New Marine Antifouling Compounds from the Red Alga Laurencia sp

Yuko Oguri; Mami Watanabe; Takafumi Ishikawa; Takashi Kamada; Charles S Vairappan; Hiroshi Matsuura; Kensuke Kaneko; Takahiro Ishii; Minoru Suzuki; Erina Yoshimura; Yasuyuki Nogata; Tatsufumi Okino

doi:10.3390/md15090267

New Marine Antifouling Compounds from the Red Alga Laurencia sp

Mar Drugs. 2017 Aug 28;15(9):267. doi: 10.3390/md15090267.

Authors

Affiliations

¹ Graduate School of Environmental Science, Hokkaido University, Sapporo 060-0810, Japan. oguri-yuu@awi.co.jp.
² Graduate School of Environmental Science, Hokkaido University, Sapporo 060-0810, Japan. watamatsu@ees.hokudai.ac.jp.
³ Graduate School of Environmental Science, Hokkaido University, Sapporo 060-0810, Japan. tishikawa947@gmail.com.
⁴ Institute for Tropical Biology and Conservation, Universiti Malaysia Sabah, Kota Kinabalu, Sabah 88400, Malaysia. takashi.kamada@ums.edu.my.
⁵ Institute for Tropical Biology and Conservation, Universiti Malaysia Sabah, Kota Kinabalu, Sabah 88400, Malaysia. csv@mes.edu.my.
⁶ National Institute of Technology, Asahikawa College, Asahikawa 071-8142, Japan. matsuura@asahikawa-nct.ac.jp.
⁷ Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. kaneko.kensuke.6a@kyoto-u.ac.jp.
⁸ Faculty of Agriculture, University of the Ryukyus, Senbaru 1, Nishihara, Okinawa 903-0213, Japan. ishiit@agr.u-ryukyu.ac.jp.
⁹ Coastal Branch of Natural History Museum and Institute, Chiba, 123 Yoshio, Katsuura, Chiba 299-5242, Japan. reiboku1965@yahoo.co.jp.
¹⁰ CERES, Inc., 1-4-5 Midori, Abiko, Chiba 270-1153, Japan. erinamusi@yahoo.co.jp.
¹¹ Environmental Science Research Laboratory, Central Research Institute of Electric Power Industry, 1646 Abiko, Abiko, Chiba 270-1194, Japan. noga@criepi.denken.or.jp.
¹² Graduate School of Environmental Science, Hokkaido University, Sapporo 060-0810, Japan. okino@ees.hokudai.ac.jp.
¹³ Faculty of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan. okino@ees.hokudai.ac.jp.

Abstract

Six new compounds, omaezol, intricatriol, hachijojimallenes A and B, debromoaplysinal, and 11,12-dihydro-3-hydroxyretinol have been isolated from four collections of Laurencia sp. These structures were determined by MS and NMR analyses. Their antifouling activities were evaluated together with eight previously known compounds isolated from the same samples. In particular, omaezol and hachijojimallene A showed potent activities (EC₅₀ = 0.15-0.23 µg/mL) against larvae of the barnacle Amphibalanus amphitrite.

Keywords: Laurencia; Rhodophyta; acetogenin; antifouling; barnacle; biofouling; terpenoid.

MeSH terms

Animals
Biofouling / prevention & control*
Diterpenes / chemistry
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Japan
Larva / drug effects*
Laurencia / chemistry*
Marine Biology
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Omeprazole / chemistry
Omeprazole / isolation & purification*
Omeprazole / pharmacology*
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Sesquiterpenes / pharmacology*
Thoracica / drug effects*
Vitamin A / analogs & derivatives

Substances

Diterpenes
Sesquiterpenes
hachijojimallene
omaezol
Vitamin A
3-hydroxyretinol
Omeprazole