A cytotoxic and antifungal 1,4-naphthoquinone and related compounds from a New Zealand brown algae, Landsburgia quercifolia.
The bioactivity-directed isolation of deoxylapachol [I] from a New Zealand brown alga, Landsburgia quercifolia, is described. Compound I was active against P-388 leukemia cells (IC50 0.6 microgm/ml) and was also antifungal. 1,4-Dimethoxy-2-(3-methyl-2-butenyl)-naphthalene [3] was the major low polarity component of extracts of this seaweed, which also contained 2,3-dihydro-2,2-bis(3-methyl-2-butenyl)-1,4-naphthalenedione [6] and 2-(3-methyl-2-butenyl)-2,3-epoxy- 1,4-naphthalenedione 4,4-dimethoxy ketal [7]. Compound 7 was converted to the 2,3-epoxide of I, which had biological activities similar to those of I.
Perry
N B
NB
Department of Chemistry, University of Canterbury, Christchurch, New Zealand.
Blunt
J W
JW
Munro
M H
MH
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification; D004354:Drug Screening Assays, Antitumor; D007941:Leukemia P388 / Q000188:drug therapy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000459:Phaeophyceae / Q000737:chemistry*
D000935:Antifungal Agents; D000972:Antineoplastic Agents, Phytogenic; D009285:Naphthoquinones