Paper · 2024 · Journal of Agricultural and Food Chemistry

Quinolizidine Alkaloids and Isoflavones from the Herb of Thermopsis lupinoides and Their Antiviral, Antifungal, and Insecticidal Activities

Tong Zhang; Cai-Yan Tian; Ji Zhang; et al.

6
claims
12
verbatim quotes
15
citations
2
research areas
—
Not open access

Abstract

As part of our ongoing investigation of natural bioactive substances from the genus Thermopsis of the tribe Fabaceae for agricultural protection, the chemical constituents of the herb Thermopsis lupinoides were systematically investigated, which led to the isolation of 39 quinolizidine alkaloids (QAs) ( 1 – 39 ), including 14 new QAs ( 1 – 14 ) and 14 isoflavones ( 40 – 53 ). Their structures were elucidated through comprehensive spectroscopic data analysis (IR, UV, NMR, HRESIMS), ECD calculations, and X-ray crystallography. The antitomato spotted wilt virus (TSWV) and antifungal (against Botrytis cinerea, Gibberella zeae, Phytophythora capsica, and Alternaria alternata ) and insecticidal (against Aphis fabae and Tetranychus urticae ) activities of the isolated compounds were screened using the lesion counting method, mycelial inhibition assay, and spray method, respectively. The bioassay results showed that 34 exhibited excellent protective activity against TSWV, with an EC 50 value of 36.04 μg/mL, which was better than that of the positive control, ningnanmycin (86.03 μg/mL). The preliminary mechanistic exploration illustrated that 34 induced systemic acquired resistance in the host plant by acting on the salicylic acid signaling pathway. Moreover, 1 showed significant antifungal activity against B. cinerea (EC 50 value of 20.83 μg/mL), while 2 exhibited good insecticidal activity against A. fabae (LC 50 value of 24.97 μg/mL). This research is promising for the invention of novel pesticides from QAs with high efficiency and satisfactory ecological compatibility.

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Claims 6

Observationobservedoriginal resultmeasured

Claim · model-written summary

The herb yielded 39 quinolizidine alkaloids, including 14 new ones.

Taxon
Thermopsis lupinoidesThermopsis fabaceat0
Outcome
quinolizidine alkaloidse0
Value
39e0

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

Thermopsis fabacea
Thermopsis fabacea · TaxonMichael Wolf · CC BY-SA 3.0 · Wikimedia Commons ↗

Verbatim

e0

“isolation of 39 quinolizidine alkaloids (QAs) ( 1 – 39 ), including 14 new QAs ( 1 – 14 )”

✓ located verbatim in the source · abstract, characters 257–346 · show in text ↑
t0

“Thermopsis lupinoides”

✓ located verbatim in the source · title, characters 57–78 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

The herb yielded 14 isoflavones.

Taxon
Thermopsis lupinoidesThermopsis fabaceat0
Outcome
isoflavonese0
Value
14e0

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

Thermopsis fabacea
Thermopsis fabacea · TaxonMichael Wolf · CC BY-SA 3.0 · Wikimedia Commons ↗

Verbatim

e0

“14 isoflavones ( 40 – 53 )”

✓ located verbatim in the source · abstract, characters 351–377 · show in text ↑
t0

“Thermopsis lupinoides”

✓ located verbatim in the source · title, characters 57–78 · show in text ↑
Intervention effectobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 34 protected against TSWV with EC50 36.04 μg/mL, better than ningnanmycin.

Taxon
Thermopsis lupinoidesThermopsis fabaceat0
Treatment
34e0
Interactor
TSWVOrthotospovirus tomatomaculaee0pathogen
Outcome
protective activity against TSWVe0
Direction
bettere0
Value
36.04 μg/mLe0
Comparator
ningnanmycine0

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

Thermopsis fabacea
Thermopsis fabacea · TaxonMichael Wolf · CC BY-SA 3.0 · Wikimedia Commons ↗
Orthotospovirus tomatomaculae
Orthotospovirus tomatomaculae · InteractorWilliam M. Brown Jr., Bugwood.org · CC BY 3.0 · Wikimedia Commons ↗

Verbatim

e0

“34 exhibited excellent protective activity against TSWV, with an EC 50 value of 36.04 μg/mL, which was better than that of the positive control, ningnanmycin (86.03 μg/mL)”

✓ located verbatim in the source · abstract, characters 922–1093 · show in text ↑
t0

“Thermopsis lupinoides”

✓ located verbatim in the source · title, characters 57–78 · show in text ↑
Mechanismauthor interpretationoriginal resultmeasured

Claim · model-written summary

Compound 34 induced systemic acquired resistance through salicylic acid signaling.

Taxon
Thermopsis lupinoidesThermopsis fabaceat0
Treatment
34e0
Compound
salicylic acide0
Outcome
systemic acquired resistancee0

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

Thermopsis fabacea
Thermopsis fabacea · TaxonMichael Wolf · CC BY-SA 3.0 · Wikimedia Commons ↗

Verbatim

e0

“34 induced systemic acquired resistance in the host plant by acting on the salicylic acid signaling pathway”

✓ located verbatim in the source · abstract, characters 1152–1259 · show in text ↑
t0

“Thermopsis lupinoides”

✓ located verbatim in the source · title, characters 57–78 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Compound 1 inhibited B. cinerea with EC50 20.83 μg/mL.

Taxon
Thermopsis lupinoidesThermopsis fabaceat0
Interactor
B. cinereaBotrytis cinereae0pathogen
Outcome
antifungal activity against B. cinereae0
Value
20.83 μg/mLe0

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

Thermopsis fabacea
Thermopsis fabacea · TaxonMichael Wolf · CC BY-SA 3.0 · Wikimedia Commons ↗
Botrytis cinerea
Botrytis cinerea · InteractorRasbak · CC BY-SA 3.0 · Wikimedia Commons ↗

Verbatim

e0

“1 showed significant antifungal activity against B. cinerea (EC 50 value of 20.83 μg/mL)”

✓ located verbatim in the source · abstract, characters 1271–1359 · show in text ↑
t0

“Thermopsis lupinoides”

✓ located verbatim in the source · title, characters 57–78 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Compound 2 had insecticidal activity against A. fabae with LC50 24.97 μg/mL.

Taxon
Thermopsis lupinoidesThermopsis fabaceat0
Interactor
A. fabaeAphis fabaee0pest
Outcome
insecticidal activity against A. fabaee0
Value
24.97 μg/mLe0

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

Thermopsis fabacea
Thermopsis fabacea · TaxonMichael Wolf · CC BY-SA 3.0 · Wikimedia Commons ↗
Aphis fabae
Aphis fabae · InteractorAlvesgaspar · CC BY-SA 3.0 · Wikimedia Commons ↗

Verbatim

e0

“2 exhibited good insecticidal activity against A. fabae (LC 50 value of 24.97 μg/mL)”

✓ located verbatim in the source · abstract, characters 1367–1451 · show in text ↑
t0

“Thermopsis lupinoides”

✓ located verbatim in the source · title, characters 57–78 · show in text ↑