Research Article
Kathy Swor
Kathy Swor
Independent
Researcher, 1432 W. Heartland Dr., Kuna, ID 83634, USA.
Ambika Poudel
Ambika Poudel
Aromatic Plant Research Center, 230 N 1200 E,
Suite 100, Lehi, UT 84043, USA.
Prabodh Satyal
Prabodh Satyal
Aromatic
Plant Research Center, 230 N 1200 E, Suite 100, Lehi, UT 84043, USA.
William N. Setzer
William N. Setzer
Corresponding Author
Aromatic
Plant Research Center, 230 N 1200 E, Suite 100, Lehi, UT 84043, USA.
And
Department
of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA.
E-mail:
setzerw@uah.edu, wsetzer@chemistry.uah.edu; Tel.: +1-256-468-2862.
Abstract
Ericameria
linearifolia, the narrowleaf goldenbush, is a
conspicuous shrub growing in mountain and desert areas of California, southern
Nevada, northwestern Arizona, and southwestern Utah. The purpose of this study was
to obtain and chemically characterize the essential oil of this plant. Aerial
parts of E. linearifolia were collected from southwestern Utah and
hydrodistilled to give yellow essential oils in 1.290-1.817% yield, which were
analyzed by gas chromatographic methods. The essential oils were dominated by
monoterpene hydrocarbons (68.7-73.2%) and oxygenated monoterpenoids
(16.2-18.7%). The major components were sabinene (13.2-14.3%), β-pinene (4.0-13.4%), β-phellandrene
(0.3-13.9%), myrcene (6.0-12.2%), terpinen-4-ol (6.3-8.1%), limonene
(1.5-15.8%), (Z)-β-ocimene
(4.6-6.1%), (E)-β-ocimene
(3.3-7.5%), and α-pinene
(4.5-8.2%). Enantioselective GC/MS revealed the (+)-enantiomers to predominate
for α-thujene, sabinene, cis-sabinene hydrate, trans-sabinene
hydrate, and terpinen-4-ol, while the (–)-enantiomers predominated for
β-phellandrene and verbenone. However, the enantiomeric distributions were not
consistent for α-pinene,
β-pinene, limonene, or α-terpineol, while
linalool was virtually racemic.
Abstract Keywords
Narrowleaf
goldenbush, Asteraceae, essential oil, gas chromatography, chemical
composition, enantiomers, chiral.
1. Introduction
The genus Ericameria Nutt. (Asteraceae) contains 41 species, which are found in southwestern and western North America [1, 2]. Ericameria linearifolia (DC.) Urbatsch & Wussow (narrow-leaf golden bush) (syn. Happlopappus linearifolius DC.) is a shrub, 40-150 cm tall, the leaves are 12-55 mm long and 0.5-3 mm wide; the flower heads appear in spring and early summer and contain 3-18 ray florets and 16-60 disc florets (Fig. 1) [3, 4]. The native range of the plant includes California, southern Nevada, southwestern Utah, western Arizona, and northern Baja California (Fig. 2) [3], and grows in rocky or sandy soils on mountainsides, dry creek beds, deserts, and mesas [4]. The Kawaiisu people of California have used E. linearifolia in their traditional medicine [5]. A decoction of leaves and flowers was applied to limbs to treat rheumatism and applied externally to relieve soreness.
Figure 1. Ericameria linearifolia (DC.) Urbatsch & Wussow (narrowleaf goldenbush).
A: Photograph of the plant at the time of collection by K. Swor.
B: Scan of the pressed plant by W.N. Setzer.
Figure 2. Native range of Ericameria linearifolia
(based on Urbatsch & Wussow, 1979 [3]).
Labdane diterpenoids (18α-succinyloxy-labd-7-en-15-oic acid and 8,17H-7,8-dehydropinifolic acid) [6] and flavonoids (kaempferol, 3-methylkaempferol, 3,4′-dimethylkaempferol, quercetin, 3-methylquercetin, 3′-methylquercetin, and 3,3′-dimethylquercetin) [7] have been isolated and characterized from E. linearifolia. As far as we are aware, however, there have been no previous investigations on the essential oil of E. linearifolia. Apparently, only two other species of Ericameria have been analyzed in terms of essential oil composition, Ericameria nauseosa (Pursh) G.L.Nesom & G.I.Baird [8–10] and Ericameria laricifolia (A.Gray) Shinners [11]. As part of our continuing interest in the essential oils of Great Basin Asteraceae, the purpose of this study is to obtain and chemically characterize the essential oil of E. linearifolia.
2.
Materials and methods
2.1.
Plant material
Three
different samples (three different plants) of E. linearifolia were
collected on 26 April 2023 near Toquerville, Utah (37°17′9″ N, 113°18′21″ W, 1180 m asl). The
plant was identified in the field by W.N. Setzer using a field guide [12]
and later verified by comparison with herbarium samples from the New York
Botanical Garden [13]. A sample of the plant was vouchered with
the University of Alabama in Huntsville herbarium (WNS-El-6980). The fresh
plant material was frozen (–20
°C) until distillation.
The aerial parts of each plant were hydrodistilled using a Likens-Nickerson
apparatus for 3 h with continuous extraction of the distillate with
dichloromethane to give yellow essential oils (Table 1).
Table 1. Details of hydrodistillation of Ericameria linearifolia.
Sample
No. |
Mass
aerial parts (g) |
Mass
essential oil (g) |
Yield
(%, w/w) |
#1 |
109.65 |
1.4144 |
1.290% |
#2 |
117.04 |
1.8910 |
1.616% |
#3 |
180.98 |
3.2888 |
1.817% |
2.2. Gas chromatographic analysis
The essential oils from the aerial
parts of E. linearifolia were analyzed by gas chromatography (GC/MS and
GC-FID) as previously described [14]. Retention indices (RI) were determined using
the linear equation of van den Dool and Kratz [15]. The essential oil components of E.
linearifolia were identified by comparing their RI values (within ten RI
units) and their MS fragmentation patterns (> 80% similarity) with those
reported in the Adams [16], FFNSC3 [17], NIST20 [18], and Satyal [19] databases. The compound percentages
were calculated from raw peak integration without standardization.
Enantioselective GC/MS was carried out as described previously [14]. The individual enantiomers were
determined by comparison of RI values with authentic samples (Sigma-Aldrich,
Milwaukee, WI, USA), which are compiled in our in-house database. Enantiomeric
distributions were calculated from raw peak areas.
3. Results and discussion
Hydrodistillation
of three different plant samples of E. linearifolia from southwestern
Utah gave yellow essential oils in yields of 1.290-1.817% (w/w). Gas
chromatographic analysis (GC/MS, GC-FID) allowed for the identification of 122
components accounting for 99.1-99.6% of the total compositions (Table 2).
Table 2. Chemical composition (percent of total) of the essential oil from the aerial parts of Ericameria linearifolia.
RIcalc |
RIdb |
Compounds |
Sample numbers |
||
#1 |
#2 |
#3 |
|||
925 |
925 |
α-Thujene |
0.6 |
0.9 |
0.9 |
933 |
933 |
α-Pinene |
4.5 |
5.1 |
8.2 |
949 |
950 |
Camphene |
tr |
tr |
tr |
953 |
953 |
Thuja-2,4(10)-diene |
0.2 |
0.2 |
0.3 |
973 |
972 |
Sabinene |
13.2 |
13.8 |
14.3 |
978 |
978 |
β-Pinene |
4.0 |
12.7 |
13.4 |
990 |
989 |
Myrcene |
12.2 |
6.4 |
6.0 |
1006 |
1006 |
3-Ethenyl-1,2-dimethylcyclohexa-1,4-diene |
tr |
tr |
0.1 |
1007 |
1007 |
α-Phellandrene |
tr |
0.1 |
0.1 |
1017 |
1017 |
α-Terpinene |
1.2 |
2.0 |
1.5 |
1025 |
1025 |
p-Cymene |
1.3 |
1.1 |
1.2 |
1030 |
1030 |
Limonene |
15.8 |
1.5 |
1.6 |
1032 |
1031 |
β-Phellandrene |
0.3 |
13.9 |
12.3 |
1035 |
1034 |
(Z)-β-Ocimene |
4.6 |
5.7 |
6.1 |
1047 |
1046 |
(E)-β-Ocimene |
7.5 |
4.8 |
3.3 |
1058 |
1058 |
γ-Terpinene |
2.4 |
3.6 |
2.8 |
1070 |
1069 |
cis-Sabinene hydrate |
0.9 |
0.7 |
0.7 |
1085 |
1086 |
Terpinolene |
0.6 |
0.9 |
0.8 |
1086 |
1086 |
trans-Linalool oxide (furanoid) |
0.1 |
0.1 |
0.2 |
1090 |
1091 |
p-Cymenene |
0.2 |
0.1 |
0.1 |
1096 |
1098 |
6-Camphenone |
tr |
- |
- |
1098 |
1098 |
Perillene |
tr |
- |
- |
1100 |
1101 |
Linalool |
0.6 |
0.3 |
0.5 |
1101 |
1101 |
trans-Sabinene hydrate |
0.6 |
0.5 |
0.4 |
1110 |
1112 |
Rose oxide |
0.1 |
0.1 |
- |
1122 |
1122 |
Chrysanthenone |
0.1 |
0.1 |
0.1 |
1125 |
1124 |
cis-p-Menth-2-en-1-ol |
0.4 |
0.6 |
0.4 |
1127 |
1127 |
α-Campholenal |
0.2 |
0.2 |
0.5 |
1128 |
1128 |
(4E,6Z)-allo-Ocimene |
0.2 |
0.2 |
0.2 |
1139 |
1139 |
Nopinone |
0.1 |
tr |
tr |
1141 |
1141 |
trans-Pinocarveol |
0.3 |
0.2 |
0.4 |
1142 |
1141 |
cis-Verbenol |
0.3 |
0.3 |
0.7 |
1143 |
1142 |
trans-p-Menth-2-en-1-ol |
0.3 |
0.3 |
0.1 |
1146 |
1146 |
trans-Verbenol |
1.5 |
1.1 |
2.3 |
1149 |
1149 |
iso-Pulegol |
0.1 |
0.1 |
- |
1151 |
1154 |
p-Mentha-1(7),2-dien-8-ol |
0.2 |
0.2 |
0.4 |
1152 |
1152 |
Citronellal |
0.2 |
0.2 |
0.1 |
1156 |
1156 |
Menthone |
tr |
0.1 |
- |
1157 |
1157 |
Sabina ketone |
tr |
tr |
0.1 |
1158 |
1157 |
iso-Isopulegol |
0.1 |
0.1 |
- |
1162 |
1164 |
Pinocarvone |
0.1 |
0.1 |
0.2 |
1173 |
1171 |
p-Mentha-1,5-dien-8-ol |
0.5 |
0.5 |
1.0 |
1176 |
1176 |
Nonanol |
0.3 |
tr |
- |
1178 |
1178 |
Octanoic acid |
0.1 |
1.4 |
0.2 |
1182 |
1180 |
Terpinen-4-ol |
6.8 |
8.1 |
6.3 |
1188 |
1188 |
p-Cymen-8-ol |
0.4 |
0.5 |
0.8 |
1196 |
1195 |
α-Terpineol |
0.5 |
0.7 |
0.7 |
1197 |
1195 |
Myrtenol |
0.3 |
0.1 |
0.3 |
1198 |
1198 |
cis-Piperitol |
0.1 |
0.1 |
0.1 |
1208 |
1208 |
Verbenone |
0.8 |
0.6 |
1.5 |
1210 |
1209 |
trans-Piperitol |
0.1 |
0.2 |
0.1 |
1220 |
1218 |
trans-Carveol |
0.1 |
0.1 |
0.2 |
1227 |
1227 |
Citronellol |
0.1 |
0.1 |
0.1 |
1243 |
1242 |
Cuminal |
tr |
tr |
tr |
1244 |
1246 |
Carvone |
tr |
tr |
0.1 |
1250 |
1249 |
Geraniol |
0.2 |
0.1 |
0.2 |
1269 |
1270 |
iso-Piperitenone |
0.1 |
0.1 |
0.1 |
1273 |
1276 |
2,3-Pinanediol |
0.1 |
0.1 |
0.2 |
1277 |
1277 |
Phellandral |
- |
tr |
tr |
1293 |
1294 |
p-Cymen-7-ol |
- |
- |
0.1 |
1331 |
1330 |
Bicycloelemene |
- |
0.1 |
0.1 |
1346 |
1348 |
α-Cubebene |
0.2 |
- |
- |
1349 |
1349 |
Citronellyl acetate |
0.1 |
0.1 |
- |
1371 |
1372 |
Decanoic acid |
2.0 |
1.4 |
0.8 |
1375 |
1375 |
α-Copaene |
tr |
- |
0.1 |
1387 |
1387 |
β-Cubebene |
0.1 |
- |
- |
1389 |
1390 |
trans-β-Elemene |
0.1 |
0.1 |
0.1 |
1419 |
1417 |
(E)-β-Caryophyllene |
0.1 |
0.6 |
0.3 |
1429 |
1433 |
β-Copaene |
- |
- |
tr |
1432 |
1432 |
trans-α-Bergamotene |
- |
tr |
tr |
1437 |
1438 |
Aromadendrene |
tr |
tr |
tr |
1449 |
1452 |
Cadina-3,5-diene |
0.1 |
tr |
- |
1452 |
1452 |
(E)-β-Farnesene |
tr |
0.1 |
tr |
1456 |
1454 |
α-Humulene |
tr |
tr |
tr |
1460 |
1457 |
allo-Aromadendrene |
0.1 |
0.2 |
0.1 |
1465 |
1463 |
γ-Decalactone |
tr |
- |
tr |
1472 |
1472 |
trans-Cadina-1(6),4-diene |
0.1 |
tr |
tr |
1475 |
1478 |
γ-Muurolene |
0.1 |
0.1 |
0.1 |
1478 |
1478 |
γ-Curcumene |
0.3 |
0.1 |
0.5 |
1481 |
1480 |
Germacrene D |
0.9 |
0.4 |
1.2 |
1489 |
1489 |
β-Selinene |
- |
tr |
- |
1491 |
1491 |
Viridiflorene |
tr |
0.1 |
0.1 |
1492 |
1490 |
γ-Amorphene |
0.2 |
tr |
tr |
1496 |
1497 |
Bicyclogermacrene |
0.4 |
0.2 |
0.3 |
1496 |
1497 |
epi-Cubebol |
0.3 |
- |
- |
1498 |
1500 |
α-Muurolene |
0.1 |
0.2 |
0.1 |
1507 |
1508 |
β-Bisabolene |
0.1 |
tr |
0.1 |
1509 |
1509 |
β-Curcumene |
tr |
- |
tr |
1513 |
1510 |
1,11-Oxidocalamenene |
- |
- |
0.1 |
1513 |
1512 |
γ-Cadinene |
0.1 |
0.2 |
0.1 |
1516 |
1515 |
Cubebol |
0.3 |
tr |
- |
1518 |
1518 |
δ-Cadinene |
1.4 |
0.8 |
0.4 |
1522 |
1519 |
trans-Calamenene |
0.1 |
- |
- |
1523 |
1521 |
Zonarene |
0.1 |
- |
- |
1533 |
1533 |
trans-Cadina-1,4-diene |
0.1 |
tr |
- |
1537 |
1538 |
α-Cadinene |
tr |
tr |
tr |
1542 |
1541 |
α-Calacorene |
0.1 |
0.1 |
0.1 |
1563 |
1560 |
Dodecanoic acid |
0.2 |
0.1 |
0.1 |
1578 |
1576 |
Spathulenol |
0.7 |
0.4 |
0.5 |
1583 |
1584 |
10-epi-Juneol |
0.1 |
- |
0.1 |
1583 |
1587 |
Caryophyllene oxide |
- |
0.2 |
- |
1587 |
1590 |
Globulol |
0.1 |
0.1 |
0.1 |
1588 |
1590 |
Gleenol |
tr |
- |
- |
1595 |
1594 |
Viridiflorol |
0.1 |
0.1 |
0.1 |
1605 |
1605 |
Ledol |
tr |
tr |
tr |
1607 |
1609 |
Rosifoliol |
tr |
- |
tr |
1616 |
1616 |
1,10-di-epi-Cubenol |
- |
tr |
- |
1629 |
1628 |
1-epi-Cubenol |
0.4 |
0.1 |
0.1 |
1633 |
1629 |
iso-Spathulenol |
0.1 |
0.1 |
0.1 |
1643 |
1643 |
τ-Cadinol |
0.4 |
0.4 |
0.5 |
1645 |
1645 |
τ-Muurolol |
0.4 |
0.5 |
0.2 |
1647 |
1645 |
α-Muurolol (= δ-Cadinol) |
0.2 |
0.1 |
0.1 |
1656 |
1655 |
α-Cadinol |
0.9 |
1.2 |
0.7 |
1686 |
1688 |
α-Bisabolol |
2.1 |
0.1 |
0.1 |
1694 |
1687 |
Shyobunol |
0.3 |
0.3 |
0.1 |
1733 |
1735 |
Oplopanone |
0.1 |
0.1 |
0.1 |
1840 |
1841 |
Phytone |
tr |
tr |
tr |
2105 |
2106 |
Phytol |
tr |
tr |
tr |
2300 |
2300 |
Tricosane |
0.2 |
0.1 |
0.1 |
2400 |
2400 |
Tetracosane |
0.1 |
tr |
tr |
2500 |
2500 |
Pentacosane |
0.1 |
0.1 |
0.1 |
2700 |
2700 |
Heptacosane |
0.1 |
tr |
0.1 |
Compound Classes |
|
|
|
||
Monoterpene hydrocarbons |
68.7 |
73.2 |
73.1 |
||
Oxygenated monoterpenoids |
16.2 |
16.4 |
18.7 |
||
Sesquiterpene hydrocarbons |
4.6 |
3.1 |
3.6 |
||
Oxygenated sesquiterpenoids |
6.6 |
3.7 |
2.9 |
||
Diterpenoids |
tr |
tr |
tr |
||
Others |
3.0 |
3.2 |
1.4 |
||
Total identified |
99.1 |
99.6 |
99.6 |
RIcalc = Retention index determined using a homologous series of n-alkanes on a ZB-5ms column. RIdb = Reference retention index from the databases. tr = trace (< 0.05%). - = not detected.
The major components in E. linearifolia essential oils were sabinene (13.2-14.3%), β-pinene (4.0-13.4%), β-phellandrene (0.3-13.9%), myrcene (6.0-12.2%), terpinen-4-ol (6.3-8.1%), limonene (1.5-15.8%), (Z)-β-ocimene (4.6-6.1%), (E)-β-ocimene (3.3-7.5%), and α-pinene (4.5-8.2%). As far as we are aware, there are only two previous reports on the essential oils of Ericameria species, E. laricifolia [11] and E. nauseosa [8–10]. The major components identified in E. laricifolia were β-phellandrene (24.3%), limonene (22.5%), β-pinene (17.5%), α-phellandrene (5.3%), and α-pinene (4.3%); while the major components (averages) in E. nauseosa were β-phellandrene (30.1%), β-pinene (10.3%), limonene (6.3%), (Z)-β-ocimene (6.4%), sabinene (4.1%), myrcene (3.6%), and (E)-β-ocimene (3.5%). Thus, there are qualitative similarities in the essential oils of the three Ericameria species, but quantitative differences. α-Pinene concentrations (average 5.9%) were higher in E. linearifolia than those reported for E. laricifolia (4.3%) or E. nauseosa (average 0.6%). Similarly, sabinene concentrations (average 13.8%) were also higher in E. linearifolia than those for E. laricifolia (not observed) or E. nauseosa (average 3.9%). β-Pinene concentrations were generally high in the Ericameria essential oils, E. linearifolia (average 10.0%), E. laricifolia (17.5%), and E. nauseosa (average 12.2%). Likewise, limonene concentrations were generally high in all three Ericameria essential oils, E. linearifolia (average 6.3%), E. laricifolia (22.5%), and E. nauseosa (average 9.0%). However, the concentration of β-phellandrene was lower in E. linearifolia (average 8.8%) than either E. laricifolia (24.3%) or E. nauseosa (average 27.7%). Terpinen-4-ol levels were high in E. linearifolia (average 7.0%), but lower in E. laricifolia (2.4%) and E. nauseosa (average 1.9%).
Several of the major components of E. linearifolia essential oil have shown relevant biological activity [20, 21]. For example, α-pinene has shown anti-inflammatory and antinociceptive activities in rodent models [22–25], while β-pinene has shown antinociceptive actions in rats [26]. Myrcene has also shown anti-inflammatory and analgesic effects in rodent models [27, 28]. Terpinen-4-ol has demonstrated antioxidant and anti-inflammatory activities as well as anti-arthritic effects attributed to the downregulation of the pro-inflammatory cytokines, IL-1ß, TNFα, IRAK, and NF-κB [29]. The anti-inflammatory and analgesic effects of the major components in E. linearifolia may account for the traditional use of this plant to treat rheumatism and other pains.
Enantioselective GC/MS was carried out to evaluate the enantiomeric distributions of chiral monoterpenoids (Table 3). The (+)-enantiomers predominated for α-thujene, sabinene, cis-sabinene hydrate, trans-sabinene hydrate, and terpinen-4-ol, while the (–)-enantiomers predominated for β-phellandrene and verbenone. Curiously, the enantiomeric distributions were not consistent between the three samples for α-pinene, β-pinene, limonene, and α-terpineol; the dominant enantiomers are switched for sample #1 compared to samples #2 and #3. Linalool was virtually racemic in the essential oils. In contrast, the essential oils of E. nauseosa showed (–)-α-thujene, (–)-α-pinene, (–)-sabinene, (–)-β-pinene, (–)-β-phellandrene, (–)-cis-sabinene hydrate, (–)-trans-sabinene hydrate, (–)-terpinen-4-ol, and (–)-α-terpineol to be the dominant stereoisomers, while (+)-limonene predominated in E. nauseosa essential oils from Idaho, but (–)-limonene was the major isomer from Utah. Thus, there are no apparent consistencies in enantiomeric distributions of monoterpenoids in Ericameria essential oils.
Table 3. Enantiomeric distribution (%) of chiral monoterpenoids in Ericameria linearifolia essential oils.
Compounds | RIdb | RIcalc | Sample numbers | ||
#1 | #2 | #3 | |||
(+)-α-Thujene | 950 | 952 | 100.0 | 88.8 | 85.6 |
(–)-α-Thujene | 951 | 954 | 0.0 | 11.2 | 14.4 |
(–)-α-Pinene | 976 | 975 | 35.6 | 68.3 | 77.9 |
(+)-α-Pinene | 982 | 981 | 64.4 | 31.7 | 22.1 |
(+)-Sabinene | 1021 | 1016 | 92.6 | 73.7 | 71.6 |
(–)-Sabinene | 1030 | 1027 | 7.4 | 26.3 | 28.4 |
(+)-β-Pinene | 1027 | 1022 | 73.0 | 16.1 | 23.4 |
(–)-β-Pinene | 1031 | 1030 | 27.0 | 83.9 | 76.6 |
(–)-α-Phellandrene | 1050 | 1051 | - | 72.1 | - |
(+)-α-Phellandrene | 1053 | 1053 | - | 27.9 | - |
(–)-Limonene | 1073 | 1073 | 2.3 | 76.3 | 82.8 |
(+)-Limonene | 1081 | 1078 | 97.7 | 23.7 | 17.2 |
(–)-β-Phellandrene | 1083 | 1080 | - | 100.0 | 100.0 |
(+)-β-Phellandrene | 1089 | - | - | 0.0 | 0.0 |
(+)-cis-Sabinene hydrate | 1199 | 1198 | 86.4 | 71.0 | 69.4 |
(–)-cis-Sabinene hydrate | 1202 | 1201 | 13.6 | 29.0 | 30.6 |
(–)-Linalool | 1228 | 1227 | 47.1 | 44.5 | 43.5 |
(+)-Linalool | 1231 | 1230 | 52.9 | 55.5 | 56.5 |
(+)-trans-Sabinene hydrate | 1231 | 1229 | 93.5 | 73.2 | 73.0 |
(–)-trans-Sabinene hydrate | 1235 | 1234 | 6.5 | 26.8 | 27.0 |
(+)-Terpinen-4-ol | 1297 | 1291 | 73.1 | 55.0 | 62.9 |
(–)-Terpinen-4-ol | 1300 | 1296 | 26.9 | 45.0 | 37.1 |
(–)-α-Terpineol | 1347 | 1346 | 29.2 | 64.1 | 58.5 |
(+)-α-Terpineol | 1356 | 1354 | 70.8 | 35.9 | 41.5 |
(–)-Verbenone | 1368 | 1369 | - | 96.2 | 96.4 |
(+)-Verbenone | 1380 | 1374 | - | 3.8 | 3.6 |
RIdb = Retention index from our in-house database. RIcalc = Calculated retention index based on a homologous series of n-alkanes on a Restek B-Dex 325 capillary column. - = compound not detected.
4. Conclusions
There is a paucity of information regarding the essential oil compositions of Ericameria. Nevertheless, there seem to be some notable components common to the genus, namely β-phellandrene (up to 13.9% in E. linearifolia and abundant in other Ericameria species), α-pinene (4.5-8.2% in E. linearifolia and abundant in other Ericameria species), β-pinene (4.0-13.4% in E. linearifolia and abundant in other Ericameria essential oils), limonene (up to 15.8% in E. linearifolia and abundant in other Ericameria species), and terpinen-4-ol. Enantioselective GC/MS, however, showed the enantiomeric distributions of chiral monoterpenoids to be inconsistent, both between Ericameria species as well as within E. linearifolia. There are 41 species of Ericameria, but apparently only three species have had the essential oils examined, E. nauseosa (three different investigations), E. laricifolia (one investigation from 1977), and E. linearifolia (this present work). Thus, there are ample opportunities for future investigations on Ericameria essential oils, which would serve to better characterize the volatile phytochemistry of this genus.
Authors’ contributions
Conceptualization, W.N.S.; Methodology, P.S. and W.N.S.; Software, P.S.; Validation, W.N.S., Formal Analysis, A.P., P.S., and W.N.S.; Investigation, K.S., A.P., P.S., and W.N.S.; Resources, P.S. and W.N.S.; Data Curation, W.N.S.; Writing – Original Draft Preparation, W.N.S.; Writing – Review & Editing, K.S., A.P., P.S., and W.N.S.; Project Administration, W.N.S.
Acknowledgements
This work was carried out as part of the activities of the Aromatic Plant Research Center (APRC, https://aromaticplant.org/).
Funding
This research received no specific grant from any funding agency.
Availability of data and materials
All data will be made available on request according to the journal policy.
Conflicts of interest
The authors declare no conflict of interest.
References
1. Mabberley, D.J. Mabberley’s Plant-Book; 3rd
ed.; Cambridge University Press: Cambridge, UK, 2008; ISBN 978-0-521-82071-4.
2. World Flora Online, W.F.O. Ericameria
Nutt. Available online: https://www.worldfloraonline.org/taxon/wfo-4000013775
(accessed on Jan 8, 2024).
3. Urbatsch, L.E.; Wussow, J.R. The taxonomic
affinities of Haplopappus linearifolius (Asteraceae-Astereae). Brittonia
1979, 31, 265–275. https://doi.org/10.2307/ 2806187.
4. eFloras.org Ericameria linearifolia
(de Candolle) Urbatsch & Wussow Available online:
http://www.efloras.org/florataxon.aspx?flora_id=1&taxon_id=250066524
(accessed on Jan 8, 2024).
5. Zigmond, M. Kawaiisu Ethnobotany; University
of Utah Press: Salt Lake City, Utah, USA, 1981; ISBN 978-0874801323.
6. Dentali, S.J.; Hoffmann, J.J.; Jolad, S.D.;
Timmermann, B.N. Diterpenes of Ericameria linearifolia. Phytochem. 1987,
26, 3025–3028. https://doi.org/10.1016/S0031-9422 (00)84585-9.
7. Wollenweber, E.; Dörr, M.; Fritz, H.; Papendieck,
S.; Yatskievych, G.; Roitman, J.N. Exudate flavonoids in Asteraceae from
Arizona, California and Mexico. Zeitschrift fur Naturforsch. Sect. C J. Biosci.
1997, 52, 301–307. https://doi.org/10.1515/znc-1997-5-604.
8. Chao, S.; Young, D.G.; Casabianca, H.;
Bertrand, M.-C. Composition of the oils of three Chrysothamnus nauseousus
varieties. J. Essent. Oil Res. 2003, 15, 425–427.
https://doi.org/10.1080/10412905.2003.9698630.
9. Tabanca, N.; Demirci, B.; Crockett, S.L.;
Başer, K.H.C.; Wedge, D.E. Chemical composition and antifungal activity of Arnica
longifolia, Aster hesperius, and Chrysothamnus nauseosus
essential oils. J. Agric. Food Chem. 2007, 55, 8430–8435. https://doi.org/10.1021/ jf071379c.
10. Stirling, J.; Platt, B.G.; Satyal, P.; Swor,
K.; Setzer, W.N. The essential oils of rubber rabbitbrush (Ericameria
nauseosa) from north-central Utah and southwestern Idaho. Nat. Prod. Commun.
2023, 18, 1934578X231 161186. https://doi.org/10.1177/1934578X231161186.
11. Wang, H.-Y. The Investigation of Essential Oil
of Ericameria laricifolia, M.S. thesis, University of Texas at El Paso,
1977.
12. Van Buren, R.; Cooper, J.G.; Shultz, L.M.;
Harper, K.T. Woody Plants of Utah; Utah State University Press: Logan, Utah,
USA, 2011, ISBN 978-0-87421-824-4.
13. New York Botanical Garden, N.Y.B.G. C. V.
Starr Virtual Herbarium Available online: https://sweetgum. nybg.org/science/vh/
(accessed on Jun 24, 2023).
14. Satyal, P.; Dosoky, N.S.; Poudel, A.; Swor,
K.; Setzer, W.N. Chemical composition of the aerial parts essential oil of Chrysothamnus
viscidiflorus from southwestern Idaho. J. Essent. Oil Plant Comp. 2023, 1,
115–121, https://doi.org/10.58985/jeopc.2023.v01i02.16.
15. van den Dool, H.; Kratz, P.D. A generalization
of the retention index system including linear temperature programmed
gas-liquid partition chromatography. J. Chromatogr. A 1963, 11, 463–471. https://doi.org/10. 1016/S0021-9673(01)80947-X.
16. Adams, R.P. Identification of Essential Oil
Components by Gas Chromatography/Mass Spectrometry; 4th ed.; Allured
Publishing: Carol Stream, IL, USA, 2007; ISBN 978-1-932633-21-4.
17. Mondello, L. FFNSC 3; Shimadzu Scientific
Instruments: Columbia, Maryland, USA, 2016.
18. NIST20; National Institute of Standards and
Technology: Gaithersburg, Maryland, USA, 2020.
19. Satyal, P. Development of GC-MS Database of
Essential Oil Components by the Analysis of Natural Essential Oils and
Synthetic Compounds and Discovery of Biologically Active Novel Chemotypes in
Essential Oils, Ph.D. dissertation, University of Alabama in Huntsville,
Huntsville, AL, USA, 2015.
20. de Sousa, D.P. Analgesic-like activity of
essential oils constituents. Molecules 2011, 16, 2233–2252. https://doi.org/10.3390/molecules16032233.
21. Guimarães, A.G.; Quintans, J.S.S.;
Quintans-Júnior, L.J. Monoterpenes with analgesic activity — A systematic review.
Phyther. Res. 2013, 27, 1–15. https://doi.org/
10.1002/ ptr.4686.
22. Santos, F.A.; Rao, V.S.N.; Silveira, E.R.
Investigations on the antinociceptive effect of Psidium guajava leaf
essential oil and its major constituents. Phyther. Res. 1998, 12, 24–27. https://doi.org/10.1002/(SICI)1099-1573(19980201)12:1<24::AID-PTR181>3.0.CO;2-B.
23. Orhan, I.; Küpeli, E.; Aslan, M.; Kartal, M.;
Yesilada, E. Bioassay-guided evaluation of anti-inflammatory and
antinociceptive activities of pistachio, Pistacia vera L. J.
Ethnopharmacol. 2006, 105, 235–240. https://doi.org/10. 1016/j.jep.2005.10.023.
24. Quintão, N.L.M.; da Silva, G.F.; Antonialli,
C.S.; Rocha, L.W.; Filho, V.C.; Cicció, J.F. Chemical composition and
evaluation of the anti-hypernociceptive effect of the essential oil extracted
from the leaves of Ugni myricoides on inflammatory and neuropathic
models of pain in mice. Planta Med. 2010, 76, 1411–1418. https://doi.org/ 10.1055/s-0029-1240891.
25. Li, X.J.; Yang, Y.-J.; Li, Y.-S.; Zhang, W.K.;
Tang, H.-B. α-Pinene, linalool, and 1-octanol contribute to the topical
anti-inflammatory and analgesic activities of frankincense by inhibiting COX-2.
J. Ethnopharmacol. 2016, 179, 22–26. http://dx.doi.org/10.1016/j.jep.2015. 12. 039.
26. Liapi, C.; Anifantis, G.; Chinou, I.;
Kourounakis, A.P.; Theodosopoulos, S.; Galanopoulou, P. Antinociceptive properties
of 1,8-cineole and β-pinene, from the essential oil of Eucalyptus
camaldulensis leaves, in rodents. Planta Med. 2007, 73, 1247–1254. https://doi. org/10.1055/s-2007-990224.
27. Lorenzetti, B.B.; Souza, G.E.P.; Sarti, S.J.;
Santos Filho, D.; Ferreira, S.H. Myrcene mimics the peripheral analgesic
activity of lemongrass tea. J. Ethnopharmacol. 1991, 34, 43–48. https://doi.org/10.1016/0378-8741(91) 90187-I.
28. McDougall, J.J.; McKenna, M.K.
Anti-inflammatory and analgesic properties of the cannabis terpene myrcene in
rat adjuvant monoarthritis. Int. J. Mol. Sci. 2022, 23, 7891. https://doi.org/10.3390/ijms23147891.
29. Aslam, S.; Younis, W.; Malik, M.N.H.; Jahan, S.; Alamgeer; Uttra, A.M.; Munir, M.U.; Roman, M. Pharmacological evaluation of anti-arthritic potential of terpinen-4-ol using in vitro and in vivo assays. Inflammopharmacology 2022, 30, 945–959. https://doi. org/10.1007/ s10787-022-00960-w.
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Abstract
Ericameria
linearifolia, the narrowleaf goldenbush, is a
conspicuous shrub growing in mountain and desert areas of California, southern
Nevada, northwestern Arizona, and southwestern Utah. The purpose of this study was
to obtain and chemically characterize the essential oil of this plant. Aerial
parts of E. linearifolia were collected from southwestern Utah and
hydrodistilled to give yellow essential oils in 1.290-1.817% yield, which were
analyzed by gas chromatographic methods. The essential oils were dominated by
monoterpene hydrocarbons (68.7-73.2%) and oxygenated monoterpenoids
(16.2-18.7%). The major components were sabinene (13.2-14.3%), β-pinene (4.0-13.4%), β-phellandrene
(0.3-13.9%), myrcene (6.0-12.2%), terpinen-4-ol (6.3-8.1%), limonene
(1.5-15.8%), (Z)-β-ocimene
(4.6-6.1%), (E)-β-ocimene
(3.3-7.5%), and α-pinene
(4.5-8.2%). Enantioselective GC/MS revealed the (+)-enantiomers to predominate
for α-thujene, sabinene, cis-sabinene hydrate, trans-sabinene
hydrate, and terpinen-4-ol, while the (–)-enantiomers predominated for
β-phellandrene and verbenone. However, the enantiomeric distributions were not
consistent for α-pinene,
β-pinene, limonene, or α-terpineol, while
linalool was virtually racemic.
Abstract Keywords
Narrowleaf
goldenbush, Asteraceae, essential oil, gas chromatography, chemical
composition, enantiomers, chiral.
This work is licensed under the
Creative Commons Attribution
4.0
License (CC BY-NC 4.0).
Editor-in-Chief
Prof. Dr. Radosław Kowalski
This work is licensed under the
Creative Commons Attribution 4.0
License.(CC BY-NC 4.0).