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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 terpenoids isolated from propolis. (A) Isocupressic acid, a labdane diterpenoid; (B) 13C-symphyoreticulic acid, a clerodane diterpenoid; (C) esters of long chain fatty acids (3-hydroxystearic acid n = 11, procrim a; 3-hydroxystearic acid n = 13, procrim b) and a pentacyclic triterpenoid (lupeol); (D) Farnesol a sesquiterpenoid, see text for references.
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fig3: Structures of terpenoids isolated from propolis. (A) Isocupressic acid, a labdane diterpenoid; (B) 13C-symphyoreticulic acid, a clerodane diterpenoid; (C) esters of long chain fatty acids (3-hydroxystearic acid n = 11, procrim a; 3-hydroxystearic acid n = 13, procrim b) and a pentacyclic triterpenoid (lupeol); (D) Farnesol a sesquiterpenoid, see text for references.

Mentions: Mono and sesquiterpenes are frequently detected in green propolis, accounting for its characteristic resinous odor and probably contributing to the antimicrobial activity. For example, farnesol (Fig. 3D) has been shown to affect the accumulation and polysaccharide content of Streptococcus mutans biofilms (35). Labdane-type diterpenes, several with hepatoprotective activity (25), such as isocupressic (Fig. 3A) and agathic acid, have been found in green propolis. Clerodane diterpenoids with anticancer activity have been isolated, such as 13-symphyoreticulic acid (36) (Fig. 3B). Non-volatile sesquiterpenes, such as dehydrocostus lactone, a compound shown to inhibit the killing function of cytotoxic T-lymphocytes (37), may also occur in green propolis (38). Triterpenoids, some with wide occurrence in plants, have been found in green propolis (38–40). Two novel esters of long chain fatty acids and the pentacyclic triterpenoid lupeol (procrims a and b, Fig. 3C) have also been obtained from green propolis (41). Notwithstanding botanical origin being a major factor affecting propolis chemistry, other aspects also seem to influence the product composition. Notable differences are often found between propolis samples, not only from distant but also from nearby, or even the same, locations. This holds either for European (42,43) or for green propolis (32,38,39), even restricting the analysis to samples of ‘typical’ green propolis. For example, 3-prenylcinnamic acid allyl ester (Fig. 2C) was only recently reported to be a major constituent of green propolis (32), despite the considerable number of previous analyses. Among samples of green propolis there seems to be a gradual variation in the proportion of mevalonate-derived substances (terpenoids, including sesqui, di and triterpenoids) and the typical shikimate-derived (phenolics, prenylated or not) compounds. For example, analyses of green propolis have detected pentacyclic triterpenoids in some samples (38,39) but not in others (32). The relative amount of triterpenoids may sometimes be evaluated by the physical appearance of the sample, which loses the hardness and depth of green, turning increasingly cream and pulverulent with increasing levels of triterpenoids and reduction in the amounts of the typical shikimate derivatives. A relatively high content of dehydrocostus lactone (a pharmacologically active sesquiterpenoid (37,44)] was found in a sample from the state of São Paulo, together with 14 pentacyclic triterpenoids, four of them unreported for propolis (39). Bauer-7-en-3-yl acetate (a triterpenoid) was found in this sample in relatively low amounts, but we found it to represent 7% of the weight of another sample in a region where green propolis predominates (unpublished results). Are such inconsistencies accounted for by behavioral shifts to alternative resin plant sources? Baccharis is a large genus, with many representative species in the Brazilian flora. Species of the genus other than B.dracunculifolia are likely providers of propolis resin, not to mention species of other plant groups, including Clusiaceae, which are known to be predominant resin sources in Venezuela and Cuba, as noted above.


Origin and Chemical Variation of Brazilian Propolis.

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

Structures of terpenoids isolated from propolis. (A) Isocupressic acid, a labdane diterpenoid; (B) 13C-symphyoreticulic acid, a clerodane diterpenoid; (C) esters of long chain fatty acids (3-hydroxystearic acid n = 11, procrim a; 3-hydroxystearic acid n = 13, procrim b) and a pentacyclic triterpenoid (lupeol); (D) Farnesol a sesquiterpenoid, see text for references.
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Related In: Results  -  Collection

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fig3: Structures of terpenoids isolated from propolis. (A) Isocupressic acid, a labdane diterpenoid; (B) 13C-symphyoreticulic acid, a clerodane diterpenoid; (C) esters of long chain fatty acids (3-hydroxystearic acid n = 11, procrim a; 3-hydroxystearic acid n = 13, procrim b) and a pentacyclic triterpenoid (lupeol); (D) Farnesol a sesquiterpenoid, see text for references.
Mentions: Mono and sesquiterpenes are frequently detected in green propolis, accounting for its characteristic resinous odor and probably contributing to the antimicrobial activity. For example, farnesol (Fig. 3D) has been shown to affect the accumulation and polysaccharide content of Streptococcus mutans biofilms (35). Labdane-type diterpenes, several with hepatoprotective activity (25), such as isocupressic (Fig. 3A) and agathic acid, have been found in green propolis. Clerodane diterpenoids with anticancer activity have been isolated, such as 13-symphyoreticulic acid (36) (Fig. 3B). Non-volatile sesquiterpenes, such as dehydrocostus lactone, a compound shown to inhibit the killing function of cytotoxic T-lymphocytes (37), may also occur in green propolis (38). Triterpenoids, some with wide occurrence in plants, have been found in green propolis (38–40). Two novel esters of long chain fatty acids and the pentacyclic triterpenoid lupeol (procrims a and b, Fig. 3C) have also been obtained from green propolis (41). Notwithstanding botanical origin being a major factor affecting propolis chemistry, other aspects also seem to influence the product composition. Notable differences are often found between propolis samples, not only from distant but also from nearby, or even the same, locations. This holds either for European (42,43) or for green propolis (32,38,39), even restricting the analysis to samples of ‘typical’ green propolis. For example, 3-prenylcinnamic acid allyl ester (Fig. 2C) was only recently reported to be a major constituent of green propolis (32), despite the considerable number of previous analyses. Among samples of green propolis there seems to be a gradual variation in the proportion of mevalonate-derived substances (terpenoids, including sesqui, di and triterpenoids) and the typical shikimate-derived (phenolics, prenylated or not) compounds. For example, analyses of green propolis have detected pentacyclic triterpenoids in some samples (38,39) but not in others (32). The relative amount of triterpenoids may sometimes be evaluated by the physical appearance of the sample, which loses the hardness and depth of green, turning increasingly cream and pulverulent with increasing levels of triterpenoids and reduction in the amounts of the typical shikimate derivatives. A relatively high content of dehydrocostus lactone (a pharmacologically active sesquiterpenoid (37,44)] was found in a sample from the state of São Paulo, together with 14 pentacyclic triterpenoids, four of them unreported for propolis (39). Bauer-7-en-3-yl acetate (a triterpenoid) was found in this sample in relatively low amounts, but we found it to represent 7% of the weight of another sample in a region where green propolis predominates (unpublished results). Are such inconsistencies accounted for by behavioral shifts to alternative resin plant sources? Baccharis is a large genus, with many representative species in the Brazilian flora. Species of the genus other than B.dracunculifolia are likely providers of propolis resin, not to mention species of other plant groups, including Clusiaceae, which are known to be predominant resin sources in Venezuela and Cuba, as noted above.

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