Algicidal Activity of Glycerolipids from Brown AlgaIshige sinicolatoward Red Tide Microalgae

Abstract

Bioassay-guided fractionation of a methanol extract of the brown alga, Ishige sinicola, led to the isolation of five algicidal compounds. Their structures were determined to be α-monoglycerides of eicosa-5Z,8Z,11Z,14Z-tetraenoic (arachidonic) acid, octadeca-6Z,9Z,12Z,15Z-tetraenoic acid, linoleic acid and oleic acid, and 1-O-palmitoyl-3-O-(6-sulfo-α-D-quinovopyranosyl)-sn-glycerol on the basis of spectroscopic data and a comparison with the data in the literature. These glycerolipids showed moderate-to-high cell lysis activity against the red tide microalgal species, Heterosigma akashiwo, Karenia mikimotoi and Alexandrium catenella, at a concentration of 20 µg/mL.

Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis Linnaeus

“…Compound 1 : 1 H NMR (CDCl 3 , 500 MHz): 5.35 (2H, m), 4.19 (1H, dd, J = 11.7, 4.5 Hz), 4.13 (1H, dd, J = 11.7, 6.0 Hz), 3.91 (1H, m), 3.68 (1H, dd, J = 11.7, 4.0 Hz), 3.58 (1H, dd, J = 11.7, 6.0 Hz), 2.33 (2H, t, J = 7.6 Hz), 2.01 (4H, m), 1.61 (2H, m), 1.29 (20H, m), 0.86 (3H, t, J = 6.9 Hz); ESIMS positive m / z (%) 357 [M + H] + (100), 735 [2M + Na] + (5), in agreement with data reported in the literature [7]. …”

“…The EtOAc fraction was partitioned as outlined in the experimental section to yield one monoacylglycerol featuring oleic acid (C18:1 Ω9) ( 1 ) and a 1:1 mixture of two MGDGs containing eicosapentaenoic acid (C20:5 Ω3) combined with octadecatetraenoic acid (C18:4 Ω3) ( 2 ) or linolenic acid (C18:3 Ω3) ( 3 ), respectively (Figure 1). Their structures and the regiochemical attachments of the acyl chains to the glycerol moiety were unambiguously elucidated on the basis of extensive NMR spectroscopic analysis and mass spectrometry and by comparison with data reported in the literature [7,21]. Previous reports include the isolation of 2 and 3 from the brown seaweed Sargassum thunbergii (Mertens ex Roth) Kuntze [21], the marine dinoflagellate Heterosigma akashiwo (Y. Hada) Y. Hada ex Y. Hara & M. Chihara [22] and from the freshwater dinoflagellate Glenodinium sanguineum (H. J. Carter) Diesing [23] and their detection in glaucocystophytes [24].…”

“…MGDGs and DGDGs constitute the most widespread non-phosphorous polar lipids in nature, accounting for about 80% of membrane lipids in green plant tissues and more than half of all lipids in algae [2,3]. Beyond their structural and chemical functions, these compounds present several promising biological properties, among which the anti-tumor [4,5], anti-viral [6], algicidal [7] and anti-inflammatory [8,9,10,11] activities can be highlighted.…”

Algicidal Sesquiterpene Hydroquinones from the Brown AlgaDictyopteris undulata

“…[1][2][3][4][5][6][7][8][9][10][11][12] In our previous study, 12) we screened eleven seaweeds collected from the coastal region of Nagasaki prefecture in Japan, involving seven Phaeophyta and four Rhodophyta, for their lysis activity toward the red tide microalgal species, Heterosigma akashiwo, and found that methanol extracts of the brown algae, Ishige sinicola and Dictyopteris undulata, had high activity. The active principles of I. sinicola have been reported to be -monoglycerides of arachidonic acid, octadeca-6Z,9Z,12Z,15Z-tetraenoic acid, linoleic acid and oleic acid, and 1-O-palmitoyl-3-O-(6-sulfo--Dquinovopyranosyl)-sn-glycerol (PSQG).…”

Regrowth of Chlorella Sorokiniana on Recycled Media With Replenished Nutrients

“…Organisms will produce allelopathic compounds to inhibit the growth of other organisms to gain a competitive advantage. Evidence of allelopathy between competing organisms has been demonstrated in multiple algal species including Chlorella vulgaris (Fergola, 2007), Cladosiphon okamuranus (Kakisawa, 1988), and Ishige sinicola (Hirao, 2012).…”