Taiwo Bamigboye J, Miller Alex H, Fielding Alistair J, Sarker Satyajit D, van Heerden Fannie R, Fatokun Amos A
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Obafemi Awolowo University, Ile-Ife, Nigeria.
Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool L3 3AF, UK.
Heliyon. 2023 Dec 10;10(1):e23335. doi: 10.1016/j.heliyon.2023.e23335. eCollection 2024 Jan 15.
(L.) Gaertn. (Bombacaceae) is popular for the quality of its wood. However, its leaf, stem bark and root bark have been popular in ethnomedicine and, apart from the inflorescence, have been subject of extensive phytochemical investigations. In this study, two compounds were isolated from the crude methanol extract of the inflorescence. Through data from UV, NMR, MS, electrochemical studies, differential scanning calorimetry, and thermogravimetric analysis, the structures were elucidated as 3---d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone () and 2---d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (mangiferin, ). They were assessed for antioxidant efficacy (DCFDA assay) and for anti-inflammatory efficacy using the lipopolysaccharide (LPS)-induced inflammation model in the RAW 264.7 macrophages (nitrite levels quantified, using Griess Assay, as surrogate for nitric oxide (NO)). Compound named ceibinin was established as a novel positional isomer of mangiferin (). While both and were antioxidant against basal and hydrogen peroxide (100 μM)-induced oxidative stress (6.25 μg/ml abrogated peroxide-induced oxidative stress), ceibinin () demonstrated no anti-inflammatory potential, unlike mangiferin () which, as previously reported, showed anti-inflammatory effect. Our work reports a positional isomer of mangiferin for the first time in and demonstrates how such isomerism could underlie differences in biological activities and thus the potential for development into therapeutics.
(L.) Gaertn.（木棉科）因其木材质量而闻名。然而，其叶子、茎皮和根皮在民族医学中颇受青睐，除了花序外，这些部位都受到了广泛的植物化学研究。在本研究中，从花序的粗甲醇提取物中分离出两种化合物。通过紫外光谱（UV）、核磁共振（NMR）、质谱（MS）、电化学研究、差示扫描量热法和热重分析的数据，确定其结构分别为3 - β - D - 吡喃葡萄糖基 - 1,3,6,7 - 四羟基呫吨酮（）和2 - β - D - 吡喃葡萄糖基 - 1,3,6,7 - 四羟基呫吨酮（芒果苷，）。使用DCFDA法评估它们的抗氧化功效，并在RAW 264.7巨噬细胞中利用脂多糖（LPS）诱导的炎症模型评估其抗炎功效（使用格里斯试剂法测定亚硝酸盐水平，作为一氧化氮（NO）的替代指标）。名为ceibinin的化合物被确定为芒果苷（）的一种新型位置异构体。虽然和对基础氧化应激以及过氧化氢（100 μM）诱导的氧化应激均具有抗氧化作用（6.25 μg/ml可消除过氧化物诱导的氧化应激），但ceibinin（）没有抗炎潜力，而芒果苷（）如先前报道的那样具有抗炎作用。我们的研究首次报道了中的芒果苷位置异构体，并证明了这种异构现象可能是生物活性差异的基础，从而具有开发成治疗药物的潜力。
