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Mar. Drugs 2017, 15(11), 344; https://doi.org/10.3390/md15110344

5-Alkylresorcinol Derivatives from the Bryozoan Schizomavella mamillata: Isolation, Synthesis, and Antioxidant Activity

Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, 11510 Puerto Real (Cádiz), Spain
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Received: 11 October 2017 / Revised: 24 October 2017 / Accepted: 30 October 2017 / Published: 2 November 2017
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Abstract

The chemical study of the bryozoan Schizomavella mamillata has led to the isolation of six new 5-alkylresorcinol derivatives, schizols A–F (16), 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. View Full-Text
Keywords: alkylresorcinols; bryozoans; Schizomavella; 1,2-dihydrocyclobutabenzene; olefination; antioxidant alkylresorcinols; bryozoans; Schizomavella; 1,2-dihydrocyclobutabenzene; olefination; antioxidant
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ortega, M.J.; Pantoja, J.J.; de los Reyes, C.; Zubía, E. 5-Alkylresorcinol Derivatives from the Bryozoan Schizomavella mamillata: Isolation, Synthesis, and Antioxidant Activity. Mar. Drugs 2017, 15, 344.

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