Syntheses and biological activities of the proposed structure of apteniol A and its derivatives

Abstract

We describe the syntheses of the proposed structure of diphenyl ether oxyneolignan, apteniol A and its derivatives. The diphenyl ether moiety of proposed apteniol A was formed via Ullmann ether synthesis, but the spectral data of the synthesized apteniol A did not agree with that in previous studies. The dimethyl ester derivative of the proposed apteniol A was found to enhance neurite outgrowth in PC12 cells and inhibit antigen-induced degranulation in RBL-2H3 cells.

Synthesis and degranulation-inhibiting activities of the proposed apteniols B, C, and G

“…5%, according to ref. 4) . It should be noted that the hydrophobic compounds showed activity, while the hydrophilic compound did not, suggesting a characteristic behavior.…”

“…1,2) Furthermore, Devi et al reported the isolation of apteniol A (1) using the marine bacterium Bacillus licheniformis SAB1 as an antimicrobial metabolite. 3) In 2014, we synthesized the compound reported as apteniol A (1), 4) and Jung and Bräse synthesized the compound reported as apteniol C (3) in 2009. 5) These two studies revealed that the spectral data for the isolated apteniols A (1) and C (3) slightly differed from those of the synthesized compounds.…”

“…Furthermore, we describe the degranulation-inhibiting activities of selected compounds synthesized during the present study, because the methyl ester of the compound proposed to be apteniol A showed strong degranulation-inhibiting activity. 4) Experimental General experimental procedures.…”

“…for C 21 H 24 O 6 : 372.1573, Found: 372.1575.4-(4-Formylphenoxy)-2-methoxybenzaldehyde (10). According to the general coupling procedure, the coupling of 4-bromo-2-methoxybenzaldehyde (1.420 g, 6.60 mmol) and4-hydroxybenzaldehyde (900 mg, 7.40 mmol) produced compound 10 as a colorless crystals with a 14.5% yield (246 mg, 0.96 mmol). Mp.…”