Chemical Diversity, Biological Activity, and Genetic Aspects of Three Ocotea Species from the Amazon
Abstract
:1. Introduction
2. Results and Discussion
2.1. Essential Oil Chemical Composition
2.2. Antimicrobial and Cytotoxic Activities
2.3. Phylogenetic Analysis
3. Materials and Methods
3.1. Plant Material
3.2. Essential Oil Extraction
3.3. Gas Chromatographic–Mass Spectral Analysis
3.4. Antibacterial Assay
3.5. Cytotoxicity Assay
3.6. Multivariate Statistical Analysis of Chemical Composition
3.7. DNA Isolation, PCR Amplification, and Sequencing
3.8. Phylogenetic Analysis
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
Abbreviations
matK | Megakaryocyte-Associated Tyrosine Kinase |
MIC | Minimum Inhibitory Concentration |
RICalc. | Calculated retention index |
RILit | Literature retention index |
IC50 | Median Inhibitory Concentration |
GC | Gas chromatography |
DMSO | Dimethylsulfoxide |
RPMI | Roswell Park Memorial Institute medium |
MTT | 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide |
HEPES | 4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid buffer |
PCR | Polymerase Chain Reaction |
References and Notes
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Species | Geographic Coordinate | Voucher | Plant Material | Sample | Oil Yield (%) |
---|---|---|---|---|---|
O. caudata | S 01.0° 44.0′ 18.8′′ | MG 216263 | Leaves | Cau-L | 0.7 |
W 51.0° 27.0′ 27.4′′ | Branches | Cau-B | 0.1 | ||
O. cujumary | S 01.0° 44.0′ 14.1′′ | MG 216269 | Leaves | Cuj-L | 0.8 |
W 51.0° 27.0′ 20.4′′ | Branches | Cuj-B | 0.5 | ||
O. caniculata | S 01.0° 44.0′ 14.1′′ | MG 216262 | Leaves | Can-L | 0.7 |
W 51.0° 27.0′ 20.4′′ | Branches | Can-B | 0.2 |
Constituents | RICalc | RILit | Cau-L | Cau-B | Cuj-L | Cuj-B | Can-L | Can-B | Flo-L * | Ver-L * | Whi-L * |
---|---|---|---|---|---|---|---|---|---|---|---|
E-2-Hexenal | 856 | 854 | 1.1 | 0.8 | |||||||
α-Thujene | 933 | 931 | 0.2 | ||||||||
α-Pinene | 936 | 932 | 9.8 | 2.1 | 22.5 | 0.7 | 12.7 | ||||
Camphene | 956 | 953 | 1.7 | 0.1 | 0.3 | ||||||
Sabinene | 979 | 976 | 0.1 | ||||||||
β-Pinene | 980 | 974 | 9.7 | 1.8 | 2.2 | 21.3 | 0.3 | 7.3 | |||
Myrcene | 995 | 991 | 0.7 | 1.1 | 0.5 | ||||||
α-Phellandrene | 1009 | 1005 | 1 | ||||||||
p-Cymene | 1028 | 1026 | 19.8 | ||||||||
Limonene | 1030 | 1024 | 2.1 | 1.8 | 20.5 | 2.7 | 1.1 | ||||
β-Phellandrene | 1032 | 1031 | 4.0 | ||||||||
1,8-Cineole | 1033 | 1033 | 1.3 | ||||||||
γ-Terpinene | 1064 | 1062 | 0.1 | ||||||||
α-Terpinolene | 1089 | 1088 | 0.1 | ||||||||
α-Pinene oxide | 1097 | 1095 | 0.1 | ||||||||
Linalool | 1104 | 1098 | 1.7 | ||||||||
Borneol | 1168 | 1165 | 0.1 | ||||||||
Terpinen-4-ol | 1178 | 1177 | 2.0 | 0.2 | |||||||
α-Terpineol | 1191 | 1189 | 0.2 | 1.3 | |||||||
Cuminal | 1238 | 1239 | 0.1 | ||||||||
2-Undecanol | 1301 | 1301 | 1.2 | 4.6 | |||||||
δ-Elemene | 1340 | 1335 | 2.2 | ||||||||
α-Cubebene | 1351 | 1345 | 2.0 | 2.0 | 0.8 | 2.2 | |||||
α-Ylangene | 1373 | 1373 | 0.8 | 5.1 | |||||||
α-Copaene | 1377 | 1374 | 1.0 | 0.1 | 0.1 | 0.8 | |||||
β-Cubebene | 1392 | 1387 | 1.6 | 0.1 | |||||||
β-Bourbonene | 1384 | 1387 | 0.7 | 0.1 | 0.1 | ||||||
δ-Elemene | 1392 | 1389 | 1.5 | 0.4 | 1.1 | 0.8 | 0.3 | 0.7 | 0.3 | ||
Z-Caryophyllene | 1416 | 1408 | 0.3 | ||||||||
β-Caryophyllene | 1421 | 1417 | 9.6 | 2.5 | 22.2 | 8.1 | 18.9 | 7.1 | 2.5 | 2.3 | 15.2 |
2,5-Dimethoxy-p-cymene | 1424 | 1424 | 0.9 | ||||||||
β-Copaene | 1428 | 1430 | 0.4 | ||||||||
β-Gurjunene | 1432 | 1432 | 0.2 | ||||||||
α-trans-Bergamotene | 1436 | 1432 | 0.9 | 1.9 | |||||||
γ-Elemene | 1435 | 1434 | 0.8 | 0.1 | |||||||
α-Guaiene | 1439 | 1439 | 0.1 | ||||||||
Aromadendrene | 1440 | 1439 | 0.1 | ||||||||
Z-β-Farnesene | 1443 | 1440 | 0.9 | ||||||||
Spirolepechinene | 1451 | 1449 | 0.7 | 1.4 | 0.6 | ||||||
α-Humulene | 1455 | 1452 | 1.8 | 2.4 | 3.8 | 2.5 | 2.5 | 1.7 | 0.3 | 1.7 | 1.7 |
Sesquisabinene | 1458 | 1457 | 0.9 | ||||||||
Dehydroaromadendrane | 1460 | 1460 | 0.6 | ||||||||
E-β-Farnesene | 1462 | 1458 | 0.9 | ||||||||
allo-Aromadendrene | 1463 | 1461 | 0.2 | ||||||||
trans-Cadina-1(6),4-diene | 1473 | 1475 | 0.5 | ||||||||
γ-Selinene | 1477 | 1470 | 0.2 | ||||||||
γ-Gurjunene | 1477 | 1475 | 0.4 | ||||||||
γ-Muurolene | 1476 | 1478 | 0.8 | 0.7 | |||||||
Widdra-2,4(14)-diene | 1483 | 1481 | 6.5 | ||||||||
Germacrene D | 1484 | 1484 | 19.9 | 8.9 | 0.9 | 5.9 | 1.2 | 0.2 | 5.5 | ||
β-Selinene | 1485 | 1489 | 2.2 | 20.3 | 12.1 | 0.3 | |||||
Valencene | 1493 | 1491 | 1.1 | ||||||||
cis-β-Guaiene | 1493 | 1492 | 8.3 | 3.0 | 5.2 | ||||||
trans-Muurola-4(14),5-diene | 1491 | 1493 | 1.1 | ||||||||
2-Tridecanone | 1497 | 1495 | 7.3 | 30.0 | |||||||
Viridiflorene | 1493 | 1496 | 9.8 | ||||||||
Bicyclogermacrene | 1500 | 1500 | 29.6 | 10.4 | 5.3 | ||||||
α-Muurolene | 1499 | 1500 | 1.7 | 1.0 | 0.1 | ||||||
Germacrene A | 1504 | 1503 | 0.2 | 2 | |||||||
β-Bisabolene | 1509 | 1505 | 0.6 | ||||||||
δ-Amorphene | 1509 | 1511 | 0.8 | 2.0 | |||||||
E,E-α-Farnesene | 1510 | 1508 | 0.3 | ||||||||
γ-Cadinene | 1517 | 1513 | 0.9 | 5.9 | 1.6 | 3.1 | 1.7 | 0.1 | 0.4 | 0.7 | |
7-epi-α-Selinene | 1517 | 1520 | 4.5 | 14.8 | 9.0 | ||||||
β-Cadinene | 1519 | 1518 | 0.7 | 0.6 | |||||||
cis-Calamenene | 1523 | 1521 | 0.6 | ||||||||
δ-Cadinene | 1526 | 1522 | 1.4 | 13.8 | 6.6 | 4.7 | 0.6 | 3.9 | 0.2 | 0.4 | 3.7 |
trans-Cadina-1,4-diene | 1532 | 1533 | 0.6 | 0.2 | 0.2 | ||||||
α-Cadinene | 1537 | 1538 | 0.1 | ||||||||
α-Calacorene | 1542 | 1544 | 0.9 | 1.5 | 0.2 | ||||||
Elemol | 1549 | 1549 | 0.1 | ||||||||
Germacrene B | 1558 | 1559 | 1.6 | 3.3 | 0.8 | 0.4 | 0.7 | ||||
E-Nerolidol | 1564 | 1561 | 1.4 | 2.5 | 3.9 | ||||||
β-Calacorene | 1564 | 1564 | 0.7 | 0.5 | |||||||
γ-Asarone | 1576 | 1572 | 0.4 | ||||||||
Spathulenol | 1579 | 1577 | 1.4 | 0.5 | 1.0 | 6 | 8.5 | 15.3 | |||
Caryophyllene oxide | 1585 | 1582 | 1.0 | 2.0 | 12.4 | 0.9 | 2.0 | ||||
Globulol | 1592 | 1590 | 0.9 | ||||||||
Viridiflorol | 1597 | 1592 | 1.2 | ||||||||
Carotol | 1586 | 1594 | 2.7 | ||||||||
6-Methoxyelemicin | 1601 | 1595 | 6.3 | ||||||||
Guaiol | 1597 | 1600 | 1.2 | 4.0 | 5.2 | ||||||
Humulene epoxide II | 1608 | 1608 | 1.0 | 1.7 | |||||||
Z-Asarone | 1625 | 1616 | 3.4 | ||||||||
1,10-di-epi-Cubenol | 1620 | 1618 | 3.0 | 1.4 | |||||||
Junenol | 1620 | 1618 | 0.6 | ||||||||
1-epi-Cubenol | 1628 | 1627 | 3.8 | 0.4 | 3.3 | ||||||
Muurola-4,10(14)-dien-1β-ol | 1628 | 1630 | 3.3 | ||||||||
epi-α-Cadinol | 1642 | 1638 | 2.0 | 0.5 | |||||||
allo-Aromadendrene epoxide | 1632 | 1639 | 1.4 | ||||||||
Caryophylla-4(12),8(13)-dien-5β-ol | 1636 | 1639 | 3.2 | ||||||||
α-Muurolol | 1642 | 1644 | 7.8 | 0.9 | 1.8 | ||||||
Cubenol | 1646 | 1645 | 2.2 | 1.5 | |||||||
α-Cadinol | 1652 | 1652 | 2.2 | 1.8 | 1.5 | 1.8 | |||||
Valerianol | 1654 | 1656 | 6.8 | ||||||||
Selin-11-en-4α-ol | 1657 | 1658 | 3.1 | 20.6 | |||||||
7-epi-α-Eudesmol | 1658 | 1662 | 4.2 | ||||||||
Bulnesol | 1662 | 1666 | 29.5 | ||||||||
14-Hydroxy-(Z)-caryophyllene | 1666 | 1666 | 2.3 | 1.5 | 0.9 | 2.1 | |||||
E-Asarone | 1683 | 1675 | 3.6 | 8.8 | |||||||
β-Sinensal | 1699 | 1699 | 0.6 | ||||||||
E,E-Farnesylacetate | 1843 | 1843 | 10.1 | ||||||||
Isohibaene | 1922 | 1923 | 0.7 | ||||||||
Kaurene | 2034 | 2034 | 34.0 |
Material | MIC (μg·mL−1) | IC50 (μg·mL−1) | ||||
---|---|---|---|---|---|---|
P. aer | E. coli | S. epi | S. aur | B. cer | MCF-7 | |
Can-L | 1250.0 | 19.5 | 625.0 | 625.0 | 625.0 | 63.9 ± 3.7 |
Cau-L | 1250.0 | 19.5 | 625.0 | 625.0 | 312.5 | 64.0 ± 3.7 |
Cuj-L | 1250.0 | 19.5 | 312.5 | 625.0 | 312.5 | 67.7 ± 3.7 |
α-Pinene | 625 | 312 | - | 312 | 625 | 69.5 ± 1.3 |
β-Pinene | 1250 | 625 | - | 625 | 312 | 71.2 ± 2.0 |
Limonene | 1250 | 625 | - | 312 | 625 | 77.4 ± 1.2 |
β-Caryophyllene | 1250 | 312 | - | 312 | 156 | 59.4 ± 5.1 |
α-Humulene | 1250 | 625 | - | 312 | 312 | 26.5 ± 5.6 |
Germacrene D | 1250 | 625 | - | 156 | 625 | 69.6 ± 2.5 |
Caryophyllene oxide | 1250 | 1250 | - | 1250 | 156 | 73.4 ± 3.7 |
Gentamicin control | 1.22 | 2.44 | <19.5 | 0.61 | 1.22 | - |
Tingenone control | <19.5 | <19.5 | - | 2.44 | 1.22 | 16.8 ± 1.7 |
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Da Silva, J.K.; Da Trindade, R.; Moreira, E.C.; Maia, J.G.S.; Dosoky, N.S.; Miller, R.S.; Cseke, L.J.; Setzer, W.N. Chemical Diversity, Biological Activity, and Genetic Aspects of Three Ocotea Species from the Amazon. Int. J. Mol. Sci. 2017, 18, 1081. https://doi.org/10.3390/ijms18051081
Da Silva JK, Da Trindade R, Moreira EC, Maia JGS, Dosoky NS, Miller RS, Cseke LJ, Setzer WN. Chemical Diversity, Biological Activity, and Genetic Aspects of Three Ocotea Species from the Amazon. International Journal of Molecular Sciences. 2017; 18(5):1081. https://doi.org/10.3390/ijms18051081
Chicago/Turabian StyleDa Silva, Joyce Kelly, Rafaela Da Trindade, Edith Cibelle Moreira, José Guilherme S. Maia, Noura S. Dosoky, Rebecca S. Miller, Leland J. Cseke, and William N. Setzer. 2017. "Chemical Diversity, Biological Activity, and Genetic Aspects of Three Ocotea Species from the Amazon" International Journal of Molecular Sciences 18, no. 5: 1081. https://doi.org/10.3390/ijms18051081