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Several natural products isolated from a red alga Gracilaria lemaneiformis and its evaluation of antialgal activity against six common red tide microalgae

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Abstract

The ethanol extracts of Gracilaria lemaneiformis that have inhibitory effects on Karenia mikimotoi and Skeletonema costatum were separated by liquid-liquid extraction using different polar solvents into five fractions with antialgal activities (petroleum ether, chloroform, ethyl acetate, n-butanol, and water-soluble fractions). These fractions were chromatographed on silica gel to give, after repeated preparative thin-layer chromatography (PTLC) purification processes, 1-β-d-ribofuranosyluracil (1), 3-hydroxymethyl-pyrrolopiperazine-2,5-dione (2), benzene-1,2-propanoic acid (3), 1-O-palmitoyl-2-O-palmitoleoyl-3-O-β-d-galactopyranosyl glycerol (4), 7-oxabicyclo[4.1.0]-heptan-3-ol (5), linoleic acid (6), 3,4-dimethoxy-6-(methoxymethyl)-tetrahydro-2H-pyran-2,5-diol (7), and 3,7,11,16-tetramethyl -2-heptadecen-1-ol (8). Five of them, natural products 1, 2, 5, 7, and 8, were isolated from Gracilaria lemaneiformis for the first time, and three natural products (3, 5, and 8) were isolated from marine macroalgae for the first time. Among them, natural products (1, 2, 3, 4, and 6) showed the most obvious inhibition activities to the growth of Karenia mikimotoi and Skeletonema costatum at the concentration of 80 μg/mL. Therefore, antialgal activities of these five natural products against Amphidinium carterae, Heterosigma akashiwo, Karenia mikimotoi, Phaeocystis globosa, Prorocentrum donghaiense, and Skeletonema costatum were further tested at different concentrations (0.4, 2, 10, and 50 μg/mL). This was the first report of antialgal activities of five natural products (1, 2, 3, 4, and 6) to these six red tide microalgae. They showed significantly selective antialgal activities against all tested red tide microalgae. At the concentration of 50 μg/mL, the growth of Amphidinium carterae, Heterosigma akashiwo, Karenia mikimotoi, and Phaeocystis globosa was obviously inhibited; for Karenia mikimotoi, natural products 1, 2, and 6 have significant antialgal activities; the growth inhibition of Skeletonema costatum that was exposed to natural products 1, 3, and 4 was remarkable. Furthermore, by analyzing and comparing EC50–96 h values, it has been determined that natural product 3 (natural product 4) showed the superior application potential than potassium dichromate and some reported natural products (such as gossonorol isolated from Porphyra yezoensis, trehalose purified from Ulva pertusa) as a characteristic antialgal agent against Amphidinium carterae (Phaeocystis globosa). In addition, natural products 1 and 3 also showed good superiority than some reported natural products in inhibiting Skeletonema costatum; however, it was a pity that they were inferior to potassium dichromate in the inhibiting this red tide microalgae. Taken together, it is not hard to conclude that Gracilaria lemaneiformis was a good source of natural products with antialgal activities against some red tide microalgae.

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The datasets used or analyzed during the current study are available from the corresponding author on reasonable request.

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Funding

This work was supported by Jiangsu Province fifth “333 project” training funding (BRA2020263); Special Foundation for A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions; Excellent Young Teachers and Principals Program of Jiangsu Province, China; Haiyan project of Lianyungang City; and Innovation Training Program for College Students of Jiangsu Ocean University.

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  1. Jiangsu Key Laboratory of Marine Biotechnology, Jiangsu Ocean University, Lianyungang, 222005, China

    Ying-ying Sun, Nai-sheng Zhang, Zi-xuan Yang & Xin Zhang

  2. Jiangsu Key Laboratory of Marine Bioresources and Eco-environment, Jiangsu Ocean University, Lianyungang, 222005, China

    Ying-ying Sun

  3. Co-Innovation Center of Jiangsu Marine Bio-industry Technology, Lianyungang, 222005, China

    Ying-ying Sun

  4. Lianyungang of Products Quality Supervision and Inspection, Lianyungang, 222006, China

    Jing Zhou & Xiu Han

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Ying-ying Sun performed the data analyses and wrote the manuscript; Jing Zhou contributed significantly to analysis and manuscript preparation; Xiu Han, Zi-xuan Yang, and Xin Zhang performed the experiment; Nai-sheng Zhang helped perform the analysis with constructive discussions.

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Sun, Yy., Zhou, J., Han, X. et al. Several natural products isolated from a red alga Gracilaria lemaneiformis and its evaluation of antialgal activity against six common red tide microalgae. Environ Sci Pollut Res 28, 22409–22426 (2021). https://doi.org/10.1007/s11356-020-11755-3

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