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Plant Origin of Green Propolis: Bee Behavior, Plant Anatomy and Chemistry.

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

Bottom Line: Its constituents have been shown to exert pharmacological effects, such as anti-microbial, anti-inflammatory and anticancer.Some compounds were found in propolis and resin mass, but not in shoot apices.Probably, green propolis composition is more complex and unpredictable than previously assumed.

View Article: PubMed Central - PubMed

ABSTRACT
Propolis, a honeybee product, has gained popularity as a food and alternative medicine. Its constituents have been shown to exert pharmacological effects, such as anti-microbial, anti-inflammatory and anticancer. Shoot apices of Baccharis dracunculifolia (alecrim plant, Asteraceae) have been pointed out as sources of resin for green propolis. The present work aimed (i) to observe the collecting behavior of bees, (ii) to test the efficacy of histological analysis in studies of propolis botanical origin and (iii) to compare the chemistries of alecrim apices, resin masses and green propolis. Bee behavior was observed, and resin and propolis were microscopically analyzed by inclusion in methacrylate. Ethanol extracts of shoot apices, resin and propolis were analyzed by gas chromatography/mass spectroscopy. Bees cut small fragments from alecrim apices, manipulate and place the resulting mass in the corbiculae. Fragments were detected in propolis and identified as alecrim vestiges by detection of alecrim structures. Prenylated and non-prenylated phenylpropanoids, terpenoids and compounds from other classes were identified. Compounds so far unreported for propolis were identified, including anthracene derivatives. Some compounds were found in propolis and resin mass, but not in shoot apices. Differences were detected between male and female apices and, among apices, resin and propolis. Alecrim apices are resin sources for green propolis. Chemical composition of alecrim apices seems to vary independently of season and phenology. Probably, green propolis composition is more complex and unpredictable than previously assumed.

No MeSH data available.


Structures of some compounds identified in a sample of green propolis. (A) 2-hydroxy-7,12-dimethylbenzanthracene. (B) 1-Hydroxy-2-(1-methoxyethyl)-3-methoxyanthraquinone; (C) Dehydrocostus lactone. (D) Isomaturnin. (E) 1,4aβ-dimethyl-7-isopropyl-2,3,4,4a,9,10-hexahydrophenanthrene. (F) 1,7,7-Trimethyl-3-phenyl-2-oxabixyclo-(4.4.0)-deca-3,5-diene. (G) 4,8-Dimethyl-5-hydrindacene.
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fig7: Structures of some compounds identified in a sample of green propolis. (A) 2-hydroxy-7,12-dimethylbenzanthracene. (B) 1-Hydroxy-2-(1-methoxyethyl)-3-methoxyanthraquinone; (C) Dehydrocostus lactone. (D) Isomaturnin. (E) 1,4aβ-dimethyl-7-isopropyl-2,3,4,4a,9,10-hexahydrophenanthrene. (F) 1,7,7-Trimethyl-3-phenyl-2-oxabixyclo-(4.4.0)-deca-3,5-diene. (G) 4,8-Dimethyl-5-hydrindacene.

Mentions: Prenylated phenylpropanoids are characteristic of B.dracunculifolia and green propolis (4). A prenylated phenylpropanoid recently reported as a novel compound, allyl-3-prenylcinnamate (12), was found again as a relevant constituent, not only in propolis but also in alecrim apices (Table 1, compound 10). Dehydrocostus lactone (Table 2, compound 24; Fig. 7C), a sesquiterpene reported from an unusual sample of propolis (13), but never in a typical green propolis, was detected in the propolis sample and resin mass, although not in the shoot apices. This guaianolide lactone has been shown to exert several activities, among them antimycobacterial (14) and against Trypanosoma cruzi (15), an important cardiac parasite in rural areas of Brazil. Artepillin C (4-hydroxy-3,5-diprenyl cinnamic acid), a compound from Brazilian propolis with anti-tumor activity (16), was not found in apices and resin mass, but was detected in propolis (Table 1, compound 12). Other phenolics from Brazilian propolis possess not only cytotoxic but also hepatoprotective activity (14). Labdane diterpenes identical or similar to compounds 28–30 (Table 2; Fig. 7E) were reported from Brazilian propolis (17) and B.dracunculifolia (18). In addition, alecrim apices are probably also sources of other classes of terpenoids (Table 2), such as sesquiterpenes (farnesol, compound 23; dehydrocostus lactone, compound 24, Fig. 7C; viridiflorol, compound 25; isomaturnin, compound 26, Fig. 7D; 1H-cyclopropazulene-1a,2,3,4,4a,5,6,7b-octahydro-1,1,4,7-tetramethyl, compound 27), triterpenes (squalene, compound 31; bauer-7-en-3β-yl acetate, compound 32) and steroids (stigmasta-3,5-dien-7-one, compound 33; cholest-5-en-3β-ol, compound 34; clionasterol, compound 35).


Plant Origin of Green Propolis: Bee Behavior, Plant Anatomy and Chemistry.

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

Structures of some compounds identified in a sample of green propolis. (A) 2-hydroxy-7,12-dimethylbenzanthracene. (B) 1-Hydroxy-2-(1-methoxyethyl)-3-methoxyanthraquinone; (C) Dehydrocostus lactone. (D) Isomaturnin. (E) 1,4aβ-dimethyl-7-isopropyl-2,3,4,4a,9,10-hexahydrophenanthrene. (F) 1,7,7-Trimethyl-3-phenyl-2-oxabixyclo-(4.4.0)-deca-3,5-diene. (G) 4,8-Dimethyl-5-hydrindacene.
© Copyright Policy
Related In: Results  -  Collection

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fig7: Structures of some compounds identified in a sample of green propolis. (A) 2-hydroxy-7,12-dimethylbenzanthracene. (B) 1-Hydroxy-2-(1-methoxyethyl)-3-methoxyanthraquinone; (C) Dehydrocostus lactone. (D) Isomaturnin. (E) 1,4aβ-dimethyl-7-isopropyl-2,3,4,4a,9,10-hexahydrophenanthrene. (F) 1,7,7-Trimethyl-3-phenyl-2-oxabixyclo-(4.4.0)-deca-3,5-diene. (G) 4,8-Dimethyl-5-hydrindacene.
Mentions: Prenylated phenylpropanoids are characteristic of B.dracunculifolia and green propolis (4). A prenylated phenylpropanoid recently reported as a novel compound, allyl-3-prenylcinnamate (12), was found again as a relevant constituent, not only in propolis but also in alecrim apices (Table 1, compound 10). Dehydrocostus lactone (Table 2, compound 24; Fig. 7C), a sesquiterpene reported from an unusual sample of propolis (13), but never in a typical green propolis, was detected in the propolis sample and resin mass, although not in the shoot apices. This guaianolide lactone has been shown to exert several activities, among them antimycobacterial (14) and against Trypanosoma cruzi (15), an important cardiac parasite in rural areas of Brazil. Artepillin C (4-hydroxy-3,5-diprenyl cinnamic acid), a compound from Brazilian propolis with anti-tumor activity (16), was not found in apices and resin mass, but was detected in propolis (Table 1, compound 12). Other phenolics from Brazilian propolis possess not only cytotoxic but also hepatoprotective activity (14). Labdane diterpenes identical or similar to compounds 28–30 (Table 2; Fig. 7E) were reported from Brazilian propolis (17) and B.dracunculifolia (18). In addition, alecrim apices are probably also sources of other classes of terpenoids (Table 2), such as sesquiterpenes (farnesol, compound 23; dehydrocostus lactone, compound 24, Fig. 7C; viridiflorol, compound 25; isomaturnin, compound 26, Fig. 7D; 1H-cyclopropazulene-1a,2,3,4,4a,5,6,7b-octahydro-1,1,4,7-tetramethyl, compound 27), triterpenes (squalene, compound 31; bauer-7-en-3β-yl acetate, compound 32) and steroids (stigmasta-3,5-dien-7-one, compound 33; cholest-5-en-3β-ol, compound 34; clionasterol, compound 35).

Bottom Line: Its constituents have been shown to exert pharmacological effects, such as anti-microbial, anti-inflammatory and anticancer.Some compounds were found in propolis and resin mass, but not in shoot apices.Probably, green propolis composition is more complex and unpredictable than previously assumed.

View Article: PubMed Central - PubMed

ABSTRACT
Propolis, a honeybee product, has gained popularity as a food and alternative medicine. Its constituents have been shown to exert pharmacological effects, such as anti-microbial, anti-inflammatory and anticancer. Shoot apices of Baccharis dracunculifolia (alecrim plant, Asteraceae) have been pointed out as sources of resin for green propolis. The present work aimed (i) to observe the collecting behavior of bees, (ii) to test the efficacy of histological analysis in studies of propolis botanical origin and (iii) to compare the chemistries of alecrim apices, resin masses and green propolis. Bee behavior was observed, and resin and propolis were microscopically analyzed by inclusion in methacrylate. Ethanol extracts of shoot apices, resin and propolis were analyzed by gas chromatography/mass spectroscopy. Bees cut small fragments from alecrim apices, manipulate and place the resulting mass in the corbiculae. Fragments were detected in propolis and identified as alecrim vestiges by detection of alecrim structures. Prenylated and non-prenylated phenylpropanoids, terpenoids and compounds from other classes were identified. Compounds so far unreported for propolis were identified, including anthracene derivatives. Some compounds were found in propolis and resin mass, but not in shoot apices. Differences were detected between male and female apices and, among apices, resin and propolis. Alecrim apices are resin sources for green propolis. Chemical composition of alecrim apices seems to vary independently of season and phenology. Probably, green propolis composition is more complex and unpredictable than previously assumed.

No MeSH data available.