Chemical Investigation of Three Antarctic Marine Sponges
This thesis describes the chemical investigation of three marine sponges from Antarctica and the total syntheses of natural products erebusinone (12) and its derivative, erebusinonamine (52). Investigation of the yellow Antarctic marine sponge Isodictya setifera resulted in the isolation of two seco...
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ftunisfloridatam:oai:digitalcommons.usf.edu:etd-2189 2023-06-11T04:05:42+02:00 Chemical Investigation of Three Antarctic Marine Sponges Park, Young Chul 2004-03-19T08:00:00Z application/pdf https://digitalcommons.usf.edu/etd/1190 https://digitalcommons.usf.edu/context/etd/article/2189/viewcontent/SFE0000351.pdf unknown Digital Commons @ University of South Florida https://digitalcommons.usf.edu/etd/1190 https://digitalcommons.usf.edu/context/etd/article/2189/viewcontent/SFE0000351.pdf default USF Tampa Graduate Theses and Dissertations marine natural products tryptophan catabolism chemical defense Antarctic invertebrates erebusinone American Studies Arts and Humanities dissertation 2004 ftunisfloridatam 2023-05-04T17:59:58Z This thesis describes the chemical investigation of three marine sponges from Antarctica and the total syntheses of natural products erebusinone (12) and its derivative, erebusinonamine (52). Investigation of the yellow Antarctic marine sponge Isodictya setifera resulted in the isolation of two secondary metabolites, purine analog (32) and 3-hydroxykynurenine (24). Chemical investigation of Isodictya setifera led to the isolation of six secondary metabolites which included 5-methyl-2-deoxycytidine (25), uridine (28), 2-deoxycytidine (31), homarine (37), hydroxyquinoline (33), 3-hydroxykynurenine (24). The latter two compounds were found to be intermediates of tryptophan catabolism in crustaceans. From the Antarctic marine sponge Isodictya antractica ceramide analog (39) was isolated and its chemical structure was assigned by a combination of spectroscopic and chemical analyses. Stereochemistry was determined by modified Mosher's method. Erebusinone (12), a yellow pigment isolated from the Antarctic marine sponge Isodictya erinacea has been implicated in molt inhibition and mortality against the Antarctic crustacean amphipod, Orchomene plebs, possibly serving as a precursor of a xanthurenic acid analog. Thought to act as a 3-hydroxykynurenine 24 mimic, erebusinone (12) may be involved chemical defense. This appears to be the first example in the marine realm of an organism utilizing tryptophan catabolism to modulate molting as a defensive mechanism. To further investigate the bioactivity and ecological role of erebusinone (12), the synthesis of this pigment was carried out in an overall yield of 44% involving seven steps which were economical and convenient. Erebusinonamine (52) was also similarly synthesized in eight steps with an overall yield of 45%. Doctoral or Postdoctoral Thesis Antarc* Antarctic Antarctica Digital Commons University of South Florida (USF) Antarctic The Antarctic |
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Digital Commons University of South Florida (USF) |
op_collection_id |
ftunisfloridatam |
language |
unknown |
topic |
marine natural products tryptophan catabolism chemical defense Antarctic invertebrates erebusinone American Studies Arts and Humanities |
spellingShingle |
marine natural products tryptophan catabolism chemical defense Antarctic invertebrates erebusinone American Studies Arts and Humanities Park, Young Chul Chemical Investigation of Three Antarctic Marine Sponges |
topic_facet |
marine natural products tryptophan catabolism chemical defense Antarctic invertebrates erebusinone American Studies Arts and Humanities |
description |
This thesis describes the chemical investigation of three marine sponges from Antarctica and the total syntheses of natural products erebusinone (12) and its derivative, erebusinonamine (52). Investigation of the yellow Antarctic marine sponge Isodictya setifera resulted in the isolation of two secondary metabolites, purine analog (32) and 3-hydroxykynurenine (24). Chemical investigation of Isodictya setifera led to the isolation of six secondary metabolites which included 5-methyl-2-deoxycytidine (25), uridine (28), 2-deoxycytidine (31), homarine (37), hydroxyquinoline (33), 3-hydroxykynurenine (24). The latter two compounds were found to be intermediates of tryptophan catabolism in crustaceans. From the Antarctic marine sponge Isodictya antractica ceramide analog (39) was isolated and its chemical structure was assigned by a combination of spectroscopic and chemical analyses. Stereochemistry was determined by modified Mosher's method. Erebusinone (12), a yellow pigment isolated from the Antarctic marine sponge Isodictya erinacea has been implicated in molt inhibition and mortality against the Antarctic crustacean amphipod, Orchomene plebs, possibly serving as a precursor of a xanthurenic acid analog. Thought to act as a 3-hydroxykynurenine 24 mimic, erebusinone (12) may be involved chemical defense. This appears to be the first example in the marine realm of an organism utilizing tryptophan catabolism to modulate molting as a defensive mechanism. To further investigate the bioactivity and ecological role of erebusinone (12), the synthesis of this pigment was carried out in an overall yield of 44% involving seven steps which were economical and convenient. Erebusinonamine (52) was also similarly synthesized in eight steps with an overall yield of 45%. |
format |
Doctoral or Postdoctoral Thesis |
author |
Park, Young Chul |
author_facet |
Park, Young Chul |
author_sort |
Park, Young Chul |
title |
Chemical Investigation of Three Antarctic Marine Sponges |
title_short |
Chemical Investigation of Three Antarctic Marine Sponges |
title_full |
Chemical Investigation of Three Antarctic Marine Sponges |
title_fullStr |
Chemical Investigation of Three Antarctic Marine Sponges |
title_full_unstemmed |
Chemical Investigation of Three Antarctic Marine Sponges |
title_sort |
chemical investigation of three antarctic marine sponges |
publisher |
Digital Commons @ University of South Florida |
publishDate |
2004 |
url |
https://digitalcommons.usf.edu/etd/1190 https://digitalcommons.usf.edu/context/etd/article/2189/viewcontent/SFE0000351.pdf |
geographic |
Antarctic The Antarctic |
geographic_facet |
Antarctic The Antarctic |
genre |
Antarc* Antarctic Antarctica |
genre_facet |
Antarc* Antarctic Antarctica |
op_source |
USF Tampa Graduate Theses and Dissertations |
op_relation |
https://digitalcommons.usf.edu/etd/1190 https://digitalcommons.usf.edu/context/etd/article/2189/viewcontent/SFE0000351.pdf |
op_rights |
default |
_version_ |
1768377301166194688 |