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Chemical composition and antioxidant activity of Otostegia persica essential oil from Iran

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Zahra Tofighi at Tehran University of Medical Sciences
Zahra Tofighi
F. Alipour
F. Alipour
F. Alipour
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Narguess Yassa at Tehran University of Medical Sciences
Narguess Yassa
Abbas Hadjiakhoondi at Tehran University of Medical Sciences
Abbas Hadjiakhoondi
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Abstract and Figures

The essential oil of Otostegia persica flowers and leaves from Sistan and Baluchestan (OSB) and top flowering aerial parts from Kerman (OK) Provinces were prepared by hydrodistillation, with a yield of 0.08, 0.1, and 0.15 % v/w, respectively.The essential oils were analysed by GC and GC/MS. Seventeen compounds were recognized from the OK essential oil sample (92.06%) and it was rich in non-terpenes.The major compounds were α-copaene-8-ol (5.93%), hexadecanoic acid methyl ester (4.76%), hexadecanoic acid (31.73%) and pentacosane (29.51%). From the flower and leaf oils of OSB, 33 and 26 compounds were characterised, which represented 90.29% and 83.27% of the oils, respectively. α-Pinene (13.62%), linalool (6.76%), verbenol (9.22%), trans-carveol (4.00%), pentadecane (4.56%), caryophyllene oxide (4.84%) and hexadecane (5.52%) were the major compounds of the flower, while α-pinene (4.48%), verbenol (10.16%), trans-anethole (4.47%), geranyl acetone (6.47%), pentadecane (5.94%), hexadecane (5.86%) and hexahydrofarnesyl acetone (14.34%) were the dominant components of leaves.The antioxidant activities of the essential oils were measured using a free radical scavenging method with 2-2-diphenyl 1-picrylhydrazyl (DPPH).The IC50 of the OSB essential oil was more potent (9.76 ±1.1) than natural and synthetic antioxidants like vitamin E (12.02 ±1.8) and BHA (24.16 ±2.2).
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45
Introduction
OtostegiabelongstothefamilyLamiaceaeandcomprises
about 31 species in the world [1], among which four
speciesaregrowinginsouthIran[2,3].Otostegia persica
(Burm.)Boiss.isanendemicplantofIranandPakistan[3].
ItsoweringtimeisfromMaytoJune[4].Thepeoplein
thesouthofIranusetheoweringaerialpartsofO. persica
as a traditional medicine to treatdiabetic, inammatory
[personal communication] and rheumatic conditions
andoralinfections[5,6].Therearealsoreportsthatthe
polar extract of O. persica from Sistan and Bluchestan
Province has antimicrobial activity against some Gram-
positive strains with minimum inhibitory concentration
valuesfrom0.62 to20mg/ml [7].Inaddition, the effect
of O. persica on naloxone-induced morphine withdrawal
syndromewasstudiedinmalemice,wheretheoralandi.p.
administrationofthehydroalcoholicextractreducedthe
numberofjumping,rearing,diarrhoea,piloerection,tremor
andptosis,whilstthehexaneextractsignicantlyinhibited
diarrhoea[8].
SomeinvestigationshaveshownthatO. persicahasmany
bioactivecomponents,suchasavonoidsandtannins,but
noalkaloidsandsaponins[5].Previousstudiesfoundthat
O. persicapossessedantioxidantactivities comparable to
thoseofvitaminE,BHA,themethanolextractofgreentea
andGinkgobilobainbioassays,usingb-carotenebleaching
andferricammoniumthiocyanatemethods.Particularly,its
methanolextractexhibitedthehighestantioxidantactivity.
Five compounds were separated and puried from the
methanol extract bycolumn and paper chromatography.
Forexample,threeisolatedavonols(morin,kaempferol,
and quercetin) showed signicant antioxidant activity
comparable to BHA and vitamin E.The C-glucoavone
(isovitexin) also exhibited moderate antioxidant activity
InternationalJournalof
EssentialOilTherapeutics
www.ijeot.com
Chemical composition and antioxidant activity of
Otostegia persica essential oil from Iran
Z.Toghi,F.Alipour,N.Yassa*,A.Hadjiakhoondi,H.Hadavinia,S.Goodarzy,R.Golestani
Department of Pharmacognosy, Faculty of Pharmacy and Medicinal Plant Research Centre, Tehran University of Medical Sciences,
Tehran 14174-14411, Iran
Abstract
The essential oil of Otostegia persica owers and leaves from Sistan and Baluchestan (OSB) and top
oweringaerialpartsfromKerman(OK)Provinceswerepreparedbyhydrodistillation,withayieldof0.08,
0.1,and0.15%v/w,respectively.TheessentialoilswereanalysedbyGCandGC/MS.Seventeencompounds
wererecognizedfromtheOKessentialoilsample(92.06%)anditwasrichinnon-terpenes.Themajor
compounds were α-copaene-8-ol (5.93%), hexadecanoic acid methyl ester (4.76%), hexadecanoic acid
(31.73%)andpentacosane(29.51%).FromtheowerandleafoilsofOSB,33and26compoundswere
characterised,whichrepresented90.29%and83.27%oftheoils,respectively.α-Pinene(13.62%),linalool
(6.76%), verbenol (9.22%), trans-carveol (4.00%), pentadecane (4.56%), caryophyllene oxide (4.84%)
and hexadecane (5.52%) were the major compounds of the ower, while α-pinene (4.48%), verbenol
(10.16%),trans-anethole(4.47%),geranylacetone(6.47%),pentadecane(5.94%),hexadecane(5.86%)and
hexahydrofarnesylacetone(14.34%)werethedominantcomponentsofleaves.Theantioxidantactivitiesof
theessentialoilsweremeasuredusingafreeradicalscavengingmethodwith2-2-diphenyl1-picrylhydrazyl
(DPPH).The IC
50
of the OSB essential oil was more potent (9.76 ± 1.1) than natural and synthetic
antioxidantslikevitaminE(12.02±1.8)andBHA(24.16±2.2).
Key words:Otostegiapersica,Lamiaceae,antioxidantactivity,essentialoil,Sistan,BaluchestanandKerman
Provinces
EORC
e
rcrc
* Corresponding author.
E-mail address: yasa@sina.tums.ac.ir
©EssentialOilResourceConsultants.Allrightsreserved.
International Journal of Essential Oil Therapeutics (2009) 3, 45-48
46
butwasweakerthantheavonols.However,cinnamicacid
didnotshowactivityinthesemethods[6,9,10].
Thereissomeresearchconcerningtheotherspeciesof
Otostegia.ThemajorcomponentsofO. integrifuliaessential
oilincludeprenylbisabolaneand1-methyl-4-(5,9-dimethyl-
1-methylene-deca-4,8-dienyl) cyclohexene [11]. The
chloroform extract of the leaves yielded two labdane
type diterpenoids, 15,16-epoxy-3-α,9-α-dihydroxy-labda-
13(16),14-diene and 9(13),15(16)-diepoxy-3-α-hydroxy-
16-dihydrolabda-14-ene, plus a saturated hydrocarbon,
pentatriacontane,andstigmasterol[11].Thenewlabdane
diterpenes,otosteginA,otosteginBand15-epi-otostegin
B,wereisolatedfromtheaerialpartsofOtostegia fruticosa
[12].Threenewtricycliccis-clerodanetypediterpenoids:
limbatolideA,limbatolideBandlimbatolideChavebeen
isolated from the roots of Otostegia limbata along with
two known compounds; oleanolic acid and b-sitosterol
[12, 13]. In addition, two new tetracyclic diterpenoids
(limbatenolide D and limbatenolide E) have also been
isolatedfromOtostegia limbata[14].
Inthisstudy,theessentialoilandradicalscavengingactivity
of O. persica from Sistan and Baluchestan and Kerman
Provinces were investigated and compared with each
otherandwithotherresearch.
Materials and methods
Plant material
Otostegia persica(Burm.) Boiss.was collected during the
oweringstage,aroundtheTaftanmountainofSistanand
Baluchestan(OSB)andKerman(OK)Provinces,Iran.The
owersandleavesofOSBandthetopoweringaerialparts
of OK were dried and powdered separately.A voucher
specimenofeachplantwasdepositedinHerbariumofthe
FacultyofPharmacy,TehranUniversityofMedicalSciences,
(VoucherNo.TEH-6684andTHE-6685respectively).
Chemicals
VitaminE97%(Sigma-AldrichChemieGmbH,Steinheim,
Germany); 2,2-diphenyl 1-picrylhydrazyl (DPPH; Fluka,
Buchs, Switzerland); Butylhydroxytoluene (BHT; Merck,
Hohenbrunn, Germany); methanol were purchased form
Merck,Darmstadt,Germany.
Isolation of the essential oils
The air-dried owers and leaves of OSB and top
owering aerial parts of OK were separately subjected
tohydrodistillationforfourhoursusingaClevengertype
apparatus.The oils were collected separately, dried on
anhydrous sodium sulphate and kept in refrigerator for
GCandGC/MSanalysis.
Gas chromatography
GCanalyseswereperformedonaHewlettPackard6890
gas chromatograph equipped with a HP-5MS column
(5% phenylmethylpolysiloxane) (30 m × 0.25 mm, lm
thickness0.25 µm).Thethermal programwas40-250°C
atarateof3°C/min;splitratio:20;Injectoranddetector
(FID)temperatureswere200and250°C,respectively.The
owrateofheliumascarriergas(with99.99%purity)was
1 ml/min.The percentage compositions were computed
from the GC peak areas without any correction factor
andwerecalculatedrelatively.
GC/MS analysis
TheoilswereanalysedbyGC/MSusingaHewlettPackard
5973massselectivedetectorconnectedtoaHP6890gas
chromatograph.Theseparationwasachievedatthesame
gaschromatographicconditions.MSweretakenat70eV.
Retentionindiceswerecalculatedbasedontheretention
timesofn-alkanesthatwereinjectedaftertheoilatthe
samechromatographicconditions.Thecompounds were
identiedbycomparisonofrelativeretentionindiceswith
those reported in the literature and by comparison of
theirmassspectrawiththeWileylibraryorwithpublished
data[15,16].
Antioxidant activity
The DPPH method as modied in our laboratory was
used(17).Onemlofdifferentsamplesoftheessentialoil
(20,10,5,2.5µl/ml)wereaddedto2mlofDPPHsolution
(4×10
-5
g/mlMeOH).Thecontrolconsistedofsamplethat
was added to methanol up to 3ml;the blank consisted
of 1 ml methanol with no sample that was added to 2
ml of DPPH solution.A Shimadzu, UV/VIS model 160A
spectrophotometerwas used for UV spectrum and the
absorbanceat517nmwasmeasuredatdifferenttimes(0,
5,10,15,20,25and30min).Thepercentageofinhibition
activitywascalculatedasfollows:
Inhibition%=
100-(sampleabsorption-controlabsorption)x100
blankabsorption
Alltestsandanalyseswerecarriedoutintriplicate.
Statistical analyses
Analyses of at least four samples were carried out in
triplicate.Student’s t-testwasused to comparethedata
and all tests were considered statistically signicant at
p <0.05. Results were processed by the Excel XP 2003
(MicrosoftCorporation)computerprogramTheIC
50
was
calculatedwithCurveExpert1.3.
Results and discussion
Otostegia persica is an endemic plant that grows in the
southofIranand Pakistan and is used in the traditional
treatmentofsomediseases.TheessentialoilofO. persica
owers and leavesfromSistan and Baluchestan and top
oweredaerialpartsofKermanProvinceswereprepared
by hydrodistillation. Their chemical compositions were
determinedbyGCandGC/MS(Table1).
The essential oils of OSB have an intense odour and
pale yellow colour, but the OK essential oil appeared
waxywitha pleasant smell.TheOK essential oilsample
containedmonoterpenes(5.73%),sesquiterpenes(15.4%)
and it was rich of non-terpenes (70.93%). The major
compounds were α-copaene-8-ol (5.93%), hexadecanoic
acid methylester (4.76%), hexadecanoic acid (31.73%)
and pentacosane (29.51%). The essential oil of OSB
owersincludedmonoterpenes(52.82%),sesquiterpenes
(18.23%)andnon-terpenes(10.20%).α-Pinene(13.62%),
linalool (6.76%), verbenol (9.2%), trans-carveol (4.00%),
pentadecane (4.56%), caryophyllene oxide (4.84%) and
hexadecane (5.52%) were the dominant compounds of
the essential oil of the ower.The essential oil of OSB
leavesconsistedofmonoterpenes(44.6%),sesquiterpenes
International Journal of Essential Oil Therapeutics (2009) 3, 45-48
47
(19.24%) and non-terpenes (15.23%). α-Pinene (4.48%),
verbenol(10.16%),trans-anethole(4.47%),geranylacetone
(6.47%), pentadecane (5.94%), hexadecane (5.86%) and
hexahydrofarnesylacetone(14.34%)werethe important
componentsofleaves.
Table 1. Composition of the essential oils of Otostegia
persica.
RI compounds Fl. % Le. % Ke. %
944
α-pinene
13.62 4.48 2.36
976 verbenene 1.2 0.94 -
985 1-octen-3-ol 3.85 3.02 -
991 6-methyl-5-heptene-2-one 0.9 2.22 -
1031 p-cymene 0.57 - -
1035 limonene - - 0.25
1114 linalool 6.76 2.79 -
1123 (E)6-methyl3,5-heptadiene-
2-one
- 1.01 -
1132
α-campholenealdehyde
1.67 1.06 -
1143 trans-pinocarveol 2.76 2.58 -
1146 cis-verbenol - - 2.41
1152 trans-verbenol 9.22 10.16 -
1180 p-mentha-1,5-diene-8-ol - 1.8 0.71
1201 myrtenal 1.04 0.85 -
1203 myrtenol 0.79 0.85 -
1208 decanal - 1.06 -
1211 verbenone - 3.51 -
1222 trans-carveol 4 - -
1243 neral 0.64 1.37 -
1255 geraniol 2.46 1.64 -
1268 2-decenal 1.1 2 -
1274 geranial 1.39 - -
1290 trans-anethole 0.66 4.47 -
1302 tridecane 1.13 1.19 -
1304 carvacrol 1.24 1.63 -
1342
δ-elemene
2.04 - -
1388
trans-b-damascenone
- 2.14 3.73
1440 3,7-guaiadiene 2.24 - -
1446
cis-b-farnesene
0.52 - -
1459 geranylacetone 3.67 6.47 -
1488
α-amorphene
1.71 - -
1503 pentadecane 4.56 5.94 -
1506 cuparene - - 0.4
1517 endo-1-bourbonanol - - 1.17
1526
δ-cadinene
1.52 - -
1565 trans-nerolidol 0.87 - -
1580 spathulenol 0.85 - -
1587 caryophylleneoxide 4.84 2.76 3.77
1604 hexadecane 5.52 5.86 -
1610
α-copaene-8-ol
- - 5.93
1702 heptadecane 3.31 - -
1757 trans-trans-farnesal 1.35 - -
1795 hexahydrofarnesylacetone - 14.34 -
1804 octadecane - - 2.04
1902 n-nonadecane - - 1.83
1922 farnesylacetoneC 2.29 - -
1930 hexadecanoicacidmethyl
ester
- - 4.76
1975 hexadecanoicacid - - 31.73
2005 n-eicosane - - 1.06
2502 pentacosane - - 29.51
monoterpenehydrocarbon 15.39 5.42 2.61
monoterpeneoxygenated 37.43 39.18 3.12
sesquiterpenehydrocarbon 8.03 0 6.33
sesquiterpeneoxygenated 10.2 19.24 9.07
non-terpene 19.24 19.43 70.93
unknown 9.71 16.73 7.94
total identied 90.29 83.27 92.06
RRI: Relative Retention Indices as determined on a HP-5MS
columnusinghomologousn-alkanes.
Fl:owerOSBoil.Le:leafOSBoil;Ke:Kermanoil.
Comparisonoftheessentialoilcomponentsshowedthat
theOKsamplehadloweramountsofmonoterpenesthan
theOSBowersandleaves,anditconsistedofmorethan
70% non-terpenoids. The composition of mono, sesqui
and nonterpenes of the ower and leaf essential oils of
OSBwereclosertogether,butα-pineneandlinaloolinthe
oweressentialoilandhexahydrofarnesylacetoneinthe
leafessentialoilwerepredominant.
The antioxidant activities of the essential oils were
measured using a free radical scavenging method with
2-2-diphenyl1-picrylhydrazyl(DPPH).AnIC
50
oftheOSB
ower and leaf essential oil mixture was more potent
(9.76 ± 1.1) than natural and synthetic antioxidants like
vitaminE(12.02±1.8)andBHA(24.16±2.2)(Figure1).
TherewasnotsufcientOKessentialoilforinvestigation
ofantioxidantactivity.
Figure 1. Comparison of IC
50
of (OSB) essential oil
and positive controls at 30 min.
In conclusion, this research in combination with our
previous study showed that the top owering parts of
O. persicacouldbebenecialforthe treatmentofsome
disease, but more studies are necessary to conrm this
hypothesis.
International Journal of Essential Oil Therapeutics (2009) 3, 45-48
48
Acknowledgements
ThisresearchwassupportedbyagrantfromtheTehran
University of Medical Sciences and Health Services.The
authorswishtothankDr.SereshtiH.(DeptofChemistry,
FacultyofSciences,UniversityofTehran)forpreparingthe
GCandGC/MSspectrums.
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International Journal of Essential Oil Therapeutics (2009) 3, 45-48
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Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectroscopy
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Adams, R. P. 2007. Identification of essential oil components by gas chromatography/ mass spectrometry, 4th Edition. Allured Publ., Carol Stream, IL Is out of print, but you can obtain a free pdf of it at www.juniperus.org
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The antioxidant activity of different extracts of aerial parts of Otostegia persica (Burm.) Boiss., Labiateae were evaluated using b-carotene bleaching and lipid peroxi-dation models. The inhibitory activity of these extracts on the peroxidation of linoleic acid was measured by ammonium thiocyanate in comparison to green tea [Camellia Sinensis (L.) Kuntze] Ginkgo biloba L., and butylated hydroxyanisole (BHA). A methanol extract of the plant exhibited the highest antioxidant activity. Five compounds were separated and purified from the methanol extract by column and paper chromatography, respectively. Three isolated flavonols showed significant antioxidant activity comparable to BHA and vitamin E in both methods. These active compounds were iden-tified by UV, IR, 1 H and 13 C NMR, and MS spectrosco-pies as morin, kaempferol, and quercetin. The only identified C-glucoflavone (isovitexin) also exhibited inter-esting antioxidant activity, but weaker than the flavo-nols. trans-Cinnamic acid showed no activity in these methods.
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Antioxidant Activity of Otostegia persica (Labiatae) and its constituents
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The antioxidant activity of the different extracts and fractions of aerial parts of Otostegia persica (Burm.) Boiss. were evaluated using beta-carotene bleaching and lipid peroxidation methods. The inhibitory activity of the plant extracts on the peroxidation of linoleic acid were measured by ferric thiocyanate method in comparison to methanolic extracts of Green tee, Ginkgo biloba, Vit.E and BHA as positive controls. Methanolic extract of the plant exhibited strong antioxidant activity .Two compounds of methanolic extract which were separated by column and paper chromatography showed significant antioxidant activity comparable to butylated hydroxy anisole (BHA) and alpha tocopherol. These active compounds were identified as morin and quercetin by using UV, IR, MS, ¹H and ¹³C NMR.
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Analysis of Essential Oil by Gas Chromatography and Mass Spectrometry
Book
  • Jan 1976
The book is in two parts: first part Essential Oil includes compositae; labiatae; verbenaceae; oleaceae; umbelliferae; myrtaceae; euphorbiaceae; rutaceae; geraniaceae; rosaceae; lauraceae; myristicaceae; anonaceae; santalaceae; moraceae; piperaceae; zingiberaceae; araceae; gramineae; and cupressaceae written in English and Japanese. Part two includes essential oil; gas chromatography, and mass spectrometry written in Japanese. (DP)
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Antimicrobial activity of Otostegia persica Bioss
Article
  • Jan 2006
Plants produce a diverse array of secondary metabolites, many of which have antimicrobial activity. Otostegia persica Bioss. (Labiatae) grows in south east of Iran. No previous investigation on antimicrobial effects of this plant has been reported. Thus, the aim of this work was to examine the antimicrobial effect of O. persica extracts with different polarity on several microorganisms. Aerial parts of O. persica were collected from Sistan-Baluchestan province (Iran). Powdered aerial parts of the plant were extracted with ethanol. The extract was concentrated under reduced pressure. The dried extract was extracted with hexane, followed by chloroform and methanol, respectively. Antimicrobial activities of three extracts were tested on several microorganisms using well plate method, MIC (Minimum Inhibitory Concentration) and MBC (Minimum Bactericidal Concentration) methods. O. persica extracts showed antimicrobial activity against Gram positive strains including Listeria monocytogens, Enterococcus fecalis, Staphylococcus aureus, and Staphylococcus epidermidis with MIC values from 0.62 to 20 mg/ml. The MBC values were identical, two, four or eight times higher than MIC values for the corresponding MIC for extracts. The Gram negative strains; Escherichia coli, Pseudomonas aeruginosa, Salmonella spp., Klebsiella spp., and Proteus spp. were not inhibited by O. persica polar, semi-polar, and non-polar extracts. It can be concluded that the tested extracts of O. persica exhibit significant antibacterial activity. This investigation supports the idea of using O. persica extracts as a candidate for further antimicrobial and phytochemical researches.
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Labdane diterpenes from Otostegia fruticosa
Article
  • Sep 2000
  • PHYTOCHEMISTRY
The new labdane diterpenes otostegin A (2), otostegin B (6) and 15-egi-otostegin B (7) were isolated from the aerial parts of Otostegin fruticosa, besides the previously known labdanes preleoheterin (1), leoheterin (3), leopersin C and 15-epi-leopersin C (4, 5). ballonigrin (9) and vulgarol (11), along with the iridoid glucoside 8-O-acetylharpagide (10). The structure elucidation of all the isolated compounds was based on their spectral data and chemical derivatization. (C) 2000 Published by Elsevier Science Ltd.
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Free radical scavenging capacity and inhibition of lipid oxidation of wines, grape juices and related polyphenolic constituents
Article
  • Jul 1999
  • FOOD RES INT
The antioxidant activity of grape juices, wines made from the same lot as juices and their major polyphenolic constituents was measured by the inhibition of lipid oxidation (ferric-thiocyanate) and free radical scavenging (2,2-diphenyl-1-picrylhydrazyl) methods. dl-α-Tocopherol and 3-tertiary-butyl-4-hydroxyanisole (BHA) were used as references. The inhibition of lipid oxidation of the standards followed the order: rutin = ferulic acid > tannic acid = gallic acid = resveratrol > BHA = quercetin > dl-α-tocopherol > caffeic acid. Meanwhile, the free radical scavenging activity of gallic acid was the highest, tannic acid, caffeic acid, quercetin, BHA and rutin activities were intermediate and that for ferulic acid, dl-α-tocopherol and resveratrol were the lowest. Wines had higher activity than the corresponding grape juices and red wine showed the strongest activity among the grape products tested. The antioxidant activity of the samples seems to be based on their free radical scavenging capacity.
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Effects of Otostegia persica (Burm.) Boiss on morphine withdrawal syndrome in mice
Article
  • Jan 2004
Effect of Otostegia persica on naloxone-induced morphine withdrawal syndrome was studied in male mice. Dependence was induced using daily subcutaneous injections of morphine for three days. Morphine was injected to mice at doses of 30 and 45mg/kg on day 1 and 60 and 90mg/kg on day 2 (8:00 am and 6:00 pm). On day 3, morphine (90mg/kg) was injected 1h before oral administration and 1.5h before intraperitoneal (i.p.) injection of hydroalcoholic and hexane extracts of the plant. Naloxone was injected (5mg/kg, i.p.) 2h afterthe final dose of morphine and the withdrawal signs including jumping, rearing, diarrhoea, piloerection, tremor and ptosis were recorded during a period of 30 minutes. While oral and i.p. administration of hydroalcoholic extract reduced the number of jumping and rearing, the hexane extract could not exert any significant change. Also the hydroalcoholic extract (1500mg/kg) significantly (p<0.05) reduced diarrhoea, piloerection, tremor and ptosis. The hexane extract only significantly (p<0.05 ) inhibited diarrhoea. Results of this study indicated that the extract of Otostegia persica contained component(s) that alleviate morphinewithdrawal syndrome and the responsible constituent(s) is(are) found in polar fraction since the hexane extract had only a negligible effect.
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Terpenes from Otostegia integrifolia
Article
  • Aug 2004
  • PHYTOCHEMISTRY
The essential oil and chloroform extract of air-dried leaves of Otostegia integrifolia Benth. were investigated for the first time using analytical and preparative gas chromatography (GC), GC-mass spectrometry (MS) and NMR techniques. A total of 40 constituents including monoterpenes, sesquiterpenes, diterpenes and their derivatives were identified. A prenylbisabolane type diterpene, 1-methyl-4-(5,9-dimethyl-1-methylene-deca-4,8-dienyl)cyclohexene was identified as a major component. The chloroform extract of the leaves yielded two labdane type diterpenoids, 15,16-epoxy-3alpha,9alpha-dihydroxy-labda-13(16),14-diene and 9(13),15(16)-diepoxy-3alpha-hydroxy-16-dihydrolabda-14-ene, a saturated hydrocarbon, pentatriacontane, and stigmasterol. The structures of the isolated compounds were established by spectroscopic methods.
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