Macrolides from Streptomyces sp. SN5452 and Their Antifungal Activity against Pyricularia oryzae

Pyricularia oryzae causes rice blast, the major destructive disease in nearly all rice fields. In order to obtain highly active compounds against P. oryzae, four new 20-membered macrolides named venturicidins G–J (1–4) were isolated from the culture broth of Streptomyces sp. SN5452 along with two known ones, venturicidins A (5) and B (6). Their structures were determined by the cumulative analyses of nuclear magnetic resonance (NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry (HRESIMS) data. All isolated compounds were evaluated for their antifungal activity against P. oryzae. Interestingly, these compounds exhibited obvious inhibition to mycelial growth and conidial germination of P. oryzae. Remarkably, the EC(50) values of venturicidins A (5), B (6), and I (3) against mycelial growth were 0.11, 0.15 and 0.35 µg/mL, and their EC(50) values of conidial germination were 0.27, 0.39 and 1.14 µg/mL, respectively. The analysis of structure-activity relationships (SARs) revealed that the methylated positions might be involved in the antifungal activity of venturicidins. These results indicate that the venturicidins are prospective candidates for novel fungicides that can be applied in controlling rice blast.