Chemical Composition and Variability of the Volatile Components of Myrciaria Species Growing in the Amazon Region
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemical Variability in the Sampled Specimens
2.1.1. Myrciaria dubia
2.1.2. Myrciaria floribunda
2.1.3. Myrciaria tenella
2.1.4. Myrciaria plinioides
2.1.5. Myrciaria pilosa
2.2. Multivariate Analyses of Myrciaria Species
2.3. Biological Activities of Myrciaria Species
2.4. Bibliometric Network Data
3. Material and Methods
3.1. Plant Material
3.2. Analysis of Essential Oil Composition
3.3. Bibliographic Research Criteria
3.4. Multivariate Statistical Analyses
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Abbreviations
HCA | Hierarchical clusters analysis |
HD | Hydrodistillation |
HS-SPME | Headspace-solid phase microextraction |
IC50 | Median inhibitory concentration |
LC50 | Median lethal concentration |
LLE | Liquid-liquid extraction |
Mdub | Myrciaria dubia |
Mflo | Myrciaria floribunda |
MH | Monoterpene hydrocarbons |
Mpil | Myrciaria pilosa |
Mpli | Myrciaria plinioides |
Mten | Myrciaria tenella |
OM | Oxygenated monoterpenes |
OS | Oxygenated sesquiterpenes |
OT | Other compounds |
PCA | Principal component analysis |
SD | Steam distillation |
SDE | Simultaneous distillation-extraction |
SH | Sesquiterpene hydrocarbons |
Appendix A
Species | Occurrence | Plant Part/Extraction Type | Sample Code | Primary Components (>5%) | Oil Yield (%) | Ref. |
---|---|---|---|---|---|---|
M. dubia | Caquetá, Colombia | Fruits (LLE) | Mdub-3 | limonene (23.9%), E-caryophyllene (9.6%), hexadecanoic acid (9.2%), α-calacorene (6.2%), germacrene B (5.2%) | - | [18] |
Fruits (SDE) | Mdub-4 | limonene (32.2%), α-terpineol (22.2%) | - | |||
Fruits (HS-SPME) | Mdub-5 | limonene (40.8%), E-caryophyllene (15.9%) | - | |||
M. dubia | Morelia, Caquetá, Colombia, | Leaf (SDE) | Mdub-6 | limonene (74.3%), α-pinene (10.8%) | - | [17] |
M. dubia | Manaus, Amazonas, Brazil | Immature green fruits (HS-SPME) | Mdub-7 | E-caryophyllene (31.0%), tricyclene (14.2%), limonene (10.0%), sabinene (7.2%), heptane (6.1%), decane (5.8%) | - | [19] |
Mature green fruits (HS-SPME) | Mbub-8 | limonene (32.1%), tricyclene (23.7%), α-3-carene (9.0%), E-caryophyllene (6.0%), β-pinene (5.0%) | - | |||
Ripened Fruits (HS-SPME) | Mdub-9 | tricyclene (28.3%), limonene (27.5%), α-3-carene (7.0%), E-caryophyllene (6.1%) | - | |||
M. dubia | Manaus, Amazonas, Brazil | Fruits (headspace) | Mdub-10 | α-pinene (66.2%), limonene (23.7%) | - | [20] |
M. floribunda | Macaé, Rio de Janeiro, Brazil | Leaf (SD) | Mflo-3 | E-nerolidol (32.4%), β-selinene (9.8%), 1,8-cineole (5.8%), | 0.7 | [26] |
M. floribunda | Exu, Pernambuco, Brazil | Fruits (HD) | Mflo-4 | δ-cadinene (26.9%), γ-cadinene (15.7%), γ-muurolene (6.2%), α-selinene (6.1%), E-caryophyllene (5.5%), α-copaene (5.0%) | 0.6 | [27] |
M. floribunda | Rio de Janeiro, Brazil | Leaf (HD) | Mflo-5 | 1,8-cineole (10.4%), β-selinene (8.4), α-selinene (7.4%), E-nerolidol (5.5%), β-curcumene (5.2%) | 0.4% | [38] |
M. floribunda | Rio de Janeiro, Brazil | Leaf (HD) | Mflo-6 | 1,8-cineole (38.4%), γ-himachalene (7.0%), α-terpineol (5.5%) | [24] | |
Stems (HD) | Mflo-7 | 2E,6Z-farnesol (13.1%), 2E,6E-farnesyl acetate (19.9%), Linalool (7.0%), γ-himachalene (5.9%), zonarene (5.2%) | ||||
Flowers (HD) | Mflo-8 | 1,8-cineole (22.8%), 2E,6Z-farnesol (16.1%), 2E,6E-farnesyl acetate (13.4%), linalool (12.7%), Z-β-ocimene (7.6%), α-terpineol (5.4%) | ||||
M. floribunda | Rio de Janeiro, Brazil | Leaf (HD) | Mflo-9 | γ-himachalene (7.0%), α-terpineol (5.5%) | - | [25] |
Stems (HD) | Mflo-10 | germacra-4(15),5,10(14)-trien-1α-ol (19.9%), 2E,6E-farnesyl acetate (13.1%), p-trans-mentha-2-en-ol (7.0%), α-humulene (5.9%), epi-zonarene (5.2%) | - | |||
Flowers (HD) | Mflo-11 | 2E,6Z-farnesol (16.1%), 2E,6E-farnesyl acetate (13.4%), linalool (12.7%), Z-β-ocimene (7.6%), α-terpineol (5.4%) | - | |||
M. pilosa | Buíque, Pernambuco, Brazil | Leaf (HD) | Mpil-1 | guaiol (13.7%), E-caryophyllene (11.3%), β-eudesmol (9.2%), γ-eudesmol (6.6%) | 0.9 | [37] |
M. plinioides | Lajeado, Rio Grande do Sul, Brazil | Leaf (HD) | Mpli-1 | spathulenol (27.3%), α-copaene (9.5%), α-cadinol (8.6%), viridiflorol (8.5%), humulene epoxide II (7.2%), cubenol (6.5%) | n.d | [35] |
M. plinioides | Lajeado, Rio Grande do Sul, Brazil | Leaf (HD) | Mpli-2 | spathulenol (21.1%), caryophyllene oxide (15.2%), isolongifolan-7-α-ol (9.8%), mustakone (5.6%), α-cadinol (5.4%), | 0.05 | [36] |
M. tenella | Acará, Pará, Brazil, | Leaf/stems (HD) | Mten-3 | E-caryophyllene (32.0%), 1,8-cineole (5.4%), δ-cadinene (5.1.%) | 0.2 | [31] |
M. tenella | Mogi-Guaçu, São Paulo, Brazil | Leaf (HD) | Mten-4 | E-caryophyllene (25.1%), spathulenol (9.7%), globulol (5.9%), α-cadinol (5.2%) | 0.4 | [32] |
M. tenella | Maracanã, Pará, Brazil | Leaf (HD) | Mten-5 | E-caryophyllene (11.4%), muurola-4,10(14)-dien-1β-ol (9.4%), caryophyllene oxide (9.3%), α-pinene (6.2%), α-selinene (5.3%), aromadendrene (5.1%) | 0.7 | [33] |
M. tenella | Rio de Janeiro, Brazil | Leaf (HD) | Mten-6 | α-pinene (25.1%), β-pinene (20.9%), E-caryophyllene (10.0%), platiphyllol (8.9%) | 0.4 | [34] |
M. tenella | Valinhos, São Paulo, Brazil | Leaf (HD) | Mten-7 | β-pinene (45.7%) | 0.4 | [34] |
Appendix B
MH | MO | SH | SO | OT | Ref. | |
---|---|---|---|---|---|---|
Mten-1 | 0.7 | 0.1 | 60.9 | 25.7 | 0.2 | * |
Mten-2 | 0 | 0.1 | 36.6 | 55.3 | 0.2 | * |
Mten-3 | 4.4 | 6.0 | 62.0 | 17.5 | 0 | [31] |
Mten-4 | 2.1 | 0 | 54.6 | 30.9 | 0 | [32] |
Mten-5 | 11.8 | 2.8 | 51.1 | 27.3 | 0 | [33] |
Mten-6 | 47.9 | 8.3 | 15.6 | 13.9 | 9.8 | [34] |
Mten-7 | 53.5 | 10.8 | 1.7 | 23.2 | 1.5 | [34] |
Mflo-1 | 78.2 | 10.3 | 6.0 | 1.1 | 0 | * |
Mflo-2 | 0 | 0 | 25.5 | 31.7 | 1.5 | * |
Mflo-3 | 11.2 | 7.8 | 35.4 | 42.6 | 0.7 | [26] |
Mflo-4 | 0.19 | 0 | 92.1 | 4.57 | 0 | [27] |
Mflo-5 | 2.5 | 16.3 | 53.5 | 12.2 | 1.5 | [38] |
Mflo-6 | 5.3 | 48.6 | 31.4 | 8.2 | 0 | [24] |
Mflo-7 | 0 | 12.2 | 29.6 | 42.6 | 0 | [24] |
Mflo-8 | 13 | 42.4 | 7.7 | 29.5 | 0 | [24] |
Mflo-9 | 5.3 | 10.2 | 31.4 | 8.2 | 0 | [25] |
Mflo-10 | 2.7 | 7.0 | 36.8 | 42.1 | 0 | [25] |
Mflo-11 | 13.0 | 19.6 | 7.7 | 49.4 | 0 | [25] |
Mdub-1 | 60.2 | 13.4 | 3.0 | 16.3 | 0.6 | * |
Mdub-2 | 74.6 | 10.2 | 0.5 | 7.3 | 0 | * |
Mdub-3 | 47.2 | 2.7 | 28.4 | 4.4 | 17.0 | [18] |
Mdub-4 | 59.3 | 27.1 | 4.0 | 4.9 | 1.2 | [18] |
Mdub-5 | 73.5 | 0.6 | 34.5 | 0.7 | 0.3 | [18] |
Mdub-6 | 89.0 | 0.9 | 3.6 | 3.1 | 1.9 | [17] |
Mdub-7 | 39.6 | 0 | 31.0 | 0 | 18.6 | [19] |
Mdub-8 | 88.3 | 0 | 6.0 | 0 | 2.7 | [19] |
Mdub-9 | 85.5 | 2.6 | 6.2 | 0 | 0.0 | [19] |
Mdub-10 | 93.8 | 0 | 4.6 | 0 | 0.3 | [20] |
Mpli-1 | 0 | 0 | 44.96 | 24.1 | 0 | [35] |
Mpli-2 | 0 | 0 | 11.05 | 88.2 | 0 | [36] |
Mpil-1 | 9.39 | 6.42 | 29.83 | 49.9 | 0.1 | [37] |
Appendix C
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RIC | RIL | Constituents (%) | M. dubia | M. floribunda | M. tenella | ||||
---|---|---|---|---|---|---|---|---|---|
Mdub-1 | Mdub-2 | Mflo-1 | Mflo-2 | Mten-1 | Mten-2 | ||||
1 | 792 | 788 a | 2,4-dimethyl-3-pentanone | 0.2 | |||||
2 | 845 | 846 a | 2E-hexenal | 0.3 | |||||
3 | 847 | 850 a | 3Z-hexenol | 0.1 | 0.3 | ||||
4 | 926 | 924 a | α-thujene | 0.1 | 0.6 | 3.7 | |||
5 | 936 | 932 a | α-pinene | 54.0 | 67.2 | 2.7 | 0.6 | ||
6 | 949 | 946 a | camphene | 0.2 | 0.1 | 0.1 | |||
7 | 953 | 953 a | thuja-2,4(10)-diene | 0.2 | 0.1 | ||||
8 | 977 | 974 a | β-pinene | 0.8 | 1.5 | 0.2 | |||
9 | 989 | 988 a | myrcene | 3.4 | |||||
10 | 1005 | 1008 a | δ-3-carene | 0.1 | 0.5 | ||||
11 | 1006 | 1002 a | α-phellandrene | 17.7 | |||||
12 | 1016 | 1014 a | α-terpinene | 3.3 | |||||
13 | 1024 | 1020 a | p-cymene | 0.5 | 1.3 | 7.2 | |||
14 | 1028 | 1024 a | limonene | 3.8 | 3.7 | 0.1 | |||
15 | 1029 | 1025 a | β-phellandrene | 6.6 | |||||
16 | 1031 | 1026 a | 1,8-cineole | 1.4 | 0.1 | ||||
17 | 1035 | 1032 a | Z-β-ocimene | 0.4 | |||||
18 | 1043 | 1044 a | E-β-ocimene | 0.3 | |||||
19 | 1057 | 1054 a | γ-terpinene | 8.7 | |||||
20 | 1089 | 1086 a | terpinolene | 0.5 | 23.1 | ||||
21 | 1098 | 1095 a | linalool | 0.4 | |||||
22 | 1099 | 1099 a | α-pinene oxide | 0.4 | 2.4 | ||||
23 | 1113 | 1114 a | endo-fenchol | 0.4 | |||||
24 | 1125 | 1122 a | α-campholenal | 1.5 | 0.7 | ||||
25 | 1138 | 1135 a | trans-pinocarveol | 2.9 | 0.6 | ||||
26 | 1144 | 1140 a | trans-verbenol | 0.1 | 2.3 | ||||
27 | 1161 | 1160 a | pinocarvone | 0.2 | 0.1 | ||||
28 | 1165 | 1165 a | borneol | 0.7 | |||||
28 | 1176 | 1174 a | terpinen-4-ol | 0.3 | 3.4 | ||||
30 | 1184 | 1179 a | p-cymen-8-ol | 0.5 | 0.8 | ||||
31 | 1190 | 1186 a | α-terpineol | 3.7 | 0.6 | 4.1 | 0.1 | ||
32 | 1196 | 1194 a | myrtenol | 0.5 | 0.6 | ||||
33 | 1208 | 1204 a | verbenone | 0.3 | 0.6 | ||||
34 | 1218 | 1215 a | trans-carveol | 1.5 | 0.2 | ||||
35 | 1313 | 1316 a | Z-patchenol | 1.6 | |||||
36 | 1321 | 1325 a | p-mentha-1,4-dien-7-ol | 0.4 | |||||
37 | 1367 | 1367 a | cyclosativene | 1.6 | |||||
38 | 1371 | 1373 a | α-ylangene | 0.2 | 0.1 | ||||
39 | 1375 | 1374 a | α-copaene | 0.1 | 0.1 | 0.3 | 1.2 | ||
40 | 1392 | 1389 a | β-elemene | 0.1 | 0.1 | ||||
41 | 1406 | 1400 a | β-longipinene | 0.2 | |||||
42 | 1419 | 1417 a | E-caryophyllene | 1.9 | 0.4 | 3.8 | 0.3 | 43.2 | 19.1 |
43 | 1429 | 1430 a | β-copaene | 0.2 | 0.1 | 1.1 | |||
44 | 1438 | 1439 a | aromadendrene | 0.1 | 0.1 | 2.7 | |||
45 | 1443 | 1445 b | selina-5,11-diene | 0.2 | |||||
46 | 1453 | 1452 a | α-humulene | 0.2 | 0.3 | 0.1 | 5.3 | 2.3 | |
47 | 1456 | 1454 a | E-β-farnesene | 0.2 | |||||
48 | 1460 | 1464 a | 9-epi-E-caryophyllene | 0.3 | |||||
49 | 1461 | 1463 a | cis-cadina-1(6),4-diene | 0.2 | |||||
50 | 1475 | 1476 b | selina-4,11-diene | 0.6 | |||||
51 | 1476 | 1478 a | γ-muurolene | 0.1 | 0.1 | 1.7 | |||
52 | 1479 | 1483 a | α-amorphene | 0.1 | 0.2 | ||||
53 | 1481 | 1480 a | germacrene D | 1.0 | |||||
54 | 1486 | 1489 a | β-selinene | 0.2 | 0.2 | 3.9 | 1.3 | ||
55 | 1495 | 1498 a | α-selinene | 0.2 | 2.8 | 1.1 | |||
56 | 1499 | 1500 a | α-muurolene | 0.2 | 0.1 | 0.6 | |||
57 | 1500 | 1499 a | bicyclogermacrene | 0.6 | |||||
58 | 1502 | 1508 a | trans-β-guaiene | ||||||
59 | 1508 | 1505 a | β-bisabolene | 2.2 | |||||
60 | 1513 | 1513 a | γ-cadinene | 0.1 | 17.5 | 1.8 | |||
61 | 1515 | 1514 a | Z-γ-bisabolene | 0.3 | |||||
62 | 1517 | 1520 a | 7-epi-α-selinene | 0.2 | |||||
63 | 1522 | 1521 a | trans-calamenene | 0.1 | 1.5 | ||||
64 | 1524 | 1513 a | δ-cadinene | 0.4 | 1.7 | ||||
65 | 1525 | 1528 a | zonarene | 0.1 | 0.2 | ||||
66 | 1531 | 1529 a | E-γ-bisabolene | 0.4 | |||||
67 | 1537 | 1537 a | α-cadinene | 0.3 | |||||
68 | 1542 | 1544 a | α-calacorene | 0.1 | 0.9 | 0.3 | |||
69 | 1545 | 1533 a | flavesone | 0.6 | |||||
70 | 1559 | 1559 a | germacrene B | 0.2 | 0.8 | ||||
71 | 1561 | 1561 a | E-nerolidol | 0.2 | 0.1 | ||||
72 | 1564 | 1563 a | β-calacorene | 0.4 | |||||
73 | 1566 | 1566 a | maaliol | 0.1 | 0.1 | ||||
74 | 1569 | 1570 a | caryophyllenyl alcohol | 1.2 | 0.2 | ||||
75 | 1577 | 1577 a | spathulenol | 1.3 | 0.6 | 0.3 | 1.0 | ||
76 | 1582 | 1582 a | caryophyllene oxide | 5.8 | 5.2 | 0.4 | 4.7 | 4.4 | 41.1 |
77 | 1591 | 1592 a | viridiflorol | 0.3 | 0.3 | 0.4 | |||
78 | 1593 | 1595 a | cubeban-11-ol | 0.1 | 0.3 | 0.5 | |||
79 | 1599 | 1599 a | longiborneol | 0.7 | |||||
80 | 1600 | 1602 a | guaiol | 0.2 | |||||
81 | 1601 | 1600 a | rosifoliol | 0.2 | 0.9 | ||||
82 | 1601 | 1602 a | ledol | 0.7 | |||||
83 | 1608 | 1608 a | humulene epoxide II | 0.5 | 0.3 | 0.4 | 2.4 | ||
84 | 1617 | 1621 a | iso-leptospermone | 1.5 | 0.1 | ||||
85 | 1618 | 1612 a | 1,10-di-epi-cubenol | 1.1 | |||||
86 | 1626 | 1627 a | 1-epi-cubenol | 0.1 | 1.8 | 0.9 | 2.3 | ||
87 | 1625 | 1629 a | leptospermone | 4.0 | 1.1 | ||||
88 | 1630 | 1628 a | muurola-4,10(14)-dien-1β-ol | 1.2 | |||||
89 | 1634 | 1639 a | caryophylla-4(12),8(13)-dien-5β-ol | 0.8 | 4.8 | 1.3 | |||
90 | 1635 | 1632 a | cis-cadin-4-en-7-ol | 0.4 | |||||
91 | 1638 | 1640 a | hinesol | 1.3 | |||||
92 | 1638 | 1638 a | epi-α-cadinol | 2.2 | |||||
93 | 1640 | 1640 a | epi-α-murrolol | 0.2 | 0.1 | ||||
94 | 1644 | 1644 a | α-muurolol | 0.1 | 0.8 | 0.5 | 0.8 | ||
95 | 1646 | 1649 a | β-eudesmol | 0.1 | 0.3 | ||||
96 | 1647 | 1639 a | allo-aromadendrene epoxide | 0.7 | |||||
97 | 1650 | 1652 a | α-cadinol | 0.2 | 1.6 | ||||
98 | 1652 | 1658 a | selin-11-en-4-α-ol | 4.5 | |||||
99 | 1667 | 1656 a | valerianol | 2.2 | |||||
100 | 1663 | 1668 a | trans-calamenen-10-ol | 0.2 | |||||
101 | 1663 | 1668 a | 14-hydroxy-9-epi-E-caryophyllene | 2.9 | |||||
102 | 1665 | 1670 a | epi-β-bisabolol | 2.9 | |||||
103 | 1666 | 1661 a | allohimachalol | 0.7 | |||||
104 | 1671 | 1675 a | cadalene | 0.1 | 4.3 | 0.4 | |||
105 | 1678 | 1683 a | epi-α-bisabolol | 0.3 | |||||
106 | 1680 | 1685 a | germacra-4(15),5,10(14)-trien-1-α-ol | 0.8 | 0.1 | ||||
107 | 1702 | 1701 a | 10-nor-calamenen-10-one | 1.3 | |||||
108 | 1745 | Oxyg. sesquiterpene unidentified MW218 c | 15.0 | ||||||
109 | 1767 | 1772 a | 14-oxy-α-muurolene | 1.7 | |||||
110 | 1779 | 1775 a | guaiazulene | 0.3 | |||||
111 | 1961 | 1959 a | hexadecanoic acid | 0.2 | |||||
Monoterpene hydrocarbons | 60.3 | 74.6 | 77.9 | 0.7 | |||||
Oxygenated monoterpenoids | 13.0 | 10.1 | 10.1 | 0.1 | 0.1 | ||||
Sesquiterpene hydrocarbons | 2.4 | 0.5 | 5.9 | 25.2 | 60.3 | 36.7 | |||
Oxygenated sesquiterpenoids | 16.8 | 7.3 | 1.1 | 36.0 | 25.9 | 56.0 | |||
Others | 0.1 | 0.6 | 0.2 | ||||||
Total (%) | 92.6 | 92.5 | 95.6 | 61.2 | 87.2 | 92.8 | |||
Oil yield (%) | 0.5 | 1.1 | 1.4 | 1.5 | 2.1 | 1.2 |
Species | Code | Collection Site | Voucher Number | Coordinates Latitude/Longitude |
---|---|---|---|---|
Myrciaria dubia | Mdub-1 | Belém, PA, Brazil | MG-229429 | 1°45′64.40″ S/48°43′86.75″ W |
Mdub-2 | Castanhal, PA, Brazil | MG-063961 | 1°15′59.57″ S/48°01′7.66″ W | |
Myrciaria floribunda | Mflo-1 | Belém, PA, Brazil | MG-228739 | 1°15′53.46″ S/48°8′11.52″ W |
Mflo-2 | Belém, PA, Brazil | MG-229218 | 1°14′20.99″ S/48°26′10.24″ W | |
Myrciaria tenella | Mten-1 | Baião, PA, Brazil | MG-237483 | 2°52′01″ S/49°29′08″ W |
Mten-2 | Abaetetuba, PA, Brazil | MG-231854 | 1°45′15″ S/48°58′00″ W |
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da Costa, J.S.; Andrade, W.M.S.; de Figueiredo, R.O.; Santos, P.V.L.; Freitas, J.J.d.S.; Setzer, W.N.; da Silva, J.K.R.; Maia, J.G.S.; Figueiredo, P.L.B. Chemical Composition and Variability of the Volatile Components of Myrciaria Species Growing in the Amazon Region. Molecules 2022, 27, 2234. https://doi.org/10.3390/molecules27072234
da Costa JS, Andrade WMS, de Figueiredo RO, Santos PVL, Freitas JJdS, Setzer WN, da Silva JKR, Maia JGS, Figueiredo PLB. Chemical Composition and Variability of the Volatile Components of Myrciaria Species Growing in the Amazon Region. Molecules. 2022; 27(7):2234. https://doi.org/10.3390/molecules27072234
Chicago/Turabian Styleda Costa, Jamile Silva, Waldemir Magno S. Andrade, Raphael O. de Figueiredo, Paulo Vinicius L. Santos, Jofre Jacob da Silva Freitas, William N. Setzer, Joyce Kelly R. da Silva, José Guilherme S. Maia, and Pablo Luis B. Figueiredo. 2022. "Chemical Composition and Variability of the Volatile Components of Myrciaria Species Growing in the Amazon Region" Molecules 27, no. 7: 2234. https://doi.org/10.3390/molecules27072234