5975-86-0Relevant academic research and scientific papers
Rational Reprogramming of O-Methylation Regioselectivity for Combinatorial Biosynthetic Tailoring of Benzenediol Lactone Scaffolds
Wang, Xiaojing,Wang, Chen,Zhang, Liwen,Liu, Hang,Zhang, Wei,Chen, Ming,Lin, Min,Xu, Yuquan,Duan, Lixin,Xu, Ya-Ming,Liu, Qingpei,Gunatilaka, A. A. Leslie,Molnár, István,Mao, Tonglin
, p. 4355 - 4364 (2019)
O-Methylation modulates the pharmacokinetic and pharmacodynamic (PK/PD) properties of small-molecule natural products, affecting their bioavailability, stability, and binding to targets. Diversity-oriented combinatorial biosynthesis of new chemical entiti
Synthesis and cytotoxic activities of semisynthetic zearalenone analogues
Tadpetch, Kwanruthai,Kaewmee, Benyapa,Chantakaew, Kittisak,Kantee, Kawalee,Rukachaisirikul, Vatcharin,Phongpaichit, Souwalak
supporting information, p. 3612 - 3616 (2016/07/21)
Zearalenone is a β-resorcylic acid macrolide with various biological activities. Herein we report the synthesis and cytotoxic activities of 34 zearalenone analogues against human oral epidermoid carcinoma (KB) and human breast adenocarcinoma (MCF-7) cells as well as noncancerous Vero cells. Some zearalenone analogues showed moderately enhanced cytotoxic activities against the two cancer cell lines. We have discovered the potential lead compounds with diminished or no cytotoxicity to Vero cells. Preliminary structure–activity relationship studies revealed that the double bond at the 1′ and 2′ positions of zearalenone core was crucial for cytotoxic activities on both cell lines. In addition, for zearalenol analogues, the unprotected hydroxyl group at C-2 and an alkoxy substituent at C-4 played key roles on cytotoxic effects of both cell lines.
Pochonins A-F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata
Hellwig, Veronika,Mayer-Bartschmid, Anke,Müller, Hartwig,Greif, Gisela,Kleymann, Gerald,Zitzmann, Werner,Tichy, Hans-Volker,Stadler, Marc
, p. 829 - 837 (2007/10/03)
Monorden (1) and the novel resorcylic acid lactones pochonins A (2), B (4), C (6), D (7), and E (8) as well as tetrahydromonorden (5) and pseurotin A (22) were isolated from cultures of the clavicipitaceous hyphomycete Pochonia chlamydosporia var. catenulata strain P 0297. Fermentation of P 0297 in bromide-containing culture media led to a shift in secondary metabolite production and yielded monocillins III (3) and II (9) as major metabolites besides monorden (1) as well as the novel compounds pochonin F (10) and a monocillin II glycoside (11) as minor metabolites. Most of these compounds showed moderate activities in a cellular replication assay against Herpes Simplex Virus 1 (HSV1) and against the parasitic protozoan Eimeria tenella. In contrast to the structurally related zearalenone derivatives none of the metabolites of strain P 0297 were found to be active in a fluorescence polarization assay for determination of modulatory activities on the human estrogenic receptor ERβ. β-Zearalenol (17), but not zearalenone (15) and α-zearalenol (16), showed antiherpetic effects. We report the production, isolation, and structure elucidation of compounds 1-11 and their biological characterization.
