New Alkylitaconic Acid Derivatives from Nodulisporium sp. A21 and Their Auxin Herbicidal Activities on Weed Seeds

Abstract

Five alkylitaconic acid (AA) derivatives, including two novel compounds, epideoxysporothric acid (2) and sporochartine F (5), and three known compounds, deoxysporothric acid (1), deoxyisosporothric acid (3), and 1-undecen-2,3dicarboxylic acid (4), were obtained from the fermentation culture of the endophytic fungus Nodulisporium sp. A21. The auxin herbicidal activities of compounds 1−4 against weed seeds were investigated under laboratory conditions. In general, the tested compounds displayed radicle growth promoting activity at low doses and inhibitory activity at higher doses. Compounds 1 and 2 could significantly inhibit the radicle growth of dicotyledon weeds, Eclipta prostrata and Veronica persica, at a concentration range from 50 to 200 μg mL −1 , while 3 notably stimulated radicle growth at the same concentration range. The results suggested that these AA derivatives have the potential to be used as the lead scaffold for novel auxin herbicide development. In addition, the biosynthetic pathways of 1−4 were deduced based on 13 C labeling experiment.

Caprylic acid enhances hydroxyhexylitaconic acid production in Aspergillus niger S17‐5

“…Cao et al . (2019) verified a similar pathway for the biosynthesis of three alkylitaconic acids and one derivative; deoxysporothric, epideoxysporothric, 1‐undecen‐2,3‐dicarboxylic and deoxyisoporothric acids, using 13 C labelling experiments. Given these findings, alkylitaconic acids are generally synthesized by the condensation of acyl‐CoAs derived from fatty acids with oxaloacetic acid via similar biosynthetic pathways.…”

“…Previously, we reported that 9-HHIA and 10-HHIA produced by A. niger S17-5 have cytotoxic and polymer building block properties (Aso et al 2020;Sano et al 2020). Related studies have predicted that 9-HHIA and 10-HHIA are synthesized by the condensation of octanoyl-CoA, which is derived from caprylic acid, with oxaloacetic acid (Guti errez et al 2002;Cao et al 2019;Palys et al 2020). However, there have been no studies regarding the effects of the addition of caprylic acid on 9-HHIA and 10-HHIA production.…”

“…To clarify the synthetic pathway in detail, further analyses, such as 13 C labelling experiments (Cao et al . 2019), are required.…”

Novel metabolites from the Cercis chinensis derived endophytic fungus Alternaria alternataZHJG5 and their antibacterial activities

“…During our recent studies examining bioactive metabolites from endophytes, 15–18 Alternaria alternata ZHJG5, a Cercis chinensis ‐associated fungus, showed strong antibacterial effects against many phytopathogens. A study of the crude extract of A. alternata ZHJG5 led to the discovery of five new polyketide derivatives, isotalaroflavone ( 2 ), (+/−)‐5′‐dehydroxytalaroflavone ( 3a/3b ), (+)‐talaroflavone ( 4b ) and bialternacin G ( 7 ), along with five known compounds.…”

Eremophilane Sesquiterpenes and Benzene Derivatives from the Endophyte Microdiplodia sp. WGHS5

“…As part of our explorative effort to find structurally diverse and/or bioactive natural products from endophytic fungi, we have identified sporothriolide, prochaetoviridin A, chaetoindolin A, alkylitaconic acid (AA) derivatives (epideoxysporothric acid, and sporochartine F) [10–12] . Among them, sporothriolide exhibited potent antifungal and alkylitaconic acid derivatives reported for herbicidal activities.…”