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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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Mar. Drugs 2017, 15(11), 344; https://doi.org/10.3390/md15110344
Received: 11 October 2017 / Revised: 24 October 2017 / Accepted: 30 October 2017 / Published: 2 November 2017
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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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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Mar. Drugs, EISSN 1660-3397, Published by MDPI AG
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