Paper · 2024 · New Phytologist

Unique bibenzyl cannabinoids in the liverwort Radula marginata: parallels with Cannabis chemistry

Christelle M. Andre; Catherine E. Sansom; Blue J. Plunkett; et al.

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claims
15
verbatim quotes
4
citations
3
research areas
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Open access · cc-by-nc

Abstract

The potential of cannabinoids to address public health challenges has stimulated exploration into alternative sources and production technologies. Radula marginata, an endemic Aotearoa/New Zealand liverwort, produces the bibenzyl cannabinoid perrottetinene (PET), analogous to Cannabis psychoactive tetrahydrocannabinol (THC). Structural differences between PET and THC could alter therapeutic interactions and mitigate adverse side effects. To understand the cannabinoid production potential of R. marginata, we analyzed 75 collections from three locations across several seasons, collaborating with kaitiaki Māori (indigenous guardians). Metabolic plasticity of the phytocannabinoids and plant growth was assessed under controlled growth conditions, and in in vitro culture. Perrottetinene diol (trans-PTD), analogous to cannabidiol (trans-CBD), and its acid precursor (PTDA), were identified and fully characterized from nature for the first time. Bibenzyl-4-geranyl (BB4G), analogous to cannabigerol (CBG), and its corresponding acid (BB4GA), were also isolated. Radula marginata showed chemotypes dominated by PET, PTD, or BB4G, in striking analogy to the main Cannabis chemotypes. These site-selective chemotypes persisted after growth under artificial lighting and in in vitro progeny, suggesting genetic control. These results expand phytocannabinoid knowledge through the discovery of PTD analogous to CBD. They add a new dimension to liverwort cannabinoids and suggest convergent evolution of biosynthesis in two distant plant lineages.

Abstract from the paper’s OpenAlex record; open copy licensed cc-by-nc. Read at the source ↗

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 8

Observationobservedoriginal resultmeasured

Claim · model-written summary

Perrottetinene diol was identified and characterized from nature for the first time.

Taxon
Radula marginataRadula marginatat0
Outcome
Perrottetinene diol (trans-PTD)e0
Qualifier
identified and fully characterized from nature for the first timee0

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

Radula marginata
Radula marginata · TaxonAngus Campbell · CC BY 4.0 · iNaturalist ↗

Verbatim

e0

“Perrottetinene diol (trans-PTD), analogous to cannabidiol (trans-CBD), and its acid precursor (PTDA), were identified and fully characterized from nature for the first time.”

✓ located verbatim in the source · abstract, characters 777–950 · show in text ↑
t0

“Radula marginata”

✓ located verbatim in the source · title, characters 46–62 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

The acid precursor PTDA was identified and characterized from nature for the first time.

Taxon
Radula marginataRadula marginatat0
Outcome
PTDAe0
Qualifier
identified and fully characterized from nature for the first timee0

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

Radula marginata
Radula marginata · TaxonAngus Campbell · CC BY 4.0 · iNaturalist ↗

Verbatim

e0

“Perrottetinene diol (trans-PTD), analogous to cannabidiol (trans-CBD), and its acid precursor (PTDA), were identified and fully characterized from nature for the first time.”

✓ located verbatim in the source · abstract, characters 777–950 · show in text ↑
t0

“Radula marginata”

✓ located verbatim in the source · title, characters 46–62 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Bibenzyl-4-geranyl was isolated.

Taxon
Radula marginataRadula marginatat0
Outcome
Bibenzyl-4-geranyl (BB4G)e0

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

Radula marginata
Radula marginata · TaxonAngus Campbell · CC BY 4.0 · iNaturalist ↗

Verbatim

e0

“Bibenzyl-4-geranyl (BB4G), analogous to cannabigerol (CBG), and its corresponding acid (BB4GA), were also isolated.”

✓ located verbatim in the source · abstract, characters 951–1066 · show in text ↑
t0

“Radula marginata”

✓ located verbatim in the source · title, characters 46–62 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

The corresponding acid BB4GA was isolated.

Taxon
Radula marginataRadula marginatat0
Outcome
BB4GAe0

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

Radula marginata
Radula marginata · TaxonAngus Campbell · CC BY 4.0 · iNaturalist ↗

Verbatim

e0

“Bibenzyl-4-geranyl (BB4G), analogous to cannabigerol (CBG), and its corresponding acid (BB4GA), were also isolated.”

✓ located verbatim in the source · abstract, characters 951–1066 · show in text ↑
t0

“Radula marginata”

✓ located verbatim in the source · title, characters 46–62 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Radula marginata had PET, PTD, or BB4G dominated chemotypes.

Taxon
Radula marginataRadula marginatae0
Outcome
chemotypes dominated by PET, PTD, or BB4Ge0

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

Radula marginata
Radula marginata · TaxonAngus Campbell · CC BY 4.0 · iNaturalist ↗

Verbatim

e0

“Radula marginata showed chemotypes dominated by PET, PTD, or BB4G, in striking analogy to the main Cannabis chemotypes.”

✓ located verbatim in the source · abstract, characters 1067–1186 · show in text ↑
Observationobservedoriginal resultmeasured

Claim · model-written summary

Site-selective chemotypes persisted under artificial lighting and in vitro progeny.

Taxon
Radula marginataRadula marginatat0
Outcome
site-selective chemotypese0
Qualifier
persisted after growth under artificial lighting and in in vitro progenye0

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

Radula marginata
Radula marginata · TaxonAngus Campbell · CC BY 4.0 · iNaturalist ↗

Verbatim

e0

“These site-selective chemotypes persisted after growth under artificial lighting and in in vitro progeny, suggesting genetic control.”

✓ located verbatim in the source · abstract, characters 1187–1320 · show in text ↑
t0

“Radula marginata”

✓ located verbatim in the source · title, characters 46–62 · show in text ↑
Mechanismauthor interpretationoriginal resultmeasured

Claim · model-written summary

Persistence of chemotypes suggests genetic control.

Taxon
Radula marginataRadula marginatat0
Outcome
site-selective chemotypese0
Qualifier
genetic controle0

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

Radula marginata
Radula marginata · TaxonAngus Campbell · CC BY 4.0 · iNaturalist ↗

Verbatim

e0

“These site-selective chemotypes persisted after growth under artificial lighting and in in vitro progeny, suggesting genetic control.”

✓ located verbatim in the source · abstract, characters 1187–1320 · show in text ↑
t0

“Radula marginata”

✓ located verbatim in the source · title, characters 46–62 · show in text ↑
Mechanismauthor interpretationoriginal resultmeasured

Claim · model-written summary

The findings suggest convergent evolution of cannabinoid biosynthesis in two plant lineages.

Taxon
Radula marginataRadula marginatat0
Outcome
convergent evolution of biosynthesise0
Qualifier
two distant plant lineagese0

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

Radula marginata
Radula marginata · TaxonAngus Campbell · CC BY 4.0 · iNaturalist ↗

Verbatim

e0

“They add a new dimension to liverwort cannabinoids and suggest convergent evolution of biosynthesis in two distant plant lineages.”

✓ located verbatim in the source · abstract, characters 1416–1546 · show in text ↑
t0

“Radula marginata”

✓ located verbatim in the source · title, characters 46–62 · show in text ↑