Callyazepin and (3R)-Methylazacyclodecane, Nitrogenous Macrocycles from a Callyspongia sp. Sponge.

@article{Kim2016CallyazepinA,
  title={Callyazepin and (3R)-Methylazacyclodecane, Nitrogenous Macrocycles from a Callyspongia sp. Sponge.},
  author={Chang-Kwon Kim and Jung-Kyun Woo and Yeon-Ju Lee and Hyi-Seung Lee and Chung Ja Sim and Dong‐Chan Oh and Ki-bong Oh and Jongheon Shin},
  journal={Journal of natural products},
  year={2016},
  volume={79 4},
  pages={
          1179-83
        }
}
Callyazepin (1) and (3R)-methylazacyclodecane (2), nitrogenous macrocycles, were isolated from a tropical Callyspongia sp. sponge. The combined spectroscopic analyses revealed that the structure of 1 is a bicyclic azepane ammonium salt of a novel structural class derived from mixed biogenetic origins. The configuration of the whole molecule and the conformation of the formamide group were assigned by proton-proton coupling constants, a NOESY analysis, and the application of the phenylglycine… 
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8 Citations

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Citation Type

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TLDR
Two new sterol O-acyltransferase (SOAT) inhibitors were isolated from the Indonesian marine sponge Callyspongia sp.
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The complete absolute configuration of callyspongiolide is elucidated and unambiguously assigned its stereochemistry at the C-21 center through synthesis.
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The key elements in this total synthesis feature Kobayashi's remote asymmetric induction with vinylketene silyl N,O-acetal, Roush's asymmetric crotylboration of aldehyde, Mitsunobu's esterification and macrocyclization via Stille cross-coupling.
The journey of total synthesis toward nannocystin Ax
Abstract Herein we describe the detail on our full investigations that led to the achievement of the total synthesis of nannocystin Ax, a 21-membered macrocyclic natural product composing of a…
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The advances that Asian research groups made in the field of natural products chemistry in 2016 were summarized and compounds with unique structural features and/or promising bioactivities originating from Asian natural sources were discussed based on structural classification.
Azepines and Their Fused-Ring Derivatives

References

SHOWING 1-10 OF 30 REFERENCES
Callyspongiolide, a cytotoxic macrolide from the marine sponge Callyspongia sp.
A novel macrolide, callyspongiolide, whose structure was determined by comprehensive analysis of the NMR and HRMS spectra, was isolated from the marine sponge Callyspongia sp. collected in Indonesia.…
Callyaerins from the Marine Sponge Callyspongia aerizusa: Cyclic Peptides with Antitubercular Activity.
TLDR
Callyaerin A, which showed the strongest anti-TB activity, was not cytotoxic to THP-1 or MRC-5 cells (IC₅₀ > 10 μM), which highlights the potential of these compounds as promising anti- TB agents.
New macrolides and furan carboxylic acid derivative from the sponge-derived fungus Cladosporium herbarum.
TLDR
Bioassay-guided fractionation of organic extracts of Cladosporium herbarum yielded two new macrolide metabolites that were isolated from the marine sponge Callyspongia aerizusa and the antimicrobially active furan carboxylic acids: Sumiki's acid and its new derivative, acetyl Sumiki’s acid.
Suvanine sesterterpenes and deacyl irciniasulfonic acids from a tropical Coscinoderma sp. sponge.
The suvanines, a new suvanine salt, five new (2, 4-8) and two known sesterterpenes from the same structural class, and two new modified lipids (9 and 10) were isolated from a Coscinoderma sp. sponge…
NAKADOMARIN A, A NOVEL HEXACYCLIC MANZAMINE-RELATED ALKALOID FROM AMPHIMEDON SPONGE
A novel manzamine-related alkaloid consisting of unprecedented 8/5/5/5/15/6 ring system, nakadomarin A (1), has been isolated from an Okinawan marine sponge Amphimedon sp., and the unique structure…
Cytotoxic Metabolites from an Australian Collection of the Sponge Jaspis Species
Three new natural products, bengamide Y (1), bengamide Z (3), and bengazole Z (5), were isolated from the aqueous extract of an Australian collection of the sponge Jaspis sp. Their structures were…
Haliclonin A, a new macrocyclic diamide from the sponge Haliclona sp.
Haliclonin A (1), a macrocyclic diamide of a novel skeletal class, was isolated from the marine sponge Haliclona sp. collected from Korean waters. The structure of this compound was determined using…
Revision of the structure of haliclorensin to (S)-7-methyl-1,5-diazacyclotetradecane and confirmation of the new structure by synthesis
Abstract A reinvestigation of the marine alkaloid haliclorensin led to a revision of the proposed structure to 7-methyl-1,5-diazacyclotetradecane. The new structure was confirmed by total synthesis…
Antimicrobial activities of the bromophenols from the red alga Odonthalia corymbifera and some synthetic derivatives.
TLDR
A series of bromophenols obtained by isolation from red alga Odonthalia corymbifera and by reactions of bis(hydroxyphenyl)methanes with bromine showed potent antibacterial effect against Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, Proteus vulgaris, and Salmonella typhimurium.
Halitulin, a new cytotoxic alkaloid from the marine sponge Haliclona tulearensis
Abstract Halitulin ( 2 ), a novel bisquinolinylpyrrole has been isolated from the sponge Haliclona tulearensis . Its structure was elucidated mainly on the basis of spectroscopic data as well as…
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