Volatile Constituents of the Aerial Parts of Salvia apiana Jepson

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%).

Full text

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

M.D. Guillén and M.J. Manzanos,
Extractable components of the
aerial parts of
Salvia lavandulifolia
and composition of the liquid
smoke flavoring obtained from them.
J. Agiic. Food Chem., 47,
3016-3027(1999).
N.B. Perry, R.E.Anderson, N.J. Brennan, M.H. Douglas,A.J. Heaney,
J.A. McGimpsey and B.M. Smailfield,
Essential oils from Dalmatian
sage
(Salvia officinalis L.):
variations among individuals, plant parts,
seasons, and sites.
J. Agric. Food Chem., 47, 2048-2054 (1999).
D. Pitarokili, 0. Tzakou, A. Loukis and C. Harvala,
Volatile metabolites
from
Salvia fruticosa
as antifungal agents in soilborne pathogens.
J.
Agric. Food Chem.,
51,
3294-3301 (2003).
V.
Radulescu, S. Chiliment and E. Oprea,
Capillary gas
chromatography-mass spectrometry of volatile and semi-volatile
compounds of
Salvia officinalis. J. Chromatogr. A, 1027, 121-126
(2004).
A. Rustaiyan, S. Masoudi, A. Monfared and H. Komeilizadeh,
Volatile
constituents of three
Salvia
species grown wild in Iran.
Fla
y
. Fragr.
J.,
14,
276-278 (1999).
S.-E. Sajjadi and A. Ghannadi,
Essential oilof the Persian sage,
Salvia
rhytidea
Benth.
Acta Pharm.,
55,
321-326 (2005).
K. Neisess, Diss. Abs., 44, 3629 (1983).
W
.
A. Emboden, Jr. and H. Lewis, Terpenes as taxonomic characters
in Salvia
section
Audibertia. Bnttonia
19,
152-160 (1967).
T.T. Borek, J.M. Hochrien and A.N. Irwin,
Composition of the
essential oil
of
white sage, Salvia apiana. Fla
y
. Fragr. J., 21,571-572
(2006).
W.
Engel, W. Bahr and P. Schieberle,
Solvent assisted flavour
evaporation-a new and versatile technique for the careful and direct
isolation of aroma compounds from complex food matrices.
Eur.
Food Res. Technol.,
209,
237-241 (1999).
E. Kováts,
Gas-ChromatographischeCharakterisierung Organischer
Verbindungen Ted 1: Retentionsindices Aliphatischer Halogenide,
Alkohole, Aldehyde und Ketone.
Helv. Chim. Acta, 41, 191 5-1 932
(1958).
R.P. Adams,
Identification of Essential Oil Components by Gas
Chromatography/Mass Spectrometry,
4th Edn. Allured Pubi. Corp.,
Carol Stream, IL (2007).
U.R. Juergens, M. Stober, L. Schmidt-Schilling, T. Kleuver and H.
Vetter,Antiinflammatoryeffects of eucalyptol (1,8-cineole) in bronchial
asthma: inhibition of arachidonic acid metabolism in human blood
monocytes ex vivo. Eur. J. Med. Res., 3, 407-412 (1998).
L.A. Laude, A.H. Morice and T.J. Grattan,
The antitussive effects
of menthol, camphor, and cineole in conscious guinea pigs.
PuIm.
Pharmacol., 7, 1 7-1 84(1 994).
F.A. Santos, R.M. Silva, A.R. Tome, VS. Rao, M.M. Pompeu, M.J.
Teixeira, L.A. De Freitas and V.L. De Souza"
1,8-Cineole protects
against liver failure in an in-vivo murine model of endotoxemic shock.
J. Pharm. Pharmacol., 53,505-511(2001).
F.A. Santos and V.S.N. Rao, 1,8-Cineole, a food flavoring agent,
prevents ethanol-induced gastric injury in rats.
Dig. Dis. Sci.,
46,
331-337 (2001) -

- -
:J.ft Juergens, T. Engelen, K. Racké, M. Stöber, A. Gillissen and
H. Vetter, Inhibitory activity of 1,8-cineol (eucalyptol) on cytokine
production in cultured human lymphocytes and monotcytes.
PuIm.
Pharmacol. Ther., 17, 281-287 (2004).
A. SivropoulOs, C. Nikolaou, E. Papanikolaou, S. Kokkini, T. Lanaras
and M. Arsenakis,
Antimicrobial, cytotoxic, and antiviral activities of
Salvia fructicosa
essential oil.
J. Agric. Food Chem., 46,3197-3201
(1997).
R.G. Berger, F. Drawert, H. Kollmannsberger, S. Nitz and B.
Schraufstetter, Novel volatiles in pineapple fruit and their sensory
properties.
J. Agric. Food Chem.,
33,
232-235 (1985).
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
California Press, Berkeley, CA (1993.
2.
M:
:
Moore
,
. Medicinal Plants of the Pacific West.
pp.
266-269, Red
Crane Books, Santa
Fe, NM (1993).
3

S Foster and
C.
6
Hobbs In A Field Guide to Western Medicinal
Plants and Hrbs.
p.442, HOiighton-Mifflin Conpany, New York,
NY
(2002).-

.

.

.:'.
4.
'
'J.D. Adams and C. Garcia,
The advantages of traditional Chumash
healing;
Evid. Based Complement. Alternat. Med., 2, 19-23
(2005).,,.
5.

A.G. G6nzálei, Z.E.Aguiar, TA.
,
'Grillo and J.G. Luis,
Diterpenes
and diteéhequinohes from the mots of
Saiviä apiana. (1992).
;

hyt9chmtf,.31, 1691-1695 (1992).
6.
,
G:R. Pettit, H. Klinger, and N.-O.N. Jorgensen,
Steroids and related
natural products-XXVII.
Salviaapiana. Phytochernistry, 5, 30l-3O9
- (1966).-
7

S J Dentali and J J Hoffmann
16 Hydroxycamosicacid a diterpene
il.fi6m Salvia apiana Phytochemistry
29
993-994 (1990)
8.,; J.G;Luis,E.H.Lätuiou and
LS.Andrés,Hassananes: C23 terpenoids
with a new type of skeleton from
Salvia apiana
Jeps
Tetrahedron
62,'l

231 (1996):
9.
* JG. Luis'E.H. LhlOtj, L.S. Andrés, G. N.
1
Sod and M.M. Ripoll,
Apiananes C23 terpenoids with a new type of skeleton from
Salvia
,,apiana Tetrahedron Left 37 4213-4216(1996)
10.
C.H.MuIler, W.H. Muller and B.L. Haines,
Volatile growth inhibitors
produced by
aromatic shrubs
Science
143
471-473 (1964)
11 A Bayrak and A Akul
Composition of essential oils from Turkish
.Salvia
species.
;Pliytochemistry, 26.846-847 (1987).'
12. . J:-C:Chalchat A. Michet and B. Pasquier,
StUdyof.c/onesofSalvia
officinal L yields and chemical composition of essential oil
Flay
T1
I
1Frar.J.,i3, 68-70(1998).
244/Journal of EsentiaI OiI
'
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