Nontoxic piperamides and their synthetic analogues as novel antifouling reagents

Xiang-Zhong Huang; Ying Xu; Yi-Fan Zhang; Yu Zhang; Yue Him Wong; Zhuang Han; Yan Yin; Pei-Yuan Qian

doi:10.1080/08927014.2014.889688

Nontoxic piperamides and their synthetic analogues as novel antifouling reagents

Xiang-Zhong Huang, Ying Xu, Yi-Fan Zhang, Yu Zhang, Yue Him Wong, Zhuang Han, Yan Yin, Pei-Yuan Qian

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

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.

Original language	English (US)
Pages (from-to)	473-481
Number of pages	9
Journal	Biofouling
Volume	30
Issue number	4
DOIs	https://doi.org/10.1080/08927014.2014.889688
State	Published - Mar 25 2014
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): SA-C0040, UK-C0016
Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1080/08927014.2014.889688

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title = "Nontoxic piperamides and their synthetic analogues as novel antifouling reagents",

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. {\textcopyright} 2014 {\textcopyright} 2014 Taylor & Francis.",

author = "Xiang-Zhong Huang and Ying Xu and Yi-Fan Zhang and Yu Zhang and Wong, {Yue Him} and Zhuang Han and Yan Yin and Pei-Yuan Qian",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): SA-C0040, UK-C0016 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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T1 - Nontoxic piperamides and their synthetic analogues as novel antifouling reagents

AU - Huang, Xiang-Zhong

AU - Xu, Ying

AU - Zhang, Yi-Fan

AU - Zhang, Yu

AU - Wong, Yue Him

AU - Han, Zhuang

AU - Yin, Yan

AU - Qian, Pei-Yuan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): SA-C0040, UK-C0016 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2014/3/25

Y1 - 2014/3/25

N2 - 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.

AB - 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.

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DO - 10.1080/08927014.2014.889688

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SN - 0892-7014

VL - 30

SP - 473

EP - 481

JO - Biofouling

JF - Biofouling

IS - 4

ER -

Nontoxic piperamides and their synthetic analogues as novel antifouling reagents

Abstract

Bibliographical note

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