Regulation of the Growth of Cotton Bollworms by Metabolites from an Entomopathogenic Fungus Paecilomyces cateniobliquus

Abstract

Chemical investigation of one entomopathogenic fungus Paecilomyces cateniobliquus YMF1.01799 led to the isolation and identification of six metabolites, which include three new compounds (2-3, and 5) and three known metabolites. Their structures were established by spectroscopic studies such as 1D and 2D NMR and MS analysis. Insect growth experiments suggested that polyketide-derived compound 1 showed significant inhibitory effect on the growth of cotton bollworm Helicoverpa armigera, while terpenoid-derived metabolite 5 promoted the growth of the larvae. The findings revealed that the entomopathogenic fungus P. cateniobliquus could produce different types of metabolites to regulate growth of the insect.

Terpenoids From the Coral-Derived Fungus Trichoderma harzianum (XS-20090075) Induced by Chemical Epigenetic Manipulation

“…Compared to the rice culture control at the same culture condition, the HPLC finger-print of the EtOAc extract of the culture with sodium butyrate (10 µM) in rice medium showed new peaks at about 15, 31, and 38 min ( Figure 1A), and the main peaks of the harziane diterpenoids at 33-42 min ( Figure 1B) disappeared. Chemical investigation of the EtOAc extract led to the isolation of three new terpenoids, including one novel chlorinated cleistanthane diterpenoid, harzianolic acid A (1), one harziane diterpenoid, harzianone E (2), and one cyclonerane sesquiterpenoid, 3,7,11-trihydroxy-cycloneran (3), together with 11 known sesquiterpenoids, including eight cyclonerane sesquiterpenoids, methyl 3,7-dihydroxy-15cycloneranate (4) (Song et al, 2018), catenioblin C (5) (Wu et al, 2012), ascotrichic acid (6) (Xie et al, 2013), cyclonerotriol (7) (Kasitu et al, 1992), (10E)-12-acetoxy-10-cycloneren-3,7-diol (8) (Fang et al, 2018), cyclonerodiol (9) (Nozoe et al, 1970), cyclonerodiol oxide (10) (Fujita et al, 1984) and epicyclonerodiol oxide (11) (Fujita et al, 1984), one african sesquiterpenoid, ophioceric acid (12) (Reátegui et al, 2005), and two acoranetype sesqiuterpenoids, ent-trichoacorenol (13) (Brock and Dickschat, 2011) and trichoacorenol (14) (Huang et al, 1995) (Figure 2). These results revealed that the original main products harziane diterpenoids were replaced by cyclonerane sesquiterpenoids.…”

Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves

“…Further experiments would be needed to establish the biosynthetic relationship between the two compounds. Catenioblin A has only previously been found in 1 entomopathogenic fungus, Paecilomyces cateniobliquus YMF1.01799 (Wu et al 2012).…”

“…Phomalactone is quite insecticidal (Khambay et al 2000;Wu et al 2012). It has been isolated previously from several species of the fungal genera Nigrospora (Fukushima et al 1998;Trisuwan et al 2009;Wu et al2009), Xylaria (Jimenéz-Romero et al 2008, Aspergillus (Komai et al 2003), Verticillium (Khambay et al 2000), Drechslera (Krivobok et al 1994), Hirsutella (entomopathogenic) ( K r a s n o f f a n d G u p t a 1 9 9 4 ) , P a e c i l o m y c e s (entomopathogenic) (Wu et al 2012), and Phoma (Yamamoto et al 1970).…”

“…It has been isolated previously from several species of the fungal genera Nigrospora (Fukushima et al 1998;Trisuwan et al 2009;Wu et al2009), Xylaria (Jimenéz-Romero et al 2008, Aspergillus (Komai et al 2003), Verticillium (Khambay et al 2000), Drechslera (Krivobok et al 1994), Hirsutella (entomopathogenic) ( K r a s n o f f a n d G u p t a 1 9 9 4 ) , P a e c i l o m y c e s (entomopathogenic) (Wu et al 2012), and Phoma (Yamamoto et al 1970). Phomolactone has antifungal activity against Aspergillus fumigatus (Komai et al 2003), nematocidal activity (Khambay et al 2000), immunomodulating activity (Krivobok et al 1994), insecticide activity (Krasnoff and Gupta 1994), phytotoxic activity (Fukushima et al 1998), and weak activity against Plasmodium falciparum (Jimenéz-Romero et al 2008).…”

Cyclonerol Derivatives from Trichoderma longibrachiatum YM311505

“…During our investigation of endophytic fungi from Azadirachta indica, one strain YM311505 was isolated and identified to be Trichoderma longibrachiatum. The study on secondary metabolites of this strain led to the isolation of a new sesquiterpene, named as dihydrocyclonerotriol (1), together with two known compounds, catenioblin C (2) [2] and sohirnone A (3) [3a] (Figure 1). Cyclonerol-related terpenes have been isolated since 1970.…”