Phytochemistry of Three Ecuadorian Lamiaceae: Lepechinia heteromorpha (Briq.) Epling, Lepechinia radula (Benth.) Epling and Lepechinia paniculata (Kunth) Epling
Abstract
:1. Introduction
2. Results
2.1. EO from L. Heteromorpha Leaves
2.1.1. Chemical Analysis
2.1.2. Enantioselective GC Analysis
2.1.3. Characterization of (−)-Ledol (1)
2.1.4. Characterization of (−)-Caryophyllene Oxide (2)
2.2. Ethyl Acetate Extract of Lepechinia Radula
2.2.1. Identification of Spathulenol (3)
2.2.2. Identification of Angustanoic Acid E (4)
2.2.3. Identification of 5-hydroxy-4′,7-dimethoxy flavone (5)
2.3. Ethyl Acetate Extract of Lepechinia paniculata
2.3.1. Identification of Ledol (3) and Guaiol (6)
2.3.2. Characterization of (−)-Carnosol (7)
3. Discussion
3.1. EO of L. Heteromorpha
3.2. Ethyl Acetate Extract of L. Radula and L. Paniculata
4. Materials and Methods
4.1. General Information
4.2. Plant Material
4.3. EO of L. heteromorpha
4.3.1. Distillation of the EO
4.3.2. Qualitative and Semi-quantitative Analysis
4.3.3. Enantioselective GC Analysis
4.3.4. Purification of (−)-Ledol and (−)-Caryophyllene oxide
4.4. Ethyl Acetate Extract Components of L. radula and L. paniculata Leaves
4.4.1. Obtainment of Ethyl Acetate Extracts
4.4.2. Chlorophyll Removal
4.4.3. Preparative Isolation of Secondary Metabolites from L. radula
4.4.4. Fraction Purification and Secondary Metabolites Isolation from L. paniculata
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Reference LRIs | Calculated LRIs | Compounds | % 1 | σ |
---|---|---|---|---|
932 | 931 | α-Pinene | 1.2 | 0.71 |
946 | 946 | Camphene | 2.4 | 0.45 |
969 | 976 | β-Pinene | 0.4 | 0.18 |
988 | 988 | Myrcene | 0.4 | 0.22 |
1003 | 1003 | Mentha-1(7),8-diene | 0.4 | 0.23 |
1007 | 1005 | iso-Sylvestrene | 0.2 | 0.13 |
1020 | 1015 | p-Cymene | 0.5 | 0.26 |
1022 | 1017 | o-Cymene | 1.0 | 0.01 |
1024 | 1029 | Limonene | 1.3 | 0.41 |
1025 | 1029 | β-Phellandrene | 4.6 | 1.02 |
1141 | 1145 | Camphor | 1.7 | 0.46 |
1400 | 1404 | Sibirene | 3.2 | 0.32 |
1417 | 1411 | (E)-β-Caryophyllene | 7.1 | 0.77 |
1439 | 1439 | Aromadendrene | 1.0 | 0.18 |
1449 | 1445 | Spirolepechinene | 7.1 | 0.93 |
1458 | 1451 | allo-Aromadendrene | 6.1 | 1.00 |
1452 | 1453 | α-Humulene | 1.2 | 0.19 |
1496 | 1484 | Valencene | 1.6 | 0.23 |
- | 1487 | Undetermined (MW 204) | 3.7 | 1.84 |
1492 | 1489 | cis-β-Guaiene | 0.3 | 0.16 |
1496 | 1497 | Viridiflorene | 27.3 | 1.80 |
1505 | 1503 | (E,E)-α-Farnesene | 1.4 | 0.41 |
- | 1509 | Undetermined (MW 204) | 0.2 | 0.12 |
1511 | 1516 | δ-Amorphene | 1.0 | 0.98 |
1559 | 1549 | Germacrene B | 1.6 | 0.83 |
1592 2 | 1593 | Caryophyllene oxide | 1.0 | 0.59 |
1602 | 1601 | (−)-Ledol 3 | 21.2 | 4.32 |
Monoterpene hydrocarbons | 12.4 | |||
Oxygenated monoterpenes | 1.7 | |||
Sesquiterpene hydrocarbons | 62.8 | |||
Oxygenated sesquiterpenes | 22.2 | |||
Others | - | |||
Total identified | 99.1 |
LRIs | Enantiomers | Enantiomeric Distribution (%) | ee (%) |
---|---|---|---|
917 | (S)-α-pinene | 8.7 | 82.6 |
926 | (R)-α-pinene | 91.3 | |
1054 | (R)-limonene | 100.0 | 100.0 |
1072 | (+)-β-phellandrene | 88.3 | 76.6 |
1091 | (−)-β-phellandrene | 11.7 | |
1262 | (R)-camphor | 100.0 | 100.0 |
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Gilardoni, G.; Ramírez, J.; Montalván, M.; Quinche, W.; León, J.; Benítez, L.; Morocho, V.; Cumbicus, N.; Bicchi, C. Phytochemistry of Three Ecuadorian Lamiaceae: Lepechinia heteromorpha (Briq.) Epling, Lepechinia radula (Benth.) Epling and Lepechinia paniculata (Kunth) Epling. Plants 2019, 8, 1. https://doi.org/10.3390/plants8010001
Gilardoni G, Ramírez J, Montalván M, Quinche W, León J, Benítez L, Morocho V, Cumbicus N, Bicchi C. Phytochemistry of Three Ecuadorian Lamiaceae: Lepechinia heteromorpha (Briq.) Epling, Lepechinia radula (Benth.) Epling and Lepechinia paniculata (Kunth) Epling. Plants. 2019; 8(1):1. https://doi.org/10.3390/plants8010001
Chicago/Turabian StyleGilardoni, Gianluca, Jorge Ramírez, Mayra Montalván, Willan Quinche, Jackeline León, Lita Benítez, Vladimir Morocho, Nixon Cumbicus, and Carlo Bicchi. 2019. "Phytochemistry of Three Ecuadorian Lamiaceae: Lepechinia heteromorpha (Briq.) Epling, Lepechinia radula (Benth.) Epling and Lepechinia paniculata (Kunth) Epling" Plants 8, no. 1: 1. https://doi.org/10.3390/plants8010001