Open AccessStructural revision of sesbagrandiflorains A and B, and synthesis and biological evaluation of 6-methoxy-2-arylbenzofuran derivatives
Author(s) -
Noviany Noviany,
Arash Samadi,
Evan L. Carpenter,
Mostafa E. Abugrain,
Sutopo Hadi,
Neny Purwitasari,
Gitali Indra,
Arup K. Indra,
Taifo Mahmud
Publication year - 2020
Publication title -
natural medicines/journal of natural medicines
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 46
eISSN - 1861-0293
pISSN - 1340-3443
DOI - 10.1007/s11418-020-01445-2
Subject(s) - benzofuran , chemistry , natural product , stereochemistry , cytotoxicity , cancer cell lines , chemical structure , organic chemistry , in vitro , cancer cell , biology , cancer , biochemistry , genetics
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 IC 50 values of 22.8 and 32.7 μM, respectively.