs
StatePublished - 1992
Externally publishedYes

Fingerprint

Fiji
Seaweed
Papua New Guinea
Quinones
Stereochemistry
Sesquiterpenes
Porifera
Thailand
Cytotoxicity
Metabolites
Complex Mixtures
Inhibitory Concentration 50
In Vitro Techniques
benzoquinone
hydroquinone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The structures and stereochemistry of cytotoxic sesquiterpene quinones from dactylospongia elegans. / Rodríguez, Jaime; Quiñoá, Emilio; Riguera, Ricardo; Peters, Barbara M.; Abrell, Leif M; Crews, Phillip.

In: Tetrahedron, Vol. 48, No. 32, 1992, p. 6667-6680.

Research output: Contribution to journalArticle

Rodríguez, Jaime ; Quiñoá, Emilio ; Riguera, Ricardo ; Peters, Barbara M. ; Abrell, Leif M ; Crews, Phillip. / The structures and stereochemistry of cytotoxic sesquiterpene quinones from dactylospongia elegans. In: Tetrahedron. 1992 ; Vol. 48, No. 32. pp. 6667-6680.
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