Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum

A novel meroterpenoid cabagranin D was isolated with related neolignans cabagranins A–C from the leaves of Piper cabagranum (Costa Rica). Cabagranins A–C represent the first examples of 3,3′-neolignans isolated from the plant genus Piper, and the meroterpenoid cabagranin D displays an unprecedented...

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Main Authors: Celso R. de Oliveira, Zachary D. Ledvina, Michael D. Leonard, Samuel O. Odoh, Craig D. Dodson, Christopher S. Jeffrey
Format: Article
Language:English
Published: Frontiers Media S.A. 2024-01-01
Series:Frontiers in Natural Products
Subjects:
Online Access:https://www.frontiersin.org/articles/10.3389/fntpr.2023.1332436/full
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author Celso R. de Oliveira
Zachary D. Ledvina
Michael D. Leonard
Samuel O. Odoh
Craig D. Dodson
Christopher S. Jeffrey
author_facet Celso R. de Oliveira
Zachary D. Ledvina
Michael D. Leonard
Samuel O. Odoh
Craig D. Dodson
Christopher S. Jeffrey
author_sort Celso R. de Oliveira
collection DOAJ
description A novel meroterpenoid cabagranin D was isolated with related neolignans cabagranins A–C from the leaves of Piper cabagranum (Costa Rica). Cabagranins A–C represent the first examples of 3,3′-neolignans isolated from the plant genus Piper, and the meroterpenoid cabagranin D displays an unprecedented Diels–Alder conjugate of an unsubstituted phenylpropenone and α-phellandrene. Details of the full structural elucidation of these compounds and a discussion of their potential biosynthetic relationships are presented.
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spelling doaj.art-31a1942adc6340a6a81e8ec99c2117a82024-01-04T05:01:49ZengFrontiers Media S.A.Frontiers in Natural Products2813-26022024-01-01210.3389/fntpr.2023.13324361332436Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranumCelso R. de Oliveira0Zachary D. Ledvina1Michael D. Leonard2Samuel O. Odoh3Craig D. Dodson4Christopher S. Jeffrey5Department of Forestry and Wildlife Ecology, University of Wisconsin—Madison, Madison, WI, United StatesHitchcock Center for Chemical-Ecology, Department of Chemistry, University of Nevada—Reno, Reno, NV, United StatesTruckee Meadows Community College, Reno, NV, United StatesHitchcock Center for Chemical-Ecology, Department of Chemistry, University of Nevada—Reno, Reno, NV, United StatesHitchcock Center for Chemical-Ecology, Department of Chemistry, University of Nevada—Reno, Reno, NV, United StatesHitchcock Center for Chemical-Ecology, Department of Chemistry, University of Nevada—Reno, Reno, NV, United StatesA novel meroterpenoid cabagranin D was isolated with related neolignans cabagranins A–C from the leaves of Piper cabagranum (Costa Rica). Cabagranins A–C represent the first examples of 3,3′-neolignans isolated from the plant genus Piper, and the meroterpenoid cabagranin D displays an unprecedented Diels–Alder conjugate of an unsubstituted phenylpropenone and α-phellandrene. Details of the full structural elucidation of these compounds and a discussion of their potential biosynthetic relationships are presented.https://www.frontiersin.org/articles/10.3389/fntpr.2023.1332436/fullmeroterpeneDiels–AlderneolignanPiper cabagranumPiperaceae
spellingShingle Celso R. de Oliveira
Zachary D. Ledvina
Michael D. Leonard
Samuel O. Odoh
Craig D. Dodson
Christopher S. Jeffrey
Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum
Frontiers in Natural Products
meroterpene
Diels–Alder
neolignan
Piper cabagranum
Piperaceae
title Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum
title_full Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum
title_fullStr Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum
title_full_unstemmed Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum
title_short Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum
title_sort isolation of new neolignans and an unusual meroterpenoid from piper cabagranum
topic meroterpene
Diels–Alder
neolignan
Piper cabagranum
Piperaceae
url https://www.frontiersin.org/articles/10.3389/fntpr.2023.1332436/full
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