Discovery and Development of Natural Products from Plant and Microbial Sources: Drimane Sesquiterpenes and Abyssomicins as Mosquito Control and Antimicrobial Agents
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The Ohio State University / OhioLINK
2020
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| Online Access: | http://rave.ohiolink.edu/etdc/view?acc_num=osu1591285556969447 |
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ndltd-OhioLink-oai-etd.ohiolink.edu-osu15912855569694472021-08-03T07:15:11Z Discovery and Development of Natural Products from Plant and Microbial Sources: Drimane Sesquiterpenes and Abyssomicins as Mosquito Control and Antimicrobial Agents Manwill, Preston Kim Pharmacy Sciences Organic Chemistry Aedes aegypti Cinnamosma Cinnamosma fragrans insecticide antifeedant TRPA1 cinnamodial natural products drug discovery sesquiterpene dialdehyde Bazzania trilobata endophytes abyssomicin neoabyssomicin Since the dawn of human existence, humankind has relied on nature’s bounty for food, raiment, and medicine. Countless populations from prehistoric beginnings to the present have proven the therapeutic properties of plants to treat all manner of afflictions heaped upon them by the “unseen” organisms of this world and the pains that accompany life. The expansion of human knowledge regarding the causes of disease, organic biochemistry, medicine, and more, have led to our modern understanding and application of chemical matter to relieve pain, treat infections, kill cancer cells, and control mosquito populations.Natural products, those organic molecules obtained from living organisms (e.g., plants, bacteria, marine sponges), are a keystone to drug discovery and modern medicine. As part of an ongoing effort, at The Ohio State University College of Pharmacy, in a drug discovery project from natural sources, three spirotetronate-containing polyketides, namely, abyssomicin 4 (<b>2.142</b>), neoabyssomicin B (<b>2.143</b>), and abyssomicin 2 (<b>2.144</b>), were isolated from a Streptomyces sp. obtained from the liverwort, <i>Bazzania trilobata</i> (L.) S. F. Gray. This represents the first report of isolated and characterized compounds from a liverwort-associated, endophytic bacterium.<i>Cinnamosma fragrans</i> Baill. has been used in traditional medicine practice for many indications and has been shown to produce an array of unsaturated dialdehyde sesquiterpenoids with diverse biological activities. Notably, unsaturated dialdehyde sesquiterpenoids show promising insecticidal and repellent activity and may serve as lead compounds for the development of much-needed mosquitocidal agents capable of controlling mosquito populations and mitigating the spread of mosquito-borne diseases. The compound, cinnamodial (<b>3.20</b>), was obtained in large quantities from the root bark of C. fragrans and used as a scaffold for semi-synthetic analog generation. The prepared analogs were used to probe the structure-activity relationship of cinnamodial and the results obtained confirm the importance of the dialdehyde moiety for mosquitocidal activity and the α,ß-unsaturated carbonyl for antifeedant activity. The improved larvicidal activity observed in a prepared methyl ketone (<b>3.32</b>) derivative and a hydroquinone (<b>3.35</b>) derivative of cinnamodial (<b>3.20</b>) suggest that the development of more stable and effective insecticidal derivatives from this lead compound is possible. 2020-11-13 English text The Ohio State University / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=osu1591285556969447 http://rave.ohiolink.edu/etdc/view?acc_num=osu1591285556969447 restricted--full text unavailable until 2022-08-25 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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NDLTD |
| language |
English |
| sources |
NDLTD |
| topic |
Pharmacy Sciences Organic Chemistry Aedes aegypti Cinnamosma Cinnamosma fragrans insecticide antifeedant TRPA1 cinnamodial natural products drug discovery sesquiterpene dialdehyde Bazzania trilobata endophytes abyssomicin neoabyssomicin |
| spellingShingle |
Pharmacy Sciences Organic Chemistry Aedes aegypti Cinnamosma Cinnamosma fragrans insecticide antifeedant TRPA1 cinnamodial natural products drug discovery sesquiterpene dialdehyde Bazzania trilobata endophytes abyssomicin neoabyssomicin Manwill, Preston Kim Discovery and Development of Natural Products from Plant and Microbial Sources: Drimane Sesquiterpenes and Abyssomicins as Mosquito Control and Antimicrobial Agents |
| author |
Manwill, Preston Kim |
| author_facet |
Manwill, Preston Kim |
| author_sort |
Manwill, Preston Kim |
| title |
Discovery and Development of Natural Products from Plant and Microbial Sources: Drimane Sesquiterpenes and Abyssomicins as Mosquito Control and Antimicrobial Agents |
| title_short |
Discovery and Development of Natural Products from Plant and Microbial Sources: Drimane Sesquiterpenes and Abyssomicins as Mosquito Control and Antimicrobial Agents |
| title_full |
Discovery and Development of Natural Products from Plant and Microbial Sources: Drimane Sesquiterpenes and Abyssomicins as Mosquito Control and Antimicrobial Agents |
| title_fullStr |
Discovery and Development of Natural Products from Plant and Microbial Sources: Drimane Sesquiterpenes and Abyssomicins as Mosquito Control and Antimicrobial Agents |
| title_full_unstemmed |
Discovery and Development of Natural Products from Plant and Microbial Sources: Drimane Sesquiterpenes and Abyssomicins as Mosquito Control and Antimicrobial Agents |
| title_sort |
discovery and development of natural products from plant and microbial sources: drimane sesquiterpenes and abyssomicins as mosquito control and antimicrobial agents |
| publisher |
The Ohio State University / OhioLINK |
| publishDate |
2020 |
| url |
http://rave.ohiolink.edu/etdc/view?acc_num=osu1591285556969447 |
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AT manwillprestonkim discoveryanddevelopmentofnaturalproductsfromplantandmicrobialsourcesdrimanesesquiterpenesandabyssomicinsasmosquitocontrolandantimicrobialagents |
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1719457539147431936 |