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- Title
5-Alkylresorcinol Derivatives from the Bryozoan Schizomavella mamillata: Isolation, Synthesis, and Antioxidant Activity.
- Authors
Ortega, María J.; Pantoja, Juan J.; de los Reyes, Carolina; Zubía, Eva
- Abstract
The chemical study of the bryozoan Schizomavella mamillata has led to the isolation of six new 5-alkylresorcinol derivatives, schizols A-F (1-6), whose structures were established by spectrocospic means. Schizol A (1) exhibits a (E)-6-phenylnon-5-enyl moiety linked to the C-5 of a resorcinol ring, while in schizol B (2) the substituent at C-5 contains an unusual 1,2-dihydrocyclobutabenzene moiety. Schizols C (3) and D (4) have been characterized as the 1-sulfate derivatives of 1 and 2, respectively, and schizols E (5) and F (6) are the corresponding 1,3-disulfates. Schizol A (1) has been synthetized from 3,5-dimethoxybenzaldehyde through a sequence involving a Wittig reaction for the construction of the C-1',C-2' bond and a Julia-Kocienski olefination for the synthesis of the C-5',C-6' double bond. In the ABTS (2-2'azinobis(3-ethylbenzothiazoline-6-sulphonic acid)) antioxidant assay, the natural compounds schizol A (1) and schizol B (2) showed higher radical scavenging activity than the Trolox standard.
- Subjects
ANTIOXIDANTS; BRYOZOA; WITTIG reaction; CHEMICAL reactions; WITTIG reagents; RESORCINOL; MOLECULAR structure
- Publication
Marine Drugs, 2017, Vol 15, Issue 11, p344
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md15110344