Antifibrotic pyridine-containing monoterpene alkaloids from Caryopteris glutinosa

Zhang, Xuejian; Cao, Yu; Pan, Dabo; Yao, Xiaojun; Wang, Fei; Zhang, Guolin; Luo, Yinggang

doi:10.1016/j.phytochem.2022.113378

Cited by 5 publications

(5 citation statements)

References 22 publications

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“…Three-dimensional structures of the molecules were drawn and subjected to conformational analysis in ComputeVOA using MMFF94 as force field and the GMMX methodology on a Windows operating system machine. Geometrical optimization and energy calculation of conformers occurring in an energy window (Δ E ) of 0–3 kcal/mol were done in Gaussian 16 software by implementation of B3LYP/DGDZVP due to its high accuracy and cost-effectiveness ratio scaling factor, using the COSMO solvation algorithm due to its algorithmic simplicity and numerical stability, as shown by multiple examples of successful applicability to fused ring heterocycles. − The optimized structures (Tables S4, S5, S6, and S7, Supporting Information) were used to calculate the thermochemical parameters estimated at 298 K and 1 atm. Calculations taking into account the solvent (MeOH) were carried out starting from DFT-optimized structures.…”

Section: Experimental Sectionmentioning

confidence: 99%

Formation of Trideuteromethylated Artifacts of Pyrrole-Containing Natural Products

Orfanoudaki,

Akee,

Martínez-Fructuoso

et al. 2024

J. Nat. Prod.

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Pyrrole-containing natural products form a large group of structurally diverse compounds that occur in both terrestrial and marine organisms. In the present study the formation of trideuteromethylated artifacts of pyrrole-containing natural products was investigated, focusing on the discorhabdins. Three deuterated discorhabdins, 1, 3, and 5, were identified to be isolation procedure artifacts caused by the presence of DMSO-d 6 during NMR sample preparation and handling. Three additional semisynthetic derivatives, 7−9, were made during the investigation of the mechanism of formation, which was shown to be driven by trideuteromethyl radicals in the presence of water, methanol, TFA, and traces of iron in the deuterated solvent. Generation of trideuteromethylated artifacts was also confirmed for other classes of pyrrolecontaining metabolites, namely, makaluvamines, tambjamines, and dibromotryptamines, which had also been dissolved in DMSO-d 6 during the structure elucidation process. Semisynthetic discorhabdins were assessed for antiproliferative activity against a panel of human tumor cell lines, and 14-trideuteromethyldiscorhabdin L (3) averaged low micromolar potency.

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Section: Experimental Sectionmentioning

confidence: 99%

Formation of Trideuteromethylated Artifacts of Pyrrole-Containing Natural Products

Orfanoudaki,

Akee,

Martínez-Fructuoso

et al. 2024

J. Nat. Prod.

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“…Caryopterisines F-I (4-7) and caryopterisines C-E (16)(17)(18) were subsequently isolated from C. glutinosa Rehder. Caryopterisines F-I (4-7) are four monoterpene alkaloids containing the cyclopentyl[c]pyridine skeleton, while caryopterisines C-E (16-18) represent three novel dimeric monoterpene alkaloids and are believed to be biosynthesized via the Diels-Alder reaction followed by aromatization rearrangement and a series of subsequent reactions [23]. Of these, caryopterisine C ( 16) has an unprecedented 6/5/6/6/5 pentacyclic ring framework, while caryopterisines D (17) and E (18) both have 6/6/6/5 fused ring frameworks.…”

Section: Classes Of Terpenoidal Alkaloids 21 Monoterpenoid Alkaloidsmentioning

confidence: 99%

“…Among them, (5S*,7R*)-7-Ethoxy-6, 7-dihydro-7-methyl-5H-cyclopenta[c]pyridin-5-ol ( 8) is a monoterpene alkaloid with a cyclopenta[c]pyridine framework [24]. (5aR*,6S*,10S*,11R*,11aR*)-10,11a-Dimethyl-6,7,9,10,11,11a-hexahydro-5H-6,11-epoxycyclopenta [6,7]azuleno [1,2-c]pyridin-5,8(5aH)dione (21) and (5aR*,6S*,7aR*,8S*,11aR*)-10-Hydroxy-7a,11a-dimethyl-5a,6,7,7a,8,11ahexahydro-5H-6,8-epoxycyclopenta [6,7]azuleno [1,2-c] pyridin-5-one (22) could be formed by fusion of the cyclopenta[c]pyridine and 4-Demethyliridoid, and (5R*,5aR*,10bS*,11R*)-5-Hydroxy-10b,11-dimethyl-5,5a,10b,11-tetrahydro-6H-5,11-methanopyrido [3 ′ ,4 ′ :3,4]cyclopenta [1,2-g]isoquinolin-6-one (23) and (6S*,6aR*,11R*,11aS*)-6a-Hydroxy-11,11a-dimethyl-6,6a,11, 11a-tetrahydro-5H-6,11-methanopyrido [3 ′ ,4 ′ :4,5]cyclopenta [1,2-h]isoquinolin-5-one (24) are dimerization products of two cyclopenta[c]pyridine [24]. Caryopteris glutinosa whole plant [22] (5aR*,6S*,10S*,11R*,11aR*)-10,11a-Dimethyl-6,7,9,10,11,11a-hexahydro-5H-6,11epoxycyclopenta [6,7]azuleno [1,2-c]pyridin-5,8(5aH)-dione.…”

Section: Classes Of Terpenoidal Alkaloids 21 Monoterpenoid Alkaloidsmentioning

confidence: 99%

Exploring the Biomedical Potential of Terpenoid Alkaloids: Sources, Structures, and Activities

Wang,

Xin,

Sun

et al. 2024

Molecules

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Terpenoid alkaloids are recognized as a class of compounds with limited numbers but potent biological activities, primarily derived from plants, with a minor proportion originating from animals and microorganisms. These alkaloids are synthesized from the same prenyl unit that forms the terpene skeleton, with the nitrogen atom introduced through β-aminoethanol, ethylamine, or methylamine, leading to a range of complex and diverse structures. Based on their skeleton type, they can be categorized into monoterpenes, sesquiterpenes, diterpenes, and triterpene alkaloids. To date, 289 natural terpenoid alkaloids, excluding triterpene alkaloids, have been identified in studies published between 2019 and 2024. These compounds demonstrate a spectrum of biological activities, including anti-inflammatory, antitumor, antibacterial, analgesic, and cardioprotective effects, making them promising candidates for further development. This review provides an overview of the sources, chemical structures, and biological activities of natural terpenoid alkaloids, serving as a reference for future research and applications in this area.

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“…Inhibition activities of the nine alkaloids on collagen accumulation through a cell-based assay were carried out. Caryopterisines C ( 24 ) was indicated to be a potential lead compound with antifibrotic activities [ 16 ].…”

Section: Mtpas and Their Activitiesmentioning

confidence: 99%

Sources, Transformations, Syntheses, and Bioactivities of Monoterpene Pyridine Alkaloids and Cyclopenta[c]pyridine Derivatives

Zhang

Tao

et al. 2022

Molecules

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Monoterpene pyridine alkaloids (MTPAs) are alkaloids derived from iridoid glycosides (IGs). The common molecular structure of MTPAs is the pyridine ring, while some of them have a cyclopenta[c]pyridine skeleton. Some compounds containing this structure are potentially bioactive medicinal agents. In this paper, seven drug candidates (A–G), ninety natural source products (1–90), thirty-seven synthesized compounds (91–127), as well as twenty-six key intermediates (S1–S26) were summarized. We categorized five types of MTPAs and one type of cyclopenta[c]pyridine alkaloids in all. Additionally, their possible genetic pathways were proposed. Then, the chemical transformation, biotransformation, chemical synthesis, as well as the bioactivity of MTPAs and cyclopenta[c]pyridine derivatives were analyzed and summarized. Cyclopenta[c]pyridine derivatives can be concisely and chirally synthesized, and they have shown potentials with antibacterial, insecticidal, antiviral, anti-inflammatory, and neuropharmacological activities.

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Antifibrotic pyridine-containing monoterpene alkaloids from Caryopteris glutinosa

Cited by 5 publications

References 22 publications

Formation of Trideuteromethylated Artifacts of Pyrrole-Containing Natural Products

Formation of Trideuteromethylated Artifacts of Pyrrole-Containing Natural Products

Exploring the Biomedical Potential of Terpenoid Alkaloids: Sources, Structures, and Activities

Sources, Transformations, Syntheses, and Bioactivities of Monoterpene Pyridine Alkaloids and Cyclopenta[c]pyridine Derivatives

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