Abstract
In an ongoing effort to explore more potent antifungal pogostone (Po) analogues, we maintained the previously identified 3-acetyl-4-hydroxy-2-pyrone core motif while synthesizing a series of Po analogues with variations in the alkyl side chain. The in vitro bioassay results revealed that compound 21 was the most potent antifungal analogue with an EC 50 value of 1.1 μg/mL against Sclerotinia sclerotiorum (Lib.) de Bary. Meanwhile, its Cu(II) complex 34 manifested significantly enhanced antibacterial activity against Xanthomonas campestris pv campestris ( Xcc ) with a minimum inhibitory concentration (MIC) value of 300 μg/mL compared with 21 (MIC = 700 μg/mL). Complex 34 exhibited a striking preventive effect against S. sclerotiorum and Xcc in rape leaves, with control efficacies of 98.8% (50 μg/mL) and 80.7% (1000 μg/mL), respectively. The 3D-QSAR models generated using Topomer comparative molecular field analysis indicated that a shorter alkyl chain (carbon atom number <8), terminal rings, or electron-deficient groups on the alkyl side chain are beneficial for antifungal potency. Further, bioassay results revealed that the component of 21 in complex 34 dominated the antifungal activity, but the introduction of Cu(II) significantly enhanced its antibacterial activity. The toxicological observations demonstrated that 21 could induce abnormal mitochondrial morphology, loss of mitochondrial membrane potential, and reactive oxygen species (ROS) accumulation in S. sclerotiorum . The enzyme assay results showed that 21 is a moderate promiscuous inhibitor of mitochondrial complexes II and III. Besides, the introduction of Cu(II) to 34 could promote the disruption of the cell membrane and intracellular proteins and the ROS level in Xcc compared with 21 . In summary, these results highlight the potential of 34 as a dual antifungal and antibacterial biocide for controlling rape diseases or as a promising candidate for further optimization.
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Claims 8
Claim · model-written summary
Compound 21 was the most potent antifungal analogue against Sclerotinia sclerotiorum in vitro, with an EC50 of 1.1 μg/mL.
- Taxon
- rape
_Brassica_napus_-_Habit.jpg?width=60)
Brassica napuse0 - Interactor
- Sclerotinia sclerotiorum
Sclerotinia sclerotiorume1pathogen - Compound
- compound 21e1
- Outcome
- EC 50 valuee1
- Value
- 1.1 μg/mLe1
- Setting
- in vitroe1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
_Brassica_napus_-_Habit.jpg?width=500)
Verbatim
e1“The in vitro bioassay results revealed that compound 21 was the most potent antifungal analogue with an EC 50 value of 1.1 μg/mL against Sclerotinia sclerotiorum (Lib.) de Bary”
e0“a dual antifungal and antibacterial biocide for controlling rape diseases”
Claim · model-written summary
Cu(II) complex 34 significantly enhanced antibacterial activity against Xanthomonas campestris pv campestris compared with compound 21, with an MIC of 300 μg/mL.
- Taxon
- rapeBrassica napuse0
- Treatment
- Cu(II) complex 34e2
- Interactor
- Xanthomonas campestris pv campestris
_(25868012152).jpg?width=60)
Xanthomonas campestrise2pathogen - Outcome
- antibacterial activitye2
- Direction
- significantly enhancede2
- Value
- 300 μg/mLe2
- Comparator
- 21e2
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
_(25868012152).jpg?width=500)
Verbatim
e2“its Cu(II) complex 34 manifested significantly enhanced antibacterial activity against Xanthomonas campestris pv campestris ( Xcc ) with a minimum inhibitory concentration (MIC) value of 300 μg/mL compared with 21 (MIC = 700 μg/mL)”
e0“a dual antifungal and antibacterial biocide for controlling rape diseases”
Claim · model-written summary
Complex 34 gave a preventive control efficacy of 98.8% (50 μg/mL) against Sclerotinia sclerotiorum on rape leaves.
- Taxon
- rapeBrassica napuse3
- Organ / stage
- leavese3
- Treatment
- Complex 34e3
- Interactor
- S. sclerotiorumSclerotinia sclerotiorume3pathogen
- Outcome
- control efficaciese3
- Value
- 98.8%e3
- Qualifier
- 50 μg/mLe3
Not reportedComparatorDirection
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e3“Complex 34 exhibited a striking preventive effect against S. sclerotiorum and Xcc in rape leaves, with control efficacies of 98.8% (50 μg/mL) and 80.7% (1000 μg/mL), respectively”
Claim · model-written summary
Complex 34 gave a preventive control efficacy of 80.7% (1000 μg/mL) against Xanthomonas campestris on rape leaves.
- Taxon
- rapeBrassica napuse3
- Organ / stage
- leavese3
- Treatment
- Complex 34e3
- Interactor
- Xcce3pathogen
- Outcome
- control efficaciese3
- Value
- 80.7%e3
- Qualifier
- 1000 μg/mLe3
Not reportedComparatorDirection
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e3“Complex 34 exhibited a striking preventive effect against S. sclerotiorum and Xcc in rape leaves, with control efficacies of 98.8% (50 μg/mL) and 80.7% (1000 μg/mL), respectively”
Claim · model-written summary
Shorter alkyl chains (carbon number below 8), terminal rings or electron-deficient groups on the side chain are beneficial for antifungal potency in 3D-QSAR models.
- Taxon
- rapeBrassica napuse0
- Treatment
- shorter alkyl chain (carbon atom number <8)e4
- Outcome
- antifungal potencye4
- Direction
- increaseinferrede4
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e4“The 3D-QSAR models generated using Topomer comparative molecular field analysis indicated that a shorter alkyl chain (carbon atom number <8), terminal rings, or electron-deficient groups on the alkyl side chain are beneficial for antifungal potency”
e0“a dual antifungal and antibacterial biocide for controlling rape diseases”
Claim · model-written summary
Compound 21 could induce abnormal mitochondrial morphology, loss of mitochondrial membrane potential and ROS accumulation in Sclerotinia sclerotiorum.
- Taxon
- rapeBrassica napuse0
- Treatment
- 21e5
- Interactor
- S. sclerotiorumSclerotinia sclerotiorume5pathogen
- Outcome
- abnormal mitochondrial morphology, loss of mitochondrial membrane potential, and reactive oxygen species (ROS) accumulatione5
- Direction
- inducee5
Not reportedComparator
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e5“The toxicological observations demonstrated that 21 could induce abnormal mitochondrial morphology, loss of mitochondrial membrane potential, and reactive oxygen species (ROS) accumulation in S. sclerotiorum”
e0“a dual antifungal and antibacterial biocide for controlling rape diseases”
Claim · model-written summary
Compound 21 is a moderate promiscuous inhibitor of mitochondrial complexes II and III.
- Taxon
- rapeBrassica napuse0
- Compound
- 21e6
- Outcome
- a moderate promiscuous inhibitor of mitochondrial complexes II and IIIe6
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e6“The enzyme assay results showed that 21 is a moderate promiscuous inhibitor of mitochondrial complexes II and III”
e0“a dual antifungal and antibacterial biocide for controlling rape diseases”
Claim · model-written summary
Introducing Cu(II) to complex 34 could promote disruption of the cell membrane and intracellular proteins and raise ROS levels in Xanthomonas campestris compared with compound 21.
- Taxon
- rapeBrassica napuse0
- Treatment
- introduction of Cu(II) to 34e7
- Interactor
- Xcce7pathogen
- Outcome
- disruption of the cell membrane and intracellular proteins and the ROS levele7
- Direction
- promotee7
- Comparator
- 21e7
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e7“the introduction of Cu(II) to 34 could promote the disruption of the cell membrane and intracellular proteins and the ROS level in Xcc compared with 21”
e0“a dual antifungal and antibacterial biocide for controlling rape diseases”
The same questions in other papers
copper atom · physiology: oxidative · Brassica napus (oilseed rape)Positive and negative results
1 paper in the same direction as this paper · 3 in the opposite direction
- negative
- negative
- negative
1 paper more in this group
See all 5 papers →Claims are grouped by organism, treatment and what was measured or targeted. A paper counts as positive when any of its claims in the group is positive.