来自 Neapolitan 亚种 Hypochaeris radicata（菊科，菊苣族）的木脂素和倍半萜内酯。
Lignans and sesquiterpene lactones from Hypochaeris radicata subsp. neapolitana (Asteraceae, Cichorieae).
机构信息
Pharmazeutisches Institut, Abteilung Pharmazeutische Biologie, Christian-Albrechts-Universität zu Kiel, Gutenbergstraße 76, 24118, Kiel, Germany.
Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, 0316, Oslo, Norway.
出版信息
Phytochemistry. 2019 Sep;165:112047. doi: 10.1016/j.phytochem.2019.05.020. Epub 2019 Jun 13.
Four undescribed lignans and two undescribed sesquiterpenic acids, together with three known compounds (hypochoeroside C, hypochoeroside D, and 5-O-caffeoylshikimic acid) were isolated from the roots of Hypochaeris radicata subsp. neapolitana (Asteraceae, Cichorieae). The lignans were identified as 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside, 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranosyl-2'-O-methacrylate, (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-7,8,7',8'-tetrahydronaphtho [8,8'-c]furan-1(3H)-one, and (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-8'-(hydroxymethyl)-7,8,7',8'-tetrahydronaphthalen-8-carboxylic acid. The two sesquiterpenic acids were identified as the ring open precursors of hypochoerosides C and D. Structures were elucidated using NMR and HRMS. Absolute configurations of (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-7,8,7',8'-tetrahydronaphtho [8,8'-c]furan-1(3H)-one and (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-8'-(hydroxymethyl)-7,8,7',8'-tetrahydronaphthalen-8-carboxylic acid were determined using electronic circular dichroism (ECD) spectroscopy. 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside was evaluated for its anti-proliferative activity against myeloma cell lines MM1S, U266, and NCI-H929 and showed cytotoxicity at 100 mM against MM1S strain. No neurotoxicity was observed for major compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside, hypochoeroside C, and hypochoeroside D in a fluorescence assay measuring neurite outgrowth in dorsal root ganglion (DRG) neurons. Additionally, compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside, hypochoeroside C, hypochoeroside D, and hypochoerosidic acid D were quantified in unstressed and drought-stressed plants using HPLC-DAD. Drought-stressed plants were found to contain lower concentrations of the lignan 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-β-D-glucopyranoside and sesquiterpene lactone hypochoeroside C.
从 Hypochaeris radicata subsp. neapolitana（菊科，菊苣族）的根部分离得到四个未描述的木脂素和两个未描述的倍半萜酸，以及三个已知化合物（hypochoeroside C、hypochoeroside D 和 5-O-咖啡酰莽草酸）。这些木脂素被鉴定为 4-(3,4-二羟基苄基)-2-(3,4-二羟基苯基)四氢呋喃-3-羧酸-O-β-D-吡喃葡萄糖苷、4-(3,4-二羟基苄基)-2-(3,4-二羟基苯基)四氢呋喃-3-羧酸-O-β-D-吡喃葡萄糖基-2'-O-甲基丙烯酸酯、(7S,8R,8'R)-7-(3,4-二羟基苯基)-3',4'-二羟基-7,8,7',8'-四氢萘并[8,8'-c]呋喃-1(3H)-酮和(7S,8R,8'R)-7-(3,4-二羟基苯基)-3',4'-二羟基-8'-(羟甲基)-7,8,7',8'-四氢萘-8-羧酸。这两种倍半萜酸被鉴定为 hypochoeroside C 和 D 的环开前体。使用 NMR 和 HRMS 阐明了结构。(7S,8R,8'R)-7-(3,4-二羟基苯基)-3',4'-二羟基-7,8,7',8'-四氢萘并[8,8'-c]呋喃-1(3H)-酮和(7S,8R,8'R)-7-(3,4-二羟基苯基)-3',4'-二羟基-8'-(羟甲基)-7,8,7',8'-四氢萘-8-羧酸的绝对构型通过电子圆二色性（ECD）光谱确定。4-(3,4-二羟基苄基)-2-(3,4-二羟基苯基)四氢呋喃-3-羧酸-O-β-D-吡喃葡萄糖苷对骨髓瘤细胞系 MM1S、U266 和 NCI-H929 的增殖活性进行了评估，在 100mM 时对 MM1S 菌株显示出细胞毒性。在测量背根神经节（DRG）神经元神经突生长的荧光测定中，主要化合物 4-(3,4-二羟基苄基)-2-(3,4-二羟基苯基)四氢呋喃-3-羧酸-O-β-D-吡喃葡萄糖苷、hypochoeroside C 和 hypochoeroside D 没有表现出神经毒性。此外，使用 HPLC-DAD 在未胁迫和干旱胁迫的植物中定量了化合物 4-(3,4-二羟基苄基)-2-(3,4-二羟基苯基)四氢呋喃-3-羧酸-O-β-D-吡喃葡萄糖苷、hypochoeroside C、hypochoeroside D 和 hypochoerosidic 酸 D。发现干旱胁迫的植物中木质素 4-(3,4-二羟基苄基)-2-(3,4-二羟基苯基)四氢呋喃-3-羧酸-O-β-D-吡喃葡萄糖苷和倍半萜内酯 hypochoeroside C 的浓度较低。
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