Cytotoxic alkaloids from the root of Zanthoxylum paracanthum (mildbr) Kokwaro

Omosa, Leonidah Kerubo; Nchiozem-Ngnitedem, Vaderament-A; Mukavi, Justus; Okoko, Brenda Atieno; Nyaboke, Helder Ombui; Ibrahim, H.; Matundura, Jackson Obegi; Efferth, Thomas; Spiteller, Michael

doi:10.1080/14786419.2021.1913586

Cited by 14 publications

(3 citation statements)

References 28 publications

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“…Thus, this nucleophilic addition furnished a hemiaminal ether 3 . Compound 5 is a dimer of two molecules of dihydrochelerythrine connected at position C-6 by an ether bridge and has been isolated previously from Zanthoxylum paracanthum and Z. monophyllum [ 44 , 45 ]. Dostál et al have previously reported chelerythrine-like compounds in a thorough description of the dimerization.…”

Section: Resultsmentioning

confidence: 99%

Alkaloids of Dicranostigma franchetianum (Papaveraceae) and Berberine Derivatives as a New Class of Antimycobacterial Agents

et al. 2022

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Tuberculosis (TB) is a widespread infectious disease caused by Mycobacterium tuberculosis. The increasing incidence of multidrug-resistant (MDR) and extensively drug-resistant (XDR) strains has created a need for new antiTB agents with new chemical scaffolds to combat the disease. Thus, the key question is: how to search for new antiTB and where to look for them? One of the possibilities is to search among natural products (NPs). In order to search for new antiTB drugs, the detailed phytochemical study of the whole Dicranostigma franchetianum plant was performed isolating wide spectrum of isoquinoline alkaloids (IAs). The chemical structures of the isolated alkaloids were determined by a combination of MS, HRMS, 1D, and 2D NMR techniques, and by comparison with literature data. Alkaloids were screened against Mycobacterium tuberculosis H37Ra and four other mycobacterial strains (M. aurum, M. avium, M. kansasii, and M. smegmatis). Alkaloids 3 and 5 showed moderate antimycobacterial activity against all tested strains (MICs 15.625–31.25 µg/mL). Furthermore, ten semisynthetic berberine (16a–16k) derivatives were developed and tested for antimycobacterial activity. In general, the derivatization of berberine was connected with a significant increase in antimycobacterial activity against all tested strains (MICs 0.39–7.81 μg/mL). Two derivatives (16e, 16k) were identified as compounds with micromolar MICs against M. tuberculosis H37Ra (MIC 2.96 and 2.78 µM). All compounds were also evaluated for their in vitro hepatotoxicity on a hepatocellular carcinoma cell line (HepG2), exerting lower cytotoxicity profile than their MIC values, thereby potentially reaching an effective concentration without revealing toxic side effects.

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Section: Resultsmentioning

confidence: 99%

Alkaloids of Dicranostigma franchetianum (Papaveraceae) and Berberine Derivatives as a New Class of Antimycobacterial Agents

et al. 2022

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“…Further chemotaxonomic insights of the study have been deduced from the presence of the other compounds isolated during the current investigation of the roots of Z. gilletii. Unsurpingsly, the lignan sesamin has been isolated during our investigation as one of the major compounds and it has been mainly reported from several species of the genus Zanthoxylum including Z. chalybeum, Z. paracanthum, Z. leprieurii, Z. rigidum, Z. paracanthum, Z. zanthoxyloides, Z. nitidum and Z. heitzii (Andima et al, 2020;Chakthong et al, 2019;Kaigongi et al, 2020;Muema et al, 2021;Oloya et al, 2021;Omosa et al, 2022;Santos et al, 2020;Wangensteen et al, 2016).…”

Section: Chemotaxonomic Significance Of the Studymentioning

confidence: 88%

Benzo[c]phenanthridine alkaloids and glycosylated flavonoids from the roots of Zanthoxylum gilletii (Rutaceae)

Dzouemo¹,

Happi²,

Happi³

et al. 2022

NRFHH

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The roots of Zanthoxylum gilletii have been chemically investigated and led to the isolation and characterization of nine compounds including three benzo[c]phenanthridine alkaloids oxychelerythrine (1), angoline (2) and arnottianamide (3); two glycosylated flavonoids hesperidin (4) and its analogue neohesperidin (5) along with four common specialized metabolites including sesamin (6), lupeol (7), β-sitosterol (8) and its derivative daucosterol (9). Their structures were established based on their recorded 1D and 2D-NMR data. Some compounds (1, 2, 3, 6 and 7) did not display a cytotoxic activity until the highest concentration of 200 μM against the human cell lines MCF-7 and A549. The chemotaxonomic relevance of this study has been discussed. To the best of our knowledge, except for the five compounds 3, 6-9, all the four others have been for the first time isolated from Z. gilletii (Rutaceae).

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“…In daily life, ZB can be used as toothpaste and hand sanitizer. In a previous study, researchers focused on the chemical separation and activity evaluation of ZB [ 32 , 33 ]. ZB extract showed good anti-inflammatory and antioxidant activities.…”

Section: Discussionmentioning

confidence: 99%

Nitidine Chloride Triggers Autophagy and Apoptosis of Ovarian Cancer Cells through Akt/mTOR Signaling Pathway

Lian¹,

Huang

et al. 2023

CPD

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Ovarian cancer (OC) is the eighth most common cancer with high mortality in women worldwide. Currently, compounds derived from Chinese herbal medicine have provided a new angle for OC treatment. In this study, the cell proliferation and migration of ovarian cancer A2780/SKOV3 cells were inhibited after being treated with nitidine chloride (NC) by using MTT and Wound-Healing Assay. Flow cytometry analysis indicated NC-induced apoptosis of ovarian cancer cells, and AO and MDC staining showed that NC treatment induced the appearance of autophagosomes and autophagic lysosomes in ovarian cancer cells. Through the autophagy inhibition experiment of chloroquine, it was proved that NC significantly further promoted apoptosis in ovarian cancer cells. Furthermore, NC proved that it could significantly decrease the expression of autophagy-related genes such as Akt, mTOR, P85 S6K, P70 S6K, and 4E-BP1. Therefore, we suggest that NC could trigger autophagy and apoptosis of ovarian cancer cells through Akt/mTOR signaling pathway, and NC may potentially be a target for chemotherapy against ovarian cancer.

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Cytotoxic alkaloids from the root of Zanthoxylum paracanthum (mildbr) Kokwaro

Cited by 14 publications

References 28 publications

Alkaloids of Dicranostigma franchetianum (Papaveraceae) and Berberine Derivatives as a New Class of Antimycobacterial Agents

Alkaloids of Dicranostigma franchetianum (Papaveraceae) and Berberine Derivatives as a New Class of Antimycobacterial Agents

Benzo[<i>c</i>]phenanthridine alkaloids and glycosylated flavonoids from the roots of <i>Zanthoxylum gilletii</i> (Rutaceae)

Nitidine Chloride Triggers Autophagy and Apoptosis of Ovarian Cancer Cells through Akt/mTOR Signaling Pathway

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