Lippia graveolens is a plant used for a variety of medicinal purposes and as a seasoning. Chemical investigation of a methanol extract obtained by percolation of its leaves and flowers led to the isolation of two monoterpenes (1–2) and twelve flavonoids, including two flavonols (3–4), two flavones (5–6), four flavanones (7–10), two dihydroflavonols (11–12), and two dihydrochalcone glucosides (13–14). β-Sitosteryl glucopyranoside (15) was also isolated. The structures of all the isolates were elucidated by analysis of the NMR and MS spectra. The configuration of chiral flavonoids was determined by optical rotation and comparison with literature data. Based on the medicinal uses of the plant, the flavonoids 3–14 were tested for their ability to inhibit the activity of α-glucosidase, while the anti-inflammatory activity of 4 and 7–14 was evaluated in the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema model. As a result, only the flavone 6 was a significative inhibitor of α-glucosidase (IC₅₀ = 37.19 µM), while the flavanones 9–10 and the dihydrochalcone 14 showed the best anti-inflammatory properties with IC₅₀ values ranging from 0.72 to 1.31 µmol/ear. The cytotoxic activity of eleven of these flavonoids (3–5 and 7–14) against five cancer human cell lines was also evaluated. The flavonol 4 inhibited moderately the proliferation of the U251 (glioblastoma) and SK-LU-1 (lung adenocarcinoma) cell lines.

中文翻译：

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苜蓿（Lippiagravolens）（牛至）中黄酮的细胞毒性，抗炎和α-葡萄糖苷酶抑制作用

Grappolens Lippiagravolens是一种用于多种药用目的和调味料的植物。通过其叶和花的渗滤得到的甲醇提取物的化学调查导致了两个单萜（的隔离1 - 2）和12类黄酮，包括二黄酮醇（3 - 4），两个黄酮（5 - 6），四个黄烷酮（7 – 10），两种二氢黄酮醇（11 – 12）和两种二氢查耳酮葡萄糖苷（13 – 14）。β-谷甾醇吡喃葡萄糖苷（15）也被隔离了。通过NMR和MS光谱分析阐明了所有分离物的结构。通过旋光并与文献数据比较确定手性类黄酮的构型。根据植物的药用用途，测试了黄酮类化合物3 – 14抑制α-葡萄糖苷酶活性的能力，而在12- O-十四烷酰佛波酮-中评估了4和7 – 14的抗炎活性。13乙酸（TPA）诱导的耳水肿模型。结果，只有黄酮6是α-葡萄糖苷酶的重要抑制剂（IC ₅₀ = 37.19 µM），而黄烷酮9 – 10和二氢查耳酮14表现出最佳的抗炎特性，IC ₅₀值为0.72至1.31 µmol /耳。还评估了其中11种类黄酮（3 – 5和7 – 14）对五种癌细胞的细胞毒活性。黄酮醇4适度抑制U251（胶质母细胞瘤）和SK-LU-1（肺腺癌）细胞系的增殖。