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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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Related in: MedlinePlus

Key NOEs observed for balticolid (1), and their corresponding interatomic distances (Å).
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f2-marinedrugs-09-00844: Key NOEs observed for balticolid (1), and their corresponding interatomic distances (Å).

Mentions: The orientation of hydroxyl group at C-3 (δH 69.1) was assigned by taking into account the 1H-1H coupling constant values of H-3 (δH 1.34) with all the neighboring protons (JH2a-H3 = 3.4 Hz, JH2b-H3 = 4.7 Hz, JH3-H4 = 2.8 Hz). On the basis of vicinal coupling constant values for other protons a 3D structure for 1 was constructed as shown in Figure 2. These findings were also supported by cross peaks in ROESY spectrum and difference NOEs experiments.


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)

Key NOEs observed for balticolid (1), and their corresponding interatomic distances (Å).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f2-marinedrugs-09-00844: Key NOEs observed for balticolid (1), and their corresponding interatomic distances (Å).
Mentions: The orientation of hydroxyl group at C-3 (δH 69.1) was assigned by taking into account the 1H-1H coupling constant values of H-3 (δH 1.34) with all the neighboring protons (JH2a-H3 = 3.4 Hz, JH2b-H3 = 4.7 Hz, JH3-H4 = 2.8 Hz). On the basis of vicinal coupling constant values for other protons a 3D structure for 1 was constructed as shown in Figure 2. These findings were also supported by cross peaks in ROESY spectrum and difference NOEs experiments.

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