Table 1 Phenolic compounds detected in shoot apices of Baccharis dracunculifolia DC. (Asteraceae), resin masses from bee corbiculae and a sample of green propolis
| Compounds |
Apices
|
Propolis |
Pharmacological activities |
Ref. |
|
|
|
|
|
|
Female |
Male |
|
|
|
|
|
Cinnamic acid derivatives
|
| 1. Hydrocinnamic acid |
+ |
+ |
+ |
+ |
|
|
| 2. p-Hydroxyhydrocinnamic acid |
– |
– |
– |
+ |
|
|
| 3. p-Hydroxycinnamic acid |
+ |
+ |
+ |
+ |
Anti-inflammatory |
22 |
| 4. p-Methoxycinnamic acid |
+ |
+ |
+ |
+ |
|
|
| 5. cis-3-Methoxy-4-hydroxy-cinnamic acid |
– |
+ |
– |
+ |
|
|
| 6. cis-3,4-Dimethoxycinnamic acid |
+ |
+ |
– |
– |
|
|
| 7. trans-3-methoxy-4-hydroxy-cinnamic acid |
+ |
+ |
+ |
+ |
Antimicrobial |
1 |
|
|
|
|
|
Anti-inflammatory |
22 |
| 8. trans-3,4-Dimethoxycinnamic acid |
+ |
+ |
+ |
+ |
Anti-inflammatory |
22 |
| 9. p-Coumaric acid |
– |
– |
+ |
+ |
|
|
Prenylated cinnamic acid derivatives
|
| 10. Allyl-3-prenylcinnamate |
+ |
+ |
+ |
+ |
|
|
| 11. 4-Hydroxy-3-prenylcinnamic acid |
– |
– |
+ |
+ |
Hepatoprotection |
14 |
| 12. 4-Hydroxy-3,5-diprenylcinnamic acid (artepillin C) |
– |
– |
+ |
+ |
Antitrypanocidal |
23 |
|
|
|
|
|
Cytotoxicity |
16 |
Chromane derivatives
|
| 13. 2,2-Dimethylchromene-6-propenoic acid |
+ |
+ |
+ |
+ |
Antioxidant |
24 |
| 14. 2,2-Dimethyl-8-prenylchromene-6-propenoic acid |
+ |
+ |
+ |
+ |
Hepatoprotection |
23 |
|
|
|
|
|
Cytotoxicity |
25 |
| 15. 8-(methyl-butanechromane)-6-propenoic acid |
– |
– |
– |
+ |
|
|
| 16. 3-Hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid |
– |
– |
+ |
+ |
|
|
Naphtalene and anthracene derivatives
|
| 17. 2-t-Butylnaphto-[2,3-b]-furan-4,9-dione |
– |
– |
+ |
+ |
|
|
| 18. 2-Hydroxy-7,12-dimethyl-benzanthracene (A) |
+ |
+ |
+ |
+ |
|
|
| 19. 1-Hydroxy-2-(1-methoxyethyl)-3-methoxyanthraquinone (B) |
– |
– |
+ |
+ |
|
|
Simple benzene and phenol derivatives
|
| 20. Benzene-3,3-dimethyl-4-pentenyl |
+ |
+ |
– |
– |
|
|
| 21. p-Vinylphenol |
– |
– |
– |
+ |
|
|
| 22. p-Vinyl-o-prenylphenol |
+ |
+ |
+ |
+ |
|
|
|
Compound names in bold refer to occurrences so far unreported in propolis; letters in parenthesis correspond to structures in Fig. 7.
–, Not detected.
Table 2 Terpenoids detected in shoot apices of Baccharis dracunculifolia DC. (Asteraceae), resin masses from bee corbiculae and a sample of green propolis
| Compound |
Apices
|
Propolis |
Pharmacological activity |
Ref. |
|
|
|
|
|
|
Female |
Male |
|
|
|
|
|
Sesquiterpenes
|
| 23. Farnesol |
– |
– |
– |
+ |
Antimicrobial |
26 |
| 24. Dehydrocostus lactone (C) |
– |
– |
+ |
+ |
Trypanocidal |
15 |
|
|
|
|
|
Antimycobacterial |
27 |
| 25. Viridiflorol |
– |
– |
+ |
– |
|
|
| 26. Isomaturnin (D) |
– |
– |
+ |
+ |
|
|
| 27. 1H-Cyclopropazulene-1a,2,3,4,4a,5,-6,7b-octahydro-1,1,4,7-tetramethyl |
+ |
+ |
– |
– |
|
|
Diterpenes
|
| 28. Isocupressic acid derivative |
– |
– |
+ |
+ |
Antibacterial |
17 |
|
|
|
|
|
Cytotoxicity |
28 |
| 29. 1,4aß-Dimethyl-7-isopropyl-2,3,4,-4a,9,10-hexahydrophenanthrene (E) |
– |
– |
+ |
+ |
|
|
30. T -Hydroxysandaracopimar-8(14)-15-diene |
– |
– |
+ |
– |
|
|
Triterpenes and steroids
|
| 31. Squalene |
+ |
+ |
– |
– |
|
|
| 32. Bauer-7-en-3ß-yl acetate |
– |
– |
– |
+ |
|
|
| 33. Stigmasta-3,5-dien-7-one |
+ |
+ |
– |
– |
|
|
| 34. Cholest-5-en-3ß-ol |
+ |
+ |
+ |
– |
|
|
| 35. Clionasterol |
+ |
+ |
+ |
– |
|
|
|
Compound names in bold refer to occurrences so far unreported in propolis; letters in parenthesis correspond to structures in Fig. 7.
–, Not detected.
Table 3 Wax constituents detected in shoot apices of Baccharis dracunculifolia DC. (Asteraceae), resin masses from bee corbiculae and a sample of green propolis
| Compound |
Apices
|
Propolis |
|
|
|
|
Female |
Male |
|
|
|
Wax constituents
|
| 36. Methyl-dodecanoate |
+ |
+ |
– |
– |
| 37. Methyl-tetradecanoate |
– |
+ |
– |
– |
| 38. Hexadecanoic acid |
+ |
+ |
– |
– |
| 39. Octadecanoic acid |
– |
+ |
+ |
– |
| 40. Hexacosanoic acid |
– |
+ |
– |
– |
| 41. Docosanoic acid |
+ |
+ |
– |
– |
| 42. Tetracosanoic acid |
– |
+ |
– |
– |
| 43. Octacosanoic acid |
– |
+ |
– |
– |
| 44. Hexacosanoic acid |
– |
+ |
– |
– |
| 45. Methyl-4-methoxyoctadecanoic acid |
+ |
+ |
– |
– |
| 46. Hexanedioic acid dioctyl ester |
+ |
+ |
+ |
+ |
| 47. n-Dodecanal |
+ |
+ |
– |
– |
| 48. n-Hexadecanal |
+ |
+ |
– |
– |
| 49. 9,12-Octadecadienal |
+ |
+ |
– |
– |
| 50. (Z,Z)-9,12-octadecadienoic acid |
– |
– |
– |
+ |
| 51. Methyl-(Z)-9-Octadecenoate |
– |
– |
– |
+ |
| 52. n-Docosanol |
+ |
+ |
– |
– |
| 53. n-Tetracosanol |
+ |
+ |
– |
– |
| 54. n-Hexacosanol |
+ |
+ |
– |
– |
| 55. 4-Ethyloctane |
– |
– |
– |
+ |
| 56. 7-n-Hexyleicosane |
+ |
+ |
– |
– |
| 57. n-Hentriacontane |
+ |
+ |
– |
– |
| 58. 17-Tritriacontene |
+ |
+ |
– |
– |
| 59. 17-Pentatriacontene |
– |
– |
– |
+ |
|
No pharmacological properties have as yet been assigned to these compounds Compound names in bold refer to occurrences so far unreported in propolis.
–, Not detected.
Table 4 Compounds representative of classes other than phenolics, terpenoids and waxes, detected in shoot apices of Baccharis dracunculifolia DC. (Asteraceae), resin masses from bee corbiculae and a sample of green propolis
| Compound |
Apices
|
Propolis |
|
|
|
|
Female |
Male |
|
|
|
| 60. Quinic acid |
+ |
+ |
– |
– |
| 61. 1,7,7-Trimethyl-3-phenyl-2-oxabicyclo-(4.4.0)-deca-3,5-diene (F) |
– |
– |
– |
+ |
| 62. Allyl-n-butanoate |
– |
+ |
+ |
– |
| 63. Vinyl-butyrate |
– |
+ |
+ |
– |
| 64. 4,8-Dimethyl-5-hydrindacene (G) |
+ |
+ |
+ |
+ |
|
No pharmacological properties have as yet been assigned to these compounds Compound names in bold refer to occurrences so far unreported in propolis; letters in parenthesis correspond to structures in Fig. 7.
–, Not detected.