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Cyclic Bis-1,3-dialkylpyridiniums from the sponge Haliclona sp.

Lee Y, Jang KH, Jeon JE, Yang WY, Sim CJ, Oh KB, Shin J - Mar Drugs (2012)

Bottom Line: Eight novel cyclic bis-1,3-dialkylpyridiniums, as well as two known compounds from the cyclostellettamine class, were isolated from the sponge Haliclona sp. from Korea.Several of these compounds exhibited moderate cytotoxic and antibacterial activities against A549 cell-line and Gram-positive strains, respectively.The structure-activity relationships of cyclostellettamines are discussed based on their bioactivities.

View Article: PubMed Central - PubMed

Affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, Korea. zizel18@snu.ac.kr

ABSTRACT
Eight novel cyclic bis-1,3-dialkylpyridiniums, as well as two known compounds from the cyclostellettamine class, were isolated from the sponge Haliclona sp. from Korea. Structures of these novel compounds were determined using combined NMR and FAB-MS/MS analyses. Several of these compounds exhibited moderate cytotoxic and antibacterial activities against A549 cell-line and Gram-positive strains, respectively. The structure-activity relationships of cyclostellettamines are discussed based on their bioactivities.

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Structures of compounds 1–10.
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marinedrugs-10-02126-f001: Structures of compounds 1–10.

Mentions: The sponge Haliclona sp. specimens were lyophilized, macerated, and repeatedly extracted with CH2Cl2 and MeOH. The combined extracts were separated by solvent-partitioning followed by ODS vacuum flash chromatography. The highly polar H2O-MeOH (50:50) chromatographic fraction was further fractionated by Sephadex LH-20 gel-permeation chromatography and separated by ODS-HPLC to yield 10 compounds (Figure 1). The structures of compounds 1 and 2 were identified as cyclostellettamine N and Q, respectively, based on spectroscopic analyses and a comparison of NMR and FAB-MS/MS data [13,14].


Cyclic Bis-1,3-dialkylpyridiniums from the sponge Haliclona sp.

Lee Y, Jang KH, Jeon JE, Yang WY, Sim CJ, Oh KB, Shin J - Mar Drugs (2012)

Structures of compounds 1–10.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3475278&req=5

marinedrugs-10-02126-f001: Structures of compounds 1–10.
Mentions: The sponge Haliclona sp. specimens were lyophilized, macerated, and repeatedly extracted with CH2Cl2 and MeOH. The combined extracts were separated by solvent-partitioning followed by ODS vacuum flash chromatography. The highly polar H2O-MeOH (50:50) chromatographic fraction was further fractionated by Sephadex LH-20 gel-permeation chromatography and separated by ODS-HPLC to yield 10 compounds (Figure 1). The structures of compounds 1 and 2 were identified as cyclostellettamine N and Q, respectively, based on spectroscopic analyses and a comparison of NMR and FAB-MS/MS data [13,14].

Bottom Line: Eight novel cyclic bis-1,3-dialkylpyridiniums, as well as two known compounds from the cyclostellettamine class, were isolated from the sponge Haliclona sp. from Korea.Several of these compounds exhibited moderate cytotoxic and antibacterial activities against A549 cell-line and Gram-positive strains, respectively.The structure-activity relationships of cyclostellettamines are discussed based on their bioactivities.

View Article: PubMed Central - PubMed

Affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, Korea. zizel18@snu.ac.kr

ABSTRACT
Eight novel cyclic bis-1,3-dialkylpyridiniums, as well as two known compounds from the cyclostellettamine class, were isolated from the sponge Haliclona sp. from Korea. Structures of these novel compounds were determined using combined NMR and FAB-MS/MS analyses. Several of these compounds exhibited moderate cytotoxic and antibacterial activities against A549 cell-line and Gram-positive strains, respectively. The structure-activity relationships of cyclostellettamines are discussed based on their bioactivities.

Show MeSH