Baglyas Márton, Bozsó Zoltán, Schwarczinger Ildikó, Ott Péter G, Bakonyi József, Darcsi András, Móricz Ágnes M
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.
Int J Mol Sci. 2025 Sep 20;26(18):9187. doi: 10.3390/ijms26189187.
Three previously undescribed clerodane diterpenoids, including two -clerodanes, solidagolactone IX () and solidagoic acid K (), and one -clerodane, solidagodiol (), along with two known -clerodane diterpenoids, (-)-(5,8,9,10)-15,16-epoxy--cleroda-3,13,14-trien-18-ol () and solidagoic acid J (), were isolated and comprehensively characterized from the ethanolic and ethyl acetate root extract of Ait. (giant goldenrod). Compound has previously been reported from the roots of this species, whereas compound was identified from the leaves of but not from the roots. The bioassay-guided isolation involved thin-layer chromatography-direct bioautography (TLC-DB) with a antibacterial assay, preparative flash column chromatography, and TLC-mass spectrometry (MS). The chemical structures of the isolated compounds (-) were elucidated through extensive in-depth spectroscopic and spectrometric analyses, including one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy, high-resolution tandem mass spectrometry (HRMS/MS), and attenuated total reflectance Fourier-transform infrared (ATR-FTIR) spectroscopy. Their antimicrobial activities were evaluated using microdilution assays against and different plant pathogens. Compound was the most active against the tested Gram-positive strains, exerting particularly potent effects against with a minimal inhibitory concentration (MIC) value of 5.1 µM as well as and pv. (MIC 21 µM for both). Compound also strongly inhibited the growth of (MIC 6.3 µM). Compounds , , and displayed moderate to weak activity against and pv. with MIC values ranging from 100 to 402 µM. bacteria were moderately inhibited by compounds (MIC 41 µM) and (MIC 201 µM). Bactericidal activity was observed for compound against with a minimal bactericidal concentration (MBC) value of 83 µM. Compounds and demonstrated weak antifungal activity against . Our findings underscore the value of bioassay-guided approaches in discovering previously undescribed bioactive compounds.
从一枝黄花（巨型一枝黄花）的乙醇根提取物和乙酸乙酯根提取物中分离并全面表征了三种先前未描述的克罗烷二萜类化合物，包括两种α-克罗烷类化合物，一枝黄花内酯IX（）和一枝黄花酸K（），以及一种β-克罗烷类化合物，一枝黄花二醇（），同时还分离出两种已知的α-克罗烷二萜类化合物，（-）-（5,8,9,10）-15,16-环氧-α-克罗达-3,13,14-三烯-18-醇（）和一枝黄花酸J（）。化合物之前已从该物种的根中报道过，而化合物是从一枝黄花的叶中鉴定出来的，而非根中。生物测定导向的分离过程包括采用金黄色葡萄球菌抗菌测定的薄层色谱 - 直接生物自显影（TLC - DB）、制备型快速柱色谱和薄层色谱 - 质谱（MS）。通过广泛深入的光谱和质谱分析阐明了分离出的化合物（-）的化学结构，包括一维和二维核磁共振（NMR）光谱、高分辨率串联质谱（HRMS/MS）以及衰减全反射傅里叶变换红外（ATR - FTIR）光谱。使用微量稀释法针对金黄色葡萄球菌和不同植物病原体评估了它们的抗菌活性。化合物对测试的革兰氏阳性菌株活性最强，对金黄色葡萄球菌具有特别强效的作用，最低抑菌浓度（MIC）值为5.1μM，对枯草芽孢杆菌和胡萝卜软腐欧文氏菌胡萝卜软腐致病变种（两者的MIC均为21μM）也有强效作用。化合物还强烈抑制大肠杆菌的生长（MIC为6.3μM）。化合物、和对金黄色葡萄球菌和胡萝卜软腐欧文氏菌胡萝卜软腐致病变种表现出中度至弱的活性，MIC值范围为100至402μM。化合物（MIC为41μM）和（MIC为201μM）对大肠杆菌有中度抑制作用。观察到化合物对金黄色葡萄球菌具有杀菌活性，最低杀菌浓度（MBC）值为83μM。化合物和对白色念珠菌表现出较弱的抗真菌活性。我们的研究结果强调了生物测定导向方法在发现先前未描述的生物活性化合物方面的价值。
