Marine natural products. VII. Zonarol and isozonarol, fungitoxic hydroquinones from the brown seaweed Dictyopteris zonarioides

Abstract

actinomycin D,26 and oxytocin.27 Only in the case of c2/cZo-(Pro-Gly)s in methylene chloride do these rules fail to agree with previous conclusions, and this failure (26) D. J. Patel, et ah, unpublished results. (27) A.

Zonarol, a sesquiterpene from the brown algae Dictyopteris undulata , provides neuroprotection by activating the Nrf2/ARE pathway

“…1B), based on analysis of nuclear magnetic resonance data after bioassay-guided purification from crude extract [4]. Originally, this sesquiterpene hydroquinone from Dictyopteris undulata had been reported to be a fungitoxic compound by Fenical and Cimino in the 1970's [5]. Subsequently, the chemical structure of the hydroquinone was elucidated in 1986 [6].…”

Cosmeceuticals from algae

“…A 1,4-napthaquinone derivative (deoxy lapachol) was isolated from a New Zealand brown alga Landsburgia quercifolia by the bioactivity-guided isolation method (Perry et al , 1991). Moreover, (+)-zonarol was isolated from Dictyopteris zonaroides by Fenical et al (1973). Terpenes contain primary and secondary metabolites which are derived from 5-carbon isoprene entity.…”

“…A 1,4-napthaquinone derivative (deoxy lapachol) with excellent antifungal activity was isolated from a New Zealand brown alga, Landsburgia quercifolia , by the bioactivity-guided isolation method (Perry et al , 1991). Also (+)-zonarol showed antifungal activity (Fenical et al , 1973).…”

Diterpenoid Synthesis in Brown Seaweeds of the Family Dictyotaceae

“…Catalytically, neither the cyclopropane nor a,B-unsaturated lactone olefin appear reactive toward reduction. Lithium in ethy1amine, however, afforded complete reduction of the lactone olefin and also reduced the ester to give (8). The nmr spectrum of (8) showed the lone bridgehead proton, alpha to the ester carbonyl, as a four-line pattern at 0 2.84 (J = 14, 10 Hz), …”