Isolation and Structure Elucidation of Novel Mycosporine-like Amino Acids from the Two Intertidal Red Macroalgae <i>Bostrychia scorpioides</i> and <i>Catenella caespitosa</i>

oleh: Maria Orfanoudaki, Mostafa Alilou, Anja Hartmann, Julia Mayr, Ulf Karsten, Hieu Nguyen-Ngoc, Markus Ganzera

Format: Article
Diterbitkan: MDPI AG 2023-10-01

Deskripsi

This study presents a phytochemical survey of two common intertidal red algal species, <i>Bostrychia scorpioides</i> and <i>Catenella caespitosa</i>, regarding their MAA (mycosporine-like amino acid) composition, which are known as biogenic sunscreen compounds. Six novel MAAs from <i>Bostrychia scorpioides</i> named bostrychines and two novel MAAs from <i>Catenella caespitosa</i> named catenellines were isolated using a protocol which included silica gel column chromatography, flash chromatography on reversed phase material and semipreparative HPLC (High-Performance Liquid Chromatography). The structure of the novel MAAs was elucidated using NMR (Nuclear Magnetic Resonance) and HR-MS (High-Resolution Mass Spectrometry), and their absolute configuration was confirmed by ECD (Electronic Circular Dichroism). All isolated MAAs possess a cyclohexenimine scaffold, and the metabolites from <i>B</i>. <i>scorpioides</i> are related to the known MAAs bostrychines A-F, which contain glutamine, glutamic acid and/or threonine in their side chains. The new MAAs from <i>C</i>. <i>caespitosa</i> contain taurine, an amino sulfonic acid that is also present in another MAA isolated from this species, namely, catenelline. Previous and new data confirm that intertidal red algae are chemically rich in MAAs, which explains their high tolerance against biologically harmful ultraviolet radiation.