Moschamine-Related Indole Alkaloids

Xia, Chengfeng; Tong, Xiaogang

doi:10.1016/bs.alkal.2017.12.004

Cited by 6 publications

(5 citation statements)

References 55 publications

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“…Inhibition of NF-κB is associated with increased sensitivity to chemotherapy [33], and has therefore been proposed as a strategy for treating glioblastoma [15]. Given that CS is known to inhibit NF-κB [40], and based on the common structural characteristics and the similarity in in vitro action [41,42], NF-κB is a potent candidate for glioblastoma treatment. Several members of the NF-κB family (i.e., human RELA, human NFKB1, murine NFKB1, and human IKBKB, based on the TRRUST Database) are included among the top 10 enriched TFs in GTN genes.…”

Section: Discussionmentioning

confidence: 99%

An NF-κB- and Therapy-Related Regulatory Network in Glioma: A Potential Mechanism of Action for Natural Antiglioma Agents

et al. 2022

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High-grade gliomas are among the most aggressive malignancies, with significantly low median survival. Recent experimental research in the field has highlighted the importance of natural substances as possible antiglioma agents, also known for their antioxidant and anti-inflammatory action. We have previously shown that natural substances target several surface cluster of differentiation (CD) markers in glioma cells, as part of their mechanism of action. We analyzed the genome-wide NF-κB binding sites residing in consensus regulatory elements, based on ENCODE data. We found that NF-κB binding sites reside adjacent to the promoter regions of genes encoding CD markers targeted by antiglioma agents (namely, CD15/FUT4, CD28, CD44, CD58, CD61/SELL, CD71/TFRC, and CD122/IL2RB). Network and pathway analysis revealed that the markers are associated with a core network of genes that, altogether, participate in processes that associate tumorigenesis with inflammation and immune evasion. Our results reveal a core regulatory network that can be targeted in glioblastoma, with apparent implications in individuals that suffer from this devastating malignancy.

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Section: Discussionmentioning

confidence: 99%

An NF-κB- and Therapy-Related Regulatory Network in Glioma: A Potential Mechanism of Action for Natural Antiglioma Agents

et al. 2022

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“…The indole structure is regarded as one of the most privileged classes of heterocycles representing structural core of many natural and non-natural compounds with a range of biological activities. 1 The indole alkaloids have been a subject of intense structural, pharmacological, biosynthetic and synthetic studies, because of the structural diversity and complexity of many of its members, along with the important physiological and medicinal properties displayed by this class of compounds. 2 Similarly, natural product inspired compounds based on polycyclic indole alkaloids also exhibit interesting biological activities.…”

Section: Introductionmentioning

confidence: 99%

Aza-Annulation of 1,2,3,4-Tetrahydro-β-carboline Derived Enaminones and Nitroenamines: Synthesis of Functionalized Indolizino[8,7-b]indoles, Pyrido[1,2-a:3,4-b′]diindoles, Indolo[2,3-a]quinolizidine-4-ones and Other Tetrahydro-β-carboline Fused Heterocycles

et al. 2019

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Aza-annulation of novel 1,2,3,4-tetrahydro-β-carboline derived enaminones and nitroenamines with various 1,2- and 1,3-bis electrophiles, such as oxalyl chloride, maleic anhydride, 1,4-benzoquinone, 3-bromopropionyl chloride, itaconic anhydride, and imines (from formaldehyde and primary amines), has been investigated. These methodologies provide simple one-step pathways for efficient construction of highly functionalized tetrahydro-β-carboline 1,2-fused, five- and six-membered heterocyclic frameworks, such as indolizino[8,7-b]indoles, pyrido[1,2-a:3,4-b′]diindoles, indolo[2,3-a]quinolizidines, and pyrimido[1′,6′:1,2]pyrido[3,4-b]indoles, which are core structures of many naturally occurring indole alkaloids with diverse bioactivity.

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“…Differently, compounds 10 and 12 present an activity not affected by EDTA, suggesting they act by modulating glucose uptake via GLUT transporters. Remarkably, among sesquiterpenoids, only the germacranolides dihydrocnicin (10) and 11-epidihydroartemisiifolin (11) proved to be active. This clearly demonstrates the impact on this pharmacological activity of the carbon skeleton with structural details also being important, as demonstrated by the higher activity of 12 compared to the closely structurally related 13.…”

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confidence: 99%

“…In the frame of our ongoing interest in finding unreported natural leads with activity on metabolic syndrome, we have evaluated the isolated metabolites for their glucose uptake stimulating activity. The germacranolide dihydrocnicin (10) and the lignan salicifoliol (15) emerged for their remarkable and previously unknown activity.…”

mentioning

confidence: 99%

“…Considering this botanical richness, it is not surprising that several Centaurea species have long been used in folk medicine for a variety of ailments, such as treatment of diabetes, diarrhea, hypertension, headache, muscle pains, microbial infections, rheumatism, and malaria . Compounds virtually belonging to dozens of classes of secondary metabolites have been characterized in Centaurea species, but, undoubtedly, sesquiterpene lactones, , flavonoids, and alkaloids are the hallmark of this genus.…”

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confidence: 99%

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Glucose Uptake-Stimulating Metabolites from Aerial Parts of Centaurea sicula

Serino,

Rigano,

Bruno

et al. 2024

J. Nat. Prod.

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A comprehensive phytochemical investigation of aerial parts obtained from Centaurea sicula L. led to the isolation of 14 terpenoids (1−14) and nine polyphenols (15−23). The sesquiterpenoid group (1−11) included three structural families, namely, elemanolides (1−6), eudesmanolides (7 and 8), and germacranolides (9−11) with four unreported secondary metabolites (5−8), whose structure has been determined by extensive spectroscopic analysis, including 1D/2D NMR, HR-MS, and chemical conversion. Moreover, an unprecedented alkaloid, named siculamide (24), was structurally characterized, and a possible biogenetic origin was postulated. Inspired by the traditional use of the plant and in the frame of ongoing research on compounds with potential activity on metabolic syndrome, all the isolated compounds were evaluated for their stimulation of glucose uptake, disclosing remarkable activity for dihydrocnicin (10) and the lignan salicifoliol (15).Centaurea is one of the most emblematic plant genera of the Mediterranean area, and with its hundreds of species (between 500 and 700, depending on the classification used), it is among the most numerous and taxonomically complex in the Cardueae tribe of the Asteraceae family. Centaurea plants can be annual, biennial, or perennial, rarely dwarf shrubs, with usually unarmed leaves. Along with the Iranian region, the Mediterranean area is one of the hotspots of distribution of the genus. 1−5 Considering this botanical richness, it is not surprising that several Centaurea species have long been used in folk medicine for a variety of ailments, such as treatment of diabetes, diarrhea, hypertension, headache, muscle pains, microbial infections, rheumatism, and malaria. 6 Compounds virtually belonging to dozens of classes of secondary metabolites have been characterized in Centaurea species, but, undoubtedly, sesquiterpene lactones, 7,8 flavonoids, 9 and alkaloids 10 are the hallmark of this genus.Centaurea sicula L. is a Mediterranean species distributed in Spain, Southern Italy, Malta, Tunisia, and other countries of Northwestern Africa. 11 In Sicily, the Italian region that gives the name to the species, it is widespread in the uncultivated lands. 12 Previous phytochemical investigations on this plant have reported the occurrence of sesquiterpene lactones, 13,14 flavonoids, 15 acetylenes, 16 and its essential oil composition. 17 Recently, the antioxidant properties of the plant extracts of specimens collected in Tunisia have been investigated. 18 In the frame of our research project aimed at the phytochemical profiling of species of the genus Centaur-

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Moschamine-Related Indole Alkaloids

Cited by 6 publications

References 55 publications

An NF-κB- and Therapy-Related Regulatory Network in Glioma: A Potential Mechanism of Action for Natural Antiglioma Agents

An NF-κB- and Therapy-Related Regulatory Network in Glioma: A Potential Mechanism of Action for Natural Antiglioma Agents

Aza-Annulation of 1,2,3,4-Tetrahydro-β-carboline Derived Enaminones and Nitroenamines: Synthesis of Functionalized Indolizino[8,7-b]indoles, Pyrido[1,2-a:3,4-b′]diindoles, Indolo[2,3-a]quinolizidine-4-ones and Other Tetrahydro-β-carboline Fused Heterocycles

Glucose Uptake-Stimulating Metabolites from Aerial Parts of Centaurea sicula

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