15766-71-9Relevant academic research and scientific papers
Isolation and Structure Elucidation of a Novel Antimalarial Macrocyclic Polylactone, Menisporopsin A, from the Fungus Menisporopsis theobromae
Chinworrungsee, Maneekarn,Kittakoop, Prasat,Isaka, Masahiko,Maithip, Pacharee,Supothina, Sumalee,Thebtaranonth, Yodhathai
, p. 689 - 692 (2004)
An antimalarial macrocyclic polylactone, menisporopsin A (1), was isolated from a cell extract of the seed fungus Menisporopsis theobromae. The structure of 1 was elucidated on the basis of spectroscopic analysis and chemical transformations, with the absolute configuration established by application of the modified Mosher method and by using chiral HPLC. Menisporopsin A (1) possesses an unprecedented residue, 2,4-dihydroxy-6-(2,4-dihydroxy-n-pentyl)benzoic acid. This compound exhibited antimalarial activity, with an IC50 value of 4.0 μg mL -1, and antimycobacterial activity (MIC value of 50 μg mL -1).
Early Oxidative Transformations During the Biosynthesis of Terrein and Related Natural Products
Kahlert, Lukas,Bernardi, Darlon,Hauser, Maurice,Ióca, Laura P.,Berlinck, Roberto G. S.,Skellam, Elizabeth J.,Cox, Russell J.
supporting information, p. 11895 - 11903 (2021/06/27)
The mycotoxin terrein is derived from the C10-precursor 6-hydroxymellein (6-HM) via an oxidative ring contraction. Although the corresponding biosynthetic gene cluster (BGC) has been identified, details of the enzymatic oxidative transformations are lacking. Combining heterologous expression and in vitro studies we show that the flavin-dependent monooxygenase (FMO) TerC catalyzes the initial oxidative decarboxylation of 6-HM. The reactive intermediate is further hydroxylated by the second FMO TerD to yield a highly oxygenated aromatic species, but further reconstitution of the pathway was hampered. A related BGC was identified in the marine-derived Roussoella sp. DLM33 and confirmed by heterologous expression. These studies demonstrate that the biosynthetic pathways of terrein and related (polychlorinated) congeners diverge after oxidative decarboxylation of the lactone precursor that is catalyzed by a conserved FMO and further indicate that early dehydration of the side chain is an essential step.
Asymmetric total synthesis of dihydroisocoumarins: 6-methoxymellein, kigelin and fusarentin 6, 7 dimethyl ether by employing proline catalysed asymmetric α-aminoxylation
Mane, Baliram B.,Markad, Sachin B.,Waghmode, Suresh B.
, (2020/10/19)
A concise asymmetric total synthesis of dihydroisocoumarins such as 6-methoxymellein, kigelin and fusarentin 6,7-dimethyl ether in high enantiopurity have been achieved from non-chiral aldehydes by employing proline catalysed asymmetric α-aminoxylation reaction. The required stereochemistry of hydroxyl group have been generated by alternating L or D proline as a organocatalyst in α-aminoxylation step and lactone ring is assembled by oxa-Pictet-Spengler cyclisation reaction as the key steps.
Dihydroisocoumarins from fungi: Isolation, structure elucidation, circular dichroism and biological activity
Krohn, Karsten,Bahramsari, Rahim,Floerke, Ulrich,Ludewig, Kerstin,Kliche-Spory, Christine,Michel, Andreas,Aust, Hans-Juergen,Draeger, Siegfried,Schulz, Barbara,Antus, Sandor
, p. 313 - 320 (2007/10/03)
Five known and three new dihydroisocoumarins were isolated from different fungi. The new isocoumarins are 5-chloro-6-hydroxymellein, 5- chloro-4,6-dihydroxymellein and 5,6-dihydroxymellein. The absolute configuration of these secondary metabolites was con
