Anti-Barnacle Activities of Isothiocyanates Derived from β-Citronellol and Their Structure-Activity Relationships.
antifouling activity
barnacle
isothiocyanate
structure-activity relationship
β-citronellol
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Feb 2023
Feb 2023
Historique:
received:
05
10
2022
accepted:
23
12
2022
pubmed:
26
12
2022
medline:
25
2
2023
entrez:
25
12
2022
Statut:
ppublish
Résumé
Antifouling agents with low toxicity are in high demand for sustaining marine industries and the environment. This study aimed to synthesize 15 isothiocyanates derived from β-citronellol and evaluate their antifouling activities and toxicities against cypris larvae of the barnacle Amphibalanus amphitrite. The synthesized isothiocyanates exhibited effective antifouling activities (EC
Identifiants
pubmed: 36567259
doi: 10.1002/cbdv.202200953
doi:
Substances chimiques
citronellol
P01OUT964K
Cyanides
0
Acyclic Monoterpenes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200953Subventions
Organisme : JSPS KAKENHI
ID : 20H03072
Organisme : JSPS KAKENHI
ID : 19H00930
Organisme : JSPS KAKENHI
ID : 19 K22272
Organisme : JSPS KAKENHI
ID : 22 K05450
Informations de copyright
© 2022 Wiley-VHCA AG, Zurich, Switzerland.
Références
M. D. Richmond, R. Seed, ‘A Review of Marine Macrofouling Communities with Special Reference to Animal Fouling’, Biofouling 1991, 3, 151-168.
M. P. Schultz, J. A. Bendick, E. R. Holm, W. M. Hertel, ‘Economic Impact of Biofouling on a Naval Surface Ship’, Biofouling 2011, 27, 87-98.
I. Fitridge, T. Dempster, J. Guenther, R. de Nys, ‘The Impact and Control of Biofouling in Marine Aquaculture: A Review’, Biofouling 2012, 28, 649-669.
D. M. Yebra, S. Kiil, K. Dam-Johansen, ‘Antifouling Technology-Past, Present and Future Steps Towards Efficient and Environmentally Friendly Antifouling Coatings’, Prog. Org. Coat. 2004, 50, 75-104.
K. A. Dafforn, J. A. Lewis, E. L. Johnston, ‘Antifouling Strategies: History and Regulation, Ecological Impacts and Mitigation’, Mar. Pollut. Bull. 2011, 62, 453-465.
P.-Y. Qian, Y. Xu, N. Fusetani, ‘Natural Products as Antifouling Compounds: Recent Progress and Future Perspectives’, Biofouling 2010, 26, 223-234.
C. Alzieu, ‘Environmental Impact of TBT: The French Experience’, Sci. Total Environ. 2000, 258, 99-102.
S. M. Evans, G. J. Nicholson, ‘The Use of Imposex to Assess Tributyltin Contamination in Coastal Waters and Open Seas’, Sci. Total Environ. 2000, 258, 73-80.
M. Ramón, M. J. Amor, ‘Increasing Imposex in Populations of Bolinus brandaris (Gastropoda: Muricidae) in the North-western Mediterranean’, Mar. Environ. Res. 2001, 52, 463-475.
A. P. Negri, L. D. Smith, N. S. Webster, A. J. Heyward, ‘Understanding Ship-grounding Impacts on a Coral Reef: Potential Effects of Anti-foulant Paint Contamination on Coral Recruitment’, Mar. Pollut. Bull. 2002, 44, 111-117.
S. E. Martins, G. Fillmann, A. Lillicrap, K. V. Thomas, ‘Review: Ecotoxicity of Organic and Organo-metallic Antifouling Co-biocides and Implications for Environmental Hazard and Risk Assessments in Aquatic Ecosystems’, Biofouling 2018, 34, 34-52.
K. V. Thomas, S. Brooks, ‘The Environmental Fate and Effects of Antifouling Paint Biocides’, Biofouling 2010, 26, 73-88.
S. Ortlepp, M. Sjögren, M. Dahlström, H. Weber, R. Ebel, R. Edrada, C. Thoms, P. Schupp, L. Bohlin, P. Proksch, ‘Antifouling Activity of Bromotyrosine-Derived Sponge Metabolites and Synthetic Analogs’, Mar. Biotechnol. 2007, 9, 776-785.
P.-Y. Qian, Z. Li, Y. Xu, Y. Li, N. Fusetani, ‘Mini-review: Marine Natural Products and Their Synthetic Analogs as Antifouling Compounds: 2009-2014’, Biofouling 2015, 31, 101-122.
T. Umezawa, Y. Hasegawa, I. S. Novita, J. Suzuki, T. Morozumi, Y. Nogata, E. Yoshimura, F. Matsuda, ‘Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides’, Mar. Drugs 2017, 15, 203.
T. Umezawa, N. I. Prakoso, M. Kannaka, Y. Nogata, E. Yoshimura, T. Okino, F. Matsuda, ‘Synthesis and Structure-Activity Relationship of Omaezallene Derivatives’, Chem. Biodiversity 2019, 16, e1800451.
L. O. Casalme, K. Katayama, Y. Hayakawa, K. Nakamura, A. Yamauchi, Y. Nogata, E. Yoshimura, F. Matsuda, T. Umezawa, ‘Effective Synthesis and Antifouling Activity of Dolastatin 16 Derivatives’, Mar. Drugs 2022, 20, 124.
V. Piazza, V. Roussis, F. Garaventa, G. Greco, V. Smyrniotopoulos, C. Vagias, M. Faimali, ‘Terpenes from the Red Alga Sphaerococcus coronopifolius Inhibit the Settlement of Barnacles’, Mar. Biotechnol. 2011, 13, 764-772.
N. Fusetani, ‘Biofouling and Antifouling’, Nat. Prod. Rep. 2004, 21, 94-104.
N. Fusetani, ‘Antifouling Marine Natural Products’, Nat. Prod. Rep. 2011, 28, 400-410.
S.-H. Qi, X. Ma, ‘Antifouling Compounds from Marine Invertebrates’, Mar. Drugs 2017, 15, 263.
I. M. Prieto, A. Paola, M. Pérez, M. García, G. Blustein, L. Schejter, J. A. Palermo, ‘Antifouling Diterpenoids from the Sponge Dendrilla antarctica’, Chem. Biodiversity 2022, 19, e202100618.
T. Okino, E. Yoshimura, H. Hirota, N. Fusetani, ‘New Antifouling Sesquiterpenes from Four Nudibranchs of the Family Phyllidiidae’, Tetrahedron 1996, 52, 9447-9454.
Y. Kitano, T. Ito, T. Suzuki, Y. Nogata, K. Shinshima, E. Yoshimura, K. Chiba, M. Tada, I. Sakaguchi, ‘Synthesis and Antifouling Activity of 3-Isocyanotheonellin and Its Analogs’, J. Chem. Soc. Perkin Trans. 1 2002, 2251-2255.
Y. Kitano, A. Yokoyama, Y. Nogata, K. Shinshima, E. Yoshimura, K. Chiba, M. Tada, I. Sakaguchi, ‘Synthesis and Anti-barnacle Activities of Novel 3-Isocyanotheonellin Analogs’, Biofouling 2003, 19, 187-192.
Y. Kitano, Y. Nogata, K. Shinshima, E. Yoshimura, K. Chiba, M. Tada, I. Sakaguchi, ‘Synthesis and Anti-barnacle Activities of Novel Isocyanocyclohexane Compounds Containing an Ester or an Ether Functional Group’, Biofouling 2004, 20, 93-100.
Y. Nogata, Y. Kitano, E. Yoshimura, K. Shinshima, I. Sakaguchi, ‘Antifouling Activity of Simple Synthetic Isocyanides Against Larvae of the Barnacle Balanus amphitrite’, Biofouling 2004, 20, 87-91.
Y. Kitano, C. Akima, E. Yoshimura, Y. Nogata, ‘Anti-barnacle Activity of Novel Simple Alkyl Isocyanides Derived from Citronellol’, Biofouling 2011, 27, 201-205.
T. Fukuda, H. Wagatsuma, Y. Kominami, Y. Nogata, E. Yoshimura, K. Chiba, Y. Kitano, ‘Anti-barnacle Activity of Isocyanides Derived from Amino Acids’, Chem. Biodiversity 2016, 13, 1502-1510.
Y. Inoue, S. Takashima, Y. Nogata, E. Yoshimura, K. Chiba, Y. Kitano, ‘Isocyanides Derived from α,α-Disubstituted Amino Acids: Synthesis and Antifouling Activity Assessment’, Chem. Biodiversity 2018, 15, e1700571.
K. Ina, R. Takasawa, A. Yagi, H. Etoh, K. Sakata, ‘Isothiocyanates as an Attaching Repellent Against the Blue Mussel Mytilus edulis’, Agric. Biol. Chem. 1989, 53, 3323-3325.
H. Hirota, Y. Tomono, N. Fusetani, ‘Terpenoids with Antifouling Activity Against Barnacle Larvae from the Marine Sponge Acanthella cavernosa’, Tetrahedron 1996, 52, 2359-2368.
Y. Xu, N. Li, W.-H. Jiao, R.-P. Wang, Y. Peng, S.-H. Qi, S.-J. Song, W.-S. Chen, H.-W. Lin, ‘Antifouling and Cytotoxic Constituents from the South China Sea Sponge Acanthella cavernosa’, Tetrahedron 2012, 68, 2876-2883.
T. S. Rajan, G. R. De Nicola, R. Iori, P. Rollin, P. Bramanti, E. Mazzon, ‘Anticancer Activity of Glucomoringin Isothiocyanate in Human Malignant Astrocytoma Cells’, Fitoterapia 2016, 110, 1-7.
A. T. Dinkova-Kostova, R. V. Kostov, ‘Glucosinolates and Isothiocyanates in Health and Disease’, Trends Mol. Med. 2012, 18, 337-347.
Y. Morimitsu, K. Hayashi, Y. Nakagawa, H. Fujii, F. Horio, K. Uchida, T. Osawa, ‘Antiplatelet and Anticancer Isothiocyanates in Japanese Domestic Horseradish, Wasabi’, Mech. Ageing Dev. 2000, 116, 125-134.
D. Trachootham, Y. Zhou, H. Zhang, Y. Demizu, Z. Chen, H. Pelicano, P. J. Chiao, G. Achanta, R. B. Arlinghaus, J. Liu, P. Huang, ‘Selective Killing of Oncogenically Transformed Cells Through a ROS-mediated Mechanism by β-Phenylethyl Isothiocyanate’, Cancer Cell 2006, 10, 241-252.
K. Nieves, J. Prudhomme, K. G. Le Roch, S. G. Franzblau, A. D. Rodríguez, ‘Natural Product-based Synthesis of Novel Anti-infective Isothiocyanate- and Isoselenocyanate-functionalized Amphilectane Diterpenes’, Bioorg. Med. Chem. Lett. 2016, 26, 854-857.
I. Blažević, A. Đulović, A. Maravić, V. Č. Čulić, S. Montaut, P. Rollin, ‘Antimicrobial and Cytotoxic Activities of Lepidium latifolium L. Hydrodistillate, Extract and Its Major Sulfur Volatile Allyl Isothiocyanate’, Chem. Biodiversity 2019, 16, e1800661.
S. Fujiwara, T. Shin-Ike, N. Sonoda, M. Aoki, K. Okada, N. Miyoshi, N. Kambe, ‘Novel Selenium Catalyzed Synthesis of Isothiocyanates from Isocyanides and Elemental Sulfur’, Tetrahedron Lett. 1991, 32, 3503-3506.
Y. Kitano, K. Chiba, M. Tada, ‘A Direct Conversion of Alkenes to Isocyanides’, Synlett 1999, 3, 288-290.
S. Fujiwara, C. Akima, Y. Nogata, E. Yoshimura, K. Chiba, Y. Kitano, ‘Bio-organic and anti-barnacle studies of fluorescence-labeled probe compounds against cyprids of barnacles’, J. Exp. Mar. Biol. Ecol. 2013, 445, 88-92.
C. G. Satuito, K. Shimizu, K. Natoyama, M. Yamazaki, N. Fusetani, ‘Age-related Settlement Success by Cyprids of the Barnacle Balanus amphitrite, with Special Reference to Consumption of Cyprid Storage Protein’, Mar. Biol. 1996, 127, 125-130.
D. Rittschof, A. S. Clare, D. J. Gerhart, S. A. Mary, J. Bonaventura, ‘Barnacle In Vitro Assays for Biologically Active Substances: Toxicity and Settlement Inhibition Assays Using Mass Cultured Balanus amphitrite amphitrite Darwin’, Biofouling 1992, 6, 115-122.
H. Hirota, T. Okino, Y. Tomono, E. Yoshimura, N. Fusetani, ‘Antifouling Activity of Isocyanoterpenoids and Related Compounds Isolated from a Marine Sponge and Nudibranchs’, J. Nat. Toxins 1996, 5, 249-259.