Using a standard two-stage fermentation technique, the fungus Beauveria bassiana (ATCC 7159) was found to convert the eudesmanolide vulgarin (1) to 1α,4α-dihydroxy-5αH,6,11βH-eudesman-6,12-olide (2). The use of the yeastHansenula anomala ATCC 20170 instead, produced the less polar 4α-hydroxy-1-oxo-5αH,6,11βH-eudesman-6,12-olide(3), in addition to the more polar 3α,4α-dihydroxy-1-oxo-5αH,6,11βH-eudesman-6,12-olide (4). These metabolites were characterized on the basis of their spectral data and the identity of 4 was further confirmed by chemical synthesis.
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http://dx.doi.org/10.2174/1389557511313050013 | DOI Listing |
Molecules
April 2023
Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, El Mansoura 35516, Egypt.
The biotransformation of vulgarin , an eudesmanolides-type sesquiterpene lactone obtained from , by the microorganism, , was carried out to give three more polar metabolites; 1--tetrahydrovulgarin (1α,4α-dihydroxy-5αH,6,11βH-eudesman-6,12-olide , 20% yield, 1α,4α-dihydroxyeudesm-2-en-5αH,6,11βH-6,12-olide , 10% yield, and C-1 epimeric mixture , 4% yield, in a ratio of 4:1, . The structures of vulgarin and its metabolites were elucidated by 1 and 2D NMR spectroscopy in conjunction with HRESIMS. Metabolites and are epimers, and they are reported here for the first time as new metabolites obtained by biotransformation by selective reduction at C-1.
View Article and Find Full Text PDFInt J Mol Sci
December 2022
Department of Pharmacognosy, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia.
The current investigation assessed the effect of the eudesmanolid, Vulgarin (VGN), obtained from (), on the antidiabetic potential of glibenclamide (GLB) using streptozotocin (STZ) to induce diabetes. Seven groups of rats were used in the study; the first group received the vehicle and served as normal control. The diabetic rats of the second to the fifth groups were treated with the vehicle (negative control), GLB at 5 mg/kg (positive control), VGN at 10 mg/kg (VGN-10) and VGN at 20 mg/kg (VGN-20), respectively.
View Article and Find Full Text PDFMolecules
August 2022
Infection Biology, Department of Life Sciences, School of Life Sciences, Central University of Tamil Nadu, Thiruvarur 610 005, Tamil Nadu, India.
() is one of the major representative aetiologies of recalcitrant nosocomial infections. Genotypic and phenotypic alterations in have resulted in a significant surge in multidrug resistance (MDR). Of all the factors responsible for the development of antimicrobial resistance (AMR), efflux protein pumps play a paramount role.
View Article and Find Full Text PDFMini Rev Med Chem
April 2013
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Health Sciences Center, Kuwait University, Safat 13110, Kuwait.
Using a standard two-stage fermentation technique, the fungus Beauveria bassiana (ATCC 7159) was found to convert the eudesmanolide vulgarin (1) to 1α,4α-dihydroxy-5αH,6,11βH-eudesman-6,12-olide (2). The use of the yeastHansenula anomala ATCC 20170 instead, produced the less polar 4α-hydroxy-1-oxo-5αH,6,11βH-eudesman-6,12-olide(3), in addition to the more polar 3α,4α-dihydroxy-1-oxo-5αH,6,11βH-eudesman-6,12-olide (4). These metabolites were characterized on the basis of their spectral data and the identity of 4 was further confirmed by chemical synthesis.
View Article and Find Full Text PDFJ Org Chem
December 2000
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, 18071-Granada, Spain.
Different lipase enzymes have been tested in order to perform regioselective acetylations on the eudesmane tetrol from vulgarin. High yields (95%) of 1,12-diacetoxy derivative (4) were achieved in 1 h with Candida antarctica lipase (CAL). However, only the 12-acetyl derivative (6) was obtained in similar yield with Mucor miehei (MML) or Candida cylindracea (CCL) lipases.
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