Abstract
Through bioassay-guided isolation, eight undescribed coumarins ( 1 – 8 ), along with six reported coumarins ( 9 – 14 ), were obtained from Coriaria nepalensis. The new structures were determined by using IR, UV, NMR, HRESIMS, and ECD calculations. The results of the biological activity assays showed that compound 9 exhibited broad spectrum antifungal activities against all tested fungi in vitro and a significant inhibitory effect on Phytophthora nicotianae with an EC 50 value of 3.00 μg/mL. Notably, compound 9 demonstrated greater curative and protective effects against tobacco balack shank than those of osthol in vivo . Thus, 9 was structurally modified to obtain new promising antifungal agents, and the novel derivatives ( 17b, 17j, and 17k ) exhibited better effects on Sclerotinia sclerotiorum than did lead compound 9 . Preliminary mechanistic exploration illustrated that 9 could enhance cell membrane permeability, destroy the morphology and ultrastructure of cells, and reduce the exopolysaccharide content of P. nicotianae mycelia. Furthermore, the cytotoxicity results revealed that compound 9 exhibited relatively low cytotoxicity against HEK293 cell lines with an inhibition rate of 33.54% at 30 μg/mL. This research is promising for the discovery of new fungicides from natural coumarins with satisfactory ecological compatibility.
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Claims 10
Claim · model-written summary
Eight undescribed coumarins were isolated from Coriaria nepalensis.
- Taxon
- Coriaria nepalensis
Coriaria nepalensise0 - Outcome
- eight undescribed coumarins ( 1 – 8 )e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“eight undescribed coumarins ( 1 – 8 ), along with six reported coumarins ( 9 – 14 ), were obtained from Coriaria nepalensis”
Claim · model-written summary
Six reported coumarins were isolated from Coriaria nepalensis.
- Taxon
- Coriaria nepalensisCoriaria nepalensise0
- Outcome
- six reported coumarins ( 9 – 14 )e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“six reported coumarins ( 9 – 14 ), were obtained from Coriaria nepalensis”
Claim · model-written summary
Compound 9 had broad spectrum antifungal activity against all tested fungi in vitro.
- Taxon
- Coriaria nepalensisCoriaria nepalensist0
- Outcome
- broad spectrum antifungal activities against all tested fungie0
- Setting
- in vitroe0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“compound 9 exhibited broad spectrum antifungal activities against all tested fungi in vitro”
t0“Coriaria nepalensis”
Claim · model-written summary
Compound 9 significantly inhibited Phytophthora nicotianae with an EC 50 of 3.00 μg/mL.
- Taxon
- Coriaria nepalensisCoriaria nepalensist0
- Interactor
- Phytophthora nicotianae
Phytophthora nicotianaee0pathogen - Outcome
- inhibitory effect on Phytophthora nicotianaee0
- Value
- 3.00 μg/mLe0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“a significant inhibitory effect on Phytophthora nicotianae with an EC 50 value of 3.00 μg/mL”
t0“Coriaria nepalensis”
Claim · model-written summary
Compound 9 had greater curative effects against tobacco black shank than osthol.
- Taxon
- tobacco
Nicotiana tabacume0 - Treatment
- compound 9e0
- Interactor
- tobacco balack shanke0pathogen
- Outcome
- curativee0
- Direction
- greatere0
- Comparator
- osthole0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“compound 9 demonstrated greater curative and protective effects against tobacco balack shank than those of osthol in vivo”
Claim · model-written summary
Compound 9 had greater protective effects against tobacco black shank than osthol.
- Taxon
- tobaccoNicotiana tabacume0
- Treatment
- compound 9e0
- Outcome
- protective effects against tobacco balack shanke0
- Direction
- greatere0
- Comparator
- osthole0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“compound 9 demonstrated greater curative and protective effects against tobacco balack shank than those of osthol in vivo”
Claim · model-written summary
Each of derivatives 17b, 17j and 17k had better effects on Sclerotinia sclerotiorum than compound 9.
- Taxon
- Coriaria nepalensisCoriaria nepalensist0
- Treatment
- 17b, 17j, and 17ke0
- Interactor
- Sclerotinia sclerotiorum
Sclerotinia sclerotiorume0pathogen - Outcome
- effects on Sclerotinia sclerotiorume0
- Direction
- bettere0
- Comparator
- lead compound 9e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“novel derivatives ( 17b, 17j, and 17k ) exhibited better effects on Sclerotinia sclerotiorum than did lead compound 9”
t0“Coriaria nepalensis”
Claim · model-written summary
Compound 9 increased membrane permeability in P. nicotianae mycelia.
- Taxon
- Coriaria nepalensisCoriaria nepalensist0
- Interactor
- P. nicotianaePhytophthora nicotianaee0pathogen
- Outcome
- cell membrane permeabilitye0
- Direction
- enhancee0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“9 could enhance cell membrane permeability, destroy the morphology and ultrastructure of cells, and reduce the exopolysaccharide content of P. nicotianae mycelia”
t0“Coriaria nepalensis”
Claim · model-written summary
Compound 9 damaged P. nicotianae cell morphology and ultrastructure.
- Taxon
- Coriaria nepalensisCoriaria nepalensist0
- Interactor
- P. nicotianaePhytophthora nicotianaee0pathogen
- Outcome
- morphology and ultrastructure of cellse0
- Direction
- destroye0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“9 could enhance cell membrane permeability, destroy the morphology and ultrastructure of cells, and reduce the exopolysaccharide content of P. nicotianae mycelia”
t0“Coriaria nepalensis”
Claim · model-written summary
Compound 9 reduced exopolysaccharide content of P. nicotianae mycelia.
- Taxon
- Coriaria nepalensisCoriaria nepalensist0
- Interactor
- P. nicotianaePhytophthora nicotianaee0pathogen
- Outcome
- exopolysaccharide content of P. nicotianae myceliae0
- Direction
- reducee0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“9 could enhance cell membrane permeability, destroy the morphology and ultrastructure of cells, and reduce the exopolysaccharide content of P. nicotianae mycelia”
t0“Coriaria nepalensis”