Two New Cytotoxic Phenylallylflavanones from Mexican Propolis

Li, Feng; He, Yumin; Awale, Suresh; Kadota, Shigetoshi; Tezuka, Yasuhiro

doi:10.1248/cpb.59.1194

Cited by 17 publications

(7 citation statements)

References 23 publications

(24 reference statements)

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“…In fact, most of the chemical compounds isolated were reported to have specific biological activity (Table 1 ). Caffeic acid phenethyl ester (CAPE) and chrysin from temperate propolis, and artepillin C from Brazilian propolis, have been extensively studied and show promising therapeutic potential in the treatment of cancer, degenerative diseases, and other pathologies (Okutan et al 2005 ; Messerli et al 2009 ; Li et al 2011 ). These compounds could have significance in the biological-activity-marker-based standardisation of temperate and Brazilian propolis, respectively.…”

Section: Challenges In Propolis Quality Control: Biomarker Selectionmentioning

confidence: 99%

Propolis: chemical diversity and challenges in quality control

2022

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Propolis is a resinous natural product produced by honeybees using beeswax and plant exudates. The chemical composition of propolis is highly complex, and varies with region and season. This inherent chemical variability presents several challenges to its standardisation and quality control. The present review was aimed at highlighting marker compounds for different types of propolis, produced by the species Apis mellifera , from different geographical origins and that display different biological activities, and to discuss strategies for quality control. Over 800 compounds have been reported in the different propolises such as temperate, tropical, birch, Mediterranean, and Pacific propolis; these mainly include alcohols, acids and their esters, benzofuranes, benzopyranes, chalcones, flavonoids and their esters, glycosides (flavonoid and diterpene), glycerol and its esters, lignans, phenylpropanoids, steroids, terpenes and terpenoids. Among these, flavonoids (> 140), terpenes and terpenoids (> 160) were major components. A broad range of biological activities, such as anti-oxidant, antimicrobial, anti-inflammatory, immunomodulatory, and anticancer activities, have been ascribed to propolis constituents, as well as the potential of these compounds to be biomarkers. Several analytical techniques, including non-separation and separation methods have been described in the literature for the quality control assessment of propolis. Mass spectrometry coupled with separation methods, followed by chemometric analysis of the data, was found to be a valuable tool for the profiling and classification of propolis samples, including (bio)marker identification. Due to the rampant chemotypic variability, a multiple-marker assessment strategy considering geographical and biological activity marker(s) with chemometric analysis may be a promising approach for propolis quality assessment. Supplementary Information The online version contains supplementary material available at 10.1007/s11101-022-09816-1.

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Section: Challenges In Propolis Quality Control: Biomarker Selectionmentioning

confidence: 99%

Propolis: chemical diversity and challenges in quality control

2022

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“…Nowadays, México is one of the main honey bee producers in the world; the States of Yucatán, Campeche, Jalisco and Chiapas are the major contributors. In the case of Mexican propolis, different type of compounds have been isolated, such as, phenylallylflavanones [ 18 , 19 ], 1,3-diarylpropane, 1,3-diarylpropene derivatives, flavanones, isoflavans, and pterocarpans [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Mexican Propolis: A Source of Antioxidants and Anti-Inflammatory Compounds, and Isolation of a Novel Chalcone and ε-Caprolactone Derivative

et al. 2018

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The propolis produced by bees are used in alternative medicine for treating inflammation, and infections, presumably due to its antioxidant properties. In this context, five propolis from México were investigated to determine their inhibitory lipid peroxidation properties. The ethyl acetate extract from a red propolis from Chiapas State (4-EAEP) was the most potent (IC50 = 1.42 ± 0.07 μg/mL) in the TBARS assay, and selected for further studies. This extract afforded two new compounds, epoxypinocembrin chalcone (6), and an ε-caprolactone derivative (10), as well as pinostrobin (1), izalpinin (2), cinnamic acid (3), pinocembrin (4), kaempherol (5), 3,3-dimethylallyl caffeate in mixture with isopent-3-enyl caffeate (7a + 7b), 3,4-dimethoxycinnamic acid (8), rhamnetin (9) and caffeic acid (11). The HPLC profile, anti-mycobacterial, and antioxidant properties of this extract was also determined. Most of the isolated compounds were also tested by inhibition of reactive oxygen species (ROS) in challenged mouse bone marrow-derived mast cells (BMMCs), and DPPH. Their anti-inflammatory activity was evaluated by TPA, and MPO (myeloperoxidase) activity by ear edema test in mice. The most potent compounds were 7a + 7b in the TBARS assay (IC50 = 0.49 ± 0.06 μM), and 2 which restored the ROS baseline (3.5 μM). Our results indicate that 4-EAEP has anti-oxidant, and anti-inflammatory properties due to its active compounds, suggesting it has anti-allergy and anti-asthma potential.

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“…Propolis has been extensively researched due to its versatile pharmacological activities such as anticancer, antibacterial, , antifungal, , antiviral, immunostimulating, anti-inflammatory, and antioxidant activities. Previous studies on Brazilian red propolis, as well as Myanmar and Mexican propolis, have shown preferential cytotoxicity activity against PANC-1 human pancreatic cancer cells in nutrient-deprived medium. ,,, …”

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confidence: 99%

Chemical Constituents of Propolis from Vietnamese Trigona minor and Their Antiausterity Activity against the PANC-1 Human Pancreatic Cancer Cell Line

Nguyen¹,

Nguyen²,

Nguyen³

et al. 2017

J. Nat. Prod.

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The ethanol extract of propolis from the Vietnamese stingless bee Trigona minor possessed potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells in nutrient-deprived medium, with a PC value of 14.0 μg/mL. Chemical investigation of this extract led to the isolation of 15 cycloartane-type triterpenoids, including five new compounds (1-5), and a lanostane-type triterpenoid. The structures of the new compounds were elucidated on the basis of NMR spectroscopic analysis. Among the isolated compounds, 23-hydroxyisomangiferolic acid B (5) and 27-hydroxyisomangiferolic acid (13) exhibited the most potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under nutrition-deprived conditions, with PC values of 4.3 and 3.7 μM, respectively.

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Two New Cytotoxic Phenylallylflavanones from Mexican Propolis

Cited by 17 publications

References 23 publications

Propolis: chemical diversity and challenges in quality control

Propolis: chemical diversity and challenges in quality control

Mexican Propolis: A Source of Antioxidants and Anti-Inflammatory Compounds, and Isolation of a Novel Chalcone and ε-Caprolactone Derivative

Chemical Constituents of Propolis from Vietnamese Trigona minor and Their Antiausterity Activity against the PANC-1 Human Pancreatic Cancer Cell Line

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