Oxygenated Theonellastrols: Interpretation of Unusual Chemical Behaviors Using Quantum Mechanical Calculations and Stereochemical Reassignment of 7 alpha-Hydroxytheonellasterol SCIE SCOPUS

Cited 0 time in WEB OF SCIENCE Cited 0 time in Scopus
Title
Oxygenated Theonellastrols: Interpretation of Unusual Chemical Behaviors Using Quantum Mechanical Calculations and Stereochemical Reassignment of 7 alpha-Hydroxytheonellasterol
Author(s)
Shin, A Young; Lee, Hyi Seung; Lee, Yeon Ju; Lee, Jong Seok; Son, Arang; Choi, Changhoon; Lee, Jihoon
KIOST Author(s)
Shin, A Young(신아영)Lee, Hyi Seung(이희승)Lee, Yeon Ju(이연주)Lee, Jong Seok(이종석)Lee, Jihoon(이지훈)
Alternative Author(s)
신아영; 이희승; 이연주; 이종석; 이지훈
Publication Year
2020-11
Abstract
A total of eight new oxygenated 4-exo-methylene sterols, 1-8, together with one artifact 9 and six known sterols 11-16, were isolated from the marine sponge Theonella swinhoei collected from the Bohol province in Philippines. Structures of sterols 1-8 were determined from 1D and 2D NMR data. Among the sterols, 8 alpha-hydroxytheonellasterol (4) spontaneously underwent an allylic 1,3-hydroxyl shift to produce 15 alpha-hydroxytheonellasterol (9) as an artifact; this was rationalized by quantum mechanical calculations of the transition state. In addition, the 1,2-epoxy alcohol subunit of 8 alpha-hydroxy-14,15-beta-epoxytheonellasterol (5) was assigned using the Gauge-Independent Atomic Orbital (GIAO) NMR chemical shift calculations and subsequent DP4+ analysis. Finally, comparison of the C-13 chemical shifts of isolated 7 alpha-hydroxytheonellasterol (6) with the reported values revealed significant discrepancies at C-6, C-7, C-8, and C-14, leading to reassignment of the C-7 stereochemistry in the known structure.
ISSN
1660-3397
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/38531
DOI
10.3390/md18120607
Bibliographic Citation
MARINE DRUGS, v.18, no.12, 2020
Publisher
MDPI
Subject
CYTOTOXIC DIMERIC MACROLIDES; POTENT THROMBIN INHIBITORS; MARINE SPONGE; STRUCTURE ELUCIDATION; 5-ALPHA,8-ALPHA-EPIDIOXY STEROLS; SWINHOLIDE-A; CONICASTEROL; 4-METHYLENESTEROLS; CYCLOTHEONAMIDES; INVERTEBRATES
Keywords
Theonella swinhoei; marine natural product; oxygenated theonellasterol; GIAO NMR chemical shift calculation; anti-inflammatory activity
Type
Article
Language
English
Document Type
Article
Publisher
MDPI
Related Researcher
Research Interests

Marine Natural Products,Organic Chemistry,해양천연물,유기화학

Files in This Item:
There are no files associated with this item.

qrcode

Items in ScienceWatch@KIOST are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse