Noviany, Noviany and Hadi, Sutopo (2021) Structural revision of sesbagrandiflorains A and B, and synthesis and biological evaluation of 6‑methoxy‑2‑arylbenzofuran derivatives. Journal of Natural Medicines, 75. pp. 66-75. ISSN 1861-0293

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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.

Item Type: Article
Uncontrolled Keywords: Antibacterial activity · Cytotoxicity · sesbagrandiflorain · Sesbania grandiflora · Rhodococcus fascians
Subjects: Q Science > QD Chemistry
Divisions: Fakultas Matematika dan Ilmu Pengetahuan Alam (FMIPA) > Prodi Kimia
Depositing User: Prof. Sutopo Hadi
Date Deposited: 12 Jan 2021 06:45
Last Modified: 12 Jan 2021 06:45

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