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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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Positive FAB-MS/MS spectrum of compound 3.
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marinedrugs-10-02126-f002: Positive FAB-MS/MS spectrum of compound 3.

Mentions: The UV absorption at 267 nm was reminiscent of two di-substituted pyridine rings, which was corroborated by aromatic proton signals [δH, 8.96 (2 H, br s, H-2, H-2′), 8.45 (1 H, d, J = 7.6 Hz, H-4), 8.44 (1 H, d, J = 7.7 Hz, H-4′), 8.02 (2 H, dd, J = 7.7, 6.2 Hz, H-5, H-5′), 8.83 (1 H, dd, J = 6.0 Hz, H-6), 8.82 (1 H, dd, J = 6.0 Hz, H-6′)] and carbon signals [δC 145.5 (C-2, C-2′), δC 145.3 (C-3), δC 145.4 (C-3′), δC 147.0 (C-4), δC 146.9 (C-4′), δC 129.2 (C-5, C-5′), δC 143.4 (C-6), δC 143.5 (C-6′)] in the NMR data. Although the two and three linearly contiguous methylene units attached to the pyridinium (N-1, N-1′, C-3, and C-3′) were identified based on 1H COSY and gHMBC, only a large methylene envelope at δH 1.25–1.40 was observed in the 1H NMR spectrum, indicating that 3 was composed of two di-substituted pyridine rings and long aliphatic chains, forming a highly symmetric cyclic framework. The lengths of the methylene chains were determined based on the FAB-MS/MS data, which yielded two intense peaks at m/z 190 and 218, as shown in Figure 2. Since these daughter ions were attributable to a pair of monomeric products generated via Hoffmann-type elimination7 from their parent ion, 3 was structurally defined to be a cyclic hetero-dimer composed of C8 and C10 chains connecting the N-1 and C-3′ (also N-1′ and C-3) of pyridiniums.


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)

Positive FAB-MS/MS spectrum of compound 3.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

marinedrugs-10-02126-f002: Positive FAB-MS/MS spectrum of compound 3.
Mentions: The UV absorption at 267 nm was reminiscent of two di-substituted pyridine rings, which was corroborated by aromatic proton signals [δH, 8.96 (2 H, br s, H-2, H-2′), 8.45 (1 H, d, J = 7.6 Hz, H-4), 8.44 (1 H, d, J = 7.7 Hz, H-4′), 8.02 (2 H, dd, J = 7.7, 6.2 Hz, H-5, H-5′), 8.83 (1 H, dd, J = 6.0 Hz, H-6), 8.82 (1 H, dd, J = 6.0 Hz, H-6′)] and carbon signals [δC 145.5 (C-2, C-2′), δC 145.3 (C-3), δC 145.4 (C-3′), δC 147.0 (C-4), δC 146.9 (C-4′), δC 129.2 (C-5, C-5′), δC 143.4 (C-6), δC 143.5 (C-6′)] in the NMR data. Although the two and three linearly contiguous methylene units attached to the pyridinium (N-1, N-1′, C-3, and C-3′) were identified based on 1H COSY and gHMBC, only a large methylene envelope at δH 1.25–1.40 was observed in the 1H NMR spectrum, indicating that 3 was composed of two di-substituted pyridine rings and long aliphatic chains, forming a highly symmetric cyclic framework. The lengths of the methylene chains were determined based on the FAB-MS/MS data, which yielded two intense peaks at m/z 190 and 218, as shown in Figure 2. Since these daughter ions were attributable to a pair of monomeric products generated via Hoffmann-type elimination7 from their parent ion, 3 was structurally defined to be a cyclic hetero-dimer composed of C8 and C10 chains connecting the N-1 and C-3′ (also N-1′ and C-3) of pyridiniums.

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