Department of Organic Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, Austria.
Institute of Chemical, Environmental and Bioscience Engineering, Technische Universität Wien, Getreidemarkt 9/166, A-1060 Vienna, Austria.
Molecules. 2022 Oct 26;27(21):7284. doi: 10.3390/molecules27217284.
There is a previously neglected influence of geochemical conditions on plant phytochemistry. In particular, high concentrations of dissolved salts can affect their biosynthesis of natural products. Detoxification is most likely an important aspect for the plant, but additional natural products can also give it an expanded range of bioactivities. During the phytochemical analysis a plant collected in a sulfate-rich environment (near the Río Sucio, Costa Rica) showed an interesting natural product in this regard. The structure of this compound was determined using spectroscopic and computational methods (NMR, MS, UV, IR, CD, optical rotation, quantum chemical calculations) and resulted in a megastigmane sulfate ester possessing a β-ionone core structure, namely blumenol C sulfate (, CHOS). The levels of sulfur and sulfate ions in the leaves of the plant were determined using elemental analysis and compared to the corresponding levels in comparable plant leaves from a less sulfate-rich environments. The analyses show the leaves from which we isolated blumenol C sulfate () to contain 35% more sulfur and 80% more sulfate than the other samples. Antimicrobial and antioxidant activities of compound were tested against , ampR and as well as measured using complementary in vitro FRAP and ATBS assays, respectively. These bioactivities are comparable to those determined for structurally related megastigmanes. The sulfur and sulfate content of the plant leaves from the sulfate-rich environment was significantly higher than that of the other plants. Against this background of salt stress, we discuss a possible biosynthesis of blumenol C sulfate (). Furthermore, there appears to be no benefit for the plant in terms of extended bioactivities. Hence, the formation of blumenol C sulfate () probably primarily serves the plant detoxification process.
有一种先前被忽视的地球化学条件对植物植物化学的影响。特别是，高浓度的溶解盐会影响它们天然产物的生物合成。解毒很可能是植物的一个重要方面，但额外的天然产物也可以赋予它更广泛的生物活性。在植物化学分析过程中，从富含硫酸盐的环境（在哥斯达黎加的 Rio Sucio 附近）采集的一种植物在这方面表现出一种有趣的天然产物。该化合物的结构是通过光谱和计算方法（NMR、MS、UV、IR、CD、旋光、量子化学计算）确定的，结果表明该化合物是一种具有β-紫罗兰酮核心结构的megastigmane 硫酸盐酯，即 blumenol C 硫酸盐（，CHOS）。使用元素分析测定植物叶片中的硫和硫酸盐离子水平，并与来自硫酸盐较少环境的可比植物叶片的相应水平进行比较。分析表明，我们从分离出 blumenol C 硫酸盐（）的叶片中含有比其他样品多 35%的硫和 80%的硫酸盐。对化合物的抗菌和抗氧化活性进行了测试，分别针对、ampR 和，并使用互补的体外 FRAP 和 ATBS 测定法进行了测量。这些生物活性与结构相关的 megastigmanes 相当。富含硫酸盐环境中植物叶片的硫和硫酸盐含量明显高于其他植物。在这种盐胁迫的背景下，我们讨论了 blumenol C 硫酸盐（）的可能生物合成。此外，对于扩展的生物活性，植物似乎没有任何好处。因此，blumenol C 硫酸盐（）的形成可能主要服务于植物的解毒过程。
