Theoretical Study on the Structures,Spectral Properties,and Drugability of Xenicane-type Diterpenoids from Dictyota dichotoma  

作　　者：HUANG Luoyi SUN Xiang CHEN Mengyi YAN Pengcheng WANG Chaojie 

机构地区：[1]School of Pharmaceutical Sciences,Wenzhou Medical University,Wenzhou 325035,P.R.China [2]Department of Pharmacy,The First Affiliated Hospital of Wenzhou Medical University,Wenzhou 325000,P.R.China

出　　处：《Chemical Research in Chinese Universities》2022年第2期622-631,共10页高等学校化学研究（英文版）

基　　金：supported by the National Natural Science Foundation of China(No.21177098);the Zhejiang Provincial Natural Science Foundation,China(No.LY16B070006);the Zhejiang Traditional Chinese Medicine Science and Technology Project,China(No.2020ZB141).

摘　　要：There are few reports on the relationship between the biological activity and structure of secondary metabolites from Dictyota dichotoma. In this work, the geometric and electronic structures, infrared spectra, ultraviolet spectra, 13C and 1H NMR spectra of 16 xenicane-type diterpenoids extracted from Dictyota dichotoma were studied by the density functional theory ωB97XD/6-311+G(2d,p) method. The analysis of the reactivity indices was carried out via the conceptual density functional theory. Furthermore, a pharmacodynamic evaluation was performed using ADME/Tox. The geometric structure analysis found that all 16 diterpenoids had the same unsaturated, branched chains and could be divided into two categories according to the ring size, including nine-membered and eight-membered rings. A hydroxyl group on the lactone ring reduced the stability of the compound. In contrast, a hydroxyl group on the parent ring had little effect on the compound's stability. The electrostatic potential results preliminarily predicted active sites for nucleophilic/electrophilic reactions. The fitting results of infrared and nuclear magnetic resonance(NMR) data showed that the theoretical values obtained by this method were consistent with the experimental values. The UV-visible absorption spectra showed that the solvent effects caused different redshifts of the absorption peaks. The absorption strength was enhanced. The sixteen diterpenoids displayed a strong absorption peak in the range of 180―200 nm, but the compound containing a carbonyl group presents a weaker absorption peak in the field of 200―240 nm. Compounds 9―11, 14, and 15 have better stability and reactivity with lower chemical potentials and higher electronegativity, electrophilic index, and hardness values. The local reactivity descriptors further identified nucleophilic/electrophilic reaction sites for the sixteen compounds. Finally, the pharmacodynamic evaluation results predicted that compounds 2, 4, 8, 11, and 14―16 have optimal drugability. The theoretical re

关 键 词：Dictyota dichotoma DITERPENOID Conceptual density functional theory 

分 类 号：O62[理学—有机化学]