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Mar. Drugs 2019, 17(2), 96; https://doi.org/10.3390/md17020096

Glycerolipid Composition of the Red Macroalga Agarophyton Chilensis and Comparison to the Closely Related Agarophyton Vermiculophyllum Producing Different Types of Eicosanoids

1
Faculty of Science & Technology, Meijo University, Shiogamaguchi, Tempaku-ku, Nagoya 468-8502, Japan
2
Faculty of Fisheries Sciences, Hokkaido University, Minato-cho, Hakodate 041-0811, Japan
3
National Research Institute of Fisheries Science, Japan Fisheries Research and Education Agency, Yokohama 236-8648, Japan
4
Callaghan Innovation, 69 Gracefield Road, P.O. Box 31310, Lower Hutt 5040, New Zealand
*
Authors to whom correspondence should be addressed.
This study was carried out in Hokkaido University, Minato-cho, Hakodate 041-0811, Japan.
Received: 25 December 2018 / Revised: 25 January 2019 / Accepted: 29 January 2019 / Published: 2 February 2019
(This article belongs to the Special Issue Discovery and Application of Macroalgae-Derived Natural Products)
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Abstract

The red macroalga Agarophyton chilensis is a well-known producer of eicosanoids such as hydroxyeicosatetraenoic acids, but the alga produces almost no prostaglandins, unlike the closely related A. vermiculophyllum. This indicates that the related two algae would have different enzyme systems or substrate composition. To carry out more in-depth discussions on the metabolic pathway of eicosanoids between the two algae, we investigated the characteristics of glycerolipids, which are the substrates of eicosanoids production, of A. chilensis and compared them to the reported values of A. vermiculophyllum. In A. chilensis, monogalactosyldiacylglycerol (MGDG), digalactosyldiacylglycerol (DGDG), sulfoquinovosyldiacylglycerol (SQDG), and phosphatidylcholine (PC) were the major lipid classes and accounted for 44.4% of the total lipid extract. The predominant fatty acids were arachidonic acid (20:4n-6), an eicosanoids precursor, and palmitic acid (16:0). The 20:4n-6 content was extremely high in MGDG and PC (>70%), and the 16:0 content was extremely high in DGDG and SQDG (>40%). A chiral-phase HPLC analysis showed that fatty acids were esterified at the sn-1 and sn-2 positions of those lipids. The glycerolipid molecular species were determined by reversed-phase HPLC–ESI–MS analysis. The main glycerolipid molecular species were 20:4n-6/20:4n-6 (sn-1/sn-2) for MGDG (63.8%) and PC (48.2%), 20:4n-6/16:0 for DGDG (71.1%) and SQDG (29.4%). These lipid characteristics of A. chilensis were almost the same as those of A. vermiculophyllum. Hence, the differences of the eicosanoids producing ability between the two algae would not be due to the difference of substrate composition but the difference of enzyme system. View Full-Text
Keywords: Agarophyton chilensis; Agarophyton vermiculophyllum; lipid class; fatty acid; glycerolipid molecular species; arachidonic acid cascade Agarophyton chilensis; Agarophyton vermiculophyllum; lipid class; fatty acid; glycerolipid molecular species; arachidonic acid cascade
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Honda, M.; Ishimaru, T.; Itabashi, Y.; Vyssotski, M. Glycerolipid Composition of the Red Macroalga Agarophyton Chilensis and Comparison to the Closely Related Agarophyton Vermiculophyllum Producing Different Types of Eicosanoids. Mar. Drugs 2019, 17, 96.

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