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Structural revision of sesbagrandiflorains A and B, and synthesis and biological evaluation of 6-methoxy-2-arylbenzofuran derivatives.
Journal of Natural Medicines ( IF 3.3 ) Pub Date : 2020-08-18 , DOI: 10.1007/s11418-020-01445-2
Noviany Noviany 1 , Arash Samadi 2 , Evan L Carpenter 2 , Mostafa E Abugrain 2 , Sutopo Hadi 1 , Neny Purwitasari 3 , Gitali Indra 2 , Arup Indra 2 , Taifo Mahmud 2
Affiliation  

Sesbagrandiflorains A (1) and B (2), isolated from the stem bark of the Indonesian fabaceous plant Sesbania grandiflora, were reported to be 6-methoxy-2-(2´,3´-dihydroxy-5´-methoxyphenyl)-1-benzofuran-3-carbaldehyde and 6-hydroxy-2-(2´,3´-dihydroxy-5´-methoxyphenyl)-1-benzofuran-3-carbaldehyde, respectively. However, based on reevaluation of their 1D and 2D NMR data, the chemical structures of 1 and 2 have been revised to 4-hydroxy-2-(4´-hydroxy-2´-methoxyphenyl)-6-methoxybenzofuran-3-carbaldehyde and 4-hydroxy-2-(4´-hydroxy-2´-hydroxyphenyl)-6-methoxybenzofuran-3-carbaldehyde, respectively. In addition, seven new derivatives of 1 have been synthesized from the natural product in good yields (65 − 93%). The chemical structures of the synthetic compounds—one diester (6), four ethers (7–10), one secondary amine (11), and one oxime (12)—were confirmed by MS and NMR analysis. Compound 6 exhibited moderate antibacterial activity against the plant pathogen Rhodococcus fascians with a MIC of 0.1 mg/mL. Compounds 8 and 12 demonstrated respectable cytotoxicity against A375 melanoma cancer cells line with the relative IC50 values of 22.8 and 32.7 μM, respectively.



中文翻译:

芥兰 A 和 B 的结构修订,以及 6-甲氧基-2-芳基苯并呋喃衍生物的合成和生物学评价。

据报道,从印度尼西亚豆科植物Sesbania grandiflora的茎皮中分离出的 Sesbagrandiflorrains A (1) 和 B (2)是 6-methoxy-2-(2´,3´-dihydroxy-5´-methoxyphenyl)-1分别为 -benzofuran-3-carbaldehyde 和 6-hydroxy-2-(2´,3´-dihydroxy-5´-methoxyphenyl)-1-benzofuran-3-carbaldehyde。然而,基于对 1D 和 2D NMR 数据的重新评估,1 和 2 的化学结构已修改为 4-hydroxy-2-(4´-hydroxy-2´-methoxyphenyl)-6-methoxybenzofuran-3-carbaldehyde 和分别为 4-羟基-2-(4´-羟基-2´-羟基苯基)-6-甲氧基苯并呋喃-3-甲醛。此外,1的 7 个新衍生品已从天然产物中以良好的收率 (65 - 93%) 合成。合成化合物的化学结构——一种二酯 (6)、四种醚 (7-10)、一种仲胺 (11) 和一种肟 (12)——通过 MS 和 NMR 分析得到证实。化合物 6 对植物病原体Rhodococcus fascians表现出中等的抗菌活性,MIC 为 0.1 mg/mL。化合物 8 和 12 对 A375 黑色素瘤癌细胞系表现出可观的细胞毒性,其相对 IC 50值分别为 22.8 和 32.7 μM。

更新日期:2020-08-18
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