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Characterization of Terpenoids from the Root of Ceriops tagal with Antifouling Activity
Research Center for the Chemistry and Chemical Engineering of Marine Biological Resource, The Third Institute of Oceanography of the State Oceanic Administration, Xiamen 361005, China
Department of Biology, School of Life Sciences, Xiamen University, Xiamen 361005, China
Department of Oceanography, College of Oceanography and Environmental Science, Xiamen University, Xiamen 361005, China
* Author to whom correspondence should be addressed.
Received: 16 August 2011; in revised form: 27 September 2011 / Accepted: 28 September 2011 / Published: 6 October 2011
Abstract: One new dimeric diterpenoid, 8(14)-enyl-pimar-2'(3')-en-4'(18')-en-15'(16')-en-dolabr-16,15,2',3'-oxoan-16-one (1) and five known terpenoids: Tagalsin C (2), Tagalsin I (3), lup-20(29)-ene-3β,28-diol (4), 3-oxolup-20(29)-en-28-oic acid (5) and 28-hydroxylup-20(29)-en-3-one (6) were isolated from the roots of the mangrove plant Ceriops tagal. Their structures and relative stereochemistry were elucidated by means of extensive NMR, IR and MS analysis. The antifouling activity against larval settlement of the barnacle Balanus albicostatus were evaluated using capsaicin as a positive control. All these terpenoids exhibited antifouling activity against cyprid larvae of the barnacle without significant toxicity. The structure-activity relationship results demonstrated that the order of antifouling activity was diterpenoid (Compound 2) > triterpenoid (Compounds 4, 5 and 6) > dimeric diterpenoid (Compounds 1 and 3). The functional groups on the C-28 position of lupane triterpenoid significantly affect the antifouling activity. The diterpenoid dimmer with two identical diterpenoid subunits might display more potent antifouling activity than one with two different diterpenoid subunits. The stability test showed that Compounds 2, 4, 5 and 6 remained stable over 2-month exposure under filtered seawater.
Keywords: terpenoids; antifouling activity; barnacle; Ceriops tagal; structure-activity relationship
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Chen, J.-D.; Yi, R.-Z.; Lin, Y.-M.; Feng, D.-Q.; Zhou, H.-C.; Wang, Z.-C. Characterization of Terpenoids from the Root of Ceriops tagal with Antifouling Activity. Int. J. Mol. Sci. 2011, 12, 6517-6528.
Chen J-D, Yi R-Z, Lin Y-M, Feng D-Q, Zhou H-C, Wang Z-C. Characterization of Terpenoids from the Root of Ceriops tagal with Antifouling Activity. International Journal of Molecular Sciences. 2011; 12(10):6517-6528.
Chen, Jun-De; Yi, Rui-Zao; Lin, Yi-Ming; Feng, Dan-Qing; Zhou, Hai-Chao; Wang, Zhan-Chang. 2011. "Characterization of Terpenoids from the Root of Ceriops tagal with Antifouling Activity." Int. J. Mol. Sci. 12, no. 10: 6517-6528.