Fox Ramos Alexander E, Alcover Charlotte, Evanno Laurent, Maciuk Alexandre, Litaudon Marc, Duplais Christophe, Bernadat Guillaume, Gallard Jean-François, Jullian Jean-Christophe, Mouray Elisabeth, Grellier Philippe, Loiseau Philippe M, Pomel Sébastien, Poupon Erwan, Champy Pierre, Beniddir Mehdi A
Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay , 21 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
J Nat Prod. 2017 Apr 28;80(4):1007-1014. doi: 10.1021/acs.jnatprod.6b01013. Epub 2017 Mar 10.
Three new monoterpene indole alkaloids (1-3) have been isolated from the bark of Geissospermum laeve, together with the known alkaloids (-)-leuconolam (4), geissolosimine (5), and geissospermine (6). The structures of 1-3 were elucidated by analysis of their HRMS and NMR spectroscopic data. The absolute configuration of geissolaevine (1) was deduced from the comparison of experimental and theoretically calculated ECD spectra. The isolation workflow was guided by a molecular networking-based dereplication strategy using an in-house database of monoterpene indole alkaloids. In addition, five known compounds previously undescribed in the Geissospermum genus were dereplicated from the G. laeve alkaloid extract network and were assigned with various levels of identification confidence. The antiparasitic activities against Plasmodium falciparum and Leishmania donovani as well as the cytotoxic activity against the MRC-5 cell line were determined for compounds 1-5.
从平滑盖裂木的树皮中分离出了三种新的单萜吲哚生物碱（1-3），以及已知生物碱（-）-亮氨醇（4）、盖裂木胺（5）和盖裂木明（6）。通过对其高分辨质谱（HRMS）和核磁共振（NMR）光谱数据的分析，阐明了1-3的结构。通过比较实验和理论计算的电子圆二色光谱（ECD），推断出盖裂木碱（1）的绝对构型。分离流程以基于分子网络的去重策略为指导，使用了一个内部的单萜吲哚生物碱数据库。此外，从平滑盖裂木生物碱提取物网络中对盖裂木属中先前未描述的五种已知化合物进行了去重，并赋予了不同程度的鉴定置信度。测定了化合物1-5对恶性疟原虫和杜氏利什曼原虫的抗寄生虫活性以及对MRC-5细胞系的细胞毒性活性。
