Andropanolide

MICROBIAL METABOLISM OF AN ANTI-HIV AND ANTI-MALARIAL NATURAL PRODUCT ANDROGRAPHOLIDE[Reference: WebLink]

International Journal of Pharmacy & Pharmaceutical Sciences, 2014, 6(1):46–52.

In the present study, we first time studied the microbial metabolism of andrographolide (1) with Cunninghamella elegans (TSY 0865) and Cephalosporium aphidicola (IMI-68689).
METHODS AND RESULTS:
Microbial cultures of the C. elegans and C. aphidicola were grown on Potato dextrose agar (PDA) at 25°C and stored at 4°C. Medium for C. aphidicola was prepared by mixing Glucose (50.0 g), KH2PO4 (1.0 g), MgSO4.7H2O (2.0 g), Glycin (2.0 g), KCl (1.0 g) and Gibberella trace element solution (2.0 mL) into distilled water (1 L) and maintained pH at 5.6. While C. elegans medium was prepared by adding Glucose (10.0 g), peptone (5.0 g), KH2PO4 .Two compounds were obtained as transformed products. Based on physical and spectroscopic data, these have been identified as Andropanolide (2) and 14-deoxy-11,12-didehydro andrographolide (3). Both compounds were previously obtained by the phytochemical investigation of A. paniculata and biotransformed product as well. (5.0 g), yeast extract (5.0 g), NaCl (5.0 g) and glycerol (10 mL) into distilled water (1 L) and maintained pH at 5.6.
CONCLUSIONS:
It could be concluded that C. elegans and C. aphidicola were able to produce oxidative derivatives of 1 in a regio- and stereoselective manner. Present investigation has been conducted for the first time with C. elegans and C. aphidicola. Incubation of 1 for 9 days with fungal strains yielded isomerized and oxidative products 2 and 3. Structures of all metabolites were elucidated by using spectroscopic techniques.

J Nat Prod. 2006 Mar;69(3):403-5.

Andropanolide and isoandrographolide, minor diterpenoids from Andrographis paniculata: structure and X-ray crystallographic analysis.[Pubmed: 16562845]

METHODS AND RESULTS:
Phytochemical investigation of the leaves of Andrographis paniculata has led to the isolation of a new labdane type diterpenoid, Andropanolide (1), along with seven known diterpenoids including isoandrographolide (2), previously reported as a rearrangement product of andrographolide. The structures and stereochemistry of compounds Andropanolide and 2 were established by X-ray crystallographic analysis.