State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, PR China; University of Chinese Academy of Sciences, Beijing, 100049, PR China.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, PR China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, PR China.
Phytochemistry. 2021 Apr;184:112656. doi: 10.1016/j.phytochem.2021.112656. Epub 2021 Jan 29.
Three previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A‒C, one rare 23S,26R-hydroxylated spirostanoid saponin, and two steroidal alkaloid aglycones, solanindins A and B, derived from the acid hydrolysis of solanindiosides A‒C, were isolated from the fruits of Solanum violaceum, together with five known analogues, including two rare steroidal glycosides, two lignans and a diterpene. Structurally, they comprise a 16β-methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16β-methoxy-3,23-dideoxy-22,26-epimino-cholest-3,5-dien derivative. The hitherto undescribed structures were established on the basis of extensive spectroscopic analyses. Configurations of sugar moieties were resolved by chemical derivations. Solanindiosides A‒C, (22R,23S,25R,26R)-spirost-5-ene-3β,23,26-triol3-O-β-d-xylopyranosyl-(1→3)-β-d-glucopyranoside, solanindins A and B, and (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol showed the most potent cytotoxic activity against MCF-7 cells (IC = 4.386 ± 0.098 μM), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC value of 37.32 ± 0.793 μM. In addition, (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells.
从茄属植物果实中分离到三个以前未描述的吡啶甾体糖苷，即 solanindiosides A-C，一个罕见的 23S,26R-羟基化螺甾烷皂苷，以及两个甾体生物碱苷元，solanindins A 和 B，这是通过 solanindiosides A-C 的酸水解得到的，此外还分离到了五个已知类似物，包括两个罕见的甾体糖苷、两个木脂素和一个二萜。结构上，它们包含一个 16β-甲氧基-23-去氧-22,26-亚氨基胆甾烷骨架部分和一个 16β-甲氧基-3,23-二去氧-22,26-亚氨基胆甾-3,5-二烯衍生物。根据广泛的光谱分析确定了以前未描述的结构。糖部分的构型通过化学衍生确定。solanindiosides A-C、(22R,23S,25R,26R)-螺甾-5-烯-3β,23,26-三醇 3-O-β-D-吡喃木糖基-(1→3)-β-D-吡喃葡萄糖苷、solanindins A 和 B 以及(1S,2S)-1-(4-羟基-3-甲氧基苯基)-2-[2-甲氧基-4-[(2S,3R,4R)-四氢-4-[(4-羟基-3-甲氧基苯基)甲基]-3-(羟甲基)-2-呋喃基]苯氧基]-1,3-丙二醇，对其细胞毒性和抗菌活性进行了评价。(1S,2S)-1-(4-羟基-3-甲氧基苯基)-2-[2-甲氧基-4-[(2S,3R,4R)-四氢-4-[(4-羟基-3-甲氧基苯基)甲基]-3-(羟甲基)-2-呋喃基]苯氧基]-1,3-丙二醇对 MCF-7 细胞表现出最强的细胞毒性活性（IC=4.386±0.098μM），而 solanindin B 对金黄色葡萄球菌 Rosenbach 具有一定的抑制作用，MIC 值为 37.32±0.793μM。此外，(1S,2S)-1-(4-羟基-3-甲氧基苯基)-2-[2-甲氧基-4-[(2S,3R,4R)-四氢-4-[(4-羟基-3-甲氧基苯基)甲基]-3-(羟甲基)-2-呋喃基]苯氧基]-1,3-丙二醇在 MCF-7 细胞中诱导剂量依赖性凋亡效应。
