Laboratory of Pharmacognosy and Chemistry of Natural Products, Faculty of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, 15771 Athens, Greece.
Int J Mol Sci. 2023 Mar 3;24(5):4935. doi: 10.3390/ijms24054935.
In this study, the black fertile (BSs) and the red unfertile seeds (RSs) of the Greek endemic subsp. (Stearn) Tzanoud were studied for the first time. Nine phenolic derivatives, -resveratol, -resveratrol-4'-O-β-d-glucopyranoside, --viniferin, -gnetin H, luteolin, luteolin 3'-O-β-d-glucoside, luteolin 3',4'-di-O-β-d-glucopyranoside, and benzoic acid, along with the monoterpene glycoside paeoniflorin, have been isolated and structurally elucidated. Furthermore, 33 metabolites have been identified from BSs through UHPLC-HRMS, including 6 monoterpene glycosides of the paeoniflorin type with the characteristic cage-like terpenic skeleton found only in plants of the genus , 6 gallic acid derivatives, 10 oligostilbene compounds, and 11 flavonoid derivatives. From the RSs, through HS-SPME and GC-MS, 19 metabolites were identified, among which nopinone, myrtanal, and -myrtanol have been reported only in peonies' roots and flowers to date. The total phenolic content of both seed extracts (BS and RS) was extremely high (up to 289.97 mg GAE/g) and, moreover, they showed interesting antioxidative activity and anti-tyrosinase properties. The isolated compounds were also biologically evaluated. Especially in the case of -gnetin H, the expressed anti-tyrosinase activity was higher than that of kojic acid, which is a well-known whitening agent standard.
本研究首次对希腊特有亚种（Stearn）Tzanoud 的黑色可育（BSs）和红色不育种子（RSs）进行了研究。分离并结构鉴定了 9 种酚类衍生物：-白藜芦醇、-白藜芦醇-4'-O-β-d-吡喃葡萄糖苷、--二氢白藜芦醇、-淫羊藿素 H、木樨草素、木樨草素 3'-O-β-d-吡喃葡萄糖苷、木樨草素 3',4'-二-O-β-d-吡喃葡萄糖苷和苯甲酸，以及单萜糖苷芍药苷。此外，通过 UHPLC-HRMS 从 BSs 中鉴定出 33 种代谢物，包括 6 种以笼状萜烯骨架为特征的芍药苷型单萜糖苷，仅在毛茛科植物中发现，6 种没食子酸衍生物、10 种二苯乙烯化合物和 11 种黄酮类衍生物。通过 HS-SPME 和 GC-MS 从 RSs 中鉴定出 19 种代谢物，其中诺匹酮、桃金娘醛和-桃金娘醇迄今为止仅在牡丹的根和花中报道过。两种种子提取物（BS 和 RS）的总酚含量极高（高达 289.97 mg GAE/g），并且具有有趣的抗氧化活性和抗酪氨酸酶活性。分离得到的化合物也进行了生物学评价。特别是在-β-淫羊藿素 H 的情况下，表达的抗酪氨酸酶活性高于作为一种著名的美白剂标准的曲酸。
