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17 pages, 3108 KiB

Open AccessArticle

Purification and Screening of the Antialgal Activity of Seaweed Extracts and a New Glycolipid Derivative against Two Ichthyotoxic Red Tide Microalgae Amphidinium carterae and Karenia mikimotoi

by Yingying Sun, Hui Li, Xiao Ma, Mengxuan Pu, Yuqi Zhang, Zhuohan Dong, Peicong He and Shiyan Zheng

Mar. Drugs 2024, 22(6), 279; https://doi.org/10.3390/md22060279 - 14 Jun 2024

Viewed by 1606

Abstract

Ichthyotoxic red tide is a problem that the world is facing and needs to solve. The use of antialgal compounds from marine macroalgae to suppress ichthyotoxic red tide is considered a promising biological control method. Antialgal substances were screened and isolated from Bangia [...] Read more.

Ichthyotoxic red tide is a problem that the world is facing and needs to solve. The use of antialgal compounds from marine macroalgae to suppress ichthyotoxic red tide is considered a promising biological control method. Antialgal substances were screened and isolated from Bangia fusco-purpurea, Gelidium amansii, Gloiopeltis furcate, Hizikia fusifarme, Laminaria japonica, Palmaria palmata, and Sargassum sp. to obtain new materials for the development of algaecides against ichthyotoxic red tide microalgae using bioactivity-guided isolation methods. The fractions of seven macroalgae exhibited selective inhibitory activities against Amphidinium carterae and Karenia mikimotoi, of which the ethyl acetate fractions had the strongest and broadest antialgal activities for the two tested red tide microalgae. Their inhibitory effects on A. carterae and K. mikimotoi were even stronger than that of potassium dichromate, such as ethyl acetate fractions of B. purpurea, H. fusifarme, and Sargassum sp. Thin-layer chromatography and ultraviolet spectroscopy were further carried out to screen the ethyl acetate fraction of Sargassum sp. Finally, a new glycolipid derivative, 2-O-eicosanoyl-3-O-(6-amino-6-deoxy)-β-D-glucopyranosyl-glycerol, was isolated and identified from Sargassum sp., and it was isolated for the first time from marine macroalgae. The significant antialgal effects of 2-O-eicosanoyl-3-O-(6-amino-6-deoxy)-β-D-glucopyranosyl-glycerol on A. carterae and K. mikimotoi were determined. Full article

(This article belongs to the Section Marine Chemoecology for Drug Discovery)

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17 pages, 3131 KiB

Open AccessArticle

Absorption Spectra as Predictors of Algal Biomass and Pigment Content of the Cultured Microalgae Amphidinium carterae, Isochrysis galbana, Nephroselmis sp., and Anabaena sp.

by George N. Hotos and Vlasoula Bekiari

Int. J. Plant Biol. 2023, 14(4), 879-895; https://doi.org/10.3390/ijpb14040065 - 26 Sep 2023

Cited by 4 | Viewed by 3509

Abstract

Background: In the search of a rapid and representative method for the approximate calculation of culture density and cell content of useful pigments, the study of absorption spectra of cultures of the dinoflagellate Amphidinium carterae, the haptophyte Isochrysis galbana, the chlorophyte [...] Read more.

Background: In the search of a rapid and representative method for the approximate calculation of culture density and cell content of useful pigments, the study of absorption spectra of cultures of the dinoflagellate Amphidinium carterae, the haptophyte Isochrysis galbana, the chlorophyte Nephroselmis sp., and the filamentous cyanobacterium Anabaena sp. were selected as representative species of different taxa. Methods: The experimental cultures were established in small volumes by the discontinuous method under 20–21 °C, salinity of 30 or 40 ppt, and 2000 or 8000 lux illumination, and the absorbance spectra, density of the culture and concentration of the extracted pigments chlorophyll, total carotenoids, and phycocyanin were recorded during cultivation. Results: Algal density can be predicted sufficiently correctly because the regression equation of the correlation of the OD value of 750 nm from each absorption spectrum and the measured algal biomass was very strong. The same is true for the corresponding correlations between OD 750 nm and the detected pigments. Conclusions: Absorption spectra of microalgal cultures can be a simple, inexpensive, and non-invasive method for the growers to obtain the necessary information for predicting the right time to collect an ideal combination of maximum biomass and useful pigments, provided that the interpretation of the spectra is performed according to the method described herein. Full article

(This article belongs to the Special Issue Microalgae as a Powerful Tool for Biopharming Development)

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10 pages, 927 KiB

Open AccessArticle

Trichoderols B-G, Six New Lipids from the Marine Algicolous Fungus Trichoderma sp. Z43

by Zhen-Zhen Shi, Xiu-Li Yin and Nai-Yun Ji

Mar. Drugs 2023, 21(8), 453; https://doi.org/10.3390/md21080453 - 17 Aug 2023

Cited by 3 | Viewed by 1915

Abstract

Six new lipids, trichoderols B-G (1–6), along with a known one, triharzianin B (7), were isolated from the culture of Trichoderma sp. Z43 obtained from the surface of the marine brown alga Dictyopteris divaricata. Their structures [...] Read more.

Six new lipids, trichoderols B-G (1–6), along with a known one, triharzianin B (7), were isolated from the culture of Trichoderma sp. Z43 obtained from the surface of the marine brown alga Dictyopteris divaricata. Their structures and relative configurations were identified by interpretation of 1D/2D NMR and MS data. Compounds 1–7 were assayed for inhibiting the growth of three phytopathogenic fungi (Fusarium graminearum, Gaeumannomyces graminis, and Glomerella cingulata), four marine phytoplankton species (Amphidinium carterae, Heterocapsa circularisquama, Heterosigma akashiwo, and Prorocentrum donghaiense), and one marine zooplankton (Artemia salina). Compounds 1, 4, and 7 exhibited weak antifungal activities against three phytopathogenic fungi tested with MIC ≥ 64 μg/mL. All compounds displayed moderate antimicroalgal activity with IC₅₀ ≥ 15 μg/mL and low toxicity to the brine shrimp Artemia salina. Full article

(This article belongs to the Special Issue A Theme Issue Honoring Professor Peter Proksch's 70th Birthday: Bioactive Compounds from the Ocean)

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10 pages, 1425 KiB

Open AccessArticle

Response of the Ciliates Fabrea salina and Condylostoma sp. to Different Salinities and Microalgal Feeds

by George N. Hotos and Ioanna Touloupi

Ecologies 2022, 3(2), 225-234; https://doi.org/10.3390/ecologies3020017 - 13 Jun 2022

Cited by 1 | Viewed by 2497

Abstract

In the quest of finding local strains of marine ciliates that can be easily cultured under a broad range of salinity and fed with microalgae, Fabrea salina Henneguy, 1890 and Condylostoma sp. Bory de St. Vincent, 1826 were cultured for 22 days in [...] Read more.

In the quest of finding local strains of marine ciliates that can be easily cultured under a broad range of salinity and fed with microalgae, Fabrea salina Henneguy, 1890 and Condylostoma sp. Bory de St. Vincent, 1826 were cultured for 22 days in small volumes at a temperature of 16–18 °C and fed with flagellated microalgae. F. salina presented a clear preference for the salinity of 40 ppt and Condylostoma. sp. for 20 ppt. Rhodomonas salina Hill and Wetherbee, 1989 were the most efficient feeds, resulting in 30 ind./mL in F. salina and 73 ind./mL in Condylostoma. Dunaliella salina Teodoresco, 1905 and Nephroselmis sp. F. Stein, 1878 also resulted in considerable ciliate densities while Isochrysis galbana Parke, 1949 came last with the highest density in Condylostoma. The strain of Tetraselmis sp. F. Stein, 1878 (var. red pappas) which is transformed in immobilized palmelloid cells and the dinoflagellate Amphidinium carterae Hulburt, 1957, which is suspected of toxin production, were inappropriate for both ciliates. These ciliates can be easily cultured and can serve as useful organisms in bioassays and probably as live food in marine fish hatcheries. Full article

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23 pages, 9393 KiB

Open AccessArticle

The Effect of Various Salinities and Light Intensities on the Growth Performance of Five Locally Isolated Microalgae [Amphidinium carterae, Nephroselmis sp., Tetraselmis sp. (var. red pappas), Asteromonas gracilis and Dunaliella sp.] in Laboratory Batch Cultures

by George N. Hotos and Despoina Avramidou

J. Mar. Sci. Eng. 2021, 9(11), 1275; https://doi.org/10.3390/jmse9111275 - 16 Nov 2021

Cited by 23 | Viewed by 5432

Abstract

After a 1.5-year screening survey in the lagoons of Western Greece in order to isolate and culture sturdy species of microalgae for aquaculture or other value-added uses, as dictated primarily by satisfactory potential for their mass culture, five species emerged, and their growth [...] Read more.

After a 1.5-year screening survey in the lagoons of Western Greece in order to isolate and culture sturdy species of microalgae for aquaculture or other value-added uses, as dictated primarily by satisfactory potential for their mass culture, five species emerged, and their growth was monitored in laboratory conditions. Amphidinium carterae, Nephroselmis sp., Tetraselmis sp. (var. red pappas), Asteromonas gracilis, and Dunaliella sp. were batch cultured using low (20 ppt), sea (40 ppt), and high salinity (50 or 60 or 100 ppt) and in combination with low (2000 lux) and high (8000 lux) intensity illumination. The results exhibited that all these species can be grown adequately in all salinities and with the best growth in terms of maximum cell density, specific growth rate (SGR), and biomass yield (g dry weight/L) at high illumination (8000 lux). The five species examined exhibited different responses in the salinities used, whereby Amphidinium clearly performs best in 20 ppt, far better than 40 ppt, and even more so than 50 ppt. Nephroselmis and Tetraselmis grow almost the same in 20 and 40 ppt and less well in 60 ppt. Asteromonas performs best in 100 ppt, although it can grow quite well in both 40 and 60 ppt. Dunaliella grows equally well in all salinities (20, 40, 60 ppt). Concerning the productivity, assessed as the maximum biomass yield at the end of the culture period, the first rank is occupied by Nephroselmis with ~3.0 g d.w./L, followed by Tetraselmis (2.0 g/L), Dunaliella (1.58 g/L), Amphidinium (1.19 g/L), and Asteromonas (0.7 g/L) with all values recorded at high light (8000 lux). Full article

(This article belongs to the Section Marine Biology)

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1 pages, 181 KiB

Open AccessExtended Abstract

Amphidinolides and Iriomoteolides, Potent Anticancer Macrolides

by Lluís Bosch, Víctor Cascales, Alejandro Castro-Alvarez, Cristian Marco, Elena Petit, Anna M. Costa and Jaume Vilarrasa

Proceedings 2019, 22(1), 41; https://doi.org/10.3390/proceedings2019022041 - 8 Aug 2019

Viewed by 1509

Abstract

Amphidinolides and iriomoteolides are complex macrolides isolated from cultured marine
dinoflagellates of the genus Amphidinium sp. [1–4]. [...] Full article

(This article belongs to the Proceedings of The 2nd Molecules Medicinal Chemistry Symposium (MMCS): Facing Novel Challenges in Drug Discovery)

15 pages, 301 KiB

Open AccessArticle

Synthesis of Key Fragments of Amphidinolide Q — A Cytotoxic 12-membered Macrolide

by Kohei Kawa, Akihiro Hara, Yuichi Ishikawa and Shigeru Nishiyama

Molecules 2011, 16(7), 5422-5436; https://doi.org/10.3390/molecules16075422 - 27 Jun 2011

Cited by 6 | Viewed by 6374

Abstract

b-Hydroxy aldehyde and alkyl ketone moieties were effectively synthesized as key intermediates of amphidinolide Q, a cytotoxic macrolide from the cultured dinoflagellate Amphidinium sp.. The asymmetric center of the former derivative was produced by Sharpless asymmetric epoxidation, followed by E-selective 1,4-addition to [...] Read more.

b-Hydroxy aldehyde and alkyl ketone moieties were effectively synthesized as key intermediates of amphidinolide Q, a cytotoxic macrolide from the cultured dinoflagellate Amphidinium sp.. The asymmetric center of the former derivative was produced by Sharpless asymmetric epoxidation, followed by E-selective 1,4-addition to give the sp² methyl group. Derivatization of the L-ascorbic acid derivative by Evans asymmetric alkylation and Peterson olefination provided the latter intermediate. The coupling reaction of the segments was examined. Full article

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6 pages, 50 KiB

Open AccessArticle

Luteophanol D, New Polyhydroxyl Metabolite from Marine Dinoflagellate Amphidinium sp.

by Takaaki Kubota, Ayako Takahashi, Masashi Tsuda and Jun\'ichi Kobayashi

Mar. Drugs 2005, 3(4), 113-118; https://doi.org/10.3390/md304113 - 2 Nov 2005

Cited by 49 | Viewed by 8591

Abstract

Luteophanol D (1), a new polyhydroxyl linear carbon-chain metabolite, has been isolated from the cultured marine dinoflagellate Amphidinium sp., which was isolated from Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris. The structure of 1 was elucidated by detailed analyses of 2D NMR spectra. Luteophanol [...] Read more.

Luteophanol D (1), a new polyhydroxyl linear carbon-chain metabolite, has been isolated from the cultured marine dinoflagellate Amphidinium sp., which was isolated from Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris. The structure of 1 was elucidated by detailed analyses of 2D NMR spectra. Luteophanol D (1) possesses two tetrahydropyran rings and twenty-three hydroxyl groups on C₆₃-linear aliphatic chain with one exo-methylene and two methyl branches. Full article

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8 pages, 70 KiB

Open AccessArticle

Amphidinolides B4 and B5, Potent Cytotoxic 26-Membered Macrolides from Dinoflagellate Amphidinium Species

by Masashi Tsuda, Yuuko Kariya, Rie Iwamoto, Eri Fukushi, Jun Kawabata and Jun’ichi Kobayashi

Mar. Drugs 2005, 3(1), 1-8; https://doi.org/10.3390/md301001 - 1 Mar 2005

Cited by 26 | Viewed by 8588

Abstract

Two new cytotoxic 26-membered macrolides, amphidinolides B4 (1) and B5 (2), have been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-100), and the structures were elucidated on the basis of detailed analyses of 2D NMR data including ¹³C−¹³C correlations. Full article

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5 pages, 56 KiB

Open AccessArticle

Amphidinolide C2, New Macrolide from Marine Dinoflagellate Amphidinium Species

by Takaaki Kubota, Yusuke Sakuma, Masashi Tsuda and Jun’ichi Kobayashi

Mar. Drugs 2004, 2(3), 83-87; https://doi.org/10.3390/md203083 - 25 Aug 2004

Cited by 34 | Viewed by 9421

Abstract

A new cytotoxic 25-membered macrolide, amphidinolide C2 (1), has been isolated from marine dinoflagellate Amphidinium sp. (Y-71 strain), and the structure 1 was elucidated on the basis of spectroscopic data and chemical means. Full article

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