Enhanced Cytotoxicity in a <i>Z</i>-Photoisomer of a Benzopyran Derivative of Propolis

Hirota, Mikako; Matsuno, Tomonori; Fujiwara, Tsuyoshi; Sugiyama, Hiroshi; Mineshita, Satoru

doi:10.1021/np990463m

Cited by 20 publications

(7 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Propolis samples from tropical zones, such as Brazil with its vast biodiversity, have become a subject of increasing scientific and economic attention. From Brazilian propolis, several bioactive derivatives of hydroxycinnamic, caffeoylquinic and diterpenic acids besides benzofuranes and benzopyranes have already been characterized ( 18 , 23–25 ).…”

Section: Discussionmentioning

confidence: 99%

Brazilian Propolis: Correlation between Chemical Composition and Antimicrobial Activity

Salomão

Pereira

Campos

et al. 2007

Evidence-Based Complementary and Alternative Medicine

100

View full text Add to dashboard Cite

The chemical composition of ethanol extracts from samples of Brazilian propolis (EEPs) determined by HPLC and their activity against Trypanosoma cruzi, Staphylococcus aureus, Streptococcus pneumoniae, Klebisiella pneumoniae, Candida albicans, Sporothrix schenckii and Paracoccidioides brasiliensis were determined. Based on the predominant botanical origin in the region of samples' collection, the 10 extracts were separated into three groups: A (B. dracunculifolia + Auraucaria spp), B (B. dracunculifolia) and C (Araucaria spp). Analysis by the multiple regression of all the extracts together showed a positive correlation, higher concentrations leading to higher biological effect, of S. aureus with p-coumaric acid (PCUM) and 3-(4-hydroxy-3-(oxo-butenyl)-phenylacrylic acid (DHCA1) and of trypomastigotes of T. cruzi with 3,5-diprenyl-4-hydroxycinnamic acid derivative 4 (DHCA4) and 2,2-dimethyl-6-carboxyethenyl-2H-1-benzopyran (DCBEN). When the same approach was employed for each group, due to the small number of observations, the statistical test gave unreliable results. However, an overall analysis revealed for group A an association of S. aureus with caffeic acid (CAF) and dicaffeoylquinic acid 3 (CAFQ3), of S. pneumoniae with CAFQ3 and monocaffeoylquinic acid 2 (CAFQ2) and of T. cruzi also with CAFQ3. For group B, a higher activity against S. pneumoniae was associated DCBEN and for T. cruzi with CAF. For group C no association was observed between the anitmicrobial effect and any component of the extracts. The present study reinforces the relevance of PCUM and derivatives, especially prenylated ones and also of caffeolyquinic acids, on the biological activity of Brazilian propolis.

show abstract

Section: Discussionmentioning

confidence: 99%

Brazilian Propolis: Correlation between Chemical Composition and Antimicrobial Activity

Salomão

Pereira

Campos

et al. 2007

Evidence-Based Complementary and Alternative Medicine

100

View full text Add to dashboard Cite

show abstract

“…Seven compounds present in propolis from the south and southeast of Brazil have been identified by comparison of their tandem mass spectra with those of standards acquired commercially or isolated in relation to previous research: 18,21 para-coumaric acid, 3-methoxy-4-hydroxycinnamaldehyde, 2,2-dimethyl-6-carboxyethenyl-2H-1-benzopyran, 3-prenyl-4-hydroxycinnamic acid, chrysin, pinocembrin and 3,5-diprenyl-4-hydroxycinnamic acid (Table 1). These compounds have been reported previously in samples of Brazilian propolis and the activity of some of them against bacteria, 21 Trypanossoma cruzi 21 and Candida, 45 as well as their cytotoxic 46 and antioxidant 47 activities have been investigated. The ion of m/z 515 has been determined to be a deprotonated form of dicaffeoylquinic acid by comparison of its ESI-MS/MS mass spectrum (Fig.…”

Section: Structural Characterization Via Tandem Mass Spectrometrymentioning

confidence: 97%

Electrospray ionization mass spectrometry fingerprinting of propolis

Sawaya

Tomazela

Cunha

et al. 2004

Analyst

133

100

View full text Add to dashboard Cite

Crude ethanolic extracts of propolis, a natural resin, have been directly analysed using electrospray ionization mass (ESI-MS) and tandem mass spectrometry (ESI-MS/MS) in the negative ion mode. European, North American and African samples have been analyzed, but emphasis has been given to Brazilian propolis which displays diverse and region-dependent chemical composition. ESI-MS provides characteristic fingerprint mass spectra, with propolis samples being divided into well-defined groups directly related to their geographical origins. Chemometric multivariate analysis statistically demonstrates the reliability of the ESI-MS fingerprinting method for propolis. On-line ESI-MS/MS tandem mass spectrometry of characteristic [M - H](-) ion markers provides an additional dimension of fingerprinting selectivity, while structurally characterizing the ESI-MS marker components of propolis. By comparison with standards, eight such markers have been identified: para-coumaric acid, 3-methoxy-4-hydroxycinnamaldehyde, 2,2-dimethyl-6-carboxyethenyl-2H-1-benzopyran, 3-prenyl-4-hydroxycinnamic acid, chrysin, pinocembrin, 3,5-diprenyl-4-hydroxycinnamic acid and dicaffeoylquinic acid. The negative mode ESI-MS fingerprinting method is capable of discerning distinct composition patterns to typify, to screen the sample origin and to reveal characteristic details of the more polar and acidic chemical components of propolis samples from different regions of the world.

show abstract

“…3-(2,2-dimethyl-8-prenylbenzopyran-6-yl)propenoic acid (5) having cytotoxic activity was also isolated from Brazilian propolis (Matsuno et al, 1997b). Hirota et al (2000) isolated (Z)-2,2-dimethyl-8-prenyl-benzopyran-6-propenoic acid (25), a Z-photoisomer of 5, which displayed an approximately 7-fold stronger cytotoxicity against human lung carcinoma cells (HTL-2) than 5. Matsuno et al (1997cMatsuno et al ( , 1998) also reported the isolation from Brazilian propolis and cytotoxic activity of a similar compound, artepillin C (26).…”

Section: Antitumour Activitymentioning

confidence: 99%

Recent progress in pharmacological research of propolis

Banskota

Tezuka

Kadota

2001

Phytotherapy Research

743

553

View full text Add to dashboard Cite

Propolis is a resinous hive product collected by honeybees from various plant sources. It is a popular folk medicine possessing a broad spectrum of biological activities. It has also been used as a health drink in various Asian, European and American countries. Several groups of researchers have focused their attention on the biological activity of propolis and its active principles. Many scientific articles are published every year in different international journals related to the pharmacological properties of propolis. This review article compiles recent findings (since 1995) on the pharmacological properties of propolis focusing on its antihepatotoxic, antitumour, antioxidative, antimicrobial and antiinflammatory properties. The possible mechanism of action of propolis as well as the active compounds are discussed.

show abstract

Enhanced Cytotoxicity in a Z-Photoisomer of a Benzopyran Derivative of Propolis

Cited by 20 publications

References 15 publications

Brazilian Propolis: Correlation between Chemical Composition and Antimicrobial Activity

Brazilian Propolis: Correlation between Chemical Composition and Antimicrobial Activity

Electrospray ionization mass spectrometry fingerprinting of propolis

Recent progress in pharmacological research of propolis

Contact Info

Product

Resources

About