Abstract
Two related peptide metabolites, one a cyclic depsipeptide, hoiamide B (2), and the other a linear lipopeptide, hoiamide C (3), were isolated from two different collections of marine cyanobacteria obtained in Papua New Guinea. Their structures were elucidated by combining various techniques in spectroscopy, chromatography, and synthetic chemistry. Both metabolites belong to the unique hoiamide structural class, characterized by possessing an acetate extended and S-adenosyl methionine modified isoleucine unit, a central triheterocyclic system comprised of two α-methylated thiazolines and one thiazole, and a highly oxygenated and methylated C-15 polyketide unit. In neocortical neurons, the cyclic depsipeptide 2 stimulated sodium influx and suppressed spontaneous Ca2+ oscillations with EC50 values of 3.9 μM and 79.8 nM, respectively, while 3 had no significant effects in these assays.
| Original language | English |
|---|---|
| Pages (from-to) | 1411-1421 |
| Number of pages | 11 |
| Journal | Journal of Natural Products |
| Volume | 73 |
| Issue number | 8 |
| DOIs | |
| State | Published - Aug 27 2010 |
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All Science Journal Classification (ASJC) codes
- Drug Discovery
- Pharmacology
- Pharmaceutical Science
- Analytical Chemistry
- Organic Chemistry
- Molecular Medicine
- Complementary and alternative medicine
- Medicine(all)
Cite this
The hoiamides, structurally intriguing neurotoxic Lipopeptides from Papua New Guinea marine cyanobacteria. / Choi, Hyukjae; Pereira, Alban R.; Cao, Zhengyu; Shuman, Cynthia F.; Engene, Niclas; Byrum, Tara; Matainaho, Teatulohi; Murray, Thomas F.; Mangoni, Alfonso; Gerwick, William H.
In: Journal of Natural Products, Vol. 73, No. 8, 27.08.2010, p. 1411-1421.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The hoiamides, structurally intriguing neurotoxic Lipopeptides from Papua New Guinea marine cyanobacteria
AU - Choi, Hyukjae
AU - Pereira, Alban R.
AU - Cao, Zhengyu
AU - Shuman, Cynthia F.
AU - Engene, Niclas
AU - Byrum, Tara
AU - Matainaho, Teatulohi
AU - Murray, Thomas F.
AU - Mangoni, Alfonso
AU - Gerwick, William H.
PY - 2010/8/27
Y1 - 2010/8/27
N2 - Two related peptide metabolites, one a cyclic depsipeptide, hoiamide B (2), and the other a linear lipopeptide, hoiamide C (3), were isolated from two different collections of marine cyanobacteria obtained in Papua New Guinea. Their structures were elucidated by combining various techniques in spectroscopy, chromatography, and synthetic chemistry. Both metabolites belong to the unique hoiamide structural class, characterized by possessing an acetate extended and S-adenosyl methionine modified isoleucine unit, a central triheterocyclic system comprised of two α-methylated thiazolines and one thiazole, and a highly oxygenated and methylated C-15 polyketide unit. In neocortical neurons, the cyclic depsipeptide 2 stimulated sodium influx and suppressed spontaneous Ca2+ oscillations with EC50 values of 3.9 μM and 79.8 nM, respectively, while 3 had no significant effects in these assays.
AB - Two related peptide metabolites, one a cyclic depsipeptide, hoiamide B (2), and the other a linear lipopeptide, hoiamide C (3), were isolated from two different collections of marine cyanobacteria obtained in Papua New Guinea. Their structures were elucidated by combining various techniques in spectroscopy, chromatography, and synthetic chemistry. Both metabolites belong to the unique hoiamide structural class, characterized by possessing an acetate extended and S-adenosyl methionine modified isoleucine unit, a central triheterocyclic system comprised of two α-methylated thiazolines and one thiazole, and a highly oxygenated and methylated C-15 polyketide unit. In neocortical neurons, the cyclic depsipeptide 2 stimulated sodium influx and suppressed spontaneous Ca2+ oscillations with EC50 values of 3.9 μM and 79.8 nM, respectively, while 3 had no significant effects in these assays.
UR - http://www.scopus.com/inward/record.url?scp=77956201068&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77956201068&partnerID=8YFLogxK
U2 - 10.1021/np100468n
DO - 10.1021/np100468n
M3 - Article
C2 - 20687534
AN - SCOPUS:77956201068
VL - 73
SP - 1411
EP - 1421
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 8
ER -