Institute of Pharmacy, Pharmacognosy, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
Institute of Biological Sciences, Applied Ecology & Phycology, University of Rostock, Albert-Einstein-Str. 3, 18059 Rostock, Germany.
Mar Drugs. 2023 Oct 18;21(10):543. doi: 10.3390/md21100543.
This study presents a phytochemical survey of two common intertidal red algal species, and , regarding their MAA (mycosporine-like amino acid) composition, which are known as biogenic sunscreen compounds. Six novel MAAs from named bostrychines and two novel MAAs from 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 . 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 . 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.
本研究对两种常见的潮间带红藻 和 进行了植物化学调查,研究其 MAAs(菌孢氨酸类似物氨基酸)组成,这些化合物是已知的生物防晒化合物。从 中分离出了六种新的 MAAs,命名为 bostrychines,从 中分离出了两种新的 MAAs,命名为 catenellines,采用的方法包括硅胶柱层析、反相材料的快速色谱和半制备高效液相色谱(HPLC)。通过 NMR(核磁共振)和 HR-MS(高分辨率质谱)确定了新 MAAs 的结构,并通过 ECD(电子圆二色性)确定了它们的绝对构型。所有分离出的 MAAs 都具有环己烯亚胺骨架,而 中的代谢物与已知的 MAAs bostrychines A-F 有关,这些 MAAs 的侧链含有谷氨酰胺、谷氨酸和/或苏氨酸。 中的新 MAAs 含有牛磺酸,这是一种氨基磺酸,也存在于该物种中另一种 MAA 即 catenelline 中。先前和新的数据证实,潮间带红藻在化学上富含 MAAs,这解释了它们对生物有害的紫外线辐射的高耐受性。