Algicidal hydroxylated C18 unsaturated fatty acids from the red alga Tricleocarpa jejuensis: Identification, synthesis and biological activity

Zha, Shijiao; Kuwano, Kazuyoshi; Shibahara, Tomohiro; Ishibashi, Fumito

doi:10.1016/j.fitote.2020.104639

Cited by 7 publications

(7 citation statements)

References 35 publications

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“…Specifically 3-hydroxy fatty acids were found in Pediastrum duplex, C. reinhardtii , Chlorella pyrenoidosa , and Cyanidium caldarium ( Matsumoto and Nagashima, 1984 ; Yarkent et al, 2020 ) and mid-chain functionalized mono- and di-C 22 – 26 hydroxy fatty acids were detected in the zygospores of Chlamydomonas monoica ( Blokker et al, 1999 ). The red seaweed Tricleocarpa jejuensis contains mid-chain hydroxy C 18 : 1 with algicidal properties ( Zha et al, 2020 ) whereas ω-hydroxy fatty acids have been found in Chlorella emersonii , Tetraedron minimum , and Scenedesmus communis ( Allard et al, 2002 ). ω- and mid-chain C 30 – 34 hydroxy fatty acids have been identified in T. minimum , S. communis , and Pediastrum boryanum ( Blokker et al, 1998 ).…”

Section: Fatty Acid Derivatives From Microalgae Biosynthetic Pathways and Biotechnological Applicationsmentioning

confidence: 99%

Fatty Acids Derivatives From Eukaryotic Microalgae, Pathways and Potential Applications

Blasio

Balzano

2021

Front. Microbiol.

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The exploitation of petrochemical hydrocarbons is compromising ecosystem and human health and biotechnological research is increasingly focusing on sustainable materials from plants and, to a lesser extent, microalgae. Fatty acid derivatives include, among others, oxylipins, hydroxy fatty acids, diols, alkenones, and wax esters. They can occur as storage lipids or cell wall components and possess, in some cases, striking cosmeceutical, pharmaceutical, and nutraceutical properties. In addition, long chain (>20) fatty acid derivatives mostly contain highly reduced methylenic carbons and exhibit a combustion enthalpy higher than that of C14–20 fatty acids, being potentially suitable as biofuel candidates. Finally, being the building blocks of cell wall components, some fatty acid derivatives might also be used as starters for the industrial synthesis of different polymers. Within this context, microalgae can be a promising source of fatty acid derivatives and, in contrast with terrestrial plants, do not require arable land neither clean water for their growth. Microalgal mass culturing for the extraction and the exploitation of fatty acid derivatives, along with products that are relevant in nutraceutics (e.g., polyunsaturated fatty acids), might contribute in increasing the viability of microalgal biotechnologies. This review explores fatty acids derivatives from microalgae with applications in the field of renewable energies, biomaterials and pharmaceuticals. Nannochloropsis spp. (Eustigmatophyceae, Heterokontophyta) are particularly interesting for biotechnological applications since they grow at faster rates than many other species and possess hydroxy fatty acids and aliphatic cell wall polymers.

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Section: Fatty Acid Derivatives From Microalgae Biosynthetic Pathways and Biotechnological Applicationsmentioning

confidence: 99%

Fatty Acids Derivatives From Eukaryotic Microalgae, Pathways and Potential Applications

Blasio

Balzano

2021

Front. Microbiol.

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“…Compound A ((±)-E-12-hydroxyoctadec-10-enoic acid) and B ((±)-12-hydroxyoctadec-10-ynoic acid) were synthesised as described previously [25].…”

Section: Preparation Of Compound a And Bmentioning

confidence: 99%

“…Compound A is one of the four isomeric C18 hydroxy unsaturated fatty acids found in a methanol extract of Tricleocarpa jejuensis, which exerts algicidal activity against the red tide phytoplankton C. antiqua with >80% mortality after 24 h incubation at a concentration of 20 μg/mL [25]. To further evaluate the algicidal activity of compound A, its concentration-dependent effects on C. marina, K.…”

Section: Effects Of Compound a And B On Four Hab Speciesmentioning

confidence: 99%

“…Under these circumstances, we recently examined 17 species of macroalgae including 9 Rhodophyta, 6 Phaeophyta, and 2 Chlorophyta collected from the coastal region of Nagasaki Prefecture, Japan, based on the cytolytic activity against the raphidophycean flagellate Chattonella antiqua, and found that the red alga Tricleocarpa jejuensis had potent toxic compounds on C. antiqua [25]. NMR, IR and mass spectral analyses revealed that the active compounds are mixture of four isomers of C18 hydroxy…”

Section: Introductionmentioning

confidence: 99%

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Bioactivities of algicidal C18 hydroxy unsaturated fatty acid isolated from the red alga Tricleocarpa jejuensis and its synthesized propargylic derivative

et al. 2020

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“…Therefore, the absolute configuration of 5 is the same as that of 6 with the configuration 3R,11R,17R,21S. The known compounds were elucidated as 2,2',6'trihydroxy-4-methyl-6-methoxy-acyl-diphenylmethanone (2), [12] 2,2',6'-trihydroxy-4-hydroxymethyl-6-methanol-acyl-diphenylmethanone (3), [15] emodin (4), [16] (À )-versicolamide B (6), [14] secalonic acid A ( 7), [17] penicillixanthone A (8), [18] 7-hydroxy-3-(2-hydroxypropyl)-5-methyl-isochromen-1-one ( 9), [19] 2,5-dimethyl-7-hydroxychromone (10), [20] methyl indol-3-ylacetate ( 11), [21] (E)-12-hydroxyoctadec-10-enoic acid (12), [22] asperidine C (13), [23] L-657,398 ( 14), [24] chrysogeside E (15), [25] AGE-1 ( 16) and AGE-2 (17) [26] by comparison of their MS and NMR data with those reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

Asperbenzophenone A and Versicolamide C, New Fungal Metabolites from the Soft Coral Derived Aspergillus sp. SCSIO 41036

Long

Pang

Lin

et al. 2022

Chemistry & Biodiversity

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Two new compounds, asperbenzophenone A (1) and versicolamide C (5), together with fifteen known compounds were isolated from a soft coral derived fungus Aspergillus sp. SCSIO 41036. Their structures were elucidated by spectroscopic methods, ECD analysis, and by a comparison with data from the literature. In bioassay, compound 8 showed significant inhibitory activity against lipopolysaccharide-inducted nitric oxide (NO) in RAW264.7 cells at the concentration of 10 μM. Additionally, the anti-acetylcholinesterase activity assay showed that 14 exhibited weak inhibition with an IC 50 value of 157.8 μM.

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Algicidal hydroxylated C18 unsaturated fatty acids from the red alga Tricleocarpa jejuensis: Identification, synthesis and biological activity

Cited by 7 publications

References 35 publications

Fatty Acids Derivatives From Eukaryotic Microalgae, Pathways and Potential Applications

Fatty Acids Derivatives From Eukaryotic Microalgae, Pathways and Potential Applications

Bioactivities of algicidal C18 hydroxy unsaturated fatty acid isolated from the red alga Tricleocarpa jejuensis and its synthesized propargylic derivative

Asperbenzophenone A and Versicolamide C, New Fungal Metabolites from the Soft Coral Derived Aspergillus sp. SCSIO 41036

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