scholarly journals Costatone C—A new halogenated monoterpene from the New Zealand red alga plocamium angustum

2020 ◽  
Author(s):  
Joe Bracegirdle ◽  
Z Sohail ◽  
Michael Fairhurst ◽  
Monica Gerth ◽  
Giuseppe Zuccarello ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
New Zealand ◽  
Natural Product ◽  
Absolute Configuration ◽  
Red Algae ◽  
Red Alga ◽  
Product Distributions ◽  
Halogenated Monoterpenes ◽  
The Absolute

© 2019 by the authors Red algae of the genus Plocamium have been a rich source of halogenated monoterpenes. Herein, a new cyclic monoterpene, costatone C (7), was isolated from the extract of P. angustum collected in New Zealand, along with the previously reported (1E,5Z)-1,6-dichloro-2-methylhepta-1,5-dien-3-ol (8). Elucidation of the planar structure of 7 was achieved through conventional NMR and (−)-HR-APCI-MS techniques, and the absolute configuration by comparison of experimental and DFT-calculated ECD spectra. The absolute configuration of 8 was determined using Mosher’s method. Compound 7 showed mild antibacterial activity against Staphylococcus aureus and S. epidermidis. The state of Plocamium taxonomy and its implications upon natural product distributions, especially across samples from specimens collected in different countries, is also discussed.

scholarly journals Costatone C—A New Halogenated Monoterpene from the New Zealand Red Alga Plocamium angustum

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 418 ◽  
Author(s):  
Joe Bracegirdle ◽  
Zaineb Sohail ◽  
Michael J. Fairhurst ◽  
Monica L. Gerth ◽  
Giuseppe C. Zuccarello ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
New Zealand ◽  
Natural Product ◽  
Absolute Configuration ◽  
Red Algae ◽  
Red Alga ◽  
Product Distributions ◽  
Halogenated Monoterpenes ◽  
The Absolute

Red algae of the genus Plocamium have been a rich source of halogenated monoterpenes. Herein, a new cyclic monoterpene, costatone C (7), was isolated from the extract of P. angustum collected in New Zealand, along with the previously reported (1E,5Z)-1,6-dichloro-2-methylhepta-1,5-dien-3-ol (8). Elucidation of the planar structure of 7 was achieved through conventional NMR and (−)-HR-APCI-MS techniques, and the absolute configuration by comparison of experimental and DFT-calculated ECD spectra. The absolute configuration of 8 was determined using Mosher’s method. Compound 7 showed mild antibacterial activity against Staphylococcus aureus and S. epidermidis. The state of Plocamium taxonomy and its implications upon natural product distributions, especially across samples from specimens collected in different countries, is also discussed.

scholarly journals Costatone C—A new halogenated monoterpene from the New Zealand red alga plocamium angustum

2020 ◽  
Author(s):  
Joe Bracegirdle ◽  
Z Sohail ◽  
Michael Fairhurst ◽  
Monica Gerth ◽  
Giuseppe Zuccarello ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
New Zealand ◽  
Natural Product ◽  
Absolute Configuration ◽  
Red Algae ◽  
Red Alga ◽  
Product Distributions ◽  
Halogenated Monoterpenes ◽  
The Absolute

© 2019 by the authors Red algae of the genus Plocamium have been a rich source of halogenated monoterpenes. Herein, a new cyclic monoterpene, costatone C (7), was isolated from the extract of P. angustum collected in New Zealand, along with the previously reported (1E,5Z)-1,6-dichloro-2-methylhepta-1,5-dien-3-ol (8). Elucidation of the planar structure of 7 was achieved through conventional NMR and (−)-HR-APCI-MS techniques, and the absolute configuration by comparison of experimental and DFT-calculated ECD spectra. The absolute configuration of 8 was determined using Mosher’s method. Compound 7 showed mild antibacterial activity against Staphylococcus aureus and S. epidermidis. The state of Plocamium taxonomy and its implications upon natural product distributions, especially across samples from specimens collected in different countries, is also discussed.

scholarly journals Bromophenolics from the Red Alga Polysiphonia decipiens

Marine Drugs ◽  
2019 ◽  
Vol 17 (9) ◽  
pp. 497 ◽  
Author(s):  
James Lever ◽  
Grace Curtis ◽  
Robert Brkljača ◽  
Sylvia Urban
Keyword(s):  
Antibacterial Activity ◽  
Natural Product ◽  
Absolute Configuration ◽  
Structure Determination ◽  
Red Alga ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
The Absolute ◽  
First Time

The isolation and the structure determination of a new bromophenolic compound, polysiphonol (10), as well as five previously reported compounds, (4–8), from the red alga Polysiphonia decipiens is reported. In addition, the absolute configuration of the natural product rhodomelol (8) could be unequivocally confirmed for the first time, and on biosynthetic grounds, the absolute configuration of polysiphonol (10) was tentatively suggested. Compounds 4–8 were evaluated for their antibacterial activity against both Gram-positive and Gram-negative bacteria, but none of the compounds showed any appreciable activity.

scholarly journals Isolation and Structure Elucidation of New Secondary Metabolites from New Zealand Marine Red Algae

2021 ◽  
Author(s):  
◽  
Wendy Lynne Popplewell
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
New Zealand ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Red Algae ◽  
Structure Elucidation ◽  
Screening Tool ◽  
Product Analysis ◽  
Algal Extracts

<p>The natural product analysis of New Zealand red algae has been neglected in recent years, and there is obvious scope for the chemical re-evaluation of New Zealand marine red algae. This study describes the isolation and structure elucidation of 12 new and eight known compounds from four different genera of red algae. To aid in this process, 34 red algae were screened in order to generate a digital HSQC spectra mask, a screening tool developed by the VUW Marine Natural Products group to identify extracts of interest for further analysis. All 34 algal extracts were screened using the HSQC mask and four extracts were identified as interesting and analysed in detail. Examination of extracts of the red algae Plocamium costatum and Ballia callitricha lead to the isolation of three known metabolites. Eleven new oxylipins, labillarides A to K, are reported from the alga Phacelocarpus labillardieri. Labillarides A to H are polyunsaturated alpha-pyrone macrocycles, all of which show similarities to the previously reported compounds isolated from southern Australian collections of the algae. Labillarides E to H are of particular interest as they represent the two diastereomeric pairs associated with variation at the C-3 and C-8 chiral centres. Labillarides I and J are related enol macrocycles while labillaride K is a furan-3-one oxylipin, all of which have biogenic significance to the macrocyclic alpha-pyrones. Labillarides A, B and I exhibit moderate cytotoxicity while labillaride C shows moderate antibacterial activity. A new nitrogenous bromophenol, colensolide A, was isolated from the alga Osmundaria colensoi along with five known bromophenols. The presence of nitrogen-containing sidechains in bromophenols is unusual but not unprecedented. The bicyclic nitrogenous moiety observed in colensolide A is proposed to be of histidine origin. Several of the known bromophenols exhibit antibacterial activity and one shows moderate cytotoxicity.</p>

scholarly journals Isolation and Structure Elucidation of New Secondary Metabolites from New Zealand Marine Red Algae

2021 ◽  
Author(s):  
◽  
Wendy Lynne Popplewell
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
New Zealand ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Red Algae ◽  
Structure Elucidation ◽  
Screening Tool ◽  
Product Analysis ◽  
Algal Extracts

<p>The natural product analysis of New Zealand red algae has been neglected in recent years, and there is obvious scope for the chemical re-evaluation of New Zealand marine red algae. This study describes the isolation and structure elucidation of 12 new and eight known compounds from four different genera of red algae. To aid in this process, 34 red algae were screened in order to generate a digital HSQC spectra mask, a screening tool developed by the VUW Marine Natural Products group to identify extracts of interest for further analysis. All 34 algal extracts were screened using the HSQC mask and four extracts were identified as interesting and analysed in detail. Examination of extracts of the red algae Plocamium costatum and Ballia callitricha lead to the isolation of three known metabolites. Eleven new oxylipins, labillarides A to K, are reported from the alga Phacelocarpus labillardieri. Labillarides A to H are polyunsaturated alpha-pyrone macrocycles, all of which show similarities to the previously reported compounds isolated from southern Australian collections of the algae. Labillarides E to H are of particular interest as they represent the two diastereomeric pairs associated with variation at the C-3 and C-8 chiral centres. Labillarides I and J are related enol macrocycles while labillaride K is a furan-3-one oxylipin, all of which have biogenic significance to the macrocyclic alpha-pyrones. Labillarides A, B and I exhibit moderate cytotoxicity while labillaride C shows moderate antibacterial activity. A new nitrogenous bromophenol, colensolide A, was isolated from the alga Osmundaria colensoi along with five known bromophenols. The presence of nitrogen-containing sidechains in bromophenols is unusual but not unprecedented. The bicyclic nitrogenous moiety observed in colensolide A is proposed to be of histidine origin. Several of the known bromophenols exhibit antibacterial activity and one shows moderate cytotoxicity.</p>

scholarly journals Determination of the Absolute Configuration of the Pseudo‐Symmetric Natural Product Elatenyne by the Crystalline Sponge Method

2016 ◽  
Vol 55 (8) ◽  
pp. 2678-2682 ◽  
Author(s):  
Sylvia Urban ◽  
Robert Brkljača ◽  
Manabu Hoshino ◽  
Shoukou Lee ◽  
Makoto Fujita
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
The Absolute

scholarly journals De novo synthesis, structural assignment and biological evaluation of pseudopaline, a metallophore produced by Pseudomonas aeruginosa

2019 ◽  
Vol 10 (27) ◽  
pp. 6635-6641 ◽  
Author(s):  
Jian Zhang ◽  
Tianhu Zhao ◽  
Rongwen Yang ◽  
Ittipon Siridechakorn ◽  
Sanshan Wang ◽  
...  
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Total Synthesis ◽  
Natural Product ◽  
Absolute Configuration ◽  
De Novo ◽  
Biological Evaluation ◽  
De Novo Synthesis ◽  
Structural Assignment ◽  
The Absolute

The first total synthesis and isolation of pseudopaline was reported, which allows determination and confirmation of the absolute configuration of the natural product.

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