Volatiles, A Glutarimide Alkaloid and Antimicrobial Effects of Croton pullei (Euphorbiaceae)
Abstract
:1. Introduction
2. Results and Discussion
2.1. Volatile Compounds
Constituents | RI * | Leaf | Stem |
---|---|---|---|
α-pinene | 937 | 8.08 | 8.23 |
β-pinene | 981 | 6.63 | 9.81 |
Myrcene | 994 | 1.07 | |
1,8-cineole | 1033 | 3.72 | |
γ-terpinene | 1060 | 0.50 | |
cis-linalool furanoxide | 1074 | 0.26 | |
1-nonen-3-ol | 1080 | 0.60 | 0.71 |
trans-linalool furanoxide | 1091 | 0.32 | |
Linalool | 1105 | 24.90 | 39.72 |
α-campholenal | 1129 | 0.67 | |
α-terpineol | 1193 | 0.60 | |
trans-pinocarveol | 1142 | 0.49 | |
trans-sabinol | 1148 | 0.40 | |
terpinen-4-ol | 1180 | 0.68 | |
Myrtenal | 1200 | 0.60 | |
β-elemene | 1395 | 1.24 | |
γ-elemene | 1340 | 0.96 | |
α-cubebene | 1352 | 0.36 | |
α-copaene | 1379 | 0.31 | |
β-elemene | 1388 | 0.44 | |
Methyleugenol | 1408 | 0.48 | 0.45 |
cis-α-bergamotene | 1419 | 0.30 | |
β-caryophyllene | 1424 | 3.96 | 1.24 |
trans-α-bergamotene | 1439 | 0.27 | |
γ-elemene | 1437 | 0.73 | |
Aromadendrene | 1444 | 0.15 | |
α-humulene | 1459 | 1.84 | |
allo-aromadendrene | 1466 | 0.29 | |
γ-gurjunene | 1481 | 0.90 | 0.43 |
germacrene D | 1486 | 1.19 | |
β-selinene | 1492 | 2.91 | 1.25 |
α-selinene | 1500 | 2.67 | 1.21 |
bicyclogermacrene | 1502 | 2.67 | |
α-muurolene | 1505 | 0.15 | |
(Z)-α-bisabolene | 1510 | 0.46 | |
γ-cadinene | 1519 | 1.50 | |
δ-cadinene | 1527 | 1.12 | 0.78 |
cis-calamenene | 1537 | 1.15 | 0.69 |
trans-cadina-1,4-diene | 1545 | 0.08 | |
α-calacorene | 1545 | 0.08 | 0.45 |
(E)-nerolidol | 1564 | 3.91 | 4.62 |
Spathulenol | 1580 | 2.72 | 2.38 |
caryophyllene oxide | 1585 | 1.80 | 1.71 |
Viridiflorol | 1604 | 0.16 | |
Ledol | 1616 | 0.78 | |
Junenol | 1625 | 1.00 | |
iso-spathulenol | 1631 | 0.40 | |
epi-cadinol | 1642 | 0.57 | |
α-muurolol | 1650 | 0.57 | |
Pogostol | 1660 | 3.58 | 4.65 |
(Z)-α-santalol | 1685 | 1.63 | 2.05 |
Acorenone | 1697 | 0.53 | 1.13 |
(Z)-epi-β-santalol | 1703 | 0.80 | 0.57 |
cyclocolorenone | 1759 | 0.09 | 0.87 |
manoyl oxide | 2002 | 0.87 | |
13-epi-manoyl oxide | 2025 | 0.39 | |
2-oxo-manoyl oxide | 2243 | 0.68 |
2.2. Novel Non-Volatile Compound
δH | δC | |
---|---|---|
2 | - | 173.3 * |
3 | 4.60 (dd, J = 12.6 and 5.6 Hz) | 51.8 |
4 | 2.13–1.86 (m) | 24.8 |
5 | 2.75–2.71 (m) | 32.4 |
6 | - | 172.9 * |
1' | - | 139.9 |
2' | 7.29–7.18 (m) | 129.9 |
3' | 7.29–7.18 (m) | 129.5 |
4' | 7.29–7.18 (m) | 127.3 |
5' | 7.29–7.18 (m) | 129.5 |
6' | 7.29–7.18 (m) | 129.9 |
7' | 2.77 (t, J =7.8 Hz) | 34.8 |
8' | 3.95–3.80 (m) | 42.6 |
1'' | - | 173.7 |
2'' | 2.02 (s) | 22.5 |
2.3. Antimicrobial Activity
Organism | Hexane | MeOH | Control | |||
MIC | MMC | MIC | MMC | Nist/Chlorf | DMSO | |
Escherichia coli CCMB 261 | 5 | - | 5 | 5 | R | 5.00 |
Pseudomonas aeruginosa CCMB 268 | 5 | 10 | 1.25 | 2.5 | 0.31 | 5.00 |
Salmonella sp. CCMB 281 | 2.5 | 10 | 1.25 | 10 | 0.16 | 5.00 |
Staphylococcus aureus CCMB 262 | 0.156 | 5 | 0.078 | 2.5 | 0.31 | 5.00 |
S. aureus CCMB 263 | 1.25 | 10 | 0.078 | 5 | 0.31 | 10.00 |
S. aureus CCMB 285 | 10 | 10 | 2.5 | 5 | R | 10.00 |
Bacillus cereus CCMB 282 | 2.5 | 2.5 | 1.25 | 1.25 | 0.16 | 5.00 |
Candida albicans CCMB 286 | 2.5 | 5 | 2.5 | 5 | 0.63 | 10.00 |
C. albicans CCMB 266 | 2.5 | 10 | 2.5 | 5 | 0.08 | 10.00 |
C. parapsilosis CCMB 288 | 2.5 | 10 | 2.5 | 10 | R | 10.00 |
3. Experimental
3.1. Material and Isolation and Identification of Non-Volatile and Distillation of the Volatile Constituents
3.2. Extraction of Volatile Compounds
3.3. Analysis of the Volatiles
3.4. Isolation and Identification of Compound 4
3.5. Antimicrobial Assays
3.5.1. Microbial Strains
3.5.2. Minimum Inhibitory Concentration (MIC)
3.5.3. Minimal Microbicidal Concentration (MMC)
4. Conclusions
Acknowledgments
References
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Peixoto, R.N.S.; Guilhon, G.M.S.P.; Das Graças B. Zoghbi, M.; Araújo, I.S.; Uetanabaro, A.P.T.; Santos, L.S.; Do S. B. Brasil, D. Volatiles, A Glutarimide Alkaloid and Antimicrobial Effects of Croton pullei (Euphorbiaceae). Molecules 2013, 18, 3195-3205. https://doi.org/10.3390/molecules18033195
Peixoto RNS, Guilhon GMSP, Das Graças B. Zoghbi M, Araújo IS, Uetanabaro APT, Santos LS, Do S. B. Brasil D. Volatiles, A Glutarimide Alkaloid and Antimicrobial Effects of Croton pullei (Euphorbiaceae). Molecules. 2013; 18(3):3195-3205. https://doi.org/10.3390/molecules18033195
Chicago/Turabian StylePeixoto, Rosana N. S., Giselle M. S. P. Guilhon, Maria Das Graças B. Zoghbi, Isabella S. Araújo, Ana Paula T. Uetanabaro, Lourivaldo S. Santos, and Davi Do S. B. Brasil. 2013. "Volatiles, A Glutarimide Alkaloid and Antimicrobial Effects of Croton pullei (Euphorbiaceae)" Molecules 18, no. 3: 3195-3205. https://doi.org/10.3390/molecules18033195