Phytochemical Study of Flavaglines from <i>Aglaia perviridis</i> and Their Rapid Dereplication in Selected Tropical Plant Samples

Phytochemical Study of Flavaglines from <i>Aglaia perviridis</i> and Their Rapid Dereplication in Selected Tropical Plant Samples

Bibliographic Details
Main Author: Agarwal, Garima
Language:English
Published: The Ohio State University / OhioLINK 2019
Subjects:
Chemistry
Analytical Chemistry
Pharmacy Sciences
Online Access:http://rave.ohiolink.edu/etdc/view?acc_num=osu1574089250694739
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spelling ndltd-OhioLink-oai-etd.ohiolink.edu-osu15740892506947392021-08-03T07:13:15Z Phytochemical Study of Flavaglines from <i>Aglaia perviridis</i> and Their Rapid Dereplication in Selected Tropical Plant Samples Agarwal, Garima Chemistry Analytical Chemistry Pharmacy Sciences Cancer is the second leading cause of death globally and responsible for more than 9 million deaths worldwide. Although a new chapter in the discovery and development of novel treatment protocols through the availability of targeted therapies has increased the survival rate of patients with different cancer types in the U.S., this is not true for economically less developed countries. Thus, there is a need to make therapies available worldwide along with addressing issues such as disease recurrence and treatments for all cancer types. Nature, for centuries, has been a source of therapeutic leads for multiple diseases, inclusive more recently of cancer. Several present clinically used anticancer drugs are either natural products or natural product-derived molecules. As part of our continuing efforts to search for potential antineoplastic leads from tropical plants, a large-scale recollection of roots of <i>Aglaia perviridis</i> Hiern was made at Nui Chua National Park in Vietnam. Bioactivity-guided fractionation of the chloroform-soluble sub-fractions led to the isolation of the known and active molecules, silvestrol (<b>31</b>) and 5‴-episilvestrol (<b>51</b>, episilvestrol) previously isolated from Aglaia foveolata. Furthermore, quantification of <b>31</b> and <b>51</b> using a new developed and validated method, determined episilvestrol as the major constituent in the chloroform partition of the roots of <i>Aglaia perviridis</i>. This observation makes <i>A. perviridis</i> as not only the first major source of episilvestrol (<b>51</b>) but also only the third source of dioxanyl-ring containing cyclopenta[<i>b</i>]benzofurans. Sequential fractionation of the ethyl acetate partition from the roots of Aglaia perviridis, led to the isolation of six new compounds (<b>81-86</b>), each found to consist of a fused cyclopenta[4,5]furo[1,4]dioxino[<i>b</i>]benzofuran ring system. This is the first time this fused ring system has been reported from the genus <i>Aglaia</i>, thus their elucidation increases the number of dioxanyl-ring containing compounds found to date by over two-fold. Theoretical ECD calculations was used to determine the absolute configurations of the compounds <b>81-84</b>. Of these new compounds, only <b>85</b> and <b>86</b> showed moderate cytotoxicity against a small cancer cell panel consisting of HT-29 (colon) [IC<sub>50</sub> = 3.04 μM (<b>85</b>) and 2.27 μM (<b>86</b>)] and PC-3 (prostate) [IC<sub>50</sub> = 0.48 μM (<b>85</b>) and 2.30 μM (<b>86</b>)], thereby contributing to the cytotoxicity-activity relationship of flavaglines. Additionally, several flavaglines isolated from previous phytochemical studies in our laboratory, including compounds <b>81-86</b>, were used to propose a general mass spectrometric fragmentation pattern for the rocaglate compound class. Once the characteristic peaks were identified, methanol extracts from several <i>Aglaia</i> species samples collected in Laos, were subjected to a dereplication study that enabled the positive identification of known compounds such as didesmethylrocaglamide (<b>30</b>), silvestrol (<b>31</b>) and methyl rocaglate (<b>34</b>) in different <i>Aglaia</i> extracts. This dereplication component of this work has also led to a means of discerning potential lead <i>Aglaia</i> species in search of possible anticancer agents. 2019 English text The Ohio State University / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=osu1574089250694739 http://rave.ohiolink.edu/etdc/view?acc_num=osu1574089250694739 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws.
collection NDLTD
language English
sources NDLTD
topic Chemistry
Analytical Chemistry
Pharmacy Sciences
spellingShingle Chemistry
Analytical Chemistry
Pharmacy Sciences
Agarwal, Garima
Phytochemical Study of Flavaglines from <i>Aglaia perviridis</i> and Their Rapid Dereplication in Selected Tropical Plant Samples
author Agarwal, Garima
author_facet Agarwal, Garima
author_sort Agarwal, Garima
title Phytochemical Study of Flavaglines from <i>Aglaia perviridis</i> and Their Rapid Dereplication in Selected Tropical Plant Samples
title_short Phytochemical Study of Flavaglines from <i>Aglaia perviridis</i> and Their Rapid Dereplication in Selected Tropical Plant Samples
title_full Phytochemical Study of Flavaglines from <i>Aglaia perviridis</i> and Their Rapid Dereplication in Selected Tropical Plant Samples
title_fullStr Phytochemical Study of Flavaglines from <i>Aglaia perviridis</i> and Their Rapid Dereplication in Selected Tropical Plant Samples
title_full_unstemmed Phytochemical Study of Flavaglines from <i>Aglaia perviridis</i> and Their Rapid Dereplication in Selected Tropical Plant Samples
title_sort phytochemical study of flavaglines from <i>aglaia perviridis</i> and their rapid dereplication in selected tropical plant samples
publisher The Ohio State University / OhioLINK
publishDate 2019
url http://rave.ohiolink.edu/etdc/view?acc_num=osu1574089250694739
work_keys_str_mv AT agarwalgarima phytochemicalstudyofflavaglinesfromiaglaiaperviridisiandtheirrapiddereplicationinselectedtropicalplantsamples
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