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Mar. Drugs 2014, 12(4), 1987-2003; doi:10.3390/md12041987
Article

Neritinaceramides A–E, New Ceramides from the Marine Bryozoan Bugula neritina Inhabiting South China Sea and Their Cytotoxicity

1
, 2,3,* , 1
, 4
, 5
, 1
 and 1,*
1 Research & Development Center of Biorational Pesticide, College of Plant Protection, Northwest A&F University, Yangling 712100, China 2 Institute of Materia Medica, School of Pharmacy, Fourth Military Medical University, Xi'an 710032, China 3 Department of Pharmacy, Xijing Hospital, Fourth Military Medical University, Xi'an 710032, China 4 School of Traditional Chinese Medicines, Shenyang Pharmaceutical University, Shenyang 110016, China 5 Department of Pharmacy, Renji Hospital, Affiliated to School of Medicine, Shanghai Jiao-Tong University, Shanghai 200127, China
* Authors to whom correspondence should be addressed.
Received: 23 January 2014 / Revised: 2 March 2014 / Accepted: 13 March 2014 / Published: 2 April 2014
(This article belongs to the Special Issue Bioactive Compounds from Marine Invertebrates)
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Abstract

Five new ceramides, neritinaceramides A (1), B (2), C (3), D (4) and E (5), together with six known ceramides (611), two known alkyl glycerylethers (12 and 13) and a known nucleoside (14), were isolated from marine bryozoan Bugula neritina, which inhabits the South China Sea. The structures of the new compounds were elucidated as (2S,3R,3′S,4E,8E,10E)-2-(hexadecanoylamino)-4,8,10-octadecatriene-l,3,3′-triol (1), (2S,3R,2′R,4E,8E,10E)-2-(hexadecanoylamino)-4,8,10-octadecatriene-l,3,2′-triol (2), (2S,3R,2′R,4E,8E,10E)-2-(octadecanoylamino)-4,8,10-octadecatriene-l,3,2′-triol (3), (2S,3R,3′S,4E,8E)-2-(hexadecanoylamino)-4,8-octadecadiene-l,3,3′-triol (4) and (2S,3R,3′S,4E)-2-(hexadecanoylamino)-4-octadecene-l,3,3′-triol (5) on the basis of extensive spectral analysis and chemical evidences. The characteristic C-3′S hydroxyl group in the fatty acid moiety in compounds 1, 4 and 5, was a novel structural feature of ceramides. The rare 4E,8E,10E-triene structure in the sphingoid base of compounds 13, was found from marine bryozoans for the first time. The new ceramides 15 were evaluated for their cytotoxicity against HepG2, NCI-H460 and SGC7901 tumor cell lines, and all of them exhibited selective cytotoxicity against HepG2 and SGC7901 cells with a range of IC50 values from 47.3 μM to 58.1 μM. These chemical and cytotoxic studies on the new neritinaceramides A–E (15) added to the chemical diversity of B. neritina and expanded our knowledge of the chemical modifications and biological activity of ceramides.
Keywords: marine bryozoan; Bugula neritina; ceramide; neritinaceramide; cytotoxicity marine bryozoan; Bugula neritina; ceramide; neritinaceramide; cytotoxicity
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.

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MDPI and ACS Style

Tian, X.-R.; Tang, H.-F.; Feng, J.-T.; Li, Y.-S.; Lin, H.-W.; Fan, X.-P.; Zhang, X. Neritinaceramides A–E, New Ceramides from the Marine Bryozoan Bugula neritina Inhabiting South China Sea and Their Cytotoxicity. Mar. Drugs 2014, 12, 1987-2003.

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