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Balticolid: a new 12-membered macrolide with antiviral activity from an ascomycetous fungus of marine origin.

Shushni MA, Singh R, Mentel R, Lindequist U - Mar Drugs (2011)

Bottom Line: A new 12-membered macrolide, balticolid (1) was isolated from the EtOAc extract of the culture broth of fungal strain 222 belonging to the Ascomycota, which was found on driftwood collected from the coast of the Greifswalder Bodden, Baltic Sea, Germany.The structure of balticolid was determined to be (3R,11R), (4E,8E)-3-hydroxy-11-methyloxacyclododeca-4,8-diene-1,7-dione using extensive spectral data as well as the modified Mosher ester method.Balticolid (1) displayed anti-HSV-1 activity with an IC₅₀ value of 0.45 μM.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy, Faculty of Pharmacy, Garyounis University, P.O. Box 5341, Benghazi, Libya. muftah.shushni@yahoo.com

ABSTRACT
A new 12-membered macrolide, balticolid (1) was isolated from the EtOAc extract of the culture broth of fungal strain 222 belonging to the Ascomycota, which was found on driftwood collected from the coast of the Greifswalder Bodden, Baltic Sea, Germany. The structure of balticolid was determined to be (3R,11R), (4E,8E)-3-hydroxy-11-methyloxacyclododeca-4,8-diene-1,7-dione using extensive spectral data as well as the modified Mosher ester method. Balticolid (1) displayed anti-HSV-1 activity with an IC₅₀ value of 0.45 μM.

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Structure of balticolid (1).
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f1-marinedrugs-09-00844: Structure of balticolid (1).

Mentions: In addition, the IR spectrum showed the presence of a hydroxyl group (3435 cm−1) and trans disubstituted alkenes (1662 cm−1). An absorption band appeared at 1716 cm−1, and is due to the conjugated ketone, the absorption band of the 12-membered lactone potentially merged with the aforementioned as a single absorption band. The 1H NMR splitting pattern of 1 showed coupling between the protons at δH 1.34 and 5.11 which indicates the presence of a CH3-CH-O group. The 1H-1H COSY and ROESY spectra revealed two structural elements, one of C-2 to C-6 and the second from the unsaturated methine carbon C-8 to methyl group C-12. HMBC correlations observed from methylene protons H2-2 (δH 2.68, 2.62) and deshielded oxymethine proton H-11(δH 5.11) to carboxy carbon C-1 established the location of the ester linkage (Table 1). The HMBC correlation of H-3 (δH 4.54) with C-1, C-2 together with molecular formula C12H16O4 indicated the presence of a methine group and a hydroxyl group at C-3. The presence of a methyl group at C-11 was deduced by the HMBC correlation of H3-12 (δH 1.34) with C-9 (δC 148.1), C-10 (δC 39.6) and C-11 (δC 72.1). The geometries of C4-C5 and C8-C9 double bonds were assigned E, E on the basis of 1H-1H coupling constants (JH4-H5 = 15.9 Hz, JH8-H9 = 16.1 Hz respectively) leading to the gross structure of 1 as shown (Figure 1). Therefore, compound 1 was established as (4E,8E)-3-hydroxy-11-methyloxacyclododeca-4,8-diene-1,7-dione and named as balticolid.


Balticolid: a new 12-membered macrolide with antiviral activity from an ascomycetous fungus of marine origin.

Shushni MA, Singh R, Mentel R, Lindequist U - Mar Drugs (2011)

Structure of balticolid (1).
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3111186&req=5

f1-marinedrugs-09-00844: Structure of balticolid (1).
Mentions: In addition, the IR spectrum showed the presence of a hydroxyl group (3435 cm−1) and trans disubstituted alkenes (1662 cm−1). An absorption band appeared at 1716 cm−1, and is due to the conjugated ketone, the absorption band of the 12-membered lactone potentially merged with the aforementioned as a single absorption band. The 1H NMR splitting pattern of 1 showed coupling between the protons at δH 1.34 and 5.11 which indicates the presence of a CH3-CH-O group. The 1H-1H COSY and ROESY spectra revealed two structural elements, one of C-2 to C-6 and the second from the unsaturated methine carbon C-8 to methyl group C-12. HMBC correlations observed from methylene protons H2-2 (δH 2.68, 2.62) and deshielded oxymethine proton H-11(δH 5.11) to carboxy carbon C-1 established the location of the ester linkage (Table 1). The HMBC correlation of H-3 (δH 4.54) with C-1, C-2 together with molecular formula C12H16O4 indicated the presence of a methine group and a hydroxyl group at C-3. The presence of a methyl group at C-11 was deduced by the HMBC correlation of H3-12 (δH 1.34) with C-9 (δC 148.1), C-10 (δC 39.6) and C-11 (δC 72.1). The geometries of C4-C5 and C8-C9 double bonds were assigned E, E on the basis of 1H-1H coupling constants (JH4-H5 = 15.9 Hz, JH8-H9 = 16.1 Hz respectively) leading to the gross structure of 1 as shown (Figure 1). Therefore, compound 1 was established as (4E,8E)-3-hydroxy-11-methyloxacyclododeca-4,8-diene-1,7-dione and named as balticolid.

Bottom Line: A new 12-membered macrolide, balticolid (1) was isolated from the EtOAc extract of the culture broth of fungal strain 222 belonging to the Ascomycota, which was found on driftwood collected from the coast of the Greifswalder Bodden, Baltic Sea, Germany.The structure of balticolid was determined to be (3R,11R), (4E,8E)-3-hydroxy-11-methyloxacyclododeca-4,8-diene-1,7-dione using extensive spectral data as well as the modified Mosher ester method.Balticolid (1) displayed anti-HSV-1 activity with an IC₅₀ value of 0.45 μM.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy, Faculty of Pharmacy, Garyounis University, P.O. Box 5341, Benghazi, Libya. muftah.shushni@yahoo.com

ABSTRACT
A new 12-membered macrolide, balticolid (1) was isolated from the EtOAc extract of the culture broth of fungal strain 222 belonging to the Ascomycota, which was found on driftwood collected from the coast of the Greifswalder Bodden, Baltic Sea, Germany. The structure of balticolid was determined to be (3R,11R), (4E,8E)-3-hydroxy-11-methyloxacyclododeca-4,8-diene-1,7-dione using extensive spectral data as well as the modified Mosher ester method. Balticolid (1) displayed anti-HSV-1 activity with an IC₅₀ value of 0.45 μM.

Show MeSH
Related in: MedlinePlus