Chemical Profiling of Hedyosmum cumbalense and Hedyosmum spectabile (Chloranthaceae) Essential Oils, and Their Antimicrobial, Antioxidant, and Anticholinesterase Properties
Abstract
:1. Introduction
2. Results
2.1. Chemical Composition of EO from Leaves of H. cumbalense
2.2. Chemical Composition of EO from Leaves of H. spectabile
2.3. Enantioselective GC Analysis of the Essential Oils
2.4. Antimicrobial Activity of H. cumbalense and H. spectabile
2.5. Antioxidant Capacity
2.6. Anticholinesterase Activity
3. Discussion
4. Materials and Methods
4.1. Plant Material
4.2. Postharvest Treatments
4.3. Essential Oil Extraction
4.4. Identification of the Composition of the Essential Oils
4.4.1. Qualitative Analysis
4.4.2. Quantitative Analysis
4.4.3. Enantioselective Analysis
4.5. Antimicrobial Activity
4.6. Antioxidant Capacity
4.6.1. The 2,2-Diphenyl-1-picril hydrazyl (DPPH) Radical Scavenging Assay
4.6.2. The 2,2-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) Radical Scavenging Assay
4.7. Anticholinesterase Assay
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Nº | Compounds | LRIa | LRIb | % | CF |
---|---|---|---|---|---|
1 | α-Thujene | 920 | 924 | 0.32 ± 0.08 | C10H16 |
2 | α-Pinene | 927 | 932 | 7.91 ± 2.10 | C10H16 |
3 | Camphene | 944 | 946 | 3.01 ± 0.72 | C10H16 |
4 | Sabinene | 968 | 969 | 14.37 ± 1.64 | C10H16 |
5 | β-Pinene | 973 | 974 | 7.41 ± 1.46 | C10H16 |
6 | Myrcene | 985 | 988 | 0.56 ± 0.07 | C10H16 |
7 | α-Phellandrene | 1004 | 1002 | 0.52 ± 0.04 | C10H16 |
8 | α-Terpinene | 1014 | 1014 | 0.65 ± 0.06 | C10H16 |
9 | ρ-Cymene | 1023 | 1020 | 0.93 ± 0.02 | C10H14 |
10 | Sylvestrene | 1026 | 1025 | 2.07 ± 0.17 | C10H16 |
11 | β-Phellandrene | 1028 | 1025 | 0.18 ± 0.01 | C10H16 |
12 | 1,8-Cineole | 1029 | 1026 | 1.89 ± 0.48 | C10H18O |
13 | (Z)-β-Ocimene | 1032 | 1032 | 1.30 ± 0.08 | C10H16 |
14 | (E)-β-Ocimene | 1042 | 1044 | 0.64 ± 0.05 | C10H16 |
15 | γ-Terpinene | 1054 | 1054 | 1.23 ± 0.12 | C10H16 |
16 | cis-Sabinene hydrate (IPP vs. OH) | 1069 | 1065 | 0.59 ± 0.15 | C10H18O |
17 | Terpinolene | 1082 | 1086 | 0.37 ± 0.04 | C10H16 |
18 | 6-Camphenone | 1091 | 1095 | 0.91 ± 0.17 | C10H14O |
19 | Linalool | 1101 | 1095 | 4.94 ± 0.93 | C10H18O |
20 | trans-Sabinene hydrate (IPP vs. OH) | 1103 | 1098 | 0.31 ± 0.11 | C10H18O |
21 | Chrysanthenone | 1124 | 1124 | 0.22 ± 0.05 | C10H14O |
22 | cis-ρ-Menth-2-en-1-ol | 1125 | 1118 | 0.32 ± 0.11 | C10H18O |
23 | α-Campholenal | 1128 | 1122 | 0.42 ± 0.05 | C10H16O |
24 | trans-Pinocarveol | 1141 | 1135 | 0.30 ± 0.05 | C10H16O |
25 | trans-Verbenol | 1147 | 1140 | 1.18 ± 0.31 | C10H16O |
26 | Camphor | 1149 | 1141 | 1.17 ± 0.39 | C10H16O |
27 | Citronellal | 1153 | 1148 | 3.51 ± 0.37 | C10H18O |
28 | Eucarvone | 1157 | 1146 | 0.17 ± 0.04 | C10H14O |
29 | cis-Chrysanthenol | 1160 | 1160 | 0.43 ± 0.11 | C10H16O |
30 | Pinocarvone | 1164 | 1160 | 1.28 ± 0.32 | C10H14O |
31 | Borneol | 1173 | 1165 | 0.93 ± 0.26 | C10H18O |
32 | cis-Pinocamphone | 1178 | 1172 | 0.56 ± 0.20 | C10H16O |
33 | Terpinen-4-ol | 1181 | 1174 | 2.43 ± 0.86 | C10H18O |
34 | cis-Dihydro carvone | 1186 | 1191 | 0.33 ± 0.07 | C10H16O |
35 | neo-Dihydro carveol | 1198 | 1193 | 1.50 ± 0.38 | C10H18O |
36 | trans-Piperitol | 1212 | 1207 | 0.32 ± 0.17 | C10H18O |
37 | Thymol, methyl ether | 1231 | 1232 | 4.75 ± 0.66 | C11H16O |
38 | Neral | 1243 | 1235 | 0.99 ± 0.20 | C10H16O |
39 | Geraniol | 1255 | 1249 | 0.23 ± 0.07 | C10H18O |
40 | Geranial | 1273 | 1264 | 1.75 ± 0.24 | C10H16O |
41 | Isobornyl acetate | 1283 | 1283 | 9.12 ± 1.11 | C12H20O2 |
42 | ρ-Cymen-7-ol | 1297 | 1289 | 0.15 ± 0.09 | C10H14O |
43 | α-Terpinyl acetate | 1346 | 1346 | 0.67 ± 0.09 | C12H20O2 |
44 | Citronellyl acetate | 1350 | 1350 | 0.68 ± 0.08 | C12H22O2 |
45 | Eugenol | 1357 | 1356 | 2.55 ± 0.99 | C10H12O2 |
46 | Neryl acetate | 1359 | 1359 | 0.16 ± 0.04 | C12H20O2 |
47 | Geranyl acetate | 1379 | 1379 | 1.95 ± 0.17 | C12H20O2 |
48 | Cyperene | 1394 | 1398 | 0.20 ± 0.08 | C15H24 |
49 | Methyl eugenol | 1406 | 1403 | 0.50 ± 0.14 | C11H14O2 |
50 | (E)-Caryophyllene | 1412 | 1417 | 0.19 ± 0.04 | C15H24 |
51 | β-Copaene | 1422 | 1430 | 0.23 ± 0.05 | C15H24 |
52 | Rotundene | 1455 | 1457 | 0.15 ± 0.05 | C15H24 |
53 | allo-Aromadendrene | 1466 | 1458 | 0.23 ± 0.07 | C15H24 |
54 | Germacrene D | 1475 | 1480 | 0.70 ± 0.28 | C15H24 |
55 | α-Selinene | 1494 | 1498 | 0.19 ± 0.06 | C15H24 |
56 | δ-Amorphene | 1512 | 1511 | 0.25 ± 0.15 | C15H24 |
57 | Eugenol acetate | 1520 | 1521 | 1.60 ± 0.33 | C12H14O3 |
58 | Germacrene B | 1554 | 1559 | 0.23 ± 0.04 | C15H24 |
59 | Spathulenol | 1574 | 1577 | 0.71 ± 0.19 | C15H24O |
60 | Caryophyllene oxide | 1580 | 1582 | 0.67 ± 0.22 | C15H24O |
61 | Globulol | 1584 | 1590 | 0.12 ± 0.02 | C15H26O |
62 | Carotol | 1600 | 1594 | 0.81 ± 0.21 | C15H26O |
63 | cis-Isolongifolanone | 1611 | 1612 | 0.33 ± 0.09 | C15H24O |
64 | Silphiperfol-6-en-5-one | 1623 | 1624 | 0.15 ± 0.04 | C15H22O |
65 | Daucol | 1646 | 1641 | 0.31 ± 0.14 | C15H26O2 |
66 | Elemol acetate | 1679 | 1680 | 0.16 ± 0.07 | C17H28O2 |
HM | 21.80 | ||||
OM | 37.79 | ||||
HS | 13.08 | ||||
OS | 10.18 | ||||
Others | 13.08 | ||||
Total | 95.94 |
Nº | Compounds | LRIa | LRIb | % | CF |
---|---|---|---|---|---|
1 | α-Pinene | 928 | 932 | 1.64 ± 0.51 | C10H16 |
2 | Sabinene | 969 | 969 | 0.41 ± 0.20 | C10H16 |
3 | β-Pinene | 975 | 974 | 0.25 ± 0.12 | C10H16 |
4 | Myrcene | 987 | 988 | 0.24 ± 0.04 | C10H16 |
5 | Sylvestrene | 1027 | 1025 | 0.29 ± 0.15 | C10H16 |
6 | (Z)-β-Ocimene | 1034 | 1032 | 1.84 ± 0.53 | C10H16 |
7 | (E)-β-Ocimene | 1044 | 1044 | 5.35 ± 1.01 | C10H16 |
8 | Linalool | 1102 | 1095 | 0.99 ± 0.53 | C10H18O |
9 | Chrysanthenone | 1123 | 1124 | 0.68 ± 0.35 | C10H14O |
10 | 1,3,8-ρ-Menthatriene | 1131 | 1108 | 4.99 ± 1.15 | C10H18O |
11 | Verbenone | 1200 | 1204 | 0.31 ± 0.23 | C10H14O |
12 | Bornyl acetate | 1285 | 1284 | 0.25 ± 0.16 | C12H20O2 |
13 | Myrtenyl acetate | 1326 | 1324 | 0.84 ± 0.28 | C12H18O2 |
14 | δ-Elemene | 1331 | 1335 | 0.88 ± 0.14 | C15H24 |
15 | α-Cubebene | 1343 | 1348 | 0.35 ± 0.26 | C15H24 |
16 | α-Copaene | 1371 | 1374 | 2.48 ± 0.46 | C15H24 |
17 | β-Cubebene | 1384 | 1387 | 0.4 ± 0.17 | C15H24 |
18 | β-Elemene | 1386 | 1389 | 3.69 ± 0.87 | C15H24 |
19 | (E)-Caryophyllene | 1414 | 1417 | 1.04 ± 0.26 | C15H24 |
20 | β-Gurjunene | 1426 | 1431 | 0.15 ± 0.03 | C15H24 |
21 | 6,9-Guaiadiene | 1438 | 1442 | 0.17 ± 0.06 | C15H24 |
22 | α-Humulene | 1452 | 1452 | 0.74 ± 0.23 | C15H24 |
23 | α-neo-Clovene | 1456 | 1452 | 0.53 ± 0.10 | C15H24 |
24 | Dauca-5,8-diene | 1469 | 1471 | 0.35 ± 0.12 | C15H24 |
25 | γ-Muurolene | 1473 | 1478 | 1.94 ± 0.49 | C15H24 |
26 | cis-Muurola-4(14),5-diene | 1479 | 1479 | 17.87 ± 2.79 | C15H24O |
27 | δ-Selinene | 1484 | 1492 | 0.98 ± 0.25 | C15H24 |
28 | β-Selinene | 1486 | 1489 | 1.69 ± 0.95 | C15H24 |
29 | trans-Muurola-4(14),5-diene | 1489 | 1493 | 0.61 ± 0.14 | C15H24 |
30 | α-Zingiberene | 1493 | 1493 | 1.84 ± 0.35 | C15H24 |
31 | cis-β-Guaiene | 1496 | 1492 | 0.54 ± 0.10 | C15H24 |
32 | Valencene | 1499 | 1496 | 1.54 ± 0.37 | C15H24 |
33 | Aciphyllene | 1504 | 1501 | 5.37 ± 0.27 | C15H24 |
34 | (Z)-α-Bisabolene | 1508 | 1506 | 0.98 ± 0.44 | C15H24 |
35 | Cubebol | 1514 | 1514 | 0.7 ± 0.04 | C15H26O |
36 | δ-Amorphene | 1516 | 1511 | 2.44 ± 0.28 | C15H24 |
37 | γ-Patchoulene | 1521 | 1502 | 1.02 ± 0.46 | C15H24 |
38 | trans-Cadina-1,4-diene | 1531 | 1533 | 0.19 ± 0.10 | C15H24 |
39 | α-Cadinene | 1536 | 1537 | 0.24 ± 0.11 | C15H24 |
40 | α-Copaen-11-ol | 1544 | 1539 | 1.39 ± 0.14 | C15H24O |
41 | Germacrene B | 1558 | 1559 | 0.94 ± 0.07 | C15H24 |
42 | (E)-Nerolidol | 1561 | 1561 | 1.18 ± 0.28 | C15H26O |
43 | Spathulenol | 1579 | 1577 | 1.34 ± 0.28 | C15H24O |
44 | Globulol | 1596 | 1590 | 2.03 ± 0.57 | C15H26O |
45 | β-Oplopenone | 1606 | 1607 | 0.19 ± 0.10 | C15H24O |
46 | Guaiol | 1610 | 1600 | 0.20 ± 0.09 | C15H26O |
47 | 1,10-di-epi-Cubenol | 1613 | 1618 | 0.65 ± 0.14 | C15H26O |
48 | Isolongifolan-7-α-ol | 1621 | 1618 | 0.2 ± 0.07 | C15H26O |
49 | γ-Eudesmol | 1626 | 1630 | 1.44 ± 0.33 | C15H26O |
50 | Muurola-4,10(14)-dien-1-β-ol | 1635 | 1630 | 6.55 ± 0.58 | C15H24O |
51 | Cubenol | 1646 | 1645 | 2.77 ± 0.22 | C15H26O |
52 | Valerianol | 1654 | 1656 | 0.42 ± 0.08 | C15H26O |
53 | α-Cadinol | 1662 | 1652 | 2.12 ± 0.24 | C15H26O |
54 | neo-Intermedeol | 1666 | 1658 | 0.79 ± 0.34 | C15H26O |
55 | Germacra-4(15),5,10(14)-trien-1-α-ol | 1691 | 1685 | 2.09 ± 0.50 | C15H24O |
56 | Eudesma-4(15),7-dien-1-β-ol (impure) | 1693 | 1687 | 0.34 ± 0.19 | C15H24O |
57 | Amorpha-4,9-dien-2-ol | 1697 | 1700 | 0.90 ± 0.23 | C15H24O |
HM | 11.34 | ||||
OM | 6.48 | ||||
HS | 40.51 | ||||
OS | 30.79 | ||||
Others | 3.24 | ||||
Total | 92.37 |
Enantiomers | LRI | Enantiomeric Ratio (%) | Enantiomeric Excess (%) |
---|---|---|---|
H. cumbalense | |||
(1R,5R)-(+)-sabinene | 999 | 34.51 | 30.98 |
(1S,5S)-(–)-sabinene | 1000 | 65.49 | |
(S)-(+)-terpinen-4-ol | 1270 | 21.27 | 57.47 |
(R)-(−)-terpinen-4-ol | 1275 | 78.73 | |
H. spectabile | |||
(1R,5R)-(+)-sabinene | 999 | 47.87 | 4.25 |
(1S,5S)-(–)-sabinene | 1001 | 52.13 | |
(S)-(+)-linalool | 1198 | 0.13 | 99.74 |
(R)-(-)-linalool | 1202 | 99.87 |
Microorganism | H. cumbalense | H. spectabile | Positive Control * |
---|---|---|---|
(µg/mL) | (µg/mL) | (µg/mL) | |
Gram-positive cocci | |||
Enterococcus faecalis ATCC ® 19433 | - | - | 0.78 |
Enterococcus faecium ATCC ® 27270 | 4000 | - | <0.39 |
Staphylococcus aureus ATCC ® 25923 | 4000 | - | <0.39 |
Gram-negative bacilli | |||
Escherichia coli (O157:H7) ATCC ® 43888 | - | - | 1.56 |
Pseudomonas aeruginosa ATCC ® 10145 | - | - | <0.39 |
Yeasts and sporulated fungi | |||
Candida albicans ATTC ® 10231 | 1000 | 2000 | <0.09 |
Aspergillus niger ATCC ® 6275 | 1000 | 1000 | <0.09 |
Sample | DPPH | ABTS |
---|---|---|
SC50 (µg/mL—µM *) ± SD | ||
H. spectabile | 2366.6 ± 2.99 | 214. 41 ± 4.03 |
H. cumbalense | 209.99 ± 1.33 | 96.02 ± 0.33 |
Trolox | 29.99 ± 1.04 | 23.27 ± 1.05 |
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Guerrero, A.; Guerrero, E.; Cartuche, L.; Cumbicus, N.; Morocho, V. Chemical Profiling of Hedyosmum cumbalense and Hedyosmum spectabile (Chloranthaceae) Essential Oils, and Their Antimicrobial, Antioxidant, and Anticholinesterase Properties. Plants 2023, 12, 39. https://doi.org/10.3390/plants12010039
Guerrero A, Guerrero E, Cartuche L, Cumbicus N, Morocho V. Chemical Profiling of Hedyosmum cumbalense and Hedyosmum spectabile (Chloranthaceae) Essential Oils, and Their Antimicrobial, Antioxidant, and Anticholinesterase Properties. Plants. 2023; 12(1):39. https://doi.org/10.3390/plants12010039
Chicago/Turabian StyleGuerrero, Alisson, Emilye Guerrero, Luis Cartuche, Nixon Cumbicus, and Vladimir Morocho. 2023. "Chemical Profiling of Hedyosmum cumbalense and Hedyosmum spectabile (Chloranthaceae) Essential Oils, and Their Antimicrobial, Antioxidant, and Anticholinesterase Properties" Plants 12, no. 1: 39. https://doi.org/10.3390/plants12010039
APA StyleGuerrero, A., Guerrero, E., Cartuche, L., Cumbicus, N., & Morocho, V. (2023). Chemical Profiling of Hedyosmum cumbalense and Hedyosmum spectabile (Chloranthaceae) Essential Oils, and Their Antimicrobial, Antioxidant, and Anticholinesterase Properties. Plants, 12(1), 39. https://doi.org/10.3390/plants12010039