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Origin and Chemical Variation of Brazilian Propolis.

Salatino A, Teixeira EW, Negri G, Message D - Evid Based Complement Alternat Med (2005)

Bottom Line: However, wide variation detected in the chemical composition suggests contributions from alternative resin plant sources.Predominant components of the resin of green propolis are cinnamic acids, chiefly compounds bearing prenyl groups.Propolis research has uncovered potentialities of substances previously isolated from plants and has detected constituents of plant origin that would hardly be known otherwise.

View Article: PubMed Central - PubMed

ABSTRACT
Propolis is a hive product containing chiefly beeswax and plant-derived substances such as resin and volatile compounds. Propolis has been used as an antiseptic and wound healer since ancient times and interest for the product has increased recently. Probably few plant species contribute as major resin sources. Green propolis derives mainly from vegetative apices of Baccharis dracunculifolia (alecrim plants). However, wide variation detected in the chemical composition suggests contributions from alternative resin plant sources. Predominant components of the resin of green propolis are cinnamic acids, chiefly compounds bearing prenyl groups. Terpenoid compounds, such as sesqui, di and pentacyclic triterpenoids, have been detected in many, but not all, samples investigated. Propolis research has uncovered potentialities of substances previously isolated from plants and has detected constituents of plant origin that would hardly be known otherwise.

No MeSH data available.


Related in: MedlinePlus

Structures of phenolic compounds isolated from green propolis. (A) 2,2-Dimethyl-8-prenylchromene; (B) 4-hydroxy-3,5-diprenyl cinnamic acid (artepillin C); (C) 3-prenyl cinnamic acid allyl ester; (D) kaempferide; (E) propolis benzofuran A. See text for references.
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fig2: Structures of phenolic compounds isolated from green propolis. (A) 2,2-Dimethyl-8-prenylchromene; (B) 4-hydroxy-3,5-diprenyl cinnamic acid (artepillin C); (C) 3-prenyl cinnamic acid allyl ester; (D) kaempferide; (E) propolis benzofuran A. See text for references.

Mentions: This is not a full account of what has been done on the chemistry of green propolis, rather it is a general idea of the diversity of classes of secondary metabolites and the extent of variation that has been noted in green propolis composition. Since most analyses carried out with European propolis until the mid 1990s revealed that flavonoids predominated as resin constituents, researchers assumed that a similar picture was apt to prevail regarding Brazilian propolis, especially taking into consideration that such propolis samples were pharmacologically similar to the European counterparts. However, contrary to those expectations, the first detailed chemical analyses revealed quite distinct profiles for samples of Brazilian propolis. Prenylated phenylpropanoids were shown to be very common and abundant constituents in propolis from Brazil, mainly from the southeastern region. For example Banskota et al. (29) identified in a sample of ‘Brazilian propolis’ pharmacologically active prenylated cinnamic acid-derived compounds, four of them bearing a prenyl group making up a heterocyclic ring that gives rise to chromenes (Fig. 2A). Although no information was given as to the provenance of the propolis sample, investigation carried out in Japan with Brazilian propolis deal practically only with green propolis. Other cinnamic acid-derived compounds common in green propolis have one or two prenyl groups not involved with ring formation. Prenylated cinnamic acids turned out to be a salient chemical feature of green propolis. Among the non-chromene prenylated cinnamic acids of green propolis, artepillin C (Fig. 2B) has attracted great attention, not only for its antimicrobial (30) but also for its toxicity to tumor cells (31). Prenylated cinnamic acids may be present as esters, such as 3-prenyl-cinnamic acid allyl ester (32) (Fig. 2C). Despite not being major constituents, flavonoids do occur in green propolis, one frequent example being kaempferide (Fig. 2D), a compound shown to possess antioxidant activities (33). Interesting benzofurans (Fig. 2E), to our knowledge never detected in B.dracunculifolia, were obtained from Brazilian propolis and shown to possess cytotoxic properties (34).


Origin and Chemical Variation of Brazilian Propolis.

Salatino A, Teixeira EW, Negri G, Message D - Evid Based Complement Alternat Med (2005)

Structures of phenolic compounds isolated from green propolis. (A) 2,2-Dimethyl-8-prenylchromene; (B) 4-hydroxy-3,5-diprenyl cinnamic acid (artepillin C); (C) 3-prenyl cinnamic acid allyl ester; (D) kaempferide; (E) propolis benzofuran A. See text for references.
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Related In: Results  -  Collection

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fig2: Structures of phenolic compounds isolated from green propolis. (A) 2,2-Dimethyl-8-prenylchromene; (B) 4-hydroxy-3,5-diprenyl cinnamic acid (artepillin C); (C) 3-prenyl cinnamic acid allyl ester; (D) kaempferide; (E) propolis benzofuran A. See text for references.
Mentions: This is not a full account of what has been done on the chemistry of green propolis, rather it is a general idea of the diversity of classes of secondary metabolites and the extent of variation that has been noted in green propolis composition. Since most analyses carried out with European propolis until the mid 1990s revealed that flavonoids predominated as resin constituents, researchers assumed that a similar picture was apt to prevail regarding Brazilian propolis, especially taking into consideration that such propolis samples were pharmacologically similar to the European counterparts. However, contrary to those expectations, the first detailed chemical analyses revealed quite distinct profiles for samples of Brazilian propolis. Prenylated phenylpropanoids were shown to be very common and abundant constituents in propolis from Brazil, mainly from the southeastern region. For example Banskota et al. (29) identified in a sample of ‘Brazilian propolis’ pharmacologically active prenylated cinnamic acid-derived compounds, four of them bearing a prenyl group making up a heterocyclic ring that gives rise to chromenes (Fig. 2A). Although no information was given as to the provenance of the propolis sample, investigation carried out in Japan with Brazilian propolis deal practically only with green propolis. Other cinnamic acid-derived compounds common in green propolis have one or two prenyl groups not involved with ring formation. Prenylated cinnamic acids turned out to be a salient chemical feature of green propolis. Among the non-chromene prenylated cinnamic acids of green propolis, artepillin C (Fig. 2B) has attracted great attention, not only for its antimicrobial (30) but also for its toxicity to tumor cells (31). Prenylated cinnamic acids may be present as esters, such as 3-prenyl-cinnamic acid allyl ester (32) (Fig. 2C). Despite not being major constituents, flavonoids do occur in green propolis, one frequent example being kaempferide (Fig. 2D), a compound shown to possess antioxidant activities (33). Interesting benzofurans (Fig. 2E), to our knowledge never detected in B.dracunculifolia, were obtained from Brazilian propolis and shown to possess cytotoxic properties (34).

Bottom Line: However, wide variation detected in the chemical composition suggests contributions from alternative resin plant sources.Predominant components of the resin of green propolis are cinnamic acids, chiefly compounds bearing prenyl groups.Propolis research has uncovered potentialities of substances previously isolated from plants and has detected constituents of plant origin that would hardly be known otherwise.

View Article: PubMed Central - PubMed

ABSTRACT
Propolis is a hive product containing chiefly beeswax and plant-derived substances such as resin and volatile compounds. Propolis has been used as an antiseptic and wound healer since ancient times and interest for the product has increased recently. Probably few plant species contribute as major resin sources. Green propolis derives mainly from vegetative apices of Baccharis dracunculifolia (alecrim plants). However, wide variation detected in the chemical composition suggests contributions from alternative resin plant sources. Predominant components of the resin of green propolis are cinnamic acids, chiefly compounds bearing prenyl groups. Terpenoid compounds, such as sesqui, di and pentacyclic triterpenoids, have been detected in many, but not all, samples investigated. Propolis research has uncovered potentialities of substances previously isolated from plants and has detected constituents of plant origin that would hardly be known otherwise.

No MeSH data available.


Related in: MedlinePlus