Graduate School of Pharmaceutical Sciences, Kumamoto University.
Pharmaceutical Industries Research Division, Pharmacognosy Department, National Research Centre.
Chem Pharm Bull (Tokyo). 2021;69(8):802-805. doi: 10.1248/cpb.c21-00392.
A new rearranged nitrogenous bisabolone-type sesquiterpene, halichonic acid B (1), was isolated from a marine sponge Axinyssa sp. together with halichonic acid (2) and (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (3). The structure of 1 was determined by extensive NMR and MS analyses, revealing an unprecedented carbon framework, and its absolute configuration was elucidated by time-dependent density-functional theory (TDDFT)-based electronic circular dichroism (ECD) spectrum calculation. We propose that 1 and 2 may be biosynthesized in the same pathway, involving the reaction between farnesyl pyrophosphate and glycine, followed by cyclization.
从海绵 Axinyssa 属中分离到一种新的氮杂双醇型倍半萜，即卤虫酸 B（1），与卤虫酸（2）和（6R,7S）-7-氨基-7,8-二氢-α-毕赤醇（3）。通过广泛的 NMR 和 MS 分析确定了 1 的结构，揭示了一个前所未有的碳骨架，其绝对构型通过基于时间依赖密度泛函理论（TDDFT）的电子圆二色（ECD）光谱计算得到阐明。我们提出 1 和 2 可能通过涉及法呢基焦磷酸和甘氨酸之间的反应，然后环化，沿着相同的生物合成途径生成。
