Sign in to use this feature.

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline
remove_circle_outline

Journals

Article Types

Countries / Regions

Search Results (3)

Search Parameters:
Keywords = granatane alkaloids

Order results
Result details
Results per page
Select all
Export citation of selected articles as:
21 pages, 4353 KiB  
Article
Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity
by Damian Pawelski, Alicja Walewska, Sylwia Ksiezak, Dariusz Sredzinski, Piotr Radziwon, Marcin Moniuszko, Ramesh Gandusekar, Andrzej Eljaszewicz, Ryszard Lazny, Krzysztof Brzezinski and Marta E. Plonska-Brzezinska
Int. J. Mol. Sci. 2021, 22(21), 11384; https://doi.org/10.3390/ijms222111384 - 21 Oct 2021
Cited by 4 | Viewed by 3923
Abstract
Curcumin (CUR) is a natural compound that exhibits anti-inflammatory, anti-bacterial, and other biological properties. However, its application as an effective drug is problematic due to its poor oral bioavailability, solubility in water, and poor absorption from the gastrointestinal tract. The aim of this [...] Read more.
Curcumin (CUR) is a natural compound that exhibits anti-inflammatory, anti-bacterial, and other biological properties. However, its application as an effective drug is problematic due to its poor oral bioavailability, solubility in water, and poor absorption from the gastrointestinal tract. The aim of this work is to synthesize monocarbonyl analogs of CUR based on the 9-methyl-9-azabicyclo[3.2.1]nonan-3-one (pseudopelletierine, granatanone) scaffold to improve its bioavailability. Granatane is a homologue of tropane, whose structure is present in numerous naturally occurring alkaloids, e.g., l-cocaine and l-scopolamine. In this study, ten new pseudopelletierine-derived monocarbonyl analogs of CUR were successfully synthesized and characterized by spectral methods and X-ray crystallography. Additionally, in vitro test of the cytotoxicity and anti-inflammatory properties of the synthesized compounds were performed. Full article
(This article belongs to the Special Issue Drug Design, Synthesis and Delivery)
Show Figures

Figure 1

8 pages, 2492 KiB  
Article
Improved Synthesis of N-Methylcadaverine
by Kayla N. Anderson, Shiva Moaven, Daniel K. Unruh, Anthony F. Cozzolino and John C. D’Auria
Molecules 2018, 23(5), 1216; https://doi.org/10.3390/molecules23051216 - 19 May 2018
Cited by 1 | Viewed by 5962
Abstract
Alkaloids compose a large class of natural products, and mono-methylated polyamines are a common intermediate in their biosynthesis. In order to evaluate the role of selectively methylated natural products, synthetic strategies are needed to prepare them. Here, N-methylcadaverine is prepared in 37.3% [...] Read more.
Alkaloids compose a large class of natural products, and mono-methylated polyamines are a common intermediate in their biosynthesis. In order to evaluate the role of selectively methylated natural products, synthetic strategies are needed to prepare them. Here, N-methylcadaverine is prepared in 37.3% yield in three steps. The alternative literature two-step strategy resulted in reductive deamination to give N-methylpiperidine as determined by the single crystal structure. A straightforward strategy to obtain the mono-alkylated aliphatic diamine, cadaverine, which avoids potential side-reactions, is demonstrated. Full article
Show Figures

Graphical abstract

25 pages, 3412 KiB  
Review
Tropane and Granatane Alkaloid Biosynthesis: A Systematic Analysis
by Neill Kim, Olga Estrada, Benjamin Chavez, Charles Stewart and John C. D’Auria
Molecules 2016, 21(11), 1510; https://doi.org/10.3390/molecules21111510 - 11 Nov 2016
Cited by 57 | Viewed by 17900
Abstract
The tropane and granatane alkaloids belong to the larger pyrroline and piperidine classes of plant alkaloids, respectively. Their core structures share common moieties and their scattered distribution among angiosperms suggest that their biosynthesis may share common ancestry in some orders, while they may [...] Read more.
The tropane and granatane alkaloids belong to the larger pyrroline and piperidine classes of plant alkaloids, respectively. Their core structures share common moieties and their scattered distribution among angiosperms suggest that their biosynthesis may share common ancestry in some orders, while they may be independently derived in others. Tropane and granatane alkaloid diversity arises from the myriad modifications occurring to their core ring structures. Throughout much of human history, humans have cultivated tropane- and granatane-producing plants for their medicinal properties. This manuscript will discuss the diversity of their biological and ecological roles as well as what is known about the structural genes and enzymes responsible for their biosynthesis. In addition, modern approaches to producing some pharmaceutically important tropanes via metabolic engineering endeavors are discussed. Full article
(This article belongs to the Special Issue Diversity of Alkaloids)
Show Figures

Graphical abstract

Back to TopTop