Graduate School of Life and Environmental Sciences, Kyoto Prefectural University , Sakyo-ku, Kyoto 606-8522, Japan.
J Nat Prod. 2013 Sep 27;76(9):1737-45. doi: 10.1021/np400460m. Epub 2013 Sep 13.
Ustusorane D and penicisochromans B-D are natural isochromans isolated from Aspergillus ustus 094102 and Penicillium sp. PSU-F40, respectively. Herein, we report the syntheses of (-)-ustusorane D and (+)-penicisochroman B and the structures of penicisochromans C and D. The relative configuration of natural ustusorane D and the absolute configuration of natural penicisochroman B were determined. Two plausible structures for penicisochroman C were evaluated through synthesis, but their ¹H and ¹³C NMR data were not in agreement with those of the natural product. The structural revision and the determination of the absolute configuration of natural penicisochroman D were achieved. Structure-activity relationship studies of the synthetic compounds as well as a series of related isochromans indicated that the enone of the furanone moiety was essential for the cytotoxicity of these compounds toward HCT116 human colon cancer cells. Pseudodeflectusin, the related natural isochroman, suppressed cell growth and induced apoptosis in HCT116 cells.
Ustusorane D 和 penicisochromans B-D 是分别从 Aspergillus ustus 094102 和 Penicillium sp. PSU-F40 中分离得到的天然异chromans。本文报道了（-）-ustusorane D 和（+）-penicisochroman B 的合成以及 penicisochromans C 和 D 的结构。确定了天然 ustusorane D 的相对构型和天然 penicisochroman B 的绝对构型。通过合成评估了 penicisochroman C 的两种可能结构，但它们的 1H 和 13C NMR 数据与天然产物不一致。对天然 penicisochroman D 的结构修订和绝对构型的确定。合成化合物以及一系列相关异 chromans 的构效关系研究表明，呋喃酮部分的烯酮对于这些化合物对 HCT116 人结肠癌细胞的细胞毒性是必不可少的。相关的天然异 chroman pseudodeflectusin 抑制 HCT116 细胞的生长并诱导其凋亡。
