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New Carbonic Anhydrase-II Inhibitors from Marine Macro Brown Alga Dictyopteris hoytii Supported by In Silico Studies.

Authors :
Rafiq, Kashif
Khan, Ajmal
Ur Rehman, Najeeb
Halim, Sobia Ahsan
Khan, Majid
Ali, Liaqat
Hilal Al-Balushi, Abdullah
Al-Busaidi, Haitham Khamis
Al-Harrasi, Ahmed
Source :
Molecules; Dec2021, Vol. 26 Issue 23, p7074, 1p
Publication Year :
2021

Abstract

In continuation of phytochemical investigations of the methanolic extract of Dictyopteris hoytii, we have obtained twelve compounds (1–12) through column chromatography. Herein, three compounds, namely, dimethyl 2-bromoterepthalate (3), dimethyl 2,6-dibromoterepthalate (4), and (E)-3-(4-(dimethoxymethyl)phenyl) acrylic acid (5) are isolated for the first time as a natural product, while the rest of the compounds (1, 2, 6–12) are known and isolated for the first time from this source. The structures of the isolated compounds were elucidated by advanced spectroscopic 1D and 2D NMR techniques including <superscript>1</superscript>H, <superscript>13</superscript>C, DEPT, HSQC, HMBC, COSY, NEOSY, and HR-MS and comparison with the reported literature. Furthermore, eight compounds (13–20) previously isolated by our group from the same source along with the currently isolated compounds (1–12) were screened against the CA-II enzyme. All compounds, except 6, 8, 14, and 17, were evaluated for in vitro bovine carbonic anhydrase-II (CA-II) inhibitory activity. Eventually, eleven compounds (1, 4, 5, 7, 9, 10, 12, 13, 15, 18, and 19) exhibited significant inhibitory activity against CA-II with IC<subscript>50</subscript> values ranging from 13.4 to 71.6 μM. Additionally, the active molecules were subjected to molecular docking studies to predict the binding behavior of those compounds. It was observed that the compounds exhibit the inhibitory potential by specifically interacting with the ZN ion present in the active site of CA-II. In addition to ZN ion, two residues (His94 and Thr199) play an important role in binding with the compounds that possess a carboxylate group in their structure. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14203049
Volume :
26
Issue :
23
Database :
Complementary Index
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
154082524
Full Text :
https://doi.org/10.3390/molecules26237074