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Abstract

Volatile constituents of the aerial parts of fresh white sage (Salvia apiana Jepson) were isolated by extraction with diethyl ether followed by high vacuum distillation with a solvent assisted flavor evaporation (SAFE) apparatus. The isolated volatiles were analyzed by GC and GC/MS. A total of 84 constituents were identified (constituting 95.1% of the total area), 11 of which were tentatively identified. The volatiles were characterized by a high content of hydrocarbon and oxygenated monoterpenes. The major constituents identified were 1,8-cineole (34.5%), camphor (21.7%), β-pinene (7.4%), α-pinene (6.4%), delta-3-carene (6.4%), camphene (3.9%), limonene (3.5%), myrcene (3.2%), and terpinolene (1.3%).
Takeoka
et al.
Volatile Constituents of the Aerial Parts
of
Salvia apiana
Jepson
Gary R. Takeoka,*
Western Regional Research Center, Agricultural Research Service, US Department of Agriculture, 800 Buchanan Street,
Albany, CA 94710
Christopher Hobbs,
Department of Integrative Biology, University of California, Berkeley, California 94720-2465
Byeoung-Soo Park,
Institute of Ecological Phytochemistry, Hankyong National University, Ansung-City, Kyonggi-Do 456-749, Korea
Abstract
Volatile constituents of the aerial parts of fresh white sage (Salvia apiana
Jepson) were isolated by extraction
with diethyl ether followed by high vacuum distillation with a solvent assisted flavor evaporation (SAFE) apparatus.
The isolated volatiles were analyzed by GC and CC/MS. A total of 84 constituents were identified (constituting
95.1% of the total area), 11 of which were tentatively identified. The volatiles were characterized by a high content
of hydrocarbon and oxygenated monoterpenes. The major constituents identified were 1,8-cineole (34.5%), camphor
(21.7%), 3-pinene (7.4%), a-pinene (6.4%), -3-carene (6.4%), camphene (3.9%), limonene (3.5%), myrcene (3.2%),
and terpinolene (1.3%).
Key Word Index
Salvia apiana, white sage, Lamiaceae, essential oil composition, 1 ,8-cineole, camphor, 1 ,3,5-undecatriene isomers,
1,3,5,8-undecatetraene isomers.
Introduction
Salvia apiana
Jepson is one of approximately 900 world-
wide species of
Salvia
found in the Lamiaceae family (1). It
generally grows below 1500
in
Baja California, in the South
Coast (SCo), Transverse Ranges (TR), and Peninsular Ranges
(PR) sub-regions of southwestern California as well as in the
western edge of the Desert Province (DR) in the southeastern
portion of California (1). The plant has been used to treat chest
colds, coughs, sore throats, systemic poison oak rashes and
acute candidal vaginitis, and has been widely used by natives
(2,3) and in traditional Churnash healing (4). The leaves were
eaten, smoked and used in sweat baths by Cahuilla Indians to
treat upper respiratory infections (3). Four new
.
diterpenes,
6,7-didehydroferruginol; 6,7-didehydrosempervirol; 16-hy-
4roxy-6,7-didehydroferruginoi; 11,12,16-trihydroxy-20(10-35)
abeo-abieta-1(10),6,8,11,13-pentaene, two new diterpene quino-
nes, 16-hydroxyroyleanone and 6-deoxo-5,6-didehydrolanugon
Q as well as the known compounds, ferruginol, miltiodiol,
cryptanshinone, lanugon Q and salvicanol have been isolated
and characterized from the roots of S. apaina (5).
a-Amyrin, oleanolic acid and ursolic acid were identi-
fied in the dried aerial parts of S. apiana (6).
Dentali and
Hoffmann (7) identified two abietane acids, 16-hydroxy-
carnosic acid and carnosic acid in the leaves of
S. apiana.
Luis and co-workers (8,9) identified the new C terpenoids,
14-hydroxy-7-methoxy-11,16-diketo-apian-8-en-(22,6)-olide,
7-methoxy-11,16-diketo-apian-8,14-dien-(22,6)-olide, and
13,14-dioxo-11-hydroxy-7-methoxy-hassane-8,11,15-trien-
(22,6)-olide along with the known diterpenes, 16-hycir
o
x
y-
carnosic acid, 16-hydroxycarnosol, 16-hydroxyrosmanol,
16-hydroxy-7-methoxyrosmanol, rosmanol, 7-epirosmanol
and salvicanol in the aerial parts of
S. apiana.
The volatile
constituents from S.
apiana
Jepson leaves have been shown
to inhibit the root growth of
Cucumis sativus
and
Avenafatua
seedlings (10). It was postulated the volatiles may be deposited
when dew condenses on the seedlings in the field though the
active constituent(s) was not characterized.
While the composition of volatiles from the essential oils
of numerous
Salvia
species have been reported (11-18) there
is only limited knowledge of the volatile constituents in white
sage (19-21). The aim of this study was to provide a more
*Address for correspondence
Received: February 2008
Revised: April 2008
1041 -2905/10/0003-0241$14.00/O—© 2010 Allured Business Media
Accepted: August 2008
Vol. 22, May/June 2010
Journal of Essential Oil Research/241
S.
apiana
Constituent
(Z)-3-hexenol
hexanol
3-methy!butyl acetate
3-methyl-3-butenyl acetate
3-methyl-2-butenyl acetate
tricyàlene
ix-thujene
a-pinene
carphene
sabiriene
-pinene
2-pentylfuran
myrcene
(Z)-3-hexenyl acetate
(pmenth1(7),8diene)d
a-phellandrene
6-3-carene
a-terpinene
p-cymene
1 ,8-cineole
limonene
(Z)-f3-ocimene
(E)--ocimene
y-terpinene
cis-sabinene hydrate
trans-linalool oxide A furanoid
fenchone
2-nonanone
terpinolene
(trans-sabinene hydrate)d
linalool
campholene aldehyde
(trans-p-rnenth-2-en-1 .01)d
camphor
ipsdienol
-
bórneol.
terpinen-4-6I
1 (E,Z)-43,5-undecatriene
aterpineol
,.
(,3,E-,89,nçjpateItraefle)e
1 (E E) 3 5undecatriene
(1,3,5uridéÔàtriné)e +
i-(E,Z,Z)-3,5,84iñdecatetraene
Table I. Volatile constituents
(%)
of theaerial parts of
Salvia apiana
Jepson
DB-1
ref
%
area
Constituent
834
tr.b
cis-piperitol
860
tr.
(E)-2-octenyl acetate
866
tr.
trans-piperitol
861
tt
(Z)-3-hexenyl isovalerate
902
tr.
piperitone
918
0.1
hexyl isovalerate
922
0.3
geranial
929
6.4
bornyl acetate
941
3.9
2-undecanone
964
0.2c
(Z)-3-hexenyl tiglate
968
7.4
4-methoxyacetophenone
977
tr.
hexyl tiglate
981
3.2
eugenol
986
tr.
neryl acetate
(1004)
0.1
a-cubebene
996
0.4
geranyl acetate
1004
6.3
(Z)-jasmone
1008
0.2
cx-ylangene
1010
tr.
cx-copaene
1018
3450
a-gurjunene
1020
3.5
-caryophyllene
1026
0.7
geranylacetone
1037
0.3
guaia-6,9-diene
1048
0.4
(Selina-4(15),6-diene)
1051
0.2
a-humulene
1056
tr.
(7aH,1 03H-cadina-1(6),4-diene)t
1065
tr.
'y-muurolene
1069
tr.
a-amorphene
1077
1.3
bicyclogermacrene
(1098)
0.2
cx-muurolene
1083
0.2
-bisabolene
1103
tr.
i-cadinene
(1136)
tr.
calamenene*
1118
21.7
ö-cadinene
1126
tr.
(trans-cadina-1 ,4-diene)t
1147
0.2
(a-cadinene)t
1159
0.2
(E)-a-bisabolene
1163
0.2,
selina-3,7(1 1)-diene
1170
tr.
germacrene B
tr.
(T-cadinol)t
1172
tr.
(6(x-hydroxygermacra-1(10),4-diene)
t
1175
tr.
exptl
843
860
865
871
909
915
923
930
940
965
967
981
985
990
992
993
999
1006
1008
1016
1018
1030
1041
1049
1052
1057
1063
1073
1077
1079
1090
1097
1108
1112
1125
1144
1157
1165
1168
1172
1173
1174
DB-1
exptl
ref
%
areaa
1177
1175
1182
1191
1185
1185
1220
1219
1224
1224
1228
1228
1241
1241
1265
1268
1270
1273
1300
1300
1303
1302
1310
1310
1323
1327
1343
1342
1343
1347
1360
1360
1361
1365
1364
1370
1368
1374
1399
1408
1406
1418
1422
1427
1431
1437
1435
(1450)
1440
1449
1461
(1472)
1463
1469
1466
(1477)
1482
1489
1486
1492
1496
1500
1496
1505
1500
1508
1507
1514
1516
(1523)
1522
(1534)
1528
1532
1531
1537
1540
1550
1615
(1633)
1664
(1687)
Peak area percentage of total FID area (assuming all response factors of 1)
btr
represents a % area <0 1
/0
peak area of this constituent and the following constituent
weré cIclated 6n the basis of the GC/MS total ion chromatàgrrn;
dTentative
identifications (in parentheses) assigned based on mass spectra and
reported in Adams
(2007); 'Tentative identifications (in parentheses) assigned based on mass spectràreported in Wiley Registry of Mass Spectral Data,
8th
Edition; Tentative identifications (in
parentheses) assigned based on mass spectra and
reported in MassFinder 3 (Dr. Hochmuth Scientific Consulting Hamburg Germany)
0
This constituent and the next
eluting constituent were resolved by GC/MS but were not separated by GC FID correct isomer not identified
comprehensive;knowledge of the volatiles in
tbe,
aerial parts
stored in the dark after addition of 1-2 ppm of antioxidant 330
of S. apiana Jepson.
.
-..
(13,5-trimethy1-2,4,6-tris-f3,5-di-tert-butyl-4-hydroxybenzy11-
-
)
.
ExPerimental .
Plant material:
Freslileaves and flowering tops of S. apiana
Jesdnwee collected in the UC Davis Bbtanical Gardens in
June 2007. The samples were prepared the same day that they
were picked. A voucher specimen was deposited in the Jepson
Herbariñrn, University of California, Berkeley, CA.
Chemicals:
Diethyl ether was freshly distilled through
a
60 cth long Pyrex column packed With glassheliées and
benzene; Ethyl Corporation, Richmond, VA).
-
Extraction
of
volatiles:
The
.
plant material
(95
g)
was
crushed with a mortar and pestle under liquid nitrogen. The
material was divided into equal portion and added to two 250
mL Pyrex glass bottles with Teflon lined screw caps. Approxi-
mately 125 mL of ether was added to each bottle. The bottles
were covered with aluminum foil and were sonicated in an
ultrasonic bath for 15
mm.
The bottles were shaken throughout
the clay every 2 h and allowed to stand overnight. The dark
242/Journal of Essential Oil Research
Vol. 22, May/June 2010
Takeoka et al.
green extract was filtered through pre-rinsed (ether) filter
paper (ED fluted filter paper, grade 513, size 24 cm, Eaton-
Dikeman, Mount Holly Springs, PA). The extract was dried
overnight over anhydrous sodium sulfate (previously heated to
150°C for several hours to remove volatiles). The extract was
subjected to high vacuum distillation using a solvent assisted
flavor evaporation (SAFE; 22) apparatus. The SAFE apparatus
was heated to 40°C with a circulating water bath and the ex-
tract was added to the dropping funnel of the apparatus. The
distillation flask (500 mL) was heated to 40°C in a water bath.
The receiving flask for the distillate and the safety-cooling
trap of the SAFE apparatus were cooled with liquid nitrogen.
The SAFE apparatus was connected to a high vacuum pump
(<0.01 Pa) and then the mixture in the dropping funnel was
added in small aliquots into the distillation flask over 20 mm.
The distillate was concentrated using a Vigreux column (15 x
1 cm) and water bath at 40°C. The extract (0.6637
g)
was used
for CC and CC/MS analyses.
Gas chromatography:
A Hewlett-Packard (Avondale,
PA) 6890 gas chromatograph equipped with a flame ionization
detector (FID) was used. A 60 m X 0.32 mm DB-1 (d
1
= 0.25
gm; J&W Scientific, Folsom, CA) fused silica capillary column
was employed. The oven temperature was programed from
30°C (4 min isothermal) to 200°C at 2°C/mm (final hold was
25 mm). Split injections (1:20) were used. Helium was used as
the carrier gas at a linear velocity of 38.3 cm/s (30°C).
Gas chromatography/mass spectrometry (GC/MS):
The GC/MS system consisted of an Agilent Technologies 6890
gas chromatograph coupled to an Agilent Technologies 5973
Network MSD (Agilent Technologies, Palo Alto, CA). A 60 m
X 0.25 mm DB-1 MS fused silica capillary column was used
(d
f
= 0.25 i.tm). The CC oven was programed from 30°C (4
min isothermal) to 200°C at 2°C/mm (final hold was 35 mm).
Helium was used as the carrier gas at a headpressure of 22
psi. The injector, transfer line, ion source and quadrupole tem-
peratures were 180°C, 200°C, 170°C and 130°C, respectively.
The mass spectrometer was operated in the electron impact
mode with an ionization voltage of 70 eV. A scan range of
m/z
35-320 at 4.94 scans/s was employed.
Identification of volatiles:
Volatile constituents were
identified by comparing the component's mass spectrum and
experimental retention index (I) with that of an authentic
reference standard. The retention system proposed by Kováts
(23) was utilized. When standards were not available, tentative
identifications were assigned based on mass spectra and reten-
tion indices reported in Wiley Registry of Mass Spectral Data,
8
11
Edition (John Wiley & Sons, Inc., Hoboken, NJ), NIST/
EPAJNIH Mass Spectral Library 2005 (U.S. Department of
Commerce), MassFinder3 (Dr. Hochmuth Scientific Consult-
ing, Hamburg, Germany) and Identification of Essential Oil
Components by Gas Chromatography/Mass Spectrometry, 4"
Edition (24).
Results and Discussion
Aerial portions of S.
a.piana
Jepson were extracted with
diethyl ether and the volatiles were isolated by high vacuum
distillation using a SAFE apparatus. CC analysis of the extract
(0.6637 g) revealed that volatiles constituted
57.5%
(0.3816 g)
while ether made up 42.5% (0.2821
g).
The yield of volatiles
from the sample was 0.4%. A total of 84 constituents were
identified (constituting 95.1% of the total area), 11 of which
were tentatively identified. The major constituents identified
were 1,8-cineole(34.5%), camphor (21.7%), -pinene(7.4%), a-
pinene (6.4%), -3-carene(6.4%), camphene (3.9%),limonene
(3.5%), myrcene (3.2%), and terpinolene (1.3%). Emboden
and Lewis (20) reported similar percentages of 1,8-cineole
(39.5-46.6%), combined camphor and borneol(30.6-40.1%),
1-
pinene(6.7-7.6%), a-pinene (5.5--6.2%), camphene(3.9-4.9%)
and limonene (3.3-5.1%) in S.
apiana
subsp.
apiana oil.
A
more recent study on S.
apiana oil
(21) found similar levels
of 3-pinene (9.1%), a-pinene (9.0%), and limonene (2.0%)
but lower levels of 8-3-carene (1.3%), camphene (0.4%) and
camphor (2.1%). 1,8-Cineole was also reported as the main
constituent though its percentage (71.6%) was higher in the
previous investigation (21). 1,8-Cineole has been reported to
be useful for the treatment of brochial asthma, cough, and
liver failure induced by endotoxemic shock (25-27). This
monoterpene oxide has been shown to possess gastroprotective
activity, an effect related to both its antioxidant activity and its
lipoxygenase inhibitory effects (28). Juergens and co-workers
(29) demonstrated that 1,8-cineole was a strong inhibitor
of TNF-a and IL-1P production in stimulated lymphocytes
and monocytes. They also showed that 1,8-cineole at known
therapeutic blood concentrations had inhibitory effects on
the chemotactic cytokmne of IL-8 and IL-5. The reduction of
cytokine production suggested an anti-inflammatory mode of
action and consequently inhibition of cytokine induced airway
mucus hypersecretion rather than simple secretolytic activity.
Isolated monoterpenes such as 1,8-cineole may offer a new
opportunity for initial and long-term treatment of asthma and
chronic obstructive pulmonary disease (COPD).
Salviafructicosa oil and its major compounds, thujone and
1,8-cineole, showed relatively low antimicrobial activity against
eight bacterial strains, Escherichia coli (NCIMB 8879 and
NCIMB 12210),
Pseudomonas aeruginosa
NCIMB 12469),
Salmonella typhimurium
(NCIMB 10248),
Staphylococcus
aureus
(NCIMB 9518 and NCIMB 8625),
Rhizobiüm legu-
minosarum (NCIMB
11478), and
Bacillus subtiii.s
(NC1MB
3610), while camphor was exhibited almost no activity against
the bacteria tested (30).
Salviafructicosa oil
and 1,8-cineole,
camphor and thujone exhibited cytotoxic activity against
African Green Monkey kidney (Vero) cells and high levels of
virucidal activity against herpes simplex virus 1 (30). Pitarokili
and co-workers(15) tested the antifungal activity of 1,8-cineole
and camphor (the main constituents identified in S.
fruticosa
oil) against five phytopathogenic fungi,
Fusarium oxysporum
f. sp. dianthi, Fusarium proliferatum, Fusarium solani f. sp.
cucurbitae, Rhizoctonia solani
and
Scierotinia scierotiorum.
Camphor showed moderate activity against S.
sclerotiorum
and
R. solani
but displayed lower activity against the three
Fusarium
species. 1,8-Cineole exhibited only slight activity
against the five fungal species. The oil of
S.fruticosa exhibited
higher
antifungal
activity than camphorwhich led the research-
ers to conclude that other components exert direct activity or
possibly a synergistic effect with camphor. Three previously
reported S.
apiana
constituents, cymene, oc-pinene oxide and
3-caryophyllene oxide, were not detected in this study (21).
Vol.-22, May/June 2010
Journal of Essential Oil Research/243
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13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
S
apiana
These authors also.id not detect a- an:d:3
t
hujone which are
major
6ons
,
tittiOnts in
Salvia officinalis
L. oil (12,14,16). To
the best of these authors' knowledge this is the first time that
1,3,5.-undec'atriee and 'i;3,5,8-u'ndècatetrâene isomers have
been reported in
Salvia
species.
The poteit odor character of 1-(E,Z)-3,5-undecatriene and
1-(E,ZZ)-3,,8-undecatetraene has been described by Berger
et aL (31). The configuration of the double bond in the C-5
position is crucial as the corresponding isomers, 1-(E,E)-3,5-
undecatriene and 1-(E,Z,Z)-3,5,8-undecatetraene have odor
thresholds 106
nd
104
times higher, respectively (31). 1-(E,Z)-
3,5-Undecatriene has a balsamic, spicy, pinewood odor while
i-(E,Z,Z)-3,5,8undecateti'aene has a similar though more fruity
odor (31). .Sesquiterpene hydrocarbons were identified for the
first time in S. apiana,
though they have been reported in other
Salvia
species (13,17,18). The most abundant sesquiterpenes
were 3-caiyophyllene(1.0%), 8-cadinene(0.3%), germacrene B
(0.2%); guaia-6,9-diene(0.2%), 13-bisabolene(0.2%),y-cadinene
(0:2%), a-copaène (0.1%), a-gurjunene (0.1%), a-humulene
(0.1%), y-muurolene (0.1%), bicyclogermacrene (0.1%), and
a-muurolene (0.1%).
References
1.
D.E.Averett and K.R.
Neisess,SaIvia.
In:
The Jepson Manual: Higher
Plants of
California. Edit., J.C. Hickman,
pp.
725-729, University of
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... 1,8-cineole (1), constituting 60.65 % of the oil, was the major component [46]. Takeoka et al. [47] Various studies have demonstrated that quantitative differences in essential oil content are common in Salvia species and depend on environmental conditions, harvesting time, and geographic and climatic factors [48,49]. In S. apiana, age-dependent variations were not reported, but some variability in the composition of the volatile fraction between day and night was described [50]. ...
... Division into chemotypes in accordance with Craft and co-workers[124]; a Fresh leaves and flowering tops; extraction with diethyl ether followed by high vacuum distillation with a solvent-assisted flavor evaporation apparatus; GC/FID and GC/MS[47]; b Branches and leaves; steam distillation; GC/FID and GC/MS[46]; c Dried aerial parts; hydrodistillation with a Clevenger-type apparatus; GC/FID and GC/MS[54]; d Entire plant; steam distillation; analyzed with GC/FID and GC/MS [123]; e Dried leaves; extraction in anhydrous ethyl ether; GC [51]; f Fresh leaves; hydrodistillation with a Clevenger-type apparatus; GC/FID and GC/MS [125]; g Dried distal parts of leafy shoots; hydrodistillation with a Clevenger-type apparatus; GC/FID and GC/MS [126]; h Dried leaves; hydrodistillation, using n-hexane as collecting solvent; GC/FID and GC/MS [127]; i Tops of plant; steam distillation with a Clevenger apparatus; GC [128]; k Dried herb; hydrodistillation with a Clevenger-type apparatus and xylene as collecting solvent; GC/FID [55]; m Dried aerial parts; hydrodistillation with a Clevenger-type apparatus; GC/MS [129]; n Fresh leaves and flowers; steam distillation; GC/MS [130];°Dried leaves; hydrodistillation; GC/MS [131]; p Leaves; hydrodistillation; GC/FID [132]; q Dried aerial parts; steam distillation; GC/MS [133]; r Aerial parts; hydrodistillation; GC/MS [134]; s Dried leaves; steam distillation with a Clevenger-type apparatus; GC/MS [135]; t Dried aerial parts; hydrodistillation; GC/MS [136]; u Dried aerial parts; hydrodistillation with a Clevenger-type apparatus; GC/MS [137]; w Fresh leaves; hydrodistillation with a modified simultaneous distillation extraction apparatus; GC/MS [138]; x Fresh leaves; hydrodistillation; GC/MS [139]; y Fresh leaves; solvent-free microwave extraction; GC/MS [140]; z Composition of Spanish, Morocco and Tunisia rosemary essential oil (European Pharmacopeia 2005) [141] Krol A et al. White Sage (Salvia … Planta Med | © 2021. Thieme. ...
Article
Salvia apiana, commonly known as white sage, is an aromatic evergreen subshrub of the chaparral, commonly found in coastal plains in California and Baja California. It has been traditionally used by the Chumash people as a ritual and medicinal plant and used as a calmative, a diuretic, and a remedy for the common cold. However, until recently, relatively little has been known about the composition and biological activity of white sage. Phytochemical studies on S. apiana revealed the presence of substantial amounts of essential oil, accompanied by a variety of triterpenes, C23 terpenoids, diterpenes, and flavonoids. Extracts of the plant have been shown to exhibit antioxidative, antimicrobial, and cytotoxic effects. The influence of white sage constituents on the nervous system, including GABA, opioid, and cannabinoid receptors, has also been documented. The review aimed to compile information on the taxonomy, botany, chemical composition, and biological activities of S. apiana. White sage was compared with other representatives of the genus in terms of chemical composition. The differences and similarities between S. apiana and other sage species were noted and discussed in the context of their therapeutic applications. Reports on ethnomedicinal uses of white sage were confronted with reports on chemistry, bioactivity, and bioavailability of S. apiana constituents. Finally, a critical assessment of the available data was made and perspectives for the use of white sage preparations in modern phytomedicine were discussed.
... Salvia apiana, commonly known as white sage, can be found scattered throughout southwestern North America, with the highest concentration in Southern California (Borek et al. 2006). Natives to the Southern California region have been known to use the leaves in traditional Chumash healing involves prayer, relaxation and natural plant-based remedies to cure a variety of ailments (Takeoka et al. 2010). In this practice, white sage is infused into water in order to relax the patient (Luis, Lahlou, Andrés, Sood, et al. 1996). ...
... The plant is used for diaphoretic and diuretic effects (Dentali & Hoffmann 1990). Previous to our research, several compounds including flavonoids, mono-, sesqui-, di-and tri terpenes, have been already identified and/or isolated from S. apiana (Pettit et al. 1966;González et al. 1992;Luis, Lahlou, Andrés, Sood, et al. 1996;Dentali & Hoffmann 1990;Borek et al. 2006;Abreu et al. 2008;Takeoka et al. 2010). However, this plant has not been studied for cannabinoid or opioid receptors activity. ...
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Full-text available
Salvia apiana (white sage, Lamiaceae family) plant is native to southern California and parts of Mexico. Some Native American tribes local to this region consider S. apiana to be sacred and burn the leaves as incense for purification ceremonies. The plant has been used to treat sore throats, coughs, chest colds, upper respiratory infections and poison oak rashes. The aqueous ethanolic extract of S. apiana showed moderate CB1 activity (58.3% displacement). Chromatographic purification of the ethanolic extract on silica gel column led to isolation of nine compounds: rosmadial (I), carnosol (II), 16-hydroxycarnosol (III), sageone (IV), cirsimaritin (V), salvigenin (VI), oleanolic acid (VII), 3β,28-dihydroxy-urs-12-ene (VIII), and ursolic acid (IX). The structures of the isolated compounds were determined by their 1D, 2D NMR and MS spectral data. All the fractions and isolated compounds were tested for cannabinoid and opioid receptor binding.
... Salvia apiana, commonly known as white sage, can be found scattered throughout southwestern North America, with the highest concentration in Southern California (Borek et al. 2006). Natives to the Southern California region have been known to use the leaves in traditional Chumash healing involves prayer, relaxation and natural plant-based remedies to cure a variety of ailments (Takeoka et al. 2010 practice, white sage is infused into water in order to relax the patient (Luis, Lahlou, Andrés, Sood, et al. 1996). The plant is used for diaphoretic and diuretic effects (Dentali & Hoffmann 1990). ...
... The plant is used for diaphoretic and diuretic effects (Dentali & Hoffmann 1990). Previous to our research, several compounds including flavonoids, mono-, sesqui-, di-and tri terpenes, have been already identified and/or isolated from S. apiana (Pettit et al. 1966;González et al. 1992;Luis, Lahlou, Andrés, Sood, et al. 1996;Dentali & Hoffmann 1990;Borek et al. 2006;Abreu et al. 2008;Takeoka et al. 2010). However, this plant has not been studied for cannabinoid or opioid receptors activity. ...
Article
Full-text available
Salvia apiana (white sage, Lamiaceae family) plant is native to California. Indian tribes consider S. apiana to be sacred and burn the leaves as incense for purification ceremonies [1]. The plant has been used to treat sore throats, coughs, chest colds, upper respiratory infections, systemic poison oak rashes and acute candidal vaginitis. Native Americans widely used this plant in traditional Chumash healing [2]. Infusion of the leaves is used as a diaphoretic or diuretic [3]. The aqueous ethanolic extract of S. apiana showed moderate CB1 activity (58.3% displacement). The extract was fractionated on silica gel column chromatography using hexanes-acetone gradient to yield 15 fractions. Repeated column chromatography led to isolation of ten compounds, which were identified to be four diterpenes: rosmadial (I), carnosol (II), 16-hydroxycarnosol (III) & sageone (IV), two flavonoids: cirsimaritin (V), & salvigenin (VI), three triterpenes: oleanolic acid, erythrodiol, ursolic acid and a fatty acid: montanic acid. All the fractions and isolated compounds were submitted for biological studies to check for cannabinoid and opioid receptor binding. Acknowledgements: The project was supported by Award Number P20GM104932 from the National Institute of General Medical Sciences and in part by NCNPR. References: [1] Ali A, et al. (2015) Journal of Agriculture and Food Chemistry, 63: 447 – 456. [2]. Takeoka GR, et al. (2010) Journal of Essential Oil Research. 22: 241 – 244. [3]. Luis JG, et al. (1996) Tetrahedron Letters, 37: 4213 – 4216,
... As noted in Timmermann et al. (2019), however, exploring a range of different doses could facilitate the process of establishing correlations between neural activity data and psychometric questionnaires. Also, the use of Salvia apiana by some of the participants as a medium for DMT recrystallization could have incorporated additional psychoactive effects related to molecules such as eucalyptol, camphor, and menthol (Takeoka et al., 2010). In particular, it is known that some of these molecules can present activity at serotonergic receptors which are also targeted by DMT (Jarvis et al., 2016). ...
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Background: N,N-dimethyltryptamine is a short-acting psychedelic tryptamine found naturally in many plants and animals. Few studies to date have addressed the neural and psychological effects of N,N-dimethyltryptamine alone, either administered intravenously or inhaled in freebase form, and none have been conducted in natural settings. Aims: Our primary aim was to study the acute effects of inhaled N,N-dimethyltryptamine in natural settings, focusing on questions tuned to the advantages of conducting field research, including the effects of contextual factors (i.e. "set" and "setting"), the possibility of studying a comparatively large number of subjects, and the relaxed mental state of participants consuming N,N-dimethyltryptamine in familiar and comfortable settings. Methods: We combined state-of-the-art wireless electroencephalography with psychometric questionnaires to study the neural and subjective effects of naturalistic N,N-dimethyltryptamine use in 35 healthy and experienced participants. Results: We observed that N,N-dimethyltryptamine significantly decreased the power of alpha (8-12 Hz) oscillations throughout all scalp locations, while simultaneously increasing power of delta (1-4 Hz) and gamma (30-40 Hz) oscillations. Gamma power increases correlated with subjective reports indicative of some features of mystical-type experiences. N,N-dimethyltryptamine also increased global synchrony and metastability in the gamma band while decreasing those measures in the alpha band. Conclusions: Our results are consistent with previous studies of psychedelic action in the human brain, while at the same time the results suggest potential electroencephalography markers of mystical-type experiences in natural settings, thus highlighting the importance of investigating these compounds in the contexts where they are naturally consumed.
... When the mass spectrum of the compound in peak j ( Figure 4) was compared with the published spectra of kunzeaol, they showed essentially identical mass fragmenting patterns [38][39][40]. In addition, comparison of the experimentally determined RI with those from the terpene database MassFinder4 and the literature were in good agreement (Table 1) [39][40][41][42]. Intriguingly, kunzeaol is known to be unstable and decomposes to cadineneand muurolene-type sesquiterpenoids under acidic conditions [39]. ...
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Thapsigargin is a major terpenoid constituent of Thapsia garganica root. Due to its potent antagonistic effect on the sarco-endoplasmic reticulum Ca2+-ATPase, thapsigargin has been widely used to study Ca2+-signaling and is also a potential drug for prostate cancer. Despite its importance, thapsigargin biosynthesis in T. garganica remains unknown. In order to decipher thapsigargin biosynthesis, deep transcript sequencing (454 and Illumina) of the T. garganica root was performed, and two terpene synthases (TgTPS1/2) were identified. Functional characterization of their encoded enzymes in a metabolically engineered yeast revealed that TgTPS1 synthesised d-cadinene while TgTPS2 produced ten distinct terpenoids. However, cultivation of the TgTPS2-expressing yeast in pH-maintained conditions (pH 6-7) yielded one major oxygenated sesquiterpenoid, suggesting that formation of multiple terpenoids was caused by acidity. The major terpene product from TgTPS2 was identified as 6β-hydroxygermacra-1(10),4-diene (kunzeaol) by mass-fragmentation pattern, retention index, the nature of its acid-induced degradation, and NMR. Also, recombinant TgTPS2 efficiently catalysed the synthesis of kunzeaol in vitro from farnesyl diphosphate with a Km of 2.6 µM and a kcat of 0.03 s-1. This is the first report of a kunzeaol synthase, and a mechanism for the transformation of kunzeaol into the thapsigargin backbone is proposed.
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Chemical composition of essential oils obtained from four species of genus Salvia were analyzed by gas chromatography (GC) and gas chromatography mass spectrometry (GC-MS). Main compounds identified from Salvia species essential oils were as follows: 1,8-cineole (71.7%), -pinene (5.1%), camphor (4.4%) and -pinene (3.8%) in S. apiana; borneol (17.4%), -eudesmol (10.4%), bornyl acetate (5%) and guaiol (4.8%) in S. elegans; bornyl acetate (11.4%), -caryophyllene (6.5%), caryophyllene oxide (13.5%) and spathulenol (7.0%) in S. leucantha; -thujene (25.8%), viridiflorol (20.4%), -thujene (5.7%) and camphor (6.4%) in S. officinalis. In biting deterrent bioassays, essential oil of S. leucantha and S. elegans at 10 µg/cm2 showed activity similar to DEET (97%, N, N-diethyl-meta-toluamide) in both the species of mosquitoes whereas activity of S. officinalis and S. apiana was lower than the other oils or DEET. Pure compounds β-eudesmol and guaiol showed biting deterrent activity similar to DEET at 25 nmol/cm2 whereas activity of 13-epi-manool, caryophyllene oxide, borneol, bornyl acetate and β-caryophyllene was significantly lower than β-eudesmol, guaiol or DEET. All essential oils showed larvicidal activity except S. apiana which was inactive at the highest dose of 125 ppm against both mosquito species. Based on 95% CIs, all the essential oils showed higher toxicity in Anopheles quadrimaculatus than Aedes aegypti. Essential oil of S. leucantha with LC50 value of 6.2 ppm showed highest toxicity in An. quadrimaculatus.
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Essential oils obtained from aerial parts of Artemisia persica and Artemisia turcomanica were analyzed by GC/MS. While 28 components representing 91.01 % of A. persica were identified, the identity of 50 components, constituting 81.93 % of the total oil, was confirmed in A. turcomanica. β-thujone was the main compound (75.23%) in A. persica while the major identified phytochemicals in A. turcomanica were 1,8-cineol (19.23%), camphor (15.55%) and filifolone (15.53%). Both of the essential oils were predominantly made up of monoterpenes. Time- and dose-dependent cytotoxic effects of A. persica and A. turcomanica on MCF-7 cell line evaluated by MTT assay at 24, 48 and 72 h, showed that the highest cytotoxic effect of A. persica and A. turcomanica were appeared at 72 h incubation. At that incubation period, CI50 of A. persica was found to be 0.15 μg/ml, while that of A. turcomanica was 0.1 μg/ml. Thus, cytotoxicity of A. turcomanica was slightly higher than A. persica which could be attributed to the higher content of sesquiterpene present in A. turcomanica. As a conclusion, these volatile oils could have chemotherapeutic potentials.
Article
The new natural diterpenes, 6,7-didehydroferruginol, 6,7-didehydrosempervirol, 16-hydroxy-6,7-didehydroferruginol, 11,12,16-trihydroxy-20(10 → 5)abeo-abieta-1(10),6,8,11,13-pentaene, the diterpene quinones, 16-hydroxyroyleanone and 6-deoxo-5,6-didehydrolanugon Q plus the known compounds ferruginol, miltiodiol, cryptotanshinone, lanugon Q and salvicanol were isolated from the roots of Salvia apiana. Their structures were established by spectrometry. The co-occurrence of so many abietane diterpenes with different degrees of oxidation and modified skeletons is in accordance with the biosynthetic route previously proposed for these compounds.
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The essential oil of white sage, Salvia apiana, was obtained by steam distillation and analysed by GC-MS. A total of 13 components were identified, accounting for >99.9% of the oil. The primary component was 1,8-cineole, accounting for 71.6% of the oil.
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The pentacyclic triterpene composition of a southern California variety of Salvia apiana (fam. Labiatae) has been assessed. The presence of α-amyrin, oleanolic acid and ursolic acid has been established. Separation of α-amyrin from a closely related impurity believed to be β-amyrin was accomplished by subjecting the mixture to selenium dioxide oxidation and isolating α-amyrin by preparative thin-layer chromatography on silver nitrate-silica gel. Evidence for the presence of isomeric mixtures of two dihydroxy triterpenes and two triterpene aldehydes representing intermediate stages of oxidation from α- and β-amyrin to ursolic and oleanolic acids was presented. Isolation of ursolic acid from a Mexican variety of Salvia karwinskii was also reported.
Article
The composition of the oils from leaves and flowers of three Salvia species (S. aethiopis L., S. hypoleuca Benth. and S. multicaulis Vahl.) has been analysed by a combination of GC and GC–MS. During the flowering period, two oils (S. aethiopis and S. hypoleuca) consisted mainly of sesquiterpenes, while in S. multicaulis oil monoterpenes predominated over sesquiterpenes. The major components of the oil of S. aethiopis were β-caryophyllene (24.6%), α-copaene (15.5%) and germacrene D (13.5%). In the oil of S. hypoleuca, β-caryophyllene (22.0%), δ-elemene (15.5%) and bicyclogermacrene (15.1%) were found to be the major constituents. α-Pinene (26.0%), 1,8-cineole+limonene (20.0%) and camphor (19.0%) were the predominant compounds in the oil of S. multicaulis. Copyright © 1999 John Wiley & Sons, Ltd.
Article
The essential oil of Salvia officinalis L. in five selected clones of different origins (France, Hungary, Portugal, Romania, Czech Republic) was studied. Yields of oils from dried leaves were excellent (2–3%), and higher than those previously reported. The α:β-thujone ratio varied according to origin. Overall, some of the oils were of high quality in terms of their α- and β-thujone and camphor contents. © 1998 John Wiley & Sons, Ltd.
Article
Two new C23 terpenoids 14-hydroxy-7-methoxy-11,16-diketo-apian-8-en-(22,6)-olide 2 and 7-methoxy-11,16-diketo-apian-8,14-dien-(22,6)-olide 3 were isolated from the aerial part of Salvia apiana. This two new C23 terpenoids have a new basic skeleton 1 for wich we propose the name of apianane. The structure of 2 was confirmed by X-ray analysis.
Article
A new C23 terpenoid, 13, 14-dioxo-11-hydroxy-7-methoxy-hassane-8, 11, 15-trien-(22,6)-olide 2 was isolated from the aerial part of Salvia apiana Jeps. This new C23 terpenoid has a new basic skeleton 1 for wich we propose the name of hassanane. The structure of 2 was established from its spectroscopic data. A possible common biosynthetic origin of 2 and the previously reported apiananes is also discussed.