Isolation and Synthesis of Novel Meroterpenoids from <i>Rhodomyrtus tomentos</i>a: Investigation of a Reactive Enetrione Intermediate

Qin, Xu‐Jie; Rauwolf, Tyler J.; Li, Pan‐Pan; Liu, Hui; McNeely, James; Hua, Yan; Liu, Haiyang; Porco, John A.

doi:10.1002/ange.201814421

Cited by 7 publications

(2 citation statements)

References 59 publications

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“…Compound 51 prevented the impairment of spatial memory, reversed dendritic spine density defects, suppressed the promotion of glycogen synthase kinase-3β activity, and reversed the decrease of brain-derived neurotrophic factor and postsynaptic density protein 95. The petroleum ether extract of leaves and stems of R. tomentosa exhibited a significant acetylcholinesterase (AChE) inhibition rate (81%, 500 μg/mL) (Qin et al, 2019), and then active compounds 103, 105 and 106 were isolated from R. tomentosa and evaluated the AChE inhibitory effect, with the favorable IC50 values of 6.6, 8.8 and 6.0 μM, respectively.…”

Section: Other Activitiesmentioning

confidence: 99%

Rhodomyrtus tomentosa (Aiton.): A review of phytochemistry, pharmacology and industrial applications research progress

Zhao

Xie

et al. 2020

Food Chemistry

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Rhodomyrtus tomentosa (Aiton) is a flowering plant native to southern and southeastern Asia.Up to date, 106 chemical constituents have been isolated and identified from R. tomentosa. Among these compounds, triterpenoids, flavonoids, phenols and meroterpenoids are the major constituents. Investigations of pharmacological activities of R. tomentosa revealed that this edible medicinal herb exhibits a wide range of therapeutic potential including antibacterial, antitumor, anti-inflammatory and antioxidant activities both in vivo and in vitro. The purpose of this review is to provide an overview of R. tomentosa studies until 2019. This article also intends to review advances in the botanical, phytochemical, pharmacological studies and industrial applications of R. tomentosa, which will provide a useful bibliography for further investigations and applications of R. tomentosa in medicines and foods.

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Section: Other Activitiesmentioning

confidence: 99%

Rhodomyrtus tomentosa (Aiton.): A review of phytochemistry, pharmacology and industrial applications research progress

Zhao

Xie

et al. 2020

Food Chemistry

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“…Phloroglucinol based meroterpenoids, isolated from species of Myrtaceae family, are a class of characteristic components generally made up of a phloroglucinol derivative and a mono/sesquiterpenoid moiety. These natural products have also attracted considerable interests from our research group [7–9] . As part of our continuing efforts to search for structurally intriguing and bioactive molecules from Myrtaceae family, three new polymethylated phloroglucinol meroterpenoids (PPMs), named rhotomentodiones C−E ( Figure 1), were obtained from the twigs and leaves of Rhodomyrtus tomentosa .…”

Section: Introductionmentioning

confidence: 99%

Polymethylated Phloroglucinol Meroterpenoids from Rhodomyrtus tomentosa and Their Antibacterial and Acetylcholinesterase Inhibitory Effects

Liu

et al. 2020

Chemistry & Biodiversity

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Rhotomentodiones CÀ E, three new polymethylated phloroglucinol meroterpenoids with diverse configurations, were isolated from the twigs and leaves of Rhodomyrtus tomentosa. Their structures and absolute configurations were established mainly by means of comprehensive spectroscopic data and electron circular dichroism (ECD) calculation. Among them, Rhotomentodione D (2) exhibited both antibacterial activity with an MIC value of 12.5 μg/mL against Propionibacterium acnes and AChE inhibitory activity with an IC 50 value of 22.9 μM.

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Nitrone and Alkyne Cascade Reactions for Regio‐ and Diastereoselective 1‐Pyrroline Synthesis

et al. 2021

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The synthesis of 1-pyrrolines from N-alkenylnitrones and alkynes has been explored as ar etrosynthetic alternative to traditional approaches.T hese cascade reactions are formal [4 + 1] cycloadditions that proceed through ap roposed dipolar cycloaddition and N-alkenylisoxazoline [3,3']sigmatropic rearrangement. Av ariety of cyclic alkynes and terminal alkynes have been shown to undergo the transformation with N-alkenylnitrones under mild conditions to provide the corresponding spirocyclic and densely substituted 1-pyrrolines with high regio-and diastereoselectivity.M echanistic studies provide insight into the balance of steric and electronic effects that promote the cascade process and control the diastereo-and regioisomeric preferences of the 1-pyrroline products.D iastereoselective derivatization of the 1-pyrrolines prepared by the cascade reaction demonstrate the divergent synthetic utility of the new method.Scheme 1. N-Alkenylisoxazoline approach to 1-pyrroline synthesis.LG = leaving group. EWG = electron-withdrawing group.

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Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate

Cited by 7 publications

References 59 publications

Rhodomyrtus tomentosa (Aiton.): A review of phytochemistry, pharmacology and industrial applications research progress

Rhodomyrtus tomentosa (Aiton.): A review of phytochemistry, pharmacology and industrial applications research progress

Polymethylated Phloroglucinol Meroterpenoids from Rhodomyrtus tomentosa and Their Antibacterial and Acetylcholinesterase Inhibitory Effects

Nitrone and Alkyne Cascade Reactions for Regio‐ and Diastereoselective 1‐Pyrroline Synthesis

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