Laboratory of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
Department of Fisheries, Faculty of Agriculture, Agricultural Technology and Innovation Research Institute, Kinki University, 3327-204 Nakamachi, Nara, 631-8505, Japan.
J Antibiot (Tokyo). 2019 Jan;72(1):8-14. doi: 10.1038/s41429-018-0101-8. Epub 2018 Oct 10.
A new piperazine derivative designated helvamide was isolated as a pair of rotamers (1 and 2) from the culture broth of the fungus Aspergillus nidulans BF-0142 along with a known helvafuranone (3). The structures of 1 and 2 were elucidated based on spectroscopic analyses by the interpretation of one-dimensional and two-dimensional nuclear magnetic resonance data, ROESY (rotational Overhauser effect spectroscopy) correlations, and a chemical method. Helvamide existed as a rotameric mixture (1 and 2) in dimethyl sulfoxide. Helvamide inhibited sterol O-acyltransferases 1 and 2 (SOAT1 and SOAT2) in enzyme-based and cell-based assays using SOAT1-expressing and SOAT2-expressing Chinese hamster ovary (CHO) cells.
从真菌构巢曲霉 BF-0142 的发酵液中分离到一种新的哌嗪衍生物，命名为 helvamide，它是一对旋光异构体（1 和 2），同时还分离到一种已知的 helvafuranone（3）。通过对一维和二维核磁共振数据、ROESY（旋转过相关谱）相关谱以及化学方法的解析，确定了 1 和 2 的结构。Helvamide 以旋光异构体混合物（1 和 2）的形式存在于二甲基亚砜中。Helvamide 在基于酶和基于细胞的测定中抑制甾醇 O-酰基转移酶 1 和 2（SOAT1 和 SOAT2），该测定使用表达 SOAT1 和 SOAT2 的中国仓鼠卵巢（CHO）细胞。
