Nontoxic piperamides and their synthetic analogues as novel antifouling reagents

Handle URI:
http://hdl.handle.net/10754/599004
Title:
Nontoxic piperamides and their synthetic analogues as novel antifouling reagents
Authors:
Huang, Xiang-Zhong; Xu, Ying; Zhang, Yi-Fan; Zhang, Yu; Wong, Yue Him; Han, Zhuang; Yin, Yan; Qian, Pei-Yuan
Abstract:
Bioassay-guided isolation of an acetone extract from a terrestrial plant Piper betle produced four known piperamides with potent antifouling (AF) activities, as evidenced by inhibition of settlement of barnacle cypris larvae. The AF activities of the four piperamides and 15 synthesized analogues were compared and their structure-activity relationships were probed. Among the compounds, piperoleine B and 1-[1-oxo-7-(3′,4′-methylenedioxyphenyl)-6E-heptenyl]-piperidine (MPHP) showed strong activity against settlement of cyprids of the barnacle Balanus amphitrite, having EC50 values of 1.1 ± 0.3 and 0.5 ± 0.2 μg ml-1, respectively. No toxicity against zebra fish was observed following incubation with these two compounds. Besides being non-toxic, 91% of piperoleine B-treated cyprids and 84% of MPHP-treated cyprids at a concentration of 100 μM completed normal metamorphosis in recovery bioassays, indicating that the anti-settlement effect of these two compounds was reversible. Hydrolysis and photolysis experiments indicated that MPHP could be decomposed in the marine environment. It is concluded that piperamides are promising compounds for use in marine AF coatings. © 2014 © 2014 Taylor & Francis.
Citation:
Huang X-Z, Xu Y, Zhang Y-F, Zhang Y, Wong YH, et al. (2014) Nontoxic piperamides and their synthetic analogues as novel antifouling reagents. Biofouling 30: 473–481. Available: http://dx.doi.org/10.1080/08927014.2014.889688.
Publisher:
Informa UK Limited
Journal:
Biofouling
KAUST Grant Number:
SA-C0040; UK-C0016
Issue Date:
25-Mar-2014
DOI:
10.1080/08927014.2014.889688
PubMed ID:
24666035
Type:
Article
ISSN:
0892-7014; 1029-2454
Sponsors:
This study was supported by a grant (DY125-15-T02) from the China Ocean Mineral Resources Research and Development Association, an award (SA-C0040/UK-C0016) from the King Abdullah University of Science and Technology to Pei-Yuan Qian and the National Natural Science Foundation of China (No. 21262047). The authors are grateful to the School of Chemistry and Biotechnology, Yunnan University of Nationalities for measuring the NMR and MS spectra. They also acknowledge Dr Zilong Wen of the Hong Kong University of Science and Technology for providing zebra fish embryos.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorHuang, Xiang-Zhongen
dc.contributor.authorXu, Yingen
dc.contributor.authorZhang, Yi-Fanen
dc.contributor.authorZhang, Yuen
dc.contributor.authorWong, Yue Himen
dc.contributor.authorHan, Zhuangen
dc.contributor.authorYin, Yanen
dc.contributor.authorQian, Pei-Yuanen
dc.date.accessioned2016-02-25T13:51:00Zen
dc.date.available2016-02-25T13:51:00Zen
dc.date.issued2014-03-25en
dc.identifier.citationHuang X-Z, Xu Y, Zhang Y-F, Zhang Y, Wong YH, et al. (2014) Nontoxic piperamides and their synthetic analogues as novel antifouling reagents. Biofouling 30: 473–481. Available: http://dx.doi.org/10.1080/08927014.2014.889688.en
dc.identifier.issn0892-7014en
dc.identifier.issn1029-2454en
dc.identifier.pmid24666035en
dc.identifier.doi10.1080/08927014.2014.889688en
dc.identifier.urihttp://hdl.handle.net/10754/599004en
dc.description.abstractBioassay-guided isolation of an acetone extract from a terrestrial plant Piper betle produced four known piperamides with potent antifouling (AF) activities, as evidenced by inhibition of settlement of barnacle cypris larvae. The AF activities of the four piperamides and 15 synthesized analogues were compared and their structure-activity relationships were probed. Among the compounds, piperoleine B and 1-[1-oxo-7-(3′,4′-methylenedioxyphenyl)-6E-heptenyl]-piperidine (MPHP) showed strong activity against settlement of cyprids of the barnacle Balanus amphitrite, having EC50 values of 1.1 ± 0.3 and 0.5 ± 0.2 μg ml-1, respectively. No toxicity against zebra fish was observed following incubation with these two compounds. Besides being non-toxic, 91% of piperoleine B-treated cyprids and 84% of MPHP-treated cyprids at a concentration of 100 μM completed normal metamorphosis in recovery bioassays, indicating that the anti-settlement effect of these two compounds was reversible. Hydrolysis and photolysis experiments indicated that MPHP could be decomposed in the marine environment. It is concluded that piperamides are promising compounds for use in marine AF coatings. © 2014 © 2014 Taylor & Francis.en
dc.description.sponsorshipThis study was supported by a grant (DY125-15-T02) from the China Ocean Mineral Resources Research and Development Association, an award (SA-C0040/UK-C0016) from the King Abdullah University of Science and Technology to Pei-Yuan Qian and the National Natural Science Foundation of China (No. 21262047). The authors are grateful to the School of Chemistry and Biotechnology, Yunnan University of Nationalities for measuring the NMR and MS spectra. They also acknowledge Dr Zilong Wen of the Hong Kong University of Science and Technology for providing zebra fish embryos.en
dc.publisherInforma UK Limiteden
dc.subjectactivity relationshipen
dc.subjectantifouling compoundsen
dc.subjecthydrolysis and photolysisen
dc.subjectPiper betleen
dc.subjectpiperamidesen
dc.titleNontoxic piperamides and their synthetic analogues as novel antifouling reagentsen
dc.typeArticleen
dc.identifier.journalBiofoulingen
dc.contributor.institutionHong Kong University of Science and Technology, Hong Kong, Chinaen
dc.contributor.institutionYunnan University, Kunming, Chinaen
kaust.grant.numberSA-C0040en
kaust.grant.numberUK-C0016en

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