Neritinaceramides A-E, new ceramides from the marine bryozoan Bugula neritina inhabiting South China Sea and their cytotoxicity.
Five new ceramides, neritinaceramides A (1), B (2), C (3), D (4) and E (5), together with six known ceramides (6-11), 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 1-3, was found from marine bryozoans for the first time. The new ceramides 1-5 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 (1-5) added to the chemical diversity of B. neritina and expanded our knowledge of the chemical modifications and biological activity of ceramides.
Research & Development Center of Biorational Pesticide, College of Plant Protection, Northwest A&F University, Yangling 712100, China. tianxiangrong@163.com.
Xiang-Rong
XR
Tian
Institute of Materia Medica, School of Pharmacy, Fourth Military Medical University, Xi'an 710032, China. tanghaifeng71@163.com.
Hai-Feng
HF
Tang
Research & Development Center of Biorational Pesticide, College of Plant Protection, Northwest A&F University, Yangling 712100, China. fengjt@nwsuaf.edu.cn.
Jun-Tao
JT
Feng
School of Traditional Chinese Medicines, Shenyang Pharmaceutical University, Shenyang 110016, China. liyushan8888@yahoo.com.cn.
Yu-Shan
YS
Li
Department of Pharmacy, Renji Hospital, Affiliated to School of Medicine, Shanghai Jiao-Tong University, Shanghai 200127, China. franklin67@126.com.
Hou-Wen
HW
Lin
Research & Development Center of Biorational Pesticide, College of Plant Protection, Northwest A&F University, Yangling 712100, China. ting2008ting2008@163.com.
Xiao-Pei
XP
Fan
Research & Development Center of Biorational Pesticide, College of Plant Protection, Northwest A&F University, Yangling 712100, China. zhxing1952@126.com.
Xing
X
Zhang
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002013:Bryozoa / Q000378:metabolism*; D045744:Cell Line, Tumor; D002518:Ceramides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002681:China; D056945:Hep G2 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D009369:Neoplasms / Q000188:drug therapy / Q000473:pathology; D009792:Oceans and Seas
D000970:Antineoplastic Agents; D002518:Ceramides