Constituents and Pharmacological Activities of Myrcia (Myrtaceae): A Review of an Aromatic and Medicinal Group of Plants
Abstract
:1. Introduction
2. Traditional Uses
3. Volatiles
Species | Part of the Plant (Yield: v/w) | Compounds (Relative Abundance, %>5) Classes of Substances; Total | Ref. |
---|---|---|---|
M. acuminatissima O.Berg | Fresh leaves (0.12%) | β-pinene (5.0), linalool (22.3), terpinen-4-ol (5.2), β-caryophyllene (8.1), spathulenol (7.5), caryophyllene oxide (5.5) MH: 13.9%, OM: 35.1%, SH: 15.7%, OS: 28.0%, T: 97.0% | [20] |
M. alagoensis O.Berg | Fresh leaves (0.3%) | β-caryophyllene (7.9), germacrene D (11.1), germacrene B (26.7), (2E,6E)-farnesoic acid (7.3) S: 79.9%, T: 80.5% | [21] |
Dry leaves (0.4%) | β-caryophyllene (7.8), germacrene D (6.4), δ-cadinene (5.4), selina-3,7(11)-diene (5.4), germacrene B (23.1) S: 75.4%, T: 75.5% | [21] | |
M. amazonica DC. | Fresh leaves (0.65%) | germacrene D (10.09), germacrene B (9.59), 1-epi-cubenol (20.22), α-muurolol (6.21) | [22] |
Dry leaves (0.96%) | germacrene D (16.56), germacrene B (11.09), 1-epi-cubenol (14.72) | [22] | |
M. arborescens O.Berg | Fresh leaves (0.2%) | α-muurolol (6.2), caryophyllene oxide (26.3), spathulenol (8.9), globulol (15.9), 5-epi-7-epi-α-eudesmol (5.9) S: 94.8%, T: 96.2% | [23] |
M. bombycina (O.Berg) Nied. | Fresh leaves (0.95%) | α-pinene (23.9), β-pinene (12.4), limonene (7.0), γ-eudesmol (7.8) MH: 53.0%, OM: 5.4%, SH: 8.0%, OS: 24.0%, T: 93.5% | [20] |
M. bracteata DC. | Leaves (0.71%) | α-bisabolol oxide (10.37), α-bisabolol (45.86) SH: 13.76%, OS: 63.49%, S: 77.25% | [24] |
Leaves and fine stems (0.1%) a | (E)-nerolidol (80.8) | [25] | |
Leaves and fine stems (0.3%) a | (E)-β-farnesene (33.9), β-curcumene (9.8), β-bisabolol (8.2) | [25] | |
Leaves and fine stems (0.1%) a | germacrene B (8.8), spathulenol (31.0) | [25] | |
M. cuprea (O.Berg) Kiaersk. | Leaves (<0.05%) | β-caryophyllene (9.57), α-humulene (7.03), γ-selinene (21.75), α-selinene (11.84), (Z)-α-bisabolene (9.51), (E,E)-α-farnesene (10.52) SH: 82.41%, S: 82.41%, OTH: 11.02% | [24] |
Leaves and fine stems (0.3%) a | myrcene (48.1), β-caryophyllene (19.9), δ-cadinene (6.9) | [25] | |
Leaves and fine stems (0.1%) a | α-pinene (15.9), myrcene (19.2), β-caryophyllene (39.1) | [25] | |
Leaves and fine stems (>0.1%) a | β-caryophyllene (38.1), germacrene D (21.8), germacrene B (19.5) | [25] | |
M. fallax (Rich.) DC. | Leaves (0.09%) | α-pinene (7.68), β-pinene (11.88), β-elemene (11.21), β-caryophyllene (5.55), selin-11-en-4α-ol (7.56) MH: 22.29%, M: 24.02%, SH: 41.83%, OS: 24.20%, S: 66.03% | [24] |
Leaves (0.25%) | α-pinene (7.7), β-pinene (6.9), β-caryophyllene (6.0), carotol (9.9), guaiol (31.0) T: 83.4% | [26] | |
Flowers (0.30%) | α-pinene (6.0), guaiol (27.5), aristolene (24.5) T: 83.2% | [26] | |
Fresh leaves (0.25%) | α-bisabolol (83.8) SH: 7.2%, OS: 86.5%, T: 94.3% | [20] | |
M. aff. fosteri Croat | Leaves | β-bisabolol oxide (19.2), α-bisabolol (19.2), bisabolol oxide B (7.0), undeca-4,6-diene (5.4) SH: 8.2%, OS: 65.9%, T: 76.7% | [27] |
M. glabra (O.Berg) D.Legrand | Fresh leaves (0.11%) | α-copaene (6.1), β-caryophyllene (9.5), β-selinene (5.8), α-selinene (9.4), valerianol (13.2) SH: 54.4%, OS: 27.4%, OTH: 9.4%, T: 92.0% | [20] |
M. hatschbachii D.Legrand | Fresh leaves (0.1%) | germacrene D (6.4%), γ-cadinene (8.1), α-cadinol (6.1), β-caryophyllene (23.3) S: 95.2%, T: 97.9% | [23] |
M. lageana D.Legrand | Fresh leaves (0.3%) | (E)-nerolidyl acetate (25.3), germacrene D (23.4) S: 98.5%, T: 99.3% | [23] |
M. laruotteana Camb. | Unripe fruits (0.3%) | spathulenol (5.4), globulol (6.3), α-bisabolol oxide B (11.5), α-bisabolol (23.6), globulol (6.3), (2E,6E)-methyl farnesoate (5.8) SH: 5.8%, OS: 75.8%, T: 82.8% | [28] |
Leaves (0.05%) | spathulenol (7.3), globulol (6.2), guaiol (6.1), 1-epi-cubenol (5.0), α-cadinol (8.0), α-bisabolol (20.7), 14-hydroxy-α-muurolene (19.9) SH: 10.2%, OS: 79.6%, T: 90.4% | [29] | |
Flowers (0.07%) | spathulenol (8.6), globulol (6.6), guaiol (7.7), 1-epi-cubenol (5.0), α-cadinol (6.5), α-bisabolol (28.1), 14-hydroxy-α-muurolene (13.7) SH: 9.1%, OS: 83.1%, T: 95.5% | [29] | |
M. multiflora (Lam) DC. | Leaves (1.16%) | α-gurjunene (6.40), β-caryophyllene (10.72), γ-selinene (5.12), α-selinene (8.67), selin-11-en-4α-ol (10.67) MH: 6.14%, OS: 5.23%, M: 11.37%, SH: 53.91%, OS: 17.57%, S: 71.48% | [24] |
Fresh leaves (0.20%) | β-caryophyllene (7.5), germacrene D (8.7), bicyclogermacrene (6.3), δ-cadinene (5.2), MW 222 (7.4), cubenol (5.9) SH: 44.9%, OS: 32.3%, n.i.: 5.9%, T: 87.5% | [20] | |
M. myrtillifolia DC. | Leaves (0.14%)b | α-pinene (80.4), α-terpineol (7.0) MH: 85.4%, OM: 13.0%, T: 99.7% | [30] |
Flowers (0.26%) b | α-pinene (76.2) MH: 77.1%, OM: 9.9%, T: 88.8% | [30] | |
Fruits (0.37%) b | α-pinene (88.1) MH: 91.9%, T: 96.8% | [30] | |
M. obtecta (O.Berg) Kiaersk. | Fresh leaves (0.1%) | α-pinene (7.2), ar-curcumene (19.0), β-bisabolene (8.5), α-copaene (8.0), α-humulene (6.2) M: 16.2%, S: 79.1%, T: 95.3% | [23] |
M. obtecta (O.Berg) Kiaersk. | Leaves (0.01%) b | α-terpineol (11.2), α-guainene (5.8), trans-calamenene (29.3), 1-epi-cubenol (5.6) M: 16.7%, SH: 56.4%, OS: 20.9%, T: 95.6% | [31] |
Flowers (n.i.) | methyl salicilate (88.2) T: 97.9% | [31] | |
M. oligantha O.Berg | Fresh leaves (0.1%) | δ-cadinene (17.9), 1-epi-cubenol (7.2), cubenol (5.7), β-caryophyllene (6.5), caryophyllene oxide (5.4), bicyclogermacrene (8.3), spathulenol (10.2) S: 96.8%, T: 99.9% | [23] |
M. ovata Cambess. | Leaves (0.9%) | neral (35.8), geranial (50.4) T: 92.1% | [17,32] |
Leaves (1.27%; w/w) | OM: 91.78%, T: 93.55% | [33] | |
M. pubiflora DC. | Fresh leaves (1.1%) | tricyclene (5.27), 1,8-cineole (5.35), caryophyllene oxide (22.16), mustakone (11.34) T: 72.7% | [34] |
M. pubipetala Miq. | Fresh leaves (0.1%) | germacrene D (7.2), β-caryophyllene (13.3), bicyclogermacrene (25.2), spathulenol (31.7), n-heneicosane (14.9) OTH: 14.9%, S: 84.8%, T: 99.7% | [23] |
M. richardiana (O.Berg) Kiaersk. | Fresh leaves (0.1%) | β-caryophyllene (20.6), caryophyllene oxide (19.3), α-humulene (5.1), bicyclogermacrene (5.7) S: 90.0%, T: 90.0% | [23] |
M. rostrata DC. | Fresh leaves (0.2%) | δ-cadinene (5.7), τ-muurolol (5.1), caryophyllene oxide (13.1), bicyclogermacrene (6.8), spathulenol (17.3) S: 93.3%, T: 93.3% | [23] |
M. rufipila McVaugh | Leaves (0.42%) a | β-caryophyllene (7.07), γ-elemene (10.49), germacrene D (9.09), bicyclogermacrene (7.49), δ-cadinene (7.36), germacrene B (6.70) SH: 72.35%, OS: 19.93%, S: 92.28% | [24] |
Leaves (0.18%) a | β-caryophyllene (5.66), germacrene D (10.31), δ-cadinene (10.12), α-cadinol (6.20) SH: 65.87%, OS: 23.69%, S: 89.56% | [24] | |
M. salzmanni O.Berg | Leaves (n.i.) b | β-caryophyllene (25.9), α-humulene(12.9), MW 222 (11.7), MW 220 (14.2), MW 222 (10.0) SH: 49.2%, OS: 10.1%, NI: 36.2%, T: 95.5% | [35] |
Flowers (n.i.) | β-caryophyllene (13.8), α-humulene (10.9), MW 222 (10.0), MW 220 (12.6), cis-β-elemone (6.2), MW 222 (7.1) SH: 36.4%, OS: 20.1%, NI: 38.6%, T: 95.4% | [35] | |
M. selloii (Spreng.) N.Silveira | Fresh leaves (0.5%) | germacrene D (6.7), δ-cadinene (14.5), τ-cadinol (9.3), α-cadinol (17.2), β-caryophyllene (9.0), bicyclogermacrene (10.2) S: 99.2%, T: 99.9% | [23] |
M. splendens (Sw.) DC. | Fresh leaves (0.44%) | (Z)-α-bisabolene (79.65) SH: 94.54%, S: 98.34%, T: 98.34% | [36] |
Fresh stems (0.15%) | β-caryophyllene (23.8), germacrene D (25.3), bicyclogermacrene (7.1), caryophyllene oxide (10.5) T: 97.2% | [37] | |
Leaves (n.i.) | trans-2-hexenal (9.5), germacrene D (35.9), δ-cadinene (5.8), epi-α-cadinol (6.8), valerianol (16.3) SH: 55.7%, OS: 31.8%, T: 96.9% | [38] | |
M. sylvatica (G.Mey) DC. | Leaves and fine stems (>0.1%) a | spathulenol (13.8), caryophyllene oxide (16.6), selin-11-en-4α-ol (24.7) | [25] |
Leaves and fine stems (0.3%) a | cis-calamenene (30.1), α-calacorene (11.5), spathulenol (18.7) | [25] | |
Leaves and fine stems (>0.1%) a | β-bisabolene (14.7), spathulenol (40.2) | [25] | |
M. tomentosa (Aubl.) DC. | Aerial parts (0.54%) b | (E)-β-farnesene (6.94), γ-muurolene (18.04), bicyclogermacrene (11.51), (2E,6E)-methyl farnesoate (36.95) SH: 47.22%, OS: 52.02%, T: 99.24% | [39] |
Fresh flowers (0.31%) | spathulenol (7.36), globulol (5.97), (2Z,6Z)-farnesal (6.86), (2Z,6Z)-farnesol (10.65), (2E,6E)-farnesal (5.36), (2E,6E)-methyl farnesoate (14.28), benzyl salicylate (5.99) OS: 46.69%, OTH: 24.61%, T: 72.71% | [39] | |
Stem bark (0.31%) | (2E,6E)-methyl farnesoate (14.39), hexadecanoic acid (22.05) SH: 6.26%, OS: 9.06%, OTH: 60.4%, T: 76.27% | [39] | |
Leaves (0.1–0.8) b | spathulenol (18.35), globulol (7.66), (2E,6E)-methyl farnesoate (46.38) | [40] | |
Leaves (0.1–0.8) b | γ-muurolene (14.20), bicyclogermacrene (14.38), δ-amorphene (18.83) | [40] | |
Leaves (0.1–0.8) b | γ-muurolene (6.62), bicyclogermacrene (8.04), globulol (57.48) | [40] | |
Leaves (0.1–0.8) b | γ-muurolene (7.67), bicyclogermacrene (5.85), (2E,6E)-methyl farnesoate (60.69) | [40] | |
Leaves (0.1–0.8) b | β-caryophyllene (12.66), γ-muurolene (40.16), bicyclogermacrene (13.74), δ-amorphene (6.31) | [40] |
4. Biological and Antioxidant Activities of the Essential Oils of Myrcia Species and Their Major Constituents
4.1. Anti-Inflammatory and Antinociceptive Effect
4.2. Antimicrobial Activity
4.3. Larvicidal Activity
4.4. Antiproliferative Activity
4.5. Antioxidant Capacity
5. Activity of the Major Compounds from Myrcia Essential Oils
6. Non-Volatiles
6.1. Flavonoids
Compound | R1 | R2 | R3 |
---|---|---|---|
1 | H | H | O-β-d-glucopyranosyl |
2 | CH3 | H | O-β-d-glucopyranosyl |
3 | H | O-β-d-glucopyranosyl | H |
4 | H | H | (6ʹʹ-O-p-coumaroyl)-O-β-d-glucopyranosyl |
5 | H | H | (6ʹʹ-O-p-hydroxybenzoyl)-O-β-d-glucopyranosyl |
Compound | R1 | R2 | R3 | R4 |
---|---|---|---|---|
6 | OH | H | OH | O-α-l-rhamnopyranosyl |
7 | OH | CH3 | OH | O-α-l-rhamnopyranosyl |
8 | OH | H | OH | O-α-l-rhamnopyranosyl |
9 | OH | H | OH | (2ʹʹ-O-galloyl)-O-α-l-rhamnopiranosyl |
10 | OH | H | H | O-α-l-arabinopyranosyl |
11 | OH | H | H | O-α-l-arabinofuranosyl |
12 | H | H | H | O-α-l-arabinofuranosyl |
13 | OH | H | OH | OH |
14 | H | H | H | O-Deoxyhexosyl |
15 | H | H | H | O-Hexosyl |
16 | OH | H | OH | O-β-d-galactopyranosyl |
17 | OH | H | OH | O-α-arabinofuranosyl |
18 | OH | H | OH | O-α-arabinopyranosyl |
19 | OH | H | OH | (O-galloyl)-O-hexosyl |
20 | H | H | OH | OH |
21 | H | H | OH | O-β-d-galactopyranosyl |
22 | H | H | OH | O-β-d-xylofuranosyl |
23 | H | H | OH | O-β-d-xylopyranosyl |
24 | H | H | OH | O-α-l-arabinofuranosyl |
25 | H | H | OH | (6ʹʹ-O-galloyl)-O-β-galactopyranosyl |
26 | H | H | OH | (O-galloyl)-pentosyl |
27 | OH | H | OH | (6ʹʹ-O-galloyl)-O-β-d-galactopyranosyl |
28 | OH | H | OH | O-β-d-xylopyranosyl |
29 | H | H | OH | O-α-l-arabinopyranosyl |
30 | H | H | OH | O-α-l-rhamnopyranosyl |
31 | H | H | H | O-β-d-galactopyranosyl |
6.2. Terpenoids
6.3. Organic Acids
6.4. Acetophenones and Related Compounds
6.5. Tannins
Compound | R1 | R2 | R3 |
---|---|---|---|
63 | H | H | Acetyl |
64 | Acetyl | H | Acetyl |
65 | Acetyl | Acetyl | H |
66 | H | Acetyl | Acetyl |
67 | Acetyl | Acetyl | Acetyl |
6.6. Alkaloid
7. Pharmacological Effects of Myrcia Extracts and Isolated Compounds
7.1. Hypoglycemic Potential
7.2. Antiobesity and Mixed Hypolipidemic Effects
7.3. Anti-Hemorrhagic Activity
7.4. Phytotoxic Effect and Allelophatic Potential
7.5. Hepatoprotective Effect
7.6. Antioxidant Effects
7.7. Others
8. Concluding Remarks
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Cascaes, M.M.; Guilhon, G.M.S.P.; Andrade, E.H.d.A.; Zoghbi, M.D.G.B.; Santos, L.D.S. Constituents and Pharmacological Activities of Myrcia (Myrtaceae): A Review of an Aromatic and Medicinal Group of Plants. Int. J. Mol. Sci. 2015, 16, 23881-23904. https://doi.org/10.3390/ijms161023881
Cascaes MM, Guilhon GMSP, Andrade EHdA, Zoghbi MDGB, Santos LDS. Constituents and Pharmacological Activities of Myrcia (Myrtaceae): A Review of an Aromatic and Medicinal Group of Plants. International Journal of Molecular Sciences. 2015; 16(10):23881-23904. https://doi.org/10.3390/ijms161023881
Chicago/Turabian StyleCascaes, Márcia Moraes, Giselle Maria Skelding Pinheiro Guilhon, Eloisa Helena de Aguiar Andrade, Maria Das Graças Bichara Zoghbi, and Lourivaldo Da Silva Santos. 2015. "Constituents and Pharmacological Activities of Myrcia (Myrtaceae): A Review of an Aromatic and Medicinal Group of Plants" International Journal of Molecular Sciences 16, no. 10: 23881-23904. https://doi.org/10.3390/ijms161023881