A systematic review of proaporphine alkaloids and a pharmacological update
Background: Proaporphine alkaloids are present in many plant families. They are often considered as metabolic precursors to aporphines. They generally contain a cyclohexadienone system and can rearrange to aporphines on treatment with acid. Typical proaporphines include the alkaloids pronuciferine,...
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Elsevier
2025-02-01
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| Series: | Phytomedicine Plus |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2667031324001635 |
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| author | Christian Bailly |
| author_facet | Christian Bailly |
| author_sort | Christian Bailly |
| collection | DOAJ |
| description | Background: Proaporphine alkaloids are present in many plant families. They are often considered as metabolic precursors to aporphines. They generally contain a cyclohexadienone system and can rearrange to aporphines on treatment with acid. Typical proaporphines include the alkaloids pronuciferine, stepharine, crotsparine, glaziovine and many analogues with different substitution patterns. The proaporphine glaziovine has been used in human as a tranquilizer to treat anxiety and depression but otherwise proaporphines have received little attention as medicinal products. Proaporphines have been neglected compared to aporphines. Purpose: The present review provides a survey of a hundred of proaporphine alkaloids isolated from plants, divided into three groups: conventional proaporphines (including mecambrine, roemeronine and orientalinone among others), homoproaporphines with a tetracyclic or pentacyclic core (such as kreysiginone and robustamine), and various proaporphine hybrid molecules (roemeridine, magnostepharine and diverse analogues). Results: The structural diversity of proaporphines is presented. The properties of prototypic proaporphine alkaloids are discussed, and their mechanisms of action are underlined. The case of atypical but promising proaporphine dimers, such as distepharinamide targeting tumor infiltrating T regulatory cells, is also addressed. Conclusion: The analysis offers a survey of the proaporphine landscape with the goal to highlight the molecular diversity in the family and to encourage further researches into their mechanism of action and medicinal properties. |
| format | Article |
| id | doaj-art-f3b0a35785cd4f8f9031310979c22999 |
| institution | Kabale University |
| issn | 2667-0313 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Phytomedicine Plus |
| spelling | doaj-art-f3b0a35785cd4f8f9031310979c229992025-02-10T04:35:08ZengElsevierPhytomedicine Plus2667-03132025-02-0151100689A systematic review of proaporphine alkaloids and a pharmacological updateChristian Bailly0CNRS, Inserm, CHU Lille, UMR9020-U1277-CANTHER—Cancer Heterogeneity Plasticity and Resistance to Therapies, OncoLille Institut, University of Lille, F-59000 Lille, France; Institute of Pharmaceutical Chemistry Albert Lespagnol (ICPAL), Faculty of Pharmacy, University of Lille, F-59006 Lille, France; OncoWitan, Scientific Consulting Office, F-59290 Lille, France; Correspondence author.Background: Proaporphine alkaloids are present in many plant families. They are often considered as metabolic precursors to aporphines. They generally contain a cyclohexadienone system and can rearrange to aporphines on treatment with acid. Typical proaporphines include the alkaloids pronuciferine, stepharine, crotsparine, glaziovine and many analogues with different substitution patterns. The proaporphine glaziovine has been used in human as a tranquilizer to treat anxiety and depression but otherwise proaporphines have received little attention as medicinal products. Proaporphines have been neglected compared to aporphines. Purpose: The present review provides a survey of a hundred of proaporphine alkaloids isolated from plants, divided into three groups: conventional proaporphines (including mecambrine, roemeronine and orientalinone among others), homoproaporphines with a tetracyclic or pentacyclic core (such as kreysiginone and robustamine), and various proaporphine hybrid molecules (roemeridine, magnostepharine and diverse analogues). Results: The structural diversity of proaporphines is presented. The properties of prototypic proaporphine alkaloids are discussed, and their mechanisms of action are underlined. The case of atypical but promising proaporphine dimers, such as distepharinamide targeting tumor infiltrating T regulatory cells, is also addressed. Conclusion: The analysis offers a survey of the proaporphine landscape with the goal to highlight the molecular diversity in the family and to encourage further researches into their mechanism of action and medicinal properties.http://www.sciencedirect.com/science/article/pii/S2667031324001635AlkaloidsGlaziovineNatural productsHomoproaporphineProaporphinePronuciferine |
| spellingShingle | Christian Bailly A systematic review of proaporphine alkaloids and a pharmacological update Phytomedicine Plus Alkaloids Glaziovine Natural products Homoproaporphine Proaporphine Pronuciferine |
| title | A systematic review of proaporphine alkaloids and a pharmacological update |
| title_full | A systematic review of proaporphine alkaloids and a pharmacological update |
| title_fullStr | A systematic review of proaporphine alkaloids and a pharmacological update |
| title_full_unstemmed | A systematic review of proaporphine alkaloids and a pharmacological update |
| title_short | A systematic review of proaporphine alkaloids and a pharmacological update |
| title_sort | systematic review of proaporphine alkaloids and a pharmacological update |
| topic | Alkaloids Glaziovine Natural products Homoproaporphine Proaporphine Pronuciferine |
| url | http://www.sciencedirect.com/science/article/pii/S2667031324001635 |
| work_keys_str_mv | AT christianbailly asystematicreviewofproaporphinealkaloidsandapharmacologicalupdate AT christianbailly systematicreviewofproaporphinealkaloidsandapharmacologicalupdate |