Department of Pharmacognosy, Faculty of Pharmacy, University of Sadat City, Sadat, 32897, Egypt.
Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut-Branch, Assiut, 71524, Egypt.
Sci Rep. 2022 Jul 22;12(1):12539. doi: 10.1038/s41598-022-16552-1.
Heliotropium is a genus of the Boraginaceae family. Its members are used in many traditional and folklore medicines to treat several ailments. Despite this widespread usage, only a few evidence-based scientific studies investigated and identified its phytoconstituents. Herein, we documented the chemical profile of the Heliotropium ramosissimum methanolic extract using gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-tandem mass spectrometry (LC-ESI-MS/MS) and assessed its antioxidant and cytotoxic effects. The methanolic extract exhibited high phenolic content (179.74 ± 0.58 µg/mL) and high flavonoid content (53.18 ± 0.60 µg/mL). The GC-MS analysis of the lipoidal matter allowed us to identify 41 compounds with high percentages of 1,2-benzenedicarboxylic acid, bis(2-methoxyethyl) ester (23.91%), and 6,10,14-trimethylpentadecan-2-one (18.74%). Thirty-two phytomolecules were tentatively identified from the methanolic extract of H. ramosissimum using LC-MS/MS. These compounds belonged to several phytochemical classes such as phenolic acids, alkaloids, coumarins, and flavonoids. Furthermore, we assessed the antioxidant activity of the methanolic extract by DPPH assay and oxygen radical absorbance capacity assay, which yielded IC values of 414.30 µg/mL and 170.03 ± 44.40 µM TE/equivalent, respectively. We also assessed the cytotoxicity of the methanolic extract on seven different cell lines; Colo-205, A-375, HeLa, HepG-2, H-460, and OEC showed that it selectively killed cancer cells with particularly potent cytotoxicity against Colo-205 without affecting normal cells. Further studies revealed that the extract induced apoptosis and/or necrosis on Colo-205 cell line at an IC of 18.60 µg/mL. Finally, we conducted molecular docking on the LC-ESI-MS/MS-identified compounds against colon cancer antigen 10 to find potentially cytotoxic compounds. Binding score energy analysis showed that isochlorogenic acid and orientin had the highest affinity for the colon cancer antigen 10 protein, with binding scores of (- 13.2001) and (- 13.5655) kcal/mol, respectively. These findings suggest that Heliotropium ramosissimum contains potent therapeutic candidates for colorectal cancer treatment.
天芥菜是紫草科的一个属。其成员被广泛用于许多传统和民间医学中，以治疗多种疾病。尽管有这种广泛的应用，但只有少数基于证据的科学研究调查和鉴定了其植物成分。本文采用气相色谱-质谱联用（GC-MS）和液相色谱-串联质谱联用（LC-ESI-MS/MS）对天芥菜的甲醇提取物进行了化学成分分析，并评估了其抗氧化和细胞毒性作用。甲醇提取物表现出高酚含量（179.74±0.58µg/mL）和高黄酮含量（53.18±0.60µg/mL）。脂质物质的 GC-MS 分析鉴定出 41 种化合物，其中 1,2-苯二甲酸，双（2-甲氧基乙基）酯（23.91%）和 6,10,14-三甲基十五烷-2-酮（18.74%）的百分比最高。利用 LC-MS/MS 从天芥菜甲醇提取物中鉴定出 32 种植物分子。这些化合物属于几种植物化学类，如酚酸、生物碱、香豆素和类黄酮。此外，我们通过 DPPH 法和氧自由基吸收能力测定法评估了甲醇提取物的抗氧化活性，得到的 IC 值分别为 414.30µg/mL 和 170.03±44.40µM TE/当量。我们还评估了甲醇提取物对七种不同细胞系的细胞毒性；Colo-205、A-375、HeLa、HepG-2、H-460 和 OEC 表明，它选择性地杀死癌细胞，对 Colo-205 具有特别强的细胞毒性，而不影响正常细胞。进一步的研究表明，该提取物在 18.60µg/mL 的 IC 下诱导 Colo-205 细胞系凋亡和/或坏死。最后，我们对 LC-ESI-MS/MS 鉴定的化合物进行了针对结肠癌抗原 10 的分子对接，以寻找潜在的细胞毒性化合物。结合评分能量分析表明，异绿原酸和Orientin 对结肠癌抗原 10 蛋白具有最高的亲和力，结合评分分别为（-13.2001）和（-13.5655）kcal/mol。这些发现表明，天芥菜含有治疗结直肠癌的潜在治疗候选物。
