Fruitful Decades for Canthin-6-ones from 1952 to 2015: Biosynthesis, Chemistry, and Biological Activities

Dai, Jiangkun; Li, Na; Wang, Junru; Schneider, Uwe

doi:10.3390/molecules21040493

Cited by 31 publications

(20 citation statements)

References 78 publications

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“…The EtOAc layer was dried over anhydrous Na 2 SO 4 and then concentrated under reduced pressure (0.5 L). This extract (30 g) was initially subjected to an acid-base extraction [ 11 ] to give CHCl 3 alkaloid (2.0 g).…”

Section: Methodsmentioning

confidence: 99%

“…Meanwhile, more than 60 canthin-6-one alkaloids have been isolated from natural sources, mainly plants from the Rutaceae and Simaroubaceae families [ 10 ]. A broad range of biological activities has been reported for canthin-6-ones, such as antitumor, antibacterial, antifungal, antiparasitic, antiviral, anti-inflammatory, antiproliferative, and aphrodisiacal properties [ 11 ]. In this paper, we report the results of an investigation of the stem barks of Picrolemma huberi .…”

Section: Introductionmentioning

confidence: 99%

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Huberine, a New Canthin-6-One Alkaloid from the Bark of Picrolemma huberi

et al. 2018

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A new alkaloid, Canthin-6-one, Huberine (1), together with three known compounds including 1-Hydroxy-canthin-6-one (2), Canthin-6-one (3) and stigma sterol (4), were isolated from the stem bark of Picrolemma huberi. The isolation was achieved by chromatographic techniques and the purification was performed on a C18 column using acetonitrile/water (90:10, v/v) with 0.1% formic acid as the mobile phase. The structural elucidation was performed via spectroscopic methods, notably 1D- and 2D-NMR, UV, IR, MS and HRMS. The antiplasmodial activity of the compounds was studied.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Huberine, a New Canthin-6-One Alkaloid from the Bark of Picrolemma huberi

et al. 2018

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“…But the molecule decreased β-catenin even in the presence of CK1α-siRNA, suggesting the action through Wnt signalling by the activation of GSK3β independently of CK1α. 51 Selected Canthin-6-one alkaloids were tested in an Nf1-and p53-defective mouse malignant glioma tumor cell and the results indicated that the majority of the canthin-6-one alkaloids inhibited cell growth and exhibited toxicity. 52 Canthin-6-one reduced the phospho-and total-AKT from the malignant glioma stems cells TG1 and TG10 at a concentration of 300µM.…”

Section: Molecular Mechanisms Leading To Cancer Cell Death By Phytochmentioning

confidence: 99%

Therapeutic Potential of Phytochemicals Isolated from Simarouba glauca DC for Inhibiting Cancers: A Review

Jose¹,

Elango²,

Kumar³

et al. 2018

SRP

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Simarouba glauca DC (Family: Simaroubaceae, abbreviated as S. glauca / SG), commonly known as 'Laxmitaru' or 'Paradise tree' is an eco-friendly tree that grows in tropical areas of America, The West Indies and Brazil. Nutritionally, SG has been used as a potential source of edible oil. Medicinally, the decoction prepared from SG leaves has been demonstrated to exhibit antitumor, antimalarial, antiviral activities. Objectives: Address various existing gaps in the research on Simarouba glauca and provide future directions to promote address these grey areas. Methods: Literature pertaining to Simarouba glauca and various related plants was collected using PubMed search engine with key words Simarouba glauca, Simaroubaceae, Paradise tree, Laxmitaru. Articles pertaining to anti-cancer activity were filtered and information collected for preparing the review article. Although pharmacological potential of Simarouba glauca is well documented; not much is known about the mechanism(s) of action of the isolated phytoconstituents. In addition, many gaps pertaining to the efficacy of pharmacological agents for inhibiting cancers does exist. Therefore, future studies should focus on (a) screening and isolating key pharmacological agents that exhibit better safety and efficacy profiles for treating cancers; (b) evaluating the pharmacodynamic and pharmacokinetic properties of phytochemicals in experimental animal models; (c) testing the compounds in clinical trials; and (d) developing better strategies to effectively deliver the isolated compounds from SG. Studies are also warranted to determine whether isolated compounds of SG are better or the crude extracts that contain a combination of agents are better. Extensive research is required to address various unanswered questions. Therefore, future studies should focus on providing answers to fill the existing gaps about the utility of Simarouba glauca phytochemicals for treating cancers.

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“…Canthi-6-one alkaloids occur in plants from families Rutaceae, Simaroubareace, Amaranthaceae, Caryophyllaceae and Zygophylaceae [1][2][3]. More than 60 members of this type of alkaloid were isolated from natural sources since first report in 1952 [4].…”

Section: Introductionmentioning

confidence: 99%

NMR analysis of a new canthin-6-one alkaloid from Simaba bahiensis (Simaroubaceae)

Costa

Fontes

Abreu

et al. 2017

Proceedings of MOL2NET 2017, International Conference on Multidisciplinary Sciences, 3rd Edition

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Graphical Abstract Abstract.Alkaloids of the canthi-6-one type have been reported in differents natural sources. These alkaloids have showed a wide range of pharmacological properties including cytotoxic, antibacterial, antifungal, antiparasict, antiviral, anti-inflammatory and beside it, some of them show excellent photophysical properties that gives an interesting use as fluorescent dye probe in florescent cellular microscopy. Because it, new studies have been carrying out in an attempt to identify new alkaloids with pharmacological properties. Some researchers have been trying to synthesize new derivatives or identify new compounds in natural sources. Among the >60 canthin-6-one alkaloids already reported in natural sources, more the half are present in plants of the family Simaroubaceae. In the Simaba genus, up to the present, only eighteen alkaloids was described in seven species, but other plants of the genus that occur in the brazilian's flora haven't been studied yet. In this work we describe the first phytochemical study of the specie Simaba bahiensis (Simaroubaceae), collected at the city of Camaçari, Bahia State, Brazil. Also, it's related complete structural determination using differents NMR experiments and HRMS of a new canthin-6-one alkaloid in addition to two others already known MOL2NET, 2017, 3, doi:10.3390/mol2net-03-xxxx IntroductionCanthi-6-one alkaloids occur in plants from families Rutaceae, Simaroubareace, Amaranthaceae, Caryophyllaceae and Zygophylaceae [1][2][3]. More than 60 members of this type of alkaloid were isolated from natural sources since first report in 1952 [4]. These alkaloids have shown a wide range of pharmacological properties including cytotoxic, antibacterial, antifungal, antiparasict, antiviral, antiinflammatory and beside it, some of them show interesting photophysical properties that gives an interesting use the fluorescent dye probe in florescent cellular microscopy. New studies have been carring out in an attempt to identify new alkaloids with pharmacological properties by synthesis or isolation from different natural sources [2]. In family Simaroubaceae more than 30 canthi-6-one alkaloids have already been described with different substitution patterns and it shows that the investigation of new alkaloids in this family it's an important way to search new chemical entities [2,3]. In this work we describe the first phytochemical study of Simaba bahiensis (Simaroubaceae), collected at the city of Camaçari, Bahia State, Brazil. Also, it's related complete structural determination using differents NMR experiments and HRMS of a new canthin-6-one alkaloid and two others already known.

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Fruitful Decades for Canthin-6-ones from 1952 to 2015: Biosynthesis, Chemistry, and Biological Activities

Cited by 31 publications

References 78 publications

Huberine, a New Canthin-6-One Alkaloid from the Bark of Picrolemma huberi

Huberine, a New Canthin-6-One Alkaloid from the Bark of Picrolemma huberi

Therapeutic Potential of Phytochemicals Isolated from Simarouba glauca DC for Inhibiting Cancers: A Review

NMR analysis of a new canthin-6-one alkaloid from Simaba bahiensis (Simaroubaceae)

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