Anti-phytopathogenic activity and the possible mechanisms of action of isoquinoline alkaloid sanguinarine

Zhao, Zhuanjun; Shang, Xiaofei; Lawoe, Raymond Kobla; Liu, Ying‐Qian; Zhou, Rui; Sun, Yu; Yan, Yin-Fang; Li, Juncai; Yang, Guan‐Zhou; Yang, Cheng‐Jie

doi:10.1016/j.pestbp.2019.05.015

Cited by 54 publications

(32 citation statements)

References 31 publications

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“…The authors have recently described the significant antifungal activity of sanguinarine (299) and its possible use as a bio-fungicide for crop protection. 236 From 2014 to 2018, many publications have reported the antibacterial and antifungal activities of isoquinoline alkaloids; findings are briefly discussed below or listed in Table 3. 23,57,63,66,78,101 Berberine 161 peroxidation of membrane constituents.…”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

“…A high content of berberine ( 161 ) is found in the well‐known Chinese drug ( Huangliansu ) taken to treat intestinal infections caused by Escherichia coli, Bacillus dysteriae , and other microorganisms. The authors have recently described the significant antifungal activity of sanguinarine ( 299 ) and its possible use as a bio‐fungicide for crop protection 236 . From 2014 to 2018, many publications have reported the antibacterial and antifungal activities of isoquinoline alkaloids; findings are briefly discussed below or listed in Table 3 23,57,63,66,78,101 …”

Section: Bioactivitiesmentioning

confidence: 99%

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Biologically active isoquinoline alkaloids covering 2014–2018

Shang

Yang

Morris‐Natschke

et al. 2020

Medicinal Research Reviews

145

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Isoquinoline alkaloids, an important class of N-based heterocyclic compounds, have attracted considerable attention from researchers worldwide since the early 19th century. Over the past 200 years, many compounds from this class were isolated, and most of them and their analogs possess various bioactivities. In this review, we survey the updated literature on bioactive alkaloids and highlight research achievements of this alkaloid class during the period of 2014-2018. We reviewed over 400 molecules with a broad range of bioactivities, including antitumor, antidiabetic and its complications, antibacterial, antifungal, antiviral, antiparasitic, insecticidal, anti-inflammatory, antioxidant, neuroprotective, and other activities. This review should provide new indications or directions for the discovery of new and better drugs from the original naturally occurring isoquinoline alkaloids.

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Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

Section: Bioactivitiesmentioning

confidence: 99%

Biologically active isoquinoline alkaloids covering 2014–2018

Shang

Yang

Morris‐Natschke

et al. 2020

Medicinal Research Reviews

145

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“…Recent reports show that sanguinarine exhibits low toxicity 30 and promotes apoptosis in hepatocellular carcinoma 31 and is reported to treat cervical cancer 32 and as a potent adjuvant for ovarian cancer chemotherapy 33 . In addition, sanguinarine is a potential drug against trichinellosis, a zoonotic parasitic disease, 34 and it has exhibited antifungal properties 35 . Sanguinarine plays important role as candidate for hypoxia‐inducible factor‐1 alpha/signal transducer and activator of transcription‐3 inhibition 36 .…”

Section: Resultsmentioning

confidence: 99%

Efficient extraction and purification of benzo[c]phenanthridine alkaloids from Macleaya cordata (Willd) R. Br. by combination of ultrahigh pressure extraction and pH‐zone‐refining counter‐current chromatography with anti‐breast cancer activity in vitro

Ali

Cui

et al. 2020

Phytochemical Analysis

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Introduction Macleaya cordata (Willd) R. Br. (Papaveraceae family) is a well‐known traditional Chinese medicine used to treat muscle pain, inflamed wounds, and bee bites. Benzo[c]phenanthridine alkaloids are the main active ingredients in M. cordata. In this work, sanguinarine and chelerythrine were efficiently extracted and purified by ultrahigh‐pressure extraction (UHPE) technique and pH‐zone‐refining counter‐current chromatography (PZRCCC) from M. cordata. Objective To develop an efficient UHPE method followed by an efficient separation technique using PZRCCC for benzo[c]phenanthridine alkaloids from the study plant species, and to evaluate the study samples for anti‐breast cancer activity. Methodology The optimal extraction conditions were optimised as extraction pressure 200 MPa, extraction solvent 95% ethanol, solid–liquid ratio 1:30 (g/mL) and extraction time 2 min. A two‐phase n‐hexane/ethyl acetate/i‐propanol/water (1:3:1.5:4.5, v/v) solvent system was optimised with 10 mmol triethylamine in the upper phase and 10 mmol trifluoroacetic acid in lower phase in PZRCCC. The sample loading was optimised as 2.50 g. Moreover, the samples were evaluated for anti‐breast cancer activity later on. Results The 2.50 g sample loading yielded 0.45 g of sanguinarine and 0.59 g chelerythrine in one‐step separation using PZRCCC. The anti‐breast cancer activities of sanguinarine and chelerythrine were found stronger than positive control (vincristine 5.04 μg/mL) with half‐maximal inhibitory concentration values of 0.96 and 3.00 μg/mL, respectively. Conclusion This study showed that the established methods were efficient in extraction (UHPE) and separation (PZRCCC) of the sanguinarine and chelerythrine from M. cordata.

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“…Previous phytochemical investigations have shown that the main chemical compounds of this plant are benzylisoquinoline alkaloids (BIAs), including benzophenanthridine, dihydrobenzophenanthridine and protopine 2 . Due to their antimicrobial, antifungal, anti‐inflammatory, anticancer, insecticidal, anti‐osteoporosis, antioxidant, hepatoprotective, neuroprotective, hypolipidemic, hypoglycemic and other biological activities, medicinal plants containing BIAs have attracted widespread attention 3–8 . As there has been little research on the chemical constituents of BIAs in ECH, it is necessary to comprehensively characterize the BIAs, especially those present in trace amounts.…”

Section: Introductionmentioning

confidence: 99%

Systematic characterization of alkaloids in Eomecon chionantha Hance using ultrahigh‐performance liquid chromatography–tandem quadrupole Exactive Orbitrap mass spectrometry with a four‐step screening strategy

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Eomecon chionantha Hance (ECH), a traditional folk herb, is commonly used to treat traumatic injuries based on its analgesic and anti‐inflammatory properties. Previous studies have reported that alkaloids are the major bioactive components in ECH. Therefore, identification of alkaloids from ECH contributes to the discovery of its potential active ingredients and quality control in clinic treatments. Methods A four‐step screening strategy was performed as follows. (1) Extracting the accurate masses of ions related to different molecules. (2) Screening different types of compounds using their molecular cations, protonated molecules, diagnostic product ions and fragmentation pathways. (3) Comparing the characteristic product ion formulae to obtain the type and number of substituents. (4) Using the biosynthetic pathways of isoquinoline alkaloids to determine the concentration of alkaloids. Results Ultrahigh‐performance liquid chromatography–tandem quadrupole Exactive Orbitrap mass spectrometry (UHPLC/Q‐Exactive Orbitrap MS) analysis combined with the four‐step screening strategy was used to profile the alkaloids in ECH. The structures of 95 alkaloids in ECH were unambiguously identified or reasonably assigned, of which 76 were reported in ECH for the first time. Six types of benzylisoquinoline alkaloids were identified in ECH: six benzyltetrahydroisoquinolines, nine protopines, five N‐methyltetrahydroprotoberberines, six protoberberines, eight benzophenanthridines and sixty‐one dihydrobenzophenanthridines. Conclusions This comprehensive study identified the alkaloids in ECH, thus providing a practical reference for further research. The UHPLC/Q‐Exactive Orbitrap MS method, combined with the four‐step screening strategy, which was developed and successfully applied to identify the alkaloids in ECH, may also be applicable for the efficient screening of other herbal medicines.

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Anti-phytopathogenic activity and the possible mechanisms of action of isoquinoline alkaloid sanguinarine

Cited by 54 publications

References 31 publications

Biologically active isoquinoline alkaloids covering 2014–2018

Biologically active isoquinoline alkaloids covering 2014–2018

Efficient extraction and purification of benzo[c]phenanthridine alkaloids from Macleaya cordata (Willd) R. Br. by combination of ultrahigh pressure extraction and pH‐zone‐refining counter‐current chromatography with anti‐breast cancer activity in vitro

Systematic characterization of alkaloids in Eomecon chionantha Hance using ultrahigh‐performance liquid chromatography–tandem quadrupole Exactive Orbitrap mass spectrometry with a four‐step screening strategy

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