Isolation and biological activity of azocine and azocane alkaloids

Lee, Stephanie J.; Sperry, Jonathan

doi:10.1016/j.bmc.2021.116560

Cited by 16 publications

(5 citation statements)

References 167 publications

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“…4 In particular, eight-membered nitrogenheterocycles are regarded as compelling privileged structures for drug discovery, especially for challenging targets that are difficult to modulate by conventional small molecule screening libraries. [5][6][7][8] In general, the installment of nitrogen heteroatoms in a ring system enhances the interaction with a biological target, yielding pharmaceuticals with more potent activities. 9,10 For example, (+)-balasubramide, an eight-membered lactam isolated from Clausena indica exhibits anti-neuroinflammatory properties (Scheme 1A).…”

Section: Introductionmentioning

confidence: 99%

Recent progress in the construction of eight-membered nitrogen-heterocycles

Li,

Dong,

Zhao

2024

New J. Chem.

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Section: Introductionmentioning

confidence: 99%

Recent progress in the construction of eight-membered nitrogen-heterocycles

Li,

Dong,

Zhao

2024

New J. Chem.

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“…The growth and development of microbes' resistant antibiotics prompted the research on nding alternative materials from a variety of sources. Among many potential medicinal plants, Alstonia scholaris (A. scholaris) commonly known as blackboard tree or devil tree is a native plant species found in various countries such as India (locally called saptaparni) Cambodia (called popeal khe), China (locally referred as Tang jiao shu) Indonesia (pulai as popularly called) Laos (called as dtin pet) in Malaysia (Popularly called Rejang or Pulai) Myanmar (Toungmayobeng s the local name), Philippines (Ditaa popularly called), and Vietnam (Sua, mo cua as the local name) 18,19 . It is a member of Apocyanacae that contains various metabolites such as monoterpenoid and indole alkaloids.…”

Section: Introductionmentioning

confidence: 99%

Alstonia scholaris Leaves: A Biochemical Marvel for Eco-friendly Copper Nanoparticles Synthesis

Labaran,

Zango,

Tailor

et al. 2024

Preprint

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The utilization of plants for the production of metallic nanoparticles is gaining significant attention in research. In this study, we conducted phytochemical screening of Alstonia scholaris (A. scholaris) leaves extracts using various solvents, including chloroform, ethyl acetate, n-hexane, methanol, and water. Our findings revealed higher proportions of flavonoids and alkaloids in both solvents compared to other phytochemical species. In the methanol, extract proteins, anthraquinone and reducing sugar were not detected. On the other hand, the aqueous extract demonstrated the presence of amino acids, reducing sugar, phenolic compounds, anthraquinone, and saponins. Notably, ethyl acetate and chloroform extracts displayed the highest levels of bioactive compounds among all solvents. Intrigued by these results, we proceeded to investigate the antibacterial properties of the leaf extracts against two major bacterial strains, Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus). All extracts exhibited significant zones of inhibition against both bacterial isolates, with S. aureus showing higher susceptibility compared to E. coli. Notably, the methanol extract displayed the most potent I hibitory effect against all organisms. Inspired by the bioactivity of the methanol extract, we employed it as a plant-based material for the green synthesis of copper nanoparticles (Cu-NPs). The synthesized Cu-NPs were characterized using Fourier infrared spectroscopy (FT-IR), UV-visible spectroscopic analysis, and scanning electron microscopy (SEM). The observed color changes confirmed the successful formation of Cu-NPs, while the FTIR analysis matched previously reported peaks, further verifying the synthesis. The SEM micrographs indicated the irregular shapes of the surface particles. From the result obtained by energy dispersive x-ray (EDX) spectroscopic analysis, Cu has the highest relative abundance of 67.41 wt.%. confirming the purity of the Cu-NPs colloid. These findings contribute to the growing field of eco-friendly nanotechnology and emphasize the significance of plant-mediated approaches in nanomaterial synthesis and biomedical applications.

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“…Deoxyisoaustamide alkaloids are the most common derivatives of azocinoindole found in nature [ 1 ]. To date, these compounds have only been reported as fungal metabolites.…”

Section: Introductionmentioning

confidence: 99%

New Marine Fungal Deoxy-14,15-Dehydroisoaustamide Resensitizes Prostate Cancer Cells to Enzalutamide

et al. 2023

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Marine fungi serve as a valuable source for new bioactive molecules bearing various biological activities. In this study, we report on the isolation of a new indole diketopiperazine alkaloid deoxy-14,15-dehydroisoaustamide (1) from the marine-derived fungus Penicillium dimorphosporum KMM 4689 associated with a soft coral. The structure of this metabolite, including its absolute configuration, was determined by HR-MS, 1D and 2D NMR as well as CD data. Compound 1 is a very first deoxyisoaustamide alkaloid possessing two double bonds in the proline ring. The isolated compound was noncytotoxic to a panel of human normal and cancer cell lines up to 100 µM. At the same time, compound 1 resensitized prostate cancer 22Rv1 cells to androgen receptor (AR) blocker enzalutamide. The mechanism of this phenomenon was identified as specific drug-induced degradation of androgen receptor transcription variant V7 (AR-V7), which also resulted in general suppression of AR signaling. Our data suggest that the isolated alkaloid is a promising candidate for combinational therapy of castration resistant prostate cancer, including drug-resistant subtypes.

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Isolation and biological activity of azocine and azocane alkaloids

Cited by 16 publications

References 167 publications

Recent progress in the construction of eight-membered nitrogen-heterocycles

Recent progress in the construction of eight-membered nitrogen-heterocycles

Alstonia scholaris Leaves: A Biochemical Marvel for Eco-friendly Copper Nanoparticles Synthesis

New Marine Fungal Deoxy-14,15-Dehydroisoaustamide Resensitizes Prostate Cancer Cells to Enzalutamide

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