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1. (Article ID: 9191)
Teng LL, Song TY, Chen YH, Chen YG, Zhang KQ, Li SH, Niu XM
Novel polyketide-terpenoid hybrid metabolites from a potent nematicidal Arthrobotrys oligospora mutant ΔAOL_s00215g278
Journal of Agricultural and Food Chemistry 68(41) (2020)
11449-11458
Here, we reported that detailed investigation on trace targeted metabolites from nematode-trapping fungus Arthrobotrys oligospora mutant with deletion of P450 gene AOL_s00215g278 led to isolation of 9 new polyketide-terpenoid hybrid derivatives, including four new glycosides of the key precursor farnesyl hydrotoluquinol (1) and, surprisingly, four new sesquiterpenyl epoxy-cyclohexenoids (SECs) analogues. Among them, two major target metabolites 1 and 14 displayed moderate nematode inhibitory ability. Moreover, the mutant lacking AOL_s00215g278 could form far more nematode-capturing traps within 6 h in contact with nematodes and show rapid potent nematicidal activity with killing 93.7% preys, though deletion of the P450 gene resulted in dramatic decrease in fungal colony growth and failure to produce fungal conidia. The results unequivocally revealed that gene AOL_s00215g278 should be involved in not only the SEC biosynthetic pathway in the nematode-trapping fungus A. oligospora but also fungal conidiation and nematicidal activity.
biosynthesis, Arthrobotrys oligospora, arthrosporols, nematode-trapping fungus, terpenyl epoxycyclohexone, trap formation, P450 gene AOL_s00215g278
NCBI PubMed ID: 32924475Publication DOI: 10.1021/acs.jafc.0c04713Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: Zhang KQ
ynu.edu.cn>; Li SH mail.kib.ac.cn>; Niu XM ynu.edu.cn>
Institutions: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China, State Key Laboratory for Conservation and Utilization of Bio-Resources & Key Laboratory for Microbial Resources of the Ministry of Education, School of Life Science, Yunnan University, Kunming, China
Methods: 13C NMR, 1H NMR, EI-MS, IR, PCR, TLC, ESI-MS, biological assays, HPLC, UV, microscopy, optical rotation measurement, CC, cell growth, HR-ESI-MS, DNA extraction, BLAST, HR-EI-MS
The publication contains the following compound(s):
- Compound ID: 22404
|
a-L-Rhap-(1-1)-Subst
Subst = 4,15'-dihydroxyfarnesyltoluquinol = SMILES C/C(CC/C=C(C)/CC/C=C(C)\{65}CO)=C\CC1=C{1}C(O)=C(C)C={4}C1O |
Show graphically |
Structure type: monomer
; 513.2810 [M+Na]+
C28H42O7
Compound class: glycoside
Reference(s) to other database(s): GenDB:JX244893
- Compound ID: 22405
|
a-L-Rhap-(1-4)-Subst
Subst = 4,15'-dihydroxyfarnesyltoluquinol = SMILES C/C(CC/C=C(C)/CC/C=C(C)\{65}CO)=C\CC1=C{1}C(O)=C(C)C={4}C1O |
Show graphically |
Structure type: monomer
; 489.2878 [M-H]-
C28H42O7
Compound class: glycoside
Reference(s) to other database(s): GenDB:JX244893
- Compound ID: 22406
|
a-L-Rhap-(1-4)-Subst
Subst = 4,15'-dihydroxyfarnesyltoluquinol = SMILES C/C(CC/C=C(C)/CC/C=C(C)\{65}CO)=C\CC1=C{1}C(O)=C(C)C={4}C1O |
Show graphically |
Structure type: monomer
; 489.2872 [M-H]-
C28H42O7
Compound class: glycoside
Reference(s) to other database(s): GenDB:JX244893
- Compound ID: 22407
|
a-L-Rhap-(1-4)-Subst
Subst = 4-hydroxy-15′-carboxylfarnesyltoluquinol = SMILES C/C(CC/C=C(C)/CC/C=C(C)\{65}C(O)=O)=C\CC1=C{1}C(O)=C(C)C={4}C1O |
Show graphically |
Structure type: monomer
; 503.2668 [M-H]-
C28H40O8
Compound class: glycoside
Reference(s) to other database(s): GenDB:JX244893
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