A Classic Photochemical Approach Inducing an Unexpected Rearrangement: Exploring the Photoreactivity of Pentacyclic Triterpenic Acids

Federica Rogati; Chiara Maioli; Gianluigi Lauro; DIEGO CAPRIOGLIO; DANIELA IMPERIO; Erika DEL GROSSO; Bruno Botta; Luisa Mannina; Giuseppe Bifulco; Cinzia Ingallina; Alberto MINASSI

doi:10.1021/acs.jnatprod.3c00067

A Classic Photochemical Approach Inducing an Unexpected Rearrangement: Exploring the Photoreactivity of Pentacyclic Triterpenic Acids

Federica Rogati
, Chiara Maioli
, Gianluigi Lauro
, DIEGO CAPRIOGLIO
, DANIELA IMPERIO
, Erika DEL GROSSO
, Bruno Botta
, Luisa Mannina
, Giuseppe Bifulco
, Cinzia Ingallina
, Alberto MINASSI

Research output: Contribution to journal › Article › peer-review

Abstract

The discovery of new bioactivities is closely related to the generation of novel scaffolds, and in the past few years different strategies have been proposed to obtain unknown architectures from the manipulation of known compounds. In the present study, we exploited a vintage photochemical approach for the discovery of an unexpected pathway of reactivity related to Δ1-3-oxo-pentacyclic triterpenic acids gaining access to a new class of natural–unnatural 5(10→1)abeo-pentacyclic triterpenic acids.

Original language	English
Pages (from-to)	1025-1032
Number of pages	8
Journal	Journal of Natural Products
Volume	86
Issue number	4
DOIs	https://doi.org/10.1021/acs.jnatprod.3c00067
Publication status	Published - 2023

Keywords

natural products
photochemical rearrangements
photochemistry
terpenes

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10.1021/acs.jnatprod.3c00067

https://hdl.handle.net/11579/152881

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Rogati, F., Maioli, C., Lauro, G., CAPRIOGLIO, DIEGO., IMPERIO, DANIELA., DEL GROSSO, E., Botta, B., Mannina, L., Bifulco, G., Ingallina, C., & MINASSI, A. (2023). A Classic Photochemical Approach Inducing an Unexpected Rearrangement: Exploring the Photoreactivity of Pentacyclic Triterpenic Acids. Journal of Natural Products, 86(4), 1025-1032. https://doi.org/10.1021/acs.jnatprod.3c00067

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title = "A Classic Photochemical Approach Inducing an Unexpected Rearrangement: Exploring the Photoreactivity of Pentacyclic Triterpenic Acids",

abstract = "The discovery of new bioactivities is closely related to the generation of novel scaffolds, and in the past few years different strategies have been proposed to obtain unknown architectures from the manipulation of known compounds. In the present study, we exploited a vintage photochemical approach for the discovery of an unexpected pathway of reactivity related to Δ1-3-oxo-pentacyclic triterpenic acids gaining access to a new class of natural–unnatural 5(10→1)abeo-pentacyclic triterpenic acids.",

keywords = "natural products, photochemical rearrangements, photochemistry, terpenes, natural products, photochemical rearrangements, photochemistry, terpenes",

author = "Federica Rogati and Chiara Maioli and Gianluigi Lauro and DIEGO CAPRIOGLIO and DANIELA IMPERIO and \{DEL GROSSO\}, Erika and Bruno Botta and Luisa Mannina and Giuseppe Bifulco and Cinzia Ingallina and Alberto MINASSI",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society and American Society of Pharmacognosy.",

year = "2023",

doi = "10.1021/acs.jnatprod.3c00067",

language = "English",

volume = "86",

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Rogati, F, Maioli, C, Lauro, G, CAPRIOGLIO, DIEGO , IMPERIO, DANIELA , DEL GROSSO, E, Botta, B, Mannina, L, Bifulco, G, Ingallina, C & MINASSI, A 2023, 'A Classic Photochemical Approach Inducing an Unexpected Rearrangement: Exploring the Photoreactivity of Pentacyclic Triterpenic Acids', Journal of Natural Products, vol. 86, no. 4, pp. 1025-1032. https://doi.org/10.1021/acs.jnatprod.3c00067

TY - JOUR

T1 - A Classic Photochemical Approach Inducing an Unexpected Rearrangement: Exploring the Photoreactivity of Pentacyclic Triterpenic Acids

AU - Rogati, Federica

AU - Maioli, Chiara

AU - Lauro, Gianluigi

AU - CAPRIOGLIO, DIEGO

AU - IMPERIO, DANIELA

AU - DEL GROSSO, Erika

AU - Botta, Bruno

AU - Mannina, Luisa

AU - Bifulco, Giuseppe

AU - Ingallina, Cinzia

AU - MINASSI, Alberto

PY - 2023

Y1 - 2023

N2 - The discovery of new bioactivities is closely related to the generation of novel scaffolds, and in the past few years different strategies have been proposed to obtain unknown architectures from the manipulation of known compounds. In the present study, we exploited a vintage photochemical approach for the discovery of an unexpected pathway of reactivity related to Δ1-3-oxo-pentacyclic triterpenic acids gaining access to a new class of natural–unnatural 5(10→1)abeo-pentacyclic triterpenic acids.

AB - The discovery of new bioactivities is closely related to the generation of novel scaffolds, and in the past few years different strategies have been proposed to obtain unknown architectures from the manipulation of known compounds. In the present study, we exploited a vintage photochemical approach for the discovery of an unexpected pathway of reactivity related to Δ1-3-oxo-pentacyclic triterpenic acids gaining access to a new class of natural–unnatural 5(10→1)abeo-pentacyclic triterpenic acids.

KW - natural products

KW - photochemical rearrangements

KW - photochemistry

KW - terpenes

KW - natural products

KW - photochemical rearrangements

KW - photochemistry

KW - terpenes

UR - https://iris.uniupo.it/handle/11579/152881

U2 - 10.1021/acs.jnatprod.3c00067

DO - 10.1021/acs.jnatprod.3c00067

M3 - Article

SN - 1520-6025

VL - 86

SP - 1025

EP - 1032

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 4

ER -

A Classic Photochemical Approach Inducing an Unexpected Rearrangement: Exploring the Photoreactivity of Pentacyclic Triterpenic Acids

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Keywords

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