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Antibacterial activities of a new brominated diterpene from Borneon Laurencia spp.

Vairappan CS, Ishii T, Lee TK, Suzuki M, Zhaoqi Z - Mar Drugs (2010)

Bottom Line: In our continuous interest to study the diversity of halogenated metabolites of Malaysian species of the red algal genus Laurencia, we examined the chemical composition of five populations of unrecorded Laurencia sp.A new brominated diterpene, 10-acetoxyangasiol (1), and four other known metabolites, aplysidiol (2), cupalaurenol (3), 1-methyl-2,3,5-tribromoindole (4), and chamigrane epoxide (5), were isolated and identified.Isolated metabolites exhibited potent antibacterial activities against clinical bacteria, Staphylococcus aureus, Staphylococcus sp., Streptococcus pyogenes, Salmonella sp. and Vibrio cholerae.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Natural Products Chemistry, Institute for Tropical Biology and Conservation, Universiti Malaysia Sabah, Kota Kinabalu, Sabah, Malaysia. csv@ums.edu.my

ABSTRACT
In our continuous interest to study the diversity of halogenated metabolites of Malaysian species of the red algal genus Laurencia, we examined the chemical composition of five populations of unrecorded Laurencia sp. A new brominated diterpene, 10-acetoxyangasiol (1), and four other known metabolites, aplysidiol (2), cupalaurenol (3), 1-methyl-2,3,5-tribromoindole (4), and chamigrane epoxide (5), were isolated and identified. Isolated metabolites exhibited potent antibacterial activities against clinical bacteria, Staphylococcus aureus, Staphylococcus sp., Streptococcus pyogenes, Salmonella sp. and Vibrio cholerae.

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Related in: MedlinePlus

1H-1H COSY correlations (bold lines) and key HMBC correlations (H→C) of 1.
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f2-marinedrugs-08-01743: 1H-1H COSY correlations (bold lines) and key HMBC correlations (H→C) of 1.

Mentions: Assignments were carried out based on 1H-1H COSY, HSQC and HMBC spectra data. 1H-1H COSY experiments revealed the sequences of the correlations depicted by the bold lines in Figure 2. Key HMBC correlations as shown in Figure 2 were consistent with the proposed structure of 1. Furthermore, the relative stereochemistry of 1 was elucidated by NOESY experiments as well as the coupling constants in the 1H-NMR spectrum. The coupling constant (J6,10 = 8.9 Hz) indicated the anti conformation for the H-6/H-10. The configuration at C-10 was assigned as R* on the basis of the NOESY correlations observed between H-5/H-10, H-7β/H-10, H-10/Hax-12, H-10/Hax-16 and H3-17/H3-Ac. In addition, the remaining stereochemistry of 1 was determined by NOESY correlations as shown in Figure 3 and assigned to be the same as for angasiol and its related compounds, irieols A–G [10–12]. In consequence, the structure of 10-acetoxyangasiol (1) must be represented by structure 1.


Antibacterial activities of a new brominated diterpene from Borneon Laurencia spp.

Vairappan CS, Ishii T, Lee TK, Suzuki M, Zhaoqi Z - Mar Drugs (2010)

1H-1H COSY correlations (bold lines) and key HMBC correlations (H→C) of 1.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC2901821&req=5

f2-marinedrugs-08-01743: 1H-1H COSY correlations (bold lines) and key HMBC correlations (H→C) of 1.
Mentions: Assignments were carried out based on 1H-1H COSY, HSQC and HMBC spectra data. 1H-1H COSY experiments revealed the sequences of the correlations depicted by the bold lines in Figure 2. Key HMBC correlations as shown in Figure 2 were consistent with the proposed structure of 1. Furthermore, the relative stereochemistry of 1 was elucidated by NOESY experiments as well as the coupling constants in the 1H-NMR spectrum. The coupling constant (J6,10 = 8.9 Hz) indicated the anti conformation for the H-6/H-10. The configuration at C-10 was assigned as R* on the basis of the NOESY correlations observed between H-5/H-10, H-7β/H-10, H-10/Hax-12, H-10/Hax-16 and H3-17/H3-Ac. In addition, the remaining stereochemistry of 1 was determined by NOESY correlations as shown in Figure 3 and assigned to be the same as for angasiol and its related compounds, irieols A–G [10–12]. In consequence, the structure of 10-acetoxyangasiol (1) must be represented by structure 1.

Bottom Line: In our continuous interest to study the diversity of halogenated metabolites of Malaysian species of the red algal genus Laurencia, we examined the chemical composition of five populations of unrecorded Laurencia sp.A new brominated diterpene, 10-acetoxyangasiol (1), and four other known metabolites, aplysidiol (2), cupalaurenol (3), 1-methyl-2,3,5-tribromoindole (4), and chamigrane epoxide (5), were isolated and identified.Isolated metabolites exhibited potent antibacterial activities against clinical bacteria, Staphylococcus aureus, Staphylococcus sp., Streptococcus pyogenes, Salmonella sp. and Vibrio cholerae.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Natural Products Chemistry, Institute for Tropical Biology and Conservation, Universiti Malaysia Sabah, Kota Kinabalu, Sabah, Malaysia. csv@ums.edu.my

ABSTRACT
In our continuous interest to study the diversity of halogenated metabolites of Malaysian species of the red algal genus Laurencia, we examined the chemical composition of five populations of unrecorded Laurencia sp. A new brominated diterpene, 10-acetoxyangasiol (1), and four other known metabolites, aplysidiol (2), cupalaurenol (3), 1-methyl-2,3,5-tribromoindole (4), and chamigrane epoxide (5), were isolated and identified. Isolated metabolites exhibited potent antibacterial activities against clinical bacteria, Staphylococcus aureus, Staphylococcus sp., Streptococcus pyogenes, Salmonella sp. and Vibrio cholerae.

Show MeSH
Related in: MedlinePlus