Facile Total Synthesis and Antimicrobial Activity of the Marine Fatty Acids (<i>Z</i>)-2-Methoxy-5-hexadecenoic Acid and (<i>Z</i>)-2-Methoxy-6-hexadecenoic Acid

Carballeira, Néstor M.; Emiliano, Anastacio; Hernández-Alonso, Norali; González, Fernando

doi:10.1021/np980274o

Cited by 28 publications

(23 citation statements)

References 12 publications

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“…7-Methoxydodec-4-enoic acid, which is non-cytotoxic and immunosuppressive toward KB cells, was also isolated from L. majuscula (Mesguiche et al, 1999). In addition, 2-methoxy-5-hexadecenoic acid and 2-methoxy-6-hexadecenoic acid isolated from sponges are antimicrobial (Carballeira et al, 1998).…”

Section: Inhibition Of Plamentioning

confidence: 99%

A methoxylated fatty acid isolated from the brown seaweed Ishige okamurae inhibits bacterial phospholipase A₂

Cho

Gyawali

Ahn

et al. 2008

Phytotherapy Research

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A methoxylated fatty acid that inhibits phospholipase A(2) (PLA(2); EC 3.1.1.4) was purified from the brown seaweed Ishige okamurae. Approximately 8.1 mg of the inhibitory compound, 7-methoxy-9-methylhexadeca-4,8-dienoic acid, was isolated from 1 kg of I. okamurae powder. Recombinant PLA(2) derived from the pathogenic bacterium Vibrio mimicus was used as the target enzyme. The methoxylated fatty acid compound competitively inhibited PLA(2) with a Ki value of 3.9 microg/mL. The concentrations required for 50% inhibition of PLA(2), oedema and erythema were 1.0 microg/mL, 3.6 mg/mL and 4.6 mg/mL, respectively. The compound strongly inhibited PLA(2) activity in vitro and had potent antiinflammatory activity in vivo.

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Section: Inhibition Of Plamentioning

confidence: 99%

A methoxylated fatty acid isolated from the brown seaweed Ishige okamurae inhibits bacterial phospholipase A₂

Cho

Gyawali

Ahn

et al. 2008

Phytotherapy Research

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“…Among those compounds that are being evaluated as antibacterial agents, unsaturated fatty acids have demonstrated to be biologically active towards Gram-positive bacteria, specifically against Staphylococcus aureus (Carballeira et al, 2002; Carballeira et al, 1998; Zheng et al, 2005) [DS1] . In the present study, we prepared a series of 2-alkynoic fatty acids (2-AFAs) and other synthetic analogues such as 2-tetrahydropyranyl protected alkynols and 2-alkynols aimed at establishing a structure activity relationship (SAR) with these compounds in order to find the fatty acid with better cytotoxicity against both Gram-positive and Gram-negative bacteria.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria

Sanabria‐Ríos

Rivera-Torres

Maldonado-Domínguez

et al. 2014

Chemistry and Physics of Lipids

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The first study aimed at determining the structural characteristics needed to prepare antibacterial 2-alkynoic fatty acids (2-AFAs) was accomplished by synthesizing several 2-AFAs and other analogues in 18-76% overall yields. Among all the compounds tested, the 2-hexadecynoic acid (2-HDA) displayed the best overall antibacterial activity against Gram-positive Staphylococcus aureus (MIC = 15.6 μg/mL), Staphylococcus saprophyticus (MIC = 15.5 μg/mL), and Bacillus cereus (MIC = 31.3 μg/mL), as well as against the Gram-negative Klebsiella pneumoniae (7.8 μg/mL) and Pseudomonas aeruginosa (MIC = 125 μg/mL). In addition, 2-HDA displayed significant antibacterial activity against methicillin-resistant S. aureus (MRSA) ATCC 43300 (MIC = 15.6 μg/mL) and clinical isolates of MRSA (MIC = 3.9 μg/mL). No direct relationship was found between the antibacterial activity of 2-AFAs and their critical micelle concentration (CMC) suggesting that the antibacterial properties of these fatty acids are not mediated by micelle formation. It was demonstrated that the presence of a triple bond at C-2 as well as the carboxylic acid moiety in 2-AFAs are important for their antibacterial activity. 2-HDA has the potential to be further evaluated for use in antibacterial formulations.

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“…In the present investigation, the total content of monoenoic FAs was only 6.75%. The content of 18:1('9) and 19:1 was the major among them [17]. The identification of 18:1 and 19:1 is confirmed by comparing their key mass fragments (18:1 m/z 296 M + , 264, 222, 180, 151, 137, 123, 98, 84, 69; 19:1: m/z 310 M + , 278, 236, 208, 194, 163, 152, 138, 123, 97, 69, 55) obtained by GC-MS analysis with literature data.…”

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confidence: 98%

“…Thus, in the sponge P. purpurea the content of iso and anteiso may be due to symbiotic bacteria. Only one polybranched FA was identified, i.e., 3,7,11,15-tetramethylhexadecanoic acid (br-16:0, 4.38%), which is very often found in marine sponges [17]. The identification of 3,7,11,15-tetramethyl-16:0 was finally confirmed by comparing its key mass fragments (3,7,11,15-tetramethyl-16:0: m/z 326 M + , 311, 139, 112, 101, 97, 74, 57) obtained by GC-MS analysis with literature data.…”

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confidence: 99%

Fatty Acid Profile, Sterol Composition of Lipids, and Antibacterial Study of the Marine Sponge Psammaplysilla purpurea Collected from the Bay of Bengal (Odisha Coast)

et al. 2014

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Marine sponges are the most primitive multicellular sedentary animals that produce bioactive metabolites. Among the aquatic animals, sponges are characterized by the greatest diversity of fatty acids (FA), sterols, etc. Fatty acids and sterols as lipid components of sponges have been elaborately studied by a number of investigators [1][2][3][4][5][6]. Some lipids of sponges are characterized as biologically active [7][8][9].The sponge Psammaplysilla purpurea (order Verongida, family Aplysinellidae) is a well-known source of several bromotyrosine alkaloids of unique structural features and exhibiting promising biological activities such as cytotoxicity, antimicrobial properties, etc. [10][11][12][13]. The methanol and dichloromethane extracts of this species have shown broad-spectrum larvicidal and insecticidal activity [14]. However there has been no report on the FA profile of the lipid composition of P. purpurea. This is the first report on the analysis of the FA and sterol composition of the sponge P. purpurea collected from the Bay of Bengal region of the Odisha coast. The search for FAs and sterols of the lipophilic extract of P. purpurea can give valuable information on its chemotaxonomy. Thus, these minor components appear as biomarkers for such organisms.Forty-nine fatty acids were identified in the mixture of total lipids of P. purpurea by GC-MS analysis (Table 1). Peak identification was carried out by comparison of the mass spectra with those available in the NIST and WILEY libraries and also confirmed by comparison of their chromatographic retention times as well as mass fragmentations with those of authentic standards C-4-C-24 (Supelco standard FAME mixtures). Among the identified fatty acids, saturated linear FAs account for more than 50% of the total FA content, which is an important observation. All of the acids from 12:0 to 27:0 were found except 13:0. Generally, among saturated fatty acids, 16:0 and C18:0 dominated in most of the sponges. But in the present investigation, the acids 19:0 and 16:0 were dominant. Long-chain saturated fatty acids like 22:0 to 27:0 are present, among which 26:0 is present in good amount (6.04%).In sponges, branched saturated iso/anteiso acids with a total number of carbon atoms from C-14 to C-29 were found, among which C-15-C-20 acids were the most widespread [15]. In the present investigation, 24 saturated monobranched FAs were identified (29.92%), br-16:0 and br-14:0 being the major ones. It is considered that saturated iso and anteiso C-15-C-20 acids have a bacterial origin [16]. The ratio of iso and anteiso FAs is much higher in sponges, a significant part of whose biomass is compounded by bacterial symbionts. Thus, in the sponge P. purpurea the content of iso and anteiso may be due to symbiotic bacteria. Only one polybranched FA was identified, i.e., 3,7,11,15-tetramethylhexadecanoic acid (br-16:0, 4.38%), which is very often found in marine sponges [17]. The identification of 3,7,11,15-tetramethyl-16:0 was finally confirmed by comparing its key mass fragments (...

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Facile Total Synthesis and Antimicrobial Activity of the Marine Fatty Acids (Z)-2-Methoxy-5-hexadecenoic Acid and (Z)-2-Methoxy-6-hexadecenoic Acid

Cited by 28 publications

References 12 publications

A methoxylated fatty acid isolated from the brown seaweed Ishige okamurae inhibits bacterial phospholipase A₂

A methoxylated fatty acid isolated from the brown seaweed Ishige okamurae inhibits bacterial phospholipase A₂

Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria

Fatty Acid Profile, Sterol Composition of Lipids, and Antibacterial Study of the Marine Sponge Psammaplysilla purpurea Collected from the Bay of Bengal (Odisha Coast)

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Facile Total Synthesis and Antimicrobial Activity of the Marine Fatty Acids (Z)-2-Methoxy-5-hexadecenoic Acid and (Z)-2-Methoxy-6-hexadecenoic Acid

Cited by 28 publications

References 12 publications

A methoxylated fatty acid isolated from the brown seaweed Ishige okamurae inhibits bacterial phospholipase A2

A methoxylated fatty acid isolated from the brown seaweed Ishige okamurae inhibits bacterial phospholipase A2

Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria

Fatty Acid Profile, Sterol Composition of Lipids, and Antibacterial Study of the Marine Sponge Psammaplysilla purpurea Collected from the Bay of Bengal (Odisha Coast)

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A methoxylated fatty acid isolated from the brown seaweed Ishige okamurae inhibits bacterial phospholipase A₂

A methoxylated fatty acid isolated from the brown seaweed Ishige okamurae inhibits bacterial phospholipase A₂