College of Pharmacy, Chonnam National University, Gwangju 61186, Korea.
College of Pharmacy and Natural Medicine Research Institute, Mokpo National University, Muan-gun 58554, Jeonnam, Korea.
Int J Mol Sci. 2022 Apr 3;23(7):3992. doi: 10.3390/ijms23073992.
Yakuchinone A () is a bioactive diarylheptanoid isolated from the dried fruits of Microbial transformation has been recognized as an efficient method to produce new biologically active derivatives from natural products. In the present study, microbial transformation of yakuchinone A was performed with the fungus KCTC 26779, which led to the isolation of nine new metabolites (, , , and -). Their structures were elucidated as (3)-oxyphyllacinol (), (3)- and (3)-7-hydroxyoxyphyllacinol ( and ), (3)-oxyphyllacinol-4'--β-d-glucopyranoside (), (3)-4″-hydroxyoxyphyllacinol (), (3)-3″-hydroxyoxyphyllacinol (), (3)-2″-hydroxyoxyphyllacinol (), (3)-2″-hydroxyoxyphyllacinol-2″--β-d-glucopyranoside (), and (3)-oxyphyllacinol-3--β-d-glucopyranoside () based on the comprehensive spectroscopic analyses and the application of modified Mosher's method. All compounds were evaluated for their cytotoxic activities against melanoma, as well as breast, lung, and colorectal cancer cell lines. Compound , which was -glucosylated on the diarylheptanoid alkyl chain, exhibited the most selective cytotoxic activities against melanoma cell lines with the IC values ranging from 6.09 to 9.74 μM, indicating that it might be considered as a possible anti-cancer lead compound.
新化合物 yakuchinone A 被鉴定为（3）-氧基二氢菲醇（）、（3）-和（3）-7-羟基氧基二氢菲醇（和）、（3）-氧基二氢菲醇-4'-O-β-d-吡喃葡萄糖苷（）、（3）-4″-羟基氧基二氢菲醇（）、（3）-3″-羟基氧基二氢菲醇（）、（3）-2″-羟基氧基二氢菲醇（）、（3）-2″-羟基氧基二氢菲醇-2″-O-β-d-吡喃葡萄糖苷（）和（3）-氧基二氢菲醇-3-O-β-d-吡喃葡萄糖苷（），基于全面的光谱分析和改良的 Mosher 方法的应用。所有化合物均针对黑色素瘤以及乳腺癌、肺癌和结直肠癌细胞系进行了细胞毒性评估。具有二氢菲烷基链上的葡萄糖基化的化合物，表现出对黑色素瘤细胞系最具选择性的细胞毒性活性，IC 值范围为 6.09 至 9.74 μM，表明其可能被视为一种潜在的抗癌先导化合物。
