Móricz Ágnes M, Baglyas Márton, Darcsi András, Balla József, Morlock Gertrud E
Plant Protection Institute, HUN-REN Centre for Agricultural Research, Fehérvári út 132-144, 1116 Budapest, Hungary.
Doctoral School, Semmelweis University, Üllői út 26, 1085 Budapest, Hungary.
Molecules. 2024 Nov 30;29(23):5673. doi: 10.3390/molecules29235673.
The stem bark of black locust ( L.) was extracted, and nine antioxidant compounds (-) were detected by high-performance thin-layer chromatography combined with the radical scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH•) assay, multi-detection, and heated electrospray high-resolution mass spectrometry. For structure elucidation, the methanolic crude extract was fractionated by solid-phase extraction, and the compounds were isolated by reversed-phase high-performance liquid chromatography with diode array detection. The structures of isolated compounds were elucidated by nuclear magnetic resonance and attenuated total reflectance Fourier-transform infrared spectroscopy as well as gas chromatography-mass spectrometry to determine the double bond position. 3--Caffeoyl oleanolic acid (), oleyl (), octadecyl (), gadoleyl (), eicosanyl (), ()-9-docosenyl (), docosyl (), tetracosyl (), and hexacosanyl () caffeates were identified. While has been reported in stem bark, the known , , , , and are described for the first time in this species, and the , , and are new natural compounds. All nine caffeates demonstrated antioxidant activity. The antioxidant effects of the isolated compounds - were quantified by a microplate DPPH• assay, with values ranging from 0.29 to 1.20 mol of caffeic acid equivalents per mole of isolate.
对刺槐（Robinia pseudoacacia L.）的茎皮进行提取，通过高效薄层色谱结合自由基清除2,2-二苯基-1-苦基肼（DPPH•）测定、多检测以及加热电喷雾高分辨率质谱法检测到9种抗氧化化合物（-）。为了阐明结构，将甲醇粗提物通过固相萃取进行分离，然后通过具有二极管阵列检测的反相高效液相色谱法分离化合物。通过核磁共振、衰减全反射傅里叶变换红外光谱以及气相色谱-质谱法阐明分离出的化合物的结构，以确定双键位置。鉴定出3 - 咖啡酰齐墩果酸（）、油基（）、十八烷基（）、二十碳烯基（）、二十烷基（）、（）-9-二十二碳烯基（）、二十二烷基（）、二十四烷基（）和二十六烷基（）咖啡酸酯。虽然在刺槐茎皮中已报道过，但已知的、、、和在此物种中首次被描述，并且、和是新的天然化合物。所有9种咖啡酸酯均表现出抗氧化活性。通过微孔板DPPH•测定法定量分离出的化合物 - 的抗氧化作用，每摩尔分离物的值范围为0.29至1.20摩尔咖啡酸当量。
