Paper · 2008 · Journal of Natural Products

Insect Antifeedant Sesquiterpene Acetals from the Liverwort Lepidolaena clavigera. 2. Structures, Artifacts, and Activity

Nigel B. Perry; Elaine J. Burgess; Lysa M. Foster; et al.

4
claims
8
verbatim quotes
33
citations
2
research areas
—
Not open access

Abstract

Clavigerin A ( 1) was isolated from the New Zealand liverwort Lepidolaena clavigera and shown to be a polyoxygenated bergamotane sesquiterpene with an unusual ring system. L. clavigera shows infraspecific variation, since 1 was the only clavigerin detected in a North Island collection, whereas the previously reported clavigerins B ( 2) and C ( 3) were found in South Island collections with no sign of 1. Three new clavigerins, 4- 6, were identified, but these are artifacts formed by alcoholysis of the acetoxy acetal group of the clavigerins 2 and 3, with either the extraction solvent ethanol or the RP column eluent methanol. The insect antifeedant and cytotoxic activities of these compounds are reported, and it is proposed that they act as hidden 1,4-dicarbonyl compounds.

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The text the model read, with the source record’s inline markup (italics, sub- and superscripts) rendered and its character entities decoded; quote offsets refer to the raw text.

Claims 4

Observationobservedoriginal resultmeasured

Claim · model-written summary

Clavigerin A was the only clavigerin detected in a North Island collection of Lepidolaena clavigera.

Taxon
Lepidolaena clavigeraLepidolaena clavigerae1
Outcome
clavigerin detectede2
Setting
North Island collectione2

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

Lepidolaena clavigera
Lepidolaena clavigera · TaxonStephen Thorpe · CC BY 4.0 · iNaturalist ↗

Verbatim

e1

“Lepidolaena clavigera”

✓ located verbatim in the source · abstract, characters 62–83 · show in text ↑
e2

“1 was the only clavigerin detected in a North Island collection”

✓ located verbatim in the source · abstract, characters 222–285 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Clavigerins B and C were found in South Island collections of Lepidolaena clavigera, with no sign of clavigerin A.

Taxon
Lepidolaena clavigeraLepidolaena clavigerae1
Outcome
clavigerins B ( 2) and C ( 3) were founde2
Qualifier
with no sign of 1e2
Setting
South Island collectionse2

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

Lepidolaena clavigera
Lepidolaena clavigera · TaxonStephen Thorpe · CC BY 4.0 · iNaturalist ↗

Verbatim

e1

“Lepidolaena clavigera”

✓ located verbatim in the source · abstract, characters 62–83 · show in text ↑
e2

“the previously reported clavigerins B ( 2) and C ( 3) were found in South Island collections with no sign of 1”

✓ located verbatim in the source · abstract, characters 295–405 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Three new clavigerins, 4-6, were identified; they are artifacts formed by alcoholysis of clavigerins 2 and 3 with the extraction or eluent solvent.

Taxon
Lepidolaena clavigeraLepidolaena clavigerae1
Compound
clavigerins 2 and 3e2
Outcome
Three new clavigerins, 4- 6, were identifiede2
Qualifier
artifacts formed by alcoholysis of the acetoxy acetal groupe2

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

Lepidolaena clavigera
Lepidolaena clavigera · TaxonStephen Thorpe · CC BY 4.0 · iNaturalist ↗

Verbatim

e1

“Lepidolaena clavigera”

✓ located verbatim in the source · abstract, characters 62–83 · show in text ↑
e2

“Three new clavigerins, 4- 6, were identified, but these are artifacts formed by alcoholysis of the acetoxy acetal group of the clavigerins 2 and 3”

✓ located verbatim in the source · abstract, characters 407–553 · show in text ↑
Mechanismhypothesisoriginal resultbasis n/a

Claim · model-written summary

The clavigerin artifacts are proposed to act as hidden 1,4-dicarbonyl compounds.

Taxon
Lepidolaena clavigeraLepidolaena clavigerat0
Outcome
act as hidden 1,4-dicarbonyl compoundse1
Qualifier
it is proposed thate1

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

Lepidolaena clavigera
Lepidolaena clavigera · TaxonStephen Thorpe · CC BY 4.0 · iNaturalist ↗

Verbatim

t0

“Lepidolaena clavigera”

✓ located verbatim in the source · title, characters 60–81 · show in text ↑
e1

“it is proposed that they act as hidden 1,4-dicarbonyl compounds”

✓ located verbatim in the source · abstract, characters 717–780 · show in text ↑