Microbial Transformation of Azorellane and Mulinane Diterpenoids
Microbial Transformation of Azorellane and Mulinane Diterpenoids
- Revista Brasileira de Farmacognosia. 33(2), 438-442, 2023, DOI: 10.1007/s43450-023-00364-z .
Microbial transformation is an alternate strategy to obtain novel derivatives from natural products using whole cells or enzymes because of their capability to introduce functional groups in chemically inactive carbon positions. In this investigation, the microbial transformation of two diterpenoids, azorellanol and 13?-mulin-11-en-20-oic acid, in three fungal cultures (Aspergillus alliaceus UI 315, Mucor circinelloides ATCC 7941, and Penicillium notatum ATCC 36740) and one bacterium (Nocardia iowensis NRRL 5646) was explored. The results showed that while biomodification of azorellanol by N. iowensis produced the known diterpenoid 7-deacetyl-azorellanol, P. notatum produced two new derivatives identified as 4,16-dihydroxy-azorellanol and 2?,16-dyhydroxy-14-en-azorellanol. Similarly, microbial transformation of 13?-mulin-11-en-20-oic acid by P. notatum produced the known derivative 13?,14?-dihydroxy-mulin-11-en-20-oic acid and the novel product 13?,14?,16-trihydroxy-mulin-11-en-20-oic acid. Graphical Abstract: [Figure not available: see fulltext.]. © 2023, The Author(s) under exclusive licence to Sociedade Brasileira de Farmacognosia.
APIACEAE
BIOMODIFICATION
BIOTRANSFORMATION
DITERPENES
NOCARDIA IOWENSIS
PENICILLIUM NOTATUM
Microbial transformation is an alternate strategy to obtain novel derivatives from natural products using whole cells or enzymes because of their capability to introduce functional groups in chemically inactive carbon positions. In this investigation, the microbial transformation of two diterpenoids, azorellanol and 13?-mulin-11-en-20-oic acid, in three fungal cultures (Aspergillus alliaceus UI 315, Mucor circinelloides ATCC 7941, and Penicillium notatum ATCC 36740) and one bacterium (Nocardia iowensis NRRL 5646) was explored. The results showed that while biomodification of azorellanol by N. iowensis produced the known diterpenoid 7-deacetyl-azorellanol, P. notatum produced two new derivatives identified as 4,16-dihydroxy-azorellanol and 2?,16-dyhydroxy-14-en-azorellanol. Similarly, microbial transformation of 13?-mulin-11-en-20-oic acid by P. notatum produced the known derivative 13?,14?-dihydroxy-mulin-11-en-20-oic acid and the novel product 13?,14?,16-trihydroxy-mulin-11-en-20-oic acid. Graphical Abstract: [Figure not available: see fulltext.]. © 2023, The Author(s) under exclusive licence to Sociedade Brasileira de Farmacognosia.
APIACEAE
BIOMODIFICATION
BIOTRANSFORMATION
DITERPENES
NOCARDIA IOWENSIS
PENICILLIUM NOTATUM