Paper · 2022 · Molecules

Identification of Cyclic Dipeptides and a New Compound (6-(5-Hydroxy-6-methylheptyl)-5,6-dihydro-2H-pyran-2-one) Produced by Streptomyces fungicidicus against Alternaria solani

He Liu; Mengnan An; Hongyang Si; et al.

10
claims
19
verbatim quotes
8
citations
2
research areas
✓
Open access · cc-by

Abstract

As an important microbial resource, Actinomycetes, especially Streptomyces, have important application values in medicine and biotechnology. Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato. To obtain pure active compounds, SYH3 fermentation broth was subjected to XAD-16 macroporous resin and silica gel column chromatography. Combined with the repeated preparation and separation of preparative high-performance liquid chromatography (HPLC), a total of four monomer compounds were obtained after activity tracking. Compound 4 was identified as a new six-membered lactone ring compound named 6-(5-hydroxy-6-methylheptyl)-5,6-dihydro-2H-pyran-2-one by 1D and 2D nuclear magnetic resonance (NMR) data and mass spectrometry (MS). The other three active compounds belong to the cyclodipeptide, and their half maximal inhibitory concentration (IC50) values against A. solani were 43.4, 42.9, and 30.6 μg/mL, respectively. Compound 4 significantly inhibited the spore germination and induced swollen and deformed local hyphae of A. solani with an IC50 value of 24.9 μg/mL. Compound 4 also had broad-spectrum antifungal activity and had a good antifungal effect on the tested plant-pathogenic fungi. The modes of action of new compound (4) still require further investigation, representing a novel and effective anti-fungal agent for future application.

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Claims 10

Intervention effectobservedoriginal resultpositivemeasured

Claim · model-written summary

Streptomyces fungicidicus SYH3 showed good inhibitory effects on Alternaria solani in tomato.

Treatment
Streptomyces fungicidicus SYH3e0
Interactor
Alternaria solaniAlternaria solanie0pathogen
Second interactor
Streptomyces fungicidicus SYH3Streptomyces fungicidicuse0biocontrol_agent
Outcome
inhibitory effects on Alternaria solanie0

Not reportedComparatorDirection

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗
Alternaria solani
Alternaria solani · InteractorClemson University - USDA Cooperative Extension Slide Series · CC BY 3.0 us · Wikimedia Commons ↗

Verbatim

e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Fermentation fractionation of SYH3 yielded a total of four monomer compounds.

Outcome
monomer compoundse1
Value
a total of foure1

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗

Verbatim

e1

“a total of four monomer compounds were obtained after activity tracking”

✓ located verbatim in the source · abstract, characters 547–618 · show in text ↑
e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Compound 4 was identified as a new six-membered lactone ring compound.

Compound
6-(5-hydroxy-6-methylheptyl)-5,6-dihydro-2H-pyran-2-onee2
Outcome
identified as a new six-membered lactone ring compounde2

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗

Verbatim

e2

“Compound 4 was identified as a new six-membered lactone ring compound named 6-(5-hydroxy-6-methylheptyl)-5,6-dihydro-2H-pyran-2-one”

✓ located verbatim in the source · abstract, characters 620–751 · show in text ↑
e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

One cyclodipeptide had an IC50 of 43.4 against Alternaria solani.

Interactor
A. solaniAlternaria solanie3pathogen
Compound
cyclodipeptidee3
Outcome
half maximal inhibitory concentration (IC50) values against A. solanie3
Value
43.4e3
Qualifier
μg/mLe3

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗
Alternaria solani
Alternaria solani · InteractorClemson University - USDA Cooperative Extension Slide Series · CC BY 3.0 us · Wikimedia Commons ↗

Verbatim

e3

“The other three active compounds belong to the cyclodipeptide, and their half maximal inhibitory concentration (IC50) values against A. solani were 43.4, 42.9, and 30.6 μg/mL, respectively”

✓ located verbatim in the source · abstract, characters 831–1019 · show in text ↑
e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

A second cyclodipeptide had an IC50 of 42.9 against Alternaria solani.

Interactor
A. solaniAlternaria solanie3pathogen
Compound
cyclodipeptidee3
Outcome
half maximal inhibitory concentration (IC50) values against A. solanie3
Value
42.9e3
Qualifier
μg/mLe3

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗
Alternaria solani
Alternaria solani · InteractorClemson University - USDA Cooperative Extension Slide Series · CC BY 3.0 us · Wikimedia Commons ↗

Verbatim

e3

“The other three active compounds belong to the cyclodipeptide, and their half maximal inhibitory concentration (IC50) values against A. solani were 43.4, 42.9, and 30.6 μg/mL, respectively”

✓ located verbatim in the source · abstract, characters 831–1019 · show in text ↑
e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

A third cyclodipeptide had an IC50 of 30.6 μg/mL against Alternaria solani.

Interactor
A. solaniAlternaria solanie3pathogen
Compound
cyclodipeptidee3
Outcome
half maximal inhibitory concentration (IC50) values against A. solanie3
Value
30.6 μg/mLe3

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗
Alternaria solani
Alternaria solani · InteractorClemson University - USDA Cooperative Extension Slide Series · CC BY 3.0 us · Wikimedia Commons ↗

Verbatim

e3

“The other three active compounds belong to the cyclodipeptide, and their half maximal inhibitory concentration (IC50) values against A. solani were 43.4, 42.9, and 30.6 μg/mL, respectively”

✓ located verbatim in the source · abstract, characters 831–1019 · show in text ↑
e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑
Intervention effectobservedoriginal resultpositivesignificant (as stated)measured

Claim · model-written summary

Compound 4 significantly inhibited spore germination of Alternaria solani.

Treatment
Compound 4e4
Interactor
A. solaniAlternaria solanie4pathogen
Outcome
spore germinatione4
Direction
inhibitede4

Not reportedComparator

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗
Alternaria solani
Alternaria solani · InteractorClemson University - USDA Cooperative Extension Slide Series · CC BY 3.0 us · Wikimedia Commons ↗

Verbatim

e4

“Compound 4 significantly inhibited the spore germination and induced swollen and deformed local hyphae of A. solani with an IC50 value of 24.9 μg/mL”

✓ located verbatim in the source · abstract, characters 1021–1169 · show in text ↑
e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑
Intervention effectobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 4 induced swollen and deformed local hyphae of Alternaria solani.

Treatment
Compound 4e4
Interactor
A. solaniAlternaria solanie4pathogen
Outcome
swollen and deformed local hyphaee4

Not reportedComparatorDirection

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗
Alternaria solani
Alternaria solani · InteractorClemson University - USDA Cooperative Extension Slide Series · CC BY 3.0 us · Wikimedia Commons ↗

Verbatim

e4

“Compound 4 significantly inhibited the spore germination and induced swollen and deformed local hyphae of A. solani with an IC50 value of 24.9 μg/mL”

✓ located verbatim in the source · abstract, characters 1021–1169 · show in text ↑
e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Compound 4 had an IC50 of 24.9 μg/mL against Alternaria solani.

Interactor
A. solaniAlternaria solanie4pathogen
Compound
Compound 4e4
Outcome
IC50 valuee4
Value
24.9 μg/mLe4

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗
Alternaria solani
Alternaria solani · InteractorClemson University - USDA Cooperative Extension Slide Series · CC BY 3.0 us · Wikimedia Commons ↗

Verbatim

e4

“Compound 4 significantly inhibited the spore germination and induced swollen and deformed local hyphae of A. solani with an IC50 value of 24.9 μg/mL”

✓ located verbatim in the source · abstract, characters 1021–1169 · show in text ↑
e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑
Observationobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 4 has broad-spectrum antifungal activity against tested plant-pathogenic fungi.

Interactor
plant-pathogenic fungie5pathogen
Compound
Compound 4e5
Outcome
broad-spectrum antifungal activitye5

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Solanum lycopersicum
Solanum lycopersicum · TaxonKod B · CC BY-SA 4.0 · Wikimedia Commons ↗

Verbatim

e5

“Compound 4 also had broad-spectrum antifungal activity and had a good antifungal effect on the tested plant-pathogenic fungi”

✓ located verbatim in the source · abstract, characters 1171–1295 · show in text ↑
e0

“Streptomyces fungicidicus SYH3 was isolated from soil samples in tomato-growing areas and showed good inhibitory effects on Alternaria solani in tomato”

✓ located verbatim in the source · abstract, characters 141–292 · show in text ↑

Streptomyces · Alternaria solani · Solanum lycopersicum (tomato)Results agree

4 papers: 4 positive, 0 negative or no effect

3 papers in the same direction as this paper

  1. positive
  2. positive
  3. positive
See all 4 papers →

fungicide · Alternaria solani · Solanum lycopersicum (tomato)Results agree

14 papers: 14 positive, 0 negative or no effect

13 papers in the same direction as this paper

  1. positive
  2. positive
  3. positive

10 papers more in this group

See all 14 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.