New Marine Antifouling Compounds from the Red Alga Laurencia sp.

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

doi:10.3390/md15090267

Cited by 33 publications

(24 citation statements)

References 25 publications

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“…Both compounds showed potent inhibition of barnacle larval settlemental at concentration >20 fold lower than they were toxic. 380 New brominated/chlorinated sesquiterpenes continue to be reported from red algae and include the cuparane, 8-deoxyalgoane 896 (Laurencia natalensis), 381 laurane dimers 897-899 (Laurencia okamurai) 382 and chamigranes, compositacins A-L 900-911 (Laurencia composita). 383 The structures of an additional two chamigranes, cycloelatanene A and B 912, 913 have been revised through application of the crystalline sponge method.…”

Section: Red Algaementioning

confidence: 99%

“…386 Other new non-halogenated sesquiterpenes reported were the laurane 931 (Laurencia sp. ), 380 and the monocyclofarnesols 932, 933 (Laurencia snackeyi), 387 while the relative conguration of the stereogenic centres in the known red algae metabolite palisadin A 934 also isolated from Laurencia snackeyi have now been dened. 387 A study to investigate the enzymes involved in the biosynthesis of sesquiterpenes in red algae has identied, through transcriptomics, three sesquiterpene synthases from L. pacica.…”

Section: Red Algaementioning

confidence: 99%

“…388 New diterpenes were omaezol 936 and 11,12-dihydro-3hydroxyretinol 937 (Laurencia sp. ), 380 13-acetyl pinnatol A 938 isoconcinndiol 13-acetate 939, and concinndiol 13-acetate 940 (ref. 389) (Laurencia alfredensis).…”

Section: Red Algaementioning

confidence: 99%

“…390 New polyether triterpenes intricatriol 948 (Laurencia sp.) 380 and alfredensinols A-C 949-951 (L. alfredensis) 389 were reported. This alga also contained three new oxygenated steroids, alfredensterol 952, 14a-hydroxy alfredensterol 953 and 3-deacetoxy alfredensterol 954.…”

Section: Red Algaementioning

confidence: 99%

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Marine natural products

et al. 2019

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Section: Red Algaementioning

confidence: 99%

Section: Red Algaementioning

confidence: 99%

Section: Red Algaementioning

confidence: 99%

Section: Red Algaementioning

confidence: 99%

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Marine natural products

et al. 2019

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“…Among marine organisms, algae of the genus Laurencia are considered one of the richest sources of novel compounds with a wide range of bioactive properties, such as the brominated sesquiterpenes laurinterol (1) and aplysin (2) ( Figure 1) [10]. Laurinterol has been evaluated for its antibacterial [11][12][13], cytotoxic [13][14][15], antifouling [16], anti-Acanthamoeba [17], Na/K ATPase inhibition [18], insecticidal, and repellent properties [19]. Meanwhile, aplysin has shown moderate cytotoxic activity and has been evaluated for its mechanisms of action in different biological models [20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Antimycobacterial Activity of Laurinterol and Aplysin from Laurencia johnstonii

et al. 2020

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Marine environments represent a great opportunity for the discovery of compounds with a wide spectrum of bioactive properties. Due to their large variety and functions derived from natural selection, marine natural products may allow the identification of novel drugs based not only on newly discovered bioactive metabolites but also on already known compounds not yet thoroughly investigated. Since drug resistance has caused an increase in infections by Mycobacterium tuberculosis and nontuberculous mycobacteria, the re-evaluation of known bioactive metabolites has been suggested as a good approach to addressing this problem. In this sense, this study presents an evaluation of the in vitro effect of laurinterol and aplysin, two brominated sesquiterpenes isolated from Laurencia johnstonii, against nine M. tuberculosis strains and six nontuberculous mycobacteria (NTM). Laurinterol exhibited good antimycobacterial activity, especially against nontuberculous mycobacteria, being remarkable its effect against Mycobacterium abscessus, with minimum inhibitory concentration (MIC) values lower than those of the reference drug imipenem. This study provides further evidence for the antimycobacterial activity of some sesquiterpenes from L. johnstonii, which can be considered interesting lead compounds for the discovery of novel molecules to treat NTM infections.

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Two New Halogenated Compounds from the Marine Red Alga Laurencia nipponica Yamada from the Kunashiri and Etorofu Islands

Sato

Kaneko

Kamekawa

et al. 2021

Chemistry & Biodiversity

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The red alga Laurencia nipponica comprises various chemical races distributed relative to the ocean current in Japanese coastal areas. We investigated the chemical compositions and chemical races of L. nipponica distributed from the Kunashiri and Etorofu Islands, the confluence of the Soya warm current and Oya‐shio cold current. Two new halogenated secondary metabolites, deacetylneonipponallene (1) and neopacifenol (2), along with four known compounds, deoxyprepacifenol (3), pacifenol (4), halo‐chamigrene diether (5), and isolaurallene (6) were isolated from L. nipponica collected at Chikappunai, Kunashiri Island, while Zaimokuiwa (Kunashiri Island) and Sana (Etorofu Island) populations contained 3, 7‐hydroxylaurene (7), 2,10‐dibromo‐3‐chloro‐9‐hydroxy‐α‐chamigrene (8), and (3Z)‐laurefucin (9). The structures of 1 and 2 were established using spectroscopic methods. The chemical races of L. nipponica distributed in this area were divided into 6‐ and 9‐producing races. Interestingly, both races contained 4 as an additional race‐index, as well as its derivatives, 2 and 5. To the best of our knowledge, this is the first example of a race comprising a mixture of two race‐index compounds, suggesting that the convergence of two currents causes the production of new and diverse chemical races in this species.

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New Marine Antifouling Compounds from the Red Alga Laurencia sp.

Cited by 33 publications

References 25 publications

Marine natural products

Marine natural products

Antimycobacterial Activity of Laurinterol and Aplysin from Laurencia johnstonii

Two New Halogenated Compounds from the Marine Red Alga Laurencia nipponica Yamada from the Kunashiri and Etorofu Islands

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