New luffariellolide derivatives from the Indonesian sponge Acanthodendrilla sp.
Investigation of the Indonesian sponge Acanthodendrilla sp. afforded five new luffariellolide-related sesterterpenes, acantholides A-E (1-5), in addition to luffariellolide and its 25-O-methyl and 25-O-ethyl derivatives. All structures were unambiguously established by 1D and 2D NMR and MS spectroscopy. Acantholide D and E are derivatives comprising the 1-acetylcyclopentan-5-ol moiety, which are new variants of the C(14)-C(20) segment for this type of linear sesterterpenes. Luffariellolide and its 25-O-methyl congener as well as acantholide E (5) were cytotoxic against the mouse lymphoma L5187Y cell line. Acantholide B (2), luffariellolide, and its 25-O-methyl congener were active against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, the Gram-negative bacterium Escherichia coli, the yeast Candida albicans, and the plant pathogenic fungus Cladosporium herbarum.
Elkhayat
Ehab
E
Institut für Pharmazeutische Biologie, Heinrich-Heine-Universität, Universitätsstr 1, 40225 Düsseldorf, Germany.
Edrada
RuAngelie
R
Ebel
Rainer
R
Wray
Victor
V
van Soest
Rob
R
Wiryowidagdo
Sumaryono
S
Mohamed
Mahmoud H
MH
Müller
Werner E G
WE
Proksch
Peter
P
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002963:Cladosporium / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D004926:Escherichia coli / Q000187:drug effects; D007214:Indonesia; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D054830:Sesterterpenes; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000935:Antifungal Agents; D000970:Antineoplastic Agents; D012717:Sesquiterpenes; D054830:Sesterterpenes; D013729:Terpenes; C076150:luffariellolide; C022283:acantholide