Trimeric and Dimeric Carbazole Alkaloids from Murraya microphylla

Ma, Xiuli; Chen, Hongwei; Zhu, Si-Si; Tu, Peng‐Fei; Jiang, Yong

doi:10.3390/molecules26185689

Cited by 6 publications

(2 citation statements)

References 25 publications

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“…Alkaloid dimers are relatively frequent (notably among Vinca alkaloids, for example), but tetra and pentamers are much rarer. A few trimeric indole alkaloids have been reported [216][217][218], but higherorder structures are extremely rare. For example, a tetramer and hexamer of the alkaloid terguride were isolated, but the oligomerization is limited and strongly reduces the high affinity of terguride for 5-HT2A receptors [219,220].…”

Section: Discussion and Perspectivesmentioning

confidence: 99%

Traditional Uses, Pharmacology and Phytochemistry of the Medicinal Plant Flueggea virosa (Roxb. ex Willd.) Royle

Bailly

2024

Future Pharmacology

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The white berry bush, officially Flueggea virosa (Roxb. ex Willd.) Royle is a medicinal plant distributed throughout tropical areas and traditionally used in Africa, India and China. Root decoctions are used to treat abdominal pain, whereas extracts from the aerial parts serve to treat liver and urinary diseases, inflammatory pathologies and diabetes, among other pathologies. Plant extracts have revealed antiparasitic, antimicrobial, antiepilepsy, antidiabetic, anticancer and analgesic effects. Three main categories of phytochemicals were isolated from F. virosa: polyphenols, with the lead product bergenin; terpenoids, such as the flueggenoids and related podocarpane-type diterpenoids; and many alkaloids derived from securinine and norsecurinine. A remarkable feature of S. virosa is the production of norsecurinine oligomers, including macromolecular tetramers and pentamers, such as fluevirosinines. The most potent anticancer alkaloid in the family is the dimeric indolizidine flueggine B, which was identified as a potential binder to α/β-tubulin dimer, which is a known target for securinine. This review highlights the diversity of phytochemicals identified from S. virosa and the potential therapeutic benefits of dimeric alkaloids. Studies are encouraged to further investigate the therapeutic properties of the lead compounds but also define and finesse the nutritional profile of the edible fruit.

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Section: Discussion and Perspectivesmentioning

confidence: 99%

Traditional Uses, Pharmacology and Phytochemistry of the Medicinal Plant Flueggea virosa (Roxb. ex Willd.) Royle

Bailly

2024

Future Pharmacology

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“…Microphyltrine, microphyldines A-O and microphyldine P were isolated from the stem and leaves of M. microphylla [41]. Nitric oxide production induced by LPS in BV-2 microglial cells was inhibited by phyto-carbazole alkaloids from M. tetramera and M. kwangsiensis [19,42], with IC 50 values ranging from 5.1 to 15.1 µM [43].…”

Section: Phyto-carbazole Alkaloids From the Genus Murrayamentioning

confidence: 99%

Phyto-Carbazole Alkaloids from the Rutaceae Family as Potential Protective Agents against Neurodegenerative Diseases

Tan

Sharma

2022

Antioxidants

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Plant-derived (phyto) carbazole alkaloids are an important class of compounds, presented in the family of Rutaceae (Genera Murraya, Clausena, Glycosmis, Micromelum and Zanthoxylum). Due to several significant biological activities, such as antitumor, antibacterial, antiviral, antidiabetic, anti-HIV and neuroprotective activities of the parent skeleton (3-methylcarbazole), carbazole alkaloids are recognized as an important class of potential therapeutic agents. Neurodegenerative diseases (NDs) may exhibit a vast range of conditions, affecting neurons primarily and leading ultimately to the progressive losses of normal motor and cognitive functions. The main pathophysiological indicators of NDs comprise increasing atypical protein folding, oxidative stresses, mitochondrial dysfunctions, deranged neurotransmissions and neuronal losses. Phyto-carbazole alkaloids can be investigated for exerting multitarget approaches to ameliorating NDs. This review presents a comprehensive evaluation of the available scientific literature on the neuroprotective mechanisms of phyto-carbazole alkaloids from the Rutaceae family in ameliorating NDs.

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Diastereoselective Biomimetic Synthesis of Dimeric Tetrahydrocarbazoles via a Copper(II)‐Catalyzed Cycloisomerization‐[3+2] Cyclodimerization Cascade

Roy

Baire

2023

Angewandte Chemie

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The cyclodimerization (homochiral‐ and heterochiral−) of monomeric units for the construction of stereodefined polycyclic systems is a powerful strategy in both biosynthesis and biomimetic synthesis. Herein we have discovered and developed a CuII‐ catalyzed, biomimetic, diastereoselective tandem cycloisomerization‐[3+2] cyclodimerization of 1‐(indol‐2‐yl)pent‐4‐yn‐3‐ol. This novel strategy operates under very mild conditions, providing access to structurally unprecedented dimeric tetrahydrocarbazoles fused to a tetrahydrofuran unit in excellent yields of the products. Several fruitful control experiments, isolation of the monomeric‐cycloisomerized products and their subsequent conversion into the corresponding cyclodimeric products supported their intermediacy and the possible mechanism as a cycloisomerization‐diastereoselective [3+2] cyclodimerization cascade. The cyclodimerization involves a substituent controlled, highly diastereoselective homochiral [3+2] annulation or heterochiral [3+2] annulation of in situ generated 3‐hydroxytetrahydrocarbazoles. The key and important features of this strategy are: a) construction of three new C−C bonds & one new C−O bond; b) creation of two new stereocenters, and c) construction of three new rings, in a single operation; d) low catalyst loading (1–5 mol %); e) 100 % atom economy; and f) rapid construction of structurally unprecedented natural product like polycyclic frameworks. A chiral pool version using an enantio‐ and diastereopure substrate was also demonstrated.

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Trimeric and Dimeric Carbazole Alkaloids from Murraya microphylla

Cited by 6 publications

References 25 publications

Traditional Uses, Pharmacology and Phytochemistry of the Medicinal Plant Flueggea virosa (Roxb. ex Willd.) Royle

Traditional Uses, Pharmacology and Phytochemistry of the Medicinal Plant Flueggea virosa (Roxb. ex Willd.) Royle

Phyto-Carbazole Alkaloids from the Rutaceae Family as Potential Protective Agents against Neurodegenerative Diseases

Diastereoselective Biomimetic Synthesis of Dimeric Tetrahydrocarbazoles via a Copper(II)‐Catalyzed Cycloisomerization‐[3+2] Cyclodimerization Cascade

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