Bioactive Constituents of <i>Aronia melanocarpa</i> and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i>

Bioactive Constituents of <i>Aronia melanocarpa</i> and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i>

Bibliographic Details
Main Author: Li, Jie
Language:English
Published: The Ohio State University / OhioLINK 2014
Subjects:
Pharmacy Sciences
Online Access:http://rave.ohiolink.edu/etdc/view?acc_num=osu1387764682
id ndltd-OhioLink-oai-etd.ohiolink.edu-osu1387764682
record_format oai_dc
collection NDLTD
language English
sources NDLTD
topic Pharmacy Sciences
spellingShingle Pharmacy Sciences
Li, Jie
Bioactive Constituents of <i>Aronia melanocarpa</i> and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i>
author Li, Jie
author_facet Li, Jie
author_sort Li, Jie
title Bioactive Constituents of <i>Aronia melanocarpa</i> and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i>
title_short Bioactive Constituents of <i>Aronia melanocarpa</i> and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i>
title_full Bioactive Constituents of <i>Aronia melanocarpa</i> and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i>
title_fullStr Bioactive Constituents of <i>Aronia melanocarpa</i> and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i>
title_full_unstemmed Bioactive Constituents of <i>Aronia melanocarpa</i> and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i>
title_sort bioactive constituents of <i>aronia melanocarpa</i> and <i>sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i>
publisher The Ohio State University / OhioLINK
publishDate 2014
url http://rave.ohiolink.edu/etdc/view?acc_num=osu1387764682
work_keys_str_mv AT lijie bioactiveconstituentsofiaroniamelanocarpaiandisphenostylisiimarginataisspierectai
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spelling ndltd-OhioLink-oai-etd.ohiolink.edu-osu13877646822021-08-03T06:21:06Z Bioactive Constituents of <i>Aronia melanocarpa</i> and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i> Li, Jie Pharmacy Sciences Natural products have played an important role for many decades in drug discovery to combat cancer. As part of a collaborative, multi-disciplinary approach to the discovery of new naturally occurring cancer chemopreventive or chemotherapeutic agents, two edible plants, namely, <i>Aronia melanocarpa</i> (black chokeberry) and <i>Sphenostylis</i> <i>marginata</i> ssp. <i>erecta</i> (African yellow pea), showed activity in initial hydroxyl radical-scavenging and quinone reductase-induciton screening assays, and thus were selected for further phytochemical and biological investigation.Bioassay-guided fractionation of the ethyl acetate-soluble extract of <i>A. melanocarpa</i> fruits, using hydroxyl radical-scavenging and quinone reductase-induciton assays, led to the isolation of a new depside (<b>81</b>) and two known depsides (<b>82</b> and <b>83</b>), along with an additional twenty-one known compounds (<b>64</b>-<b>66</b>, <b>70</b>, and <b>84</b>-<b>100</b>). Among the known compounds obtained, eighteen compounds (<b>81</b>-<b>87</b>, <b>89</b>, <b>90</b>, and <b>92</b>-<b>100</b>) were isolated from <i>A. melanocarpa</i> for the first time. The new compound <b>81</b> and the known compounds <b>82</b> and <b>83</b> represent a novel class of depsides that has been reported only relatively recently. In the present study, the four-bond HMBC correlations of <b>81</b>-<b>83</b> were obtained to provide direct evidence for fully unambiguous NMR assignments of these three compounds. Among all the twenty-four compounds isolated, seventeen compounds showed significant hydroxyl radical-scavenging activity, with hyperin (<b>64</b>, ED<sub>50</sub> 0.17 uM) being of the greatest potency. The new compound <b>81</b> also exhibited potent antioxidant activity (ED<sub>50</sub> 0.44 uM) in this assay. The quinone reductase-induction assay showed that protocatechuic acid (<b>84</b>, CD 4.3 uM), neochlorogenic acid methyl ester (<b>96</b>, CD 6.7 uM), and quercetin (<b>99</b>, CD 3.1 uM) doubled quinone reductase activity at concentrations less than 10 uM.The chloroform-soluble extract of the root bark of <i>S.</i> <i>marginata</i> ssp. <i>erecta</i> was also fractionated under the guidance of both hydroxyl radical-scavenging and quinone reductase-induciton assays, and resulted in the isolation of sphenostylisins A-C (<b>107</b>-<b>109</b>), three complex dimeric compounds representing two novel carbon skeletons, as well as an additional eight new compounds, sphenostylisins D-K (<b>110</b>-<b>117</b>). All these new compounds obtained were evaluated against a panel of <i>in vitro</i> bioassays. Of these isolates, eight compounds (<b>107</b>-<b>110</b> and <b>114</b>-<b>117</b>) exhibited potent hydroxyl radical-scavenging activity (ED<sub>50</sub> values range from 0.60 to 2.6 uM). Six compounds (<b>107</b>-<b>110</b>, <b>114</b>, and <b>115</b>) showed quinone reductase-inducing activity, with sphenostylisin C (<b>109</b>, CD 2.1 uM) being the most potent. Eight compounds (<b>107</b>-<b>114</b>) showed NF-kB p65 inhibitory activity. In particular, sphenostylisin A (<b>107</b>), representing a novel carbon skeleton, was found to be a very potent NF-kB p65 inhibitor with an IC<sub>50</sub> value of 6 nM. This compound (<b>107</b>) also showed cytotoxicity (IC<sub>50</sub> 1.6 uM) against the HT-29 cell line. Based on the structural features and similarities of these eleven new compounds (<b>107</b>-<b>117</b>), a plausible biogenetic pathway and a preliminary structure-activity relationship among them were discussed in the present study.In summary, considering the high abundance and potent activities of bioactive constituents present in <i>A. melanocarpa</i> and <i>S.</i> <i>marginata</i> ssp. <i>erecta</i>, these two plants can be regarded as excellent sources of lead compounds for the development of drugs to combat cancer. 2014-05-21 English text The Ohio State University / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=osu1387764682 http://rave.ohiolink.edu/etdc/view?acc_num=osu1387764682 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.

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