Triproamide and Pemukainalides, Cyclic Depsipeptides from the Marine Cyanobacterium Symploca hydnoides
A new cyclic depsipeptide, triproamide ( 1 ), containing the rare 4-phenylvaline (dolaphenvaline, Dpv) and a β-amino acid, dolamethylleucine (Dml), originally found in dolastatin 16, was isolated from the polar VLC-derived fraction of the extracts prepared from the marine cyanobacterium Symploca hyd...
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ftsmithonian:oai:figshare.com:article/18439466 2023-05-15T16:02:00+02:00 Triproamide and Pemukainalides, Cyclic Depsipeptides from the Marine Cyanobacterium Symploca hydnoides Ma Yadanar Phyo (8037719) Jun Xian Goh (8037728) Lik Tong Tan (2248375) 2022-01-14T00:00:00Z https://doi.org/10.1021/acs.jnatprod.1c00996.s001 unknown https://figshare.com/articles/journal_contribution/Triproamide_and_Pemukainalides_Cyclic_Depsipeptides_from_the_Marine_Cyanobacterium_i_Symploca_hydnoides_i_/18439466 doi:10.1021/acs.jnatprod.1c00996.s001 CC BY-NC 4.0 CC-BY-NC Biochemistry Ecology Cancer Environmental Sciences not elsewhere classified Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified two new analogues symploca hydnoides </ phase hplc analyses mass spectrometric data 1 (< b new cyclic depsipeptide b (< b known molecule kulokainalide 50 </ sub triproamide (< b (< b cyclic depsipeptides relative configurations rare 4 polar vlc planar structures marine cyanobacterium marfey ’ j -</ extracts prepared extensive nmr elucidated based dolastatin 16 determined utilizing derived fraction based configuration amino acid 6 μm Text Journal contribution 2022 ftsmithonian https://doi.org/10.1021/acs.jnatprod.1c00996.s001 2022-01-21T13:07:28Z A new cyclic depsipeptide, triproamide ( 1 ), containing the rare 4-phenylvaline (dolaphenvaline, Dpv) and a β-amino acid, dolamethylleucine (Dml), originally found in dolastatin 16, was isolated from the polar VLC-derived fraction of the extracts prepared from the marine cyanobacterium Symploca hydnoides . Triproamide ( 1 ) was isolated along with the known molecule kulokainalide-1 ( 2 ), as well as its two new analogues, pemukainalides A ( 3 ) and B ( 4 ). Their planar structures were elucidated based on extensive NMR and mass spectrometric data. The absolute and relative configurations of the compounds were determined utilizing a combination of Marfey’s method, J- based configuration, and chiral-phase HPLC analyses. Kulokainalide-1 ( 2 ) and pemukainalide A ( 3 ) exhibited cytotoxicity against the MOLT-4 leukemia cell line with IC 50 values of 5.9 and 5.6 μM, respectively. Other Non-Article Part of Journal/Newspaper DML Unknown |
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Unknown |
op_collection_id |
ftsmithonian |
language |
unknown |
topic |
Biochemistry Ecology Cancer Environmental Sciences not elsewhere classified Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified two new analogues symploca hydnoides </ phase hplc analyses mass spectrometric data 1 (< b new cyclic depsipeptide b (< b known molecule kulokainalide 50 </ sub triproamide (< b (< b cyclic depsipeptides relative configurations rare 4 polar vlc planar structures marine cyanobacterium marfey ’ j -</ extracts prepared extensive nmr elucidated based dolastatin 16 determined utilizing derived fraction based configuration amino acid 6 μm |
spellingShingle |
Biochemistry Ecology Cancer Environmental Sciences not elsewhere classified Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified two new analogues symploca hydnoides </ phase hplc analyses mass spectrometric data 1 (< b new cyclic depsipeptide b (< b known molecule kulokainalide 50 </ sub triproamide (< b (< b cyclic depsipeptides relative configurations rare 4 polar vlc planar structures marine cyanobacterium marfey ’ j -</ extracts prepared extensive nmr elucidated based dolastatin 16 determined utilizing derived fraction based configuration amino acid 6 μm Ma Yadanar Phyo (8037719) Jun Xian Goh (8037728) Lik Tong Tan (2248375) Triproamide and Pemukainalides, Cyclic Depsipeptides from the Marine Cyanobacterium Symploca hydnoides |
topic_facet |
Biochemistry Ecology Cancer Environmental Sciences not elsewhere classified Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified two new analogues symploca hydnoides </ phase hplc analyses mass spectrometric data 1 (< b new cyclic depsipeptide b (< b known molecule kulokainalide 50 </ sub triproamide (< b (< b cyclic depsipeptides relative configurations rare 4 polar vlc planar structures marine cyanobacterium marfey ’ j -</ extracts prepared extensive nmr elucidated based dolastatin 16 determined utilizing derived fraction based configuration amino acid 6 μm |
description |
A new cyclic depsipeptide, triproamide ( 1 ), containing the rare 4-phenylvaline (dolaphenvaline, Dpv) and a β-amino acid, dolamethylleucine (Dml), originally found in dolastatin 16, was isolated from the polar VLC-derived fraction of the extracts prepared from the marine cyanobacterium Symploca hydnoides . Triproamide ( 1 ) was isolated along with the known molecule kulokainalide-1 ( 2 ), as well as its two new analogues, pemukainalides A ( 3 ) and B ( 4 ). Their planar structures were elucidated based on extensive NMR and mass spectrometric data. The absolute and relative configurations of the compounds were determined utilizing a combination of Marfey’s method, J- based configuration, and chiral-phase HPLC analyses. Kulokainalide-1 ( 2 ) and pemukainalide A ( 3 ) exhibited cytotoxicity against the MOLT-4 leukemia cell line with IC 50 values of 5.9 and 5.6 μM, respectively. |
format |
Other Non-Article Part of Journal/Newspaper |
author |
Ma Yadanar Phyo (8037719) Jun Xian Goh (8037728) Lik Tong Tan (2248375) |
author_facet |
Ma Yadanar Phyo (8037719) Jun Xian Goh (8037728) Lik Tong Tan (2248375) |
author_sort |
Ma Yadanar Phyo (8037719) |
title |
Triproamide and Pemukainalides, Cyclic Depsipeptides from the Marine Cyanobacterium Symploca hydnoides |
title_short |
Triproamide and Pemukainalides, Cyclic Depsipeptides from the Marine Cyanobacterium Symploca hydnoides |
title_full |
Triproamide and Pemukainalides, Cyclic Depsipeptides from the Marine Cyanobacterium Symploca hydnoides |
title_fullStr |
Triproamide and Pemukainalides, Cyclic Depsipeptides from the Marine Cyanobacterium Symploca hydnoides |
title_full_unstemmed |
Triproamide and Pemukainalides, Cyclic Depsipeptides from the Marine Cyanobacterium Symploca hydnoides |
title_sort |
triproamide and pemukainalides, cyclic depsipeptides from the marine cyanobacterium symploca hydnoides |
publishDate |
2022 |
url |
https://doi.org/10.1021/acs.jnatprod.1c00996.s001 |
genre |
DML |
genre_facet |
DML |
op_relation |
https://figshare.com/articles/journal_contribution/Triproamide_and_Pemukainalides_Cyclic_Depsipeptides_from_the_Marine_Cyanobacterium_i_Symploca_hydnoides_i_/18439466 doi:10.1021/acs.jnatprod.1c00996.s001 |
op_rights |
CC BY-NC 4.0 |
op_rightsnorm |
CC-BY-NC |
op_doi |
https://doi.org/10.1021/acs.jnatprod.1c00996.s001 |
_version_ |
1766397654033498112 |