TY - JOUR
T1 - Berkeleylactones and a Citreohybriddione Analogue from Penicillium turbatum
AU - Stierle, Andrea A.
AU - Stierle, Donald B.
AU - Alverson, Jeremy
AU - Gibson, Nathan
N1 - Publisher Copyright:
© 2021 American Chemical Society and American Society of Pharmacognosy
PY - 2021/12/24
Y1 - 2021/12/24
N2 - In 2017 we reported the isolation and characterization of berkeleylactones A–H and A26771B from a coculture of two extremophilic Penicillium sp. isolated from an acid mine waste lake. Berkeleylactone A exhibited potent activity against several strains of multi-drug-resistant Staphylococcus aureus and Bacillus anthracis. A26771B, which is related to the berkeleylactones, also exhibited antibiotic activity. Although the berkeleylactones were novel compounds, A26771B was originally isolated by scientists at Eli Lilly Company from P. turbatum and reported in1977. We recently obtained P. turbatum and grew it in axenic culture. We isolated five new berkeleylactones (2 and 4–7), two berkeley-γ-lactones (8 and 9), and citreohybriddional (10), as well as the known compounds A26771B (1), berkeleylactone E (3), and gliovictin. The structures of the novel compounds were deduced from analysis of spectral data. Compounds 2 and 4 −7 are 16-membered macrolides, while 8 and 9 are γ-lactones that share the hexadecanoic acid skeleton. A26771B (1) and berkeleylactone I (2) were active against several strains of Staphylococcus aureus, including four multi-drug-resistant strains. Berkeleylactone N (8) was active only against Streptococcus pyogenes.
AB - In 2017 we reported the isolation and characterization of berkeleylactones A–H and A26771B from a coculture of two extremophilic Penicillium sp. isolated from an acid mine waste lake. Berkeleylactone A exhibited potent activity against several strains of multi-drug-resistant Staphylococcus aureus and Bacillus anthracis. A26771B, which is related to the berkeleylactones, also exhibited antibiotic activity. Although the berkeleylactones were novel compounds, A26771B was originally isolated by scientists at Eli Lilly Company from P. turbatum and reported in1977. We recently obtained P. turbatum and grew it in axenic culture. We isolated five new berkeleylactones (2 and 4–7), two berkeley-γ-lactones (8 and 9), and citreohybriddional (10), as well as the known compounds A26771B (1), berkeleylactone E (3), and gliovictin. The structures of the novel compounds were deduced from analysis of spectral data. Compounds 2 and 4 −7 are 16-membered macrolides, while 8 and 9 are γ-lactones that share the hexadecanoic acid skeleton. A26771B (1) and berkeleylactone I (2) were active against several strains of Staphylococcus aureus, including four multi-drug-resistant strains. Berkeleylactone N (8) was active only against Streptococcus pyogenes.
UR - http://www.scopus.com/inward/record.url?scp=85120736478&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.1c00791
DO - 10.1021/acs.jnatprod.1c00791
M3 - Review article
C2 - 34851642
AN - SCOPUS:85120736478
SN - 0163-3864
VL - 84
SP - 3064
EP - 3070
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 12
ER -