Zingiber officinale
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Zingiber officinale
CONTENTS1. Brief literature review on Zingiber officinale. (Pg.1-4)
a. Classificationb. Vernacular namesc. Part usedd. Botanical descriptione. Geographical distributionf. Traditional useg. Anatomy of the Rhizomeh. Pharmacology and Clinical studiesi. Toxicity and Adverse reactionsj. Phytochemistryk. Active Principles
2. Analytical specifications of Crude Drug (Pg.5-9)a. Macroscopic characterizationb. Identification of Crude drug by TLCc. TLC profile of Ginger oild. GC profile of Ginger oil
3. Analytical specifications for Zingiber officinale extract. (Pg.10-14)a. Identification testsb. TLC profilec. Estimation of Gingerol in Zingiber officinale extract by HPLC
4. Analytical specifications for 6-Gingerol (Pg. 15-20)a. UV Spectrumb. TLC and HPTLCc. FTIR and NMR Spectrumd. HPLC Chromatogram
5. Analytical specifications for 8-Gingerol (Pg. 21-24)a. TLC and HPTLCb. FTIR and NMR Spectrumc. HPLC Chromatogram
6. Analytical specifications for 6-Shogaol (Pg. 25-28)a. TLC and HPTLCb. FTIR and NMR Spectrumc. HPLC Chromatogram
7. References (Pg. 29-31)
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Zingiber officinale
=LQJLEHU�RIILFLQDOH�Roscoe(a) Classification:
Kingdom : PlantaeDivision : AngiospermaClass : MonocotyledoneaeOrder : ScitaminaeaFamily : ZingiberaceaeGenus : ZingiberSpecies : officinale
(b) Vernacular names:Sanskrit : Adrakam, ArdrakaHindi : Adrak,Sunthi,SonthKannada : SunthiMarathi : NisamGujarati : SuntEnglish : Ginger
(c) Part used : Rhizome
(d) Botanical description: A herbaceous rhizomatous perennial, reaching up to 90 cm in heightunder cultivation. Rhizomes are aromatic, thick lobed, pale yellowish, bearing simple alternatedistichous narrow oblong lanceolate leaves. The herb develops several lateral shoots in clumps,which begin to dry when the plant matures. Leaves are long and 2-3 cm broad with sheathing bases,the blade gradually tapering to a point. Inflorescence solitary, lateral radical pedunculate oblong-cylindrical spikes. Flowers are rare, rather small, calyx superior, gamosepalous, three toothed, opensplitting on one side, corolla of three subequal oblong to lanceolate connate greenish segments1.
(e) Geographical distribution: The plant is widely cultivated all over India, Bangladesh, Taiwan,Jamaica and Nigeria. This perennial grows in warm climates1.
(f) Traditional use: Ginger is carminative, pungent, stimulant, used widely for indigestion,stomachache, malaria and fevers. It is chiefly used to cure diseases due to morbidity of Kapha andVata. Ginger with lime juice and rock salt increases appetite and stimulates the secretion of gastricjuices. It is said to be used for abdominal pain, anorexia, arthritis, atonic dyspepsia, bleeding,cancer, chest congestion, chicken pox, cholera, chronic bronchitis, cold extremities, colic, colitis,common cold, cough, cystic fibrosis, diarrhoea, difficulty in breathing, dropsy, fever, flatulent,indigestion, disorders of gallbladder, hyperacidity, hypercholesterolemia, hyperglycemia,indigestion, morning sickness, nausea, rheumatism, sore throat, throat ache, stomach ache andvomiting. Ginger forms an important constituent of many pharmacopoeial Ayurvedicformulations1,4.
(g) Anatomy of the Rhizome: Scraped rhizome with buff external surface showing longitudinalstriations and occasional loose fibers, outer surface dark brown and more or less covered with corkwhich shows conspicuous, narrow, longitudinal and transverse ridges; the cork readily exfoliatesfrom lateral surfaces but persists between branches. Smoothed transversely cut surface exhibiting anarrow cortex separated by an endodermis from a much wider stele, numerous widely scatteredfibrovascular bundles, abundant scattered oleoresin cells with yellow contents. Starch abundant inthe thin-walled ground tissue, as flattened, ovate to subrectangular, transversely straited, simplegranules, each with the hilum in a projection towards one end. Pigments cells with dark reddish
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Zingiber officinale
brown contents occurring either singly in the ground tissue or in axial rows accompanying thevascular bundles. Vessels with spiral or reticulate thickening in the scattered vascular bundles arefound. Irregularly shaped thin-walled fibers with delicate, transverse septa, yielding only slightlythe reaction characteristic of lignin. Sclereids and calcium oxalate crystals absent1-2.
Fig. 1 Fig. 2
Fig. 3Fig.1 : Transversely cut surface of the rhizome, vascular bundles represented by circles, secretion cells by dots(x3).
Fig.2 : Transverse section in the region of the endodermis (x100)Fig.3 : Transverse section of the central part (x100) ct- cortex, end-endodermis, fr.b.vascular bundles, pg-pigment cell,
S-stele, scl.f-sclerenchymatous fibres, secr.- secretion cell.
(h) Pharmacology and Clinical Studies
Anti-emetic Activity: Early animal studies had demonstrated the anti-emetic property of freshginger1, but it was the clinical work of Mowrey and Clayson which generated a wider interest in thisuse of ginger2. They compared the effects of 1.88g of dried powdered ginger, 100mgdimenhydrinate (Dramamine) and placebo on the symptoms of motion sickness in 36 healthysubjects who reported very high susceptibility to motion sickness. Motion sickness was induced byplacing the blind folded subject in a tilted rotating chair. Ginger was found to be superior todimenhydrinate and placebo in preventing the gastrointestinal symptoms of motion sickness and theauthors postulated a local effort in the gastrointestinal tract for ginger. This was particularly likelysince it was given as a powder only 25 minutes before the test. The gingerols and shogaols weresubsequently identified as the main anti-emetic compounds in ginger3.
Improvement of digestive function: Early Chinese and Japanese research found that oral andintragastric application of fresh ginger decoction produced a stimulant action on gastric secretion1.
German scientists found that chewing 9g of crystallised ginger had a profound effect on salivaproduction4. Amylase activity was also increased and the saliva was not more watery, although itcontained slightly less mucroprotein. Intraduodenal doses of ginger extract increased bile secretionin rats5. Total secretion of bile solids was also increased, but not to the same extent as bile flow. 6-
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Zingiber officinale
gingerol and 10-gingerol were identified as the active components5. Fresh ginger also contains aproteolytic enzyme6.
Ginger, in conjunction with other pungent Ayurvedic herbs, increased the bioavailability of anumber of drugs by promoting their absorption and/or protecting them from being metabolized intheir first passage through the liver1.
Oral doses of 6-shogaol accelerated intestinal transit in rats7. Also an extract of ginger, and isolated6-shogaol and gingerols, enhanced gastrointestinal motility in mice after oral doses8.
Anti-ulcer Activity: Ginger and 6-gingerol inhibited experimental gastric ulcers in rats9-10. Freshginger decocted in water resulted in symptomatic improvement in 10 patients with peptic ulcers1.
Antiplatelet Activity: Srivastava and co-workers found that aqueous extract of ginger inhibitedplatelet aggregation induced by ADP, epinephrine, collagen and arachidonic acid in vitro11. Gingeracted by inhibiting thromboxane synthesis12-13. It also inhibited prostacyclin synthesis in rat aorta11.The antiplatelet action of 6-gingerol was also mainly due to the inhibition of thromboxaneformation14.
Anti-inflammatory Activity: Ginger extract inhibited carrageenan-induced paw swelling and wasas active as aspirin15. Essential oil of ginger inhibited chronic adjuvant arthritis in rats16.
Ginger and its pungent components are dual inhibitors of arachiodonic acid metabolism. That is,they inhibit both cyclooxygenase (prostaglandin synthetase) and lipoxygenase enzymes of theprostaglandin and leukotriene biosynthetic pathways15,17-22.
Antipyretic Activity: Ginger extract given orally reduced fever in rats by 38%, while the samedose of aspirin was effective by 44%15. The antipyretic activity of 6-shogaol and 6-gingerol has alsobeen observed7.
Cardiovascular Effects: Ginger exerted a powerful positive inotropic effect on isolated guinea pigsleft atria23. Gingerols were identified as the active components23-24.
Antioxidant Activity: Extracts of ginger have pronounced antioxidant activity comparable to thatof synthetic antioxidant preservatives25.
Other Effects: Ginger extract exhibited a prolonged hypoglycaemic activity in rabbits15.Antihepatotoxic activities of gingerols and shogaols were observed using carbon tetrachloride andgalactosamine induced cytotoxicity in cultured rat hepatocytes26. Injection of 6-shogaol showed anintense antitussive action in comparison with dihydrocodeine phosphate7.
Pharmacokinetics: After injection, 90% of 6-gingerol was bound to serum protein and eliminationwas mainly via the liver27. Oral or intraperitoneal dosage of zingerone resulted in the urinaryexcretion of metabolites within 24 hours, mainly as glucuronide and/or sulphate conjugates28.Appreciable biliary excretion (40% in 12 hours) also occurred28.
(i) Toxicity and Adverse Reactions: The mutagenic activity of ginger extracts has been observedin several strains22,29. As a result of component fractionation of ginger juice, it was found that 6-gingerol was a potent mutagen30. When mutagenicity of gingerol or shogaol was tested in thepresence of zingerone, it was observed that zingerone suppressed the mutagenic activity of bothcompounds22,31.
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Zingiber officinale
Ginger extract caused no mortality at doses of up to 2.5g/kg in mice (equivalent to about 75g/kg offresh rhizome)15. This low acute toxicity was confirmed in a separate study, which also found thatginger extract at 100mg/kg per day for three months caused no signs of chronic toxicity32.Topical application of ginger may cause contact dermatitis in sensitive patients33.
(j) Phytochemistry: Ginger has been reported to contain usually 1-3% of volatile oil, pungentprinciples viz., gingerols and shogaols and about 6-8 lipids and others. Ginger oil containsZingiberene and bisaboline as major constituents along with other sesqui and monoterpenes. Gingeroleoresin contains mainly the pungent principles gingerols and shogaols as well as zingiberone.Shogaols have recently been found to be twice as pungent as gingerols1-4.
(k) Active principles: Gingerols, Shogaols
Fig.4 Fig.5
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CH3O
O
( )n
[6] Shogaol 4 C 17H24O3 276.3
HO
[8] Shogaol 6 C 19H28O3 304.4 [10] Shogaol 8 C 21H32O3 332.1
n
CH3OH OH
O
[6] Gingerol 4 C 17H26O4 294.3
HO
[8] Gingerol 6 C 19H30O4 322.7 [10] Gingerol 8 C 21H34O4 350.2
n
( )n
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Zingiber officinale
ANALYTICAL SPECIFICATION OF THE CRUDE DRUG
Organoleptic Characters:
Colour & Appearance : Yellowish Brown or light brown. Scraped rhizomewith buff external surface showing longitudinalstriations and occasional loose fibers, outer surfacedark brown and more or less covered with cork whichshows conspicuous, narrow, longitudinal andtransverse ridges.
Odour : AromaticTaste : Pungent
Fig.6TESTS LIMITS PROTOCOLS
Tests for extraneous material Quality ControlMethods for MedicinalPlant Materials -WHO
Foreign matter < 1.0% -do-
Sand & Silica Absent -do-
Insect infestation Nil -do-
Rodent contamination Nil -do-
Physico-chemical analysis
Ash content < 8.0%w/w -do-
Acid insoluble ash < 1.0%w/w -do-
Moisture content < 12.0%w/w -do-
Volatile oil content 0.5 – 1.5%w/w -do-
Successive extractive value
Petroleum ether extractive valueChloroform extractive valueMethanol extractive value
1.5 – 2.5 % w/w3.0 - 5.0 % w/w2.0 – 4.0 % w/w
-do-
Alcohol soluble extractive value > 7.0%w/w -do-
Water soluble extractive value > 14.0%w/w -do-
Phytochemical analysis6-Gingerol 0.6 - 1.5 %w/w By HPLC
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Zingiber officinale
IDENTIFICATION OF CRUDE DRUG BY TLC
Sample detail : Zingiber officinale crude drug (dried rhizome)
Adsorbent : Precoated silicagel (Al - Sheet)
Mobile Phase : Toluene : Ethyl Acetate 93 : 7
Sample preparation : 2 gms of Zingiber officinale rhizome powderwas extracted with petroleum ether. The extractwas concentrated and diluted with chloroform.10µl was applied on different TLC plates.
Solvent front run upto : 9 cms
Application : CAMAG Linomat IV
Detection : Anisaldehyde sulphuric acid (Fig. 7) : Vanillin sulphuric acid (Fig. 8)
S T S T
Fig. 7 Fig. 8
S- StandardT- Sample
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Zingiber officinale
IDENTIFICATION OF CRUDE DRUG BY TLC
Sample detail : Zingiber officinale crude drug
Adsorbent : Precoated silicagel (Al - Sheet)
Mobile Phase : n-Hexane : Ether
40 : 60
Sample preparation : The mark from petroleum ether fraction of Zingiber officinalerhizome powder extract was successively extracted withchloroform and then by methanol. The individual extracts wereconcentrated and separately applied on different TLC plates.
Solvent front run upto : 9 cms
Application : CAMAG Linomat IV
Detection : Vanillin sulphuric acid (Fig. 9&10)
Scanninig : 254 nm (Fig. 10A)
Chloroform Methanol Fraction fraction
Fig.9 Fig.10 Fig. 10A - HPTLC of Methanolic fraction
Rf. ≅ 0.35 – Gingerols (blue spot)
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Zingiber officinale
TLC PROFILE OF GINGER OIL
Sample detail : Zingiber officinale oil
Adsorbent : Precoated silicagel (Al - Sheet)
Mobile Phase : Toluene : Ethyl Acetate
93 : 7
Sample preparation : 1 gm of Zingiber officinale oil was dissolved in chloroformand 10µl applied on the TLC plate.
Solvent front run upto : 9 cms
Detection : Anisaldihyde Sulphuric acid reagent (Fig.11)
Vanillin sulphuric acid reagent (Fig.12)
Fig. 11 Fig. 12
Rf. ≅ 0.9 – Zingiberene (red spot)
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Zingiber officinale
Chromatographic conditions
1. Column : DB wax 0.25 mm (diameter) 30 mtr (length)
2. Temperature Capillary injector port : 2600C FID Detector : 2750C Column oven : 400 C initial for 2 min. Program > column oven : 40C /min up to 2250C Hold time : 5 min Total time : 53 min.3. Control mode : Split
Split ratio : 1 : 504. Column pressure : 134 kPa5. Column flow : 2.2 ml / min.6. Detector : F.I.D.7. Carrier gas : Nitrogen
GC PROFILE OF GINGER OIL
TESTS LIMITSColour and appearance Light yellow to greenish yellow liquid
Odour Sharp lemony top note with persistent dry spicy note
Relative density at 27O C 0.866 – 0.880
Fig.13
FIG. 13A - MASS SPECTRUM OF ZINGIBERENE
Fig. 13B - MASS SPECTRUM OF ar-CURCUMENE
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Zingiber officinale
ANALYTICAL SPECIFICATIONS FOR THEZINGIBER OFFICINALE - EXTRACT
Item : Zingiber officinale extract (≥20% Gingerols)
Description : Brown to dark brown liquid with characteristic odour and taste.
Identification : 1) Comparison with the standard TLC profile.2) Positive for Gingerol
TESTS LIMITS PROTOCOLPhysico-chemical analysis
Moisture content < 4% w/w As per I.P / B.P
Ash content 3.5 % w/w As per I.P / B.P
Acid insoluble ash < 1% w/w As per I.P / B.P
Heavy metal analysis
Lead < 10ppm By A.A.S.
Cadmium < 2ppm By A.A.S.
Arsenic < 2ppm As per U.S.P
Microbiological tests
Total Viable Aerobic Count < 104 cfu g-1 As per I.P / B.P
Total Fungal count < 102 cfu g-1 As per I.P / B.P
Total Enterobacteriaceae < 102 cfu g-1 As per B.P.
E. Coli Absent As per I.P / B.P
Salmonella typhi Absent As per I.P / B.P
S. aureus Absent As per I.P / B.P
Solvent residuesOrganic solvents < 200 ppm By GC
Mycotoxin analysis
Aflatoxins(Total B1,B2,G1,G2)
< 5 ppb As perA.O.A.C
Phytochemical analysis
Gingerols ≥ 20.0%w/w HPLC(High PerformanceLiquid Chromatography)
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TLC PROFILE
Sample detail : Zingiber officinale extract
Adsorbant : Precoated silicagel (Al - Sheet)
Solvent system : n Hexane : Ether 40 : 60
Sample preparation : 1 gm of Zingiber officinale extract wasdissolved in 25 ml of methanol. 10µl of thissolution was applied on the TLC plate.
Solvent front run upto : 9 cms
Detection : Vanillin sulphuric acid reagent. (Fig.14)
Scanning : Densitometer 254 nm (Fig. 15)
Application : CAMAG Linomat IV
S T Fig. 14 Fig. 15
S = Standard
T = Sample
Rf. ≅ 0.9 – Zingiberene (dark purple spot) Fig.14
Rf. ≅ 0.3 – Gingerols (violet spot) Fig.14
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Zingiber officinale
ESTIMATION OF GINGEROL IN ZINGIBER OFFICINALE EXTRACT BY HPLC
Summary: Gingerol is separated from its related compounds like Shagaol, by reverse phasechromatography. The separated compounds are identified with the retention times in comparisonwith the pure compound and quantified with the corresponding peak area. The results were found tobe accurate and reproducible.
Analysis
Chromatographic system: High Performance Liquid Chromatographic system equipped withLC8A pump, SPD-M 10Avp Photo Array Detector in combination with Class LC 10A software.
Mobile phase: Acetonitrile : Water 55 : 45
Column : C18 - ODS (Octadecylsilane) (Lichrocart 250-4, Lichrospher RP-18e-5µ (Merck) Art.No: 1.50216
Detector : SPD-M 10Avp Photo diode array detector
Flow rate : 1.3 ml/min
Wave length : 280 nm
Injection volume : 10 µL
Standard preparation: Weigh accurately 100mg of working standard (contains 40% w/w ofGingerol) to a 25ml volumetric flask. Dissolve and make upto 25ml with HPLC grade methanol.
Sample preparation: Weigh accurately a sample quantity equivalent to 40 mg of gingerol to a 25ml volumetric flask. Dissolve and make upto 25ml with HPLC grade methanol.
Procedure:
Set the instrument as per the chromatographic condition prescribed above. By means of suitablesyringe inject 10 µl of standard solution. Record the chromatogram repeat the injections for another4 times and calculate the RSD of the area. It should not be more than 2%. Inject 10µL of samplepreparation and record the chromatogram.
Calculate the % of gingerol from the peak areas.
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HPLC PROFILEWORKING STANDARD
Fig.16 Fig.17Chromatogram PDA Spectrum of 6-Gingerol
Fig.18
3-D View
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Zingiber officinale
HPLC PROFILESAMPLE (Zingiber officinale extract 20% Gingerols)
Fig.19 Fig.20
Chromatogram PDA Spectrum of 6-Gingerol
Fig.21
3-D View
PKNO R.TIME k' NAME Plate # Tailing 1 4.75 4.7 6-Gingerol 7357 1.022 10.275 3.47 11281 0.91
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Zingiber officinale
ANALYTICAL SPECIFICATION
OF 6-GINGEROL
(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone
6-Gingerol is the major phenol and most important pungent and active principle isolated from therhizome of Zingiber officinale Roscoe. Normally obtained as yellow oil1.
2
+�&2
+2
2+
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Mol. Formula: C 17H26O4 Mol. Wt. 294.39
TESTS RESULTSDescription Yellow oily liquid
Solubility1 Sparingly soluble in petroleum ether, soluble in alcohol,chloroform, ether and almost insoluble in water.
Identification (by Spectroscopy & Chromatography)
Light absorption(UV absorption)1
Exhibits maxima at 282nm
TLC & HPTLC2 Gives a single spot
FTIR2 Characteristic of 6-Gingerol
NMR2 Characteristic of 6-Gingerol
HPLC (using PDA detector)
UV spectra of the principal peak matches with the 6-Gingerol
MASS SPECTRUM Characteristic of 6-Gingerol
Moisture content < 0.5%w/w
Purity > 97%w/w
References:
1. Merck Index. 12th edn., 19962. D.W. Connell et al., Aust. J. Chem., 1969; 22 : 1033-1043
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UV SPECTRUM
Fig. 22
UV absorption of 0.01788 % w/v solution in alcohol
ε reported at : 282nm 2560
ε calculated at : 282nm 2620
Created : 09:06 09/07/99
Data : Original
Measuring mode : Abs.
Scan speed : Fast
Slit width : 1.0
Sampling interval : 0.2
No. Wavelength (nm) Abs.
1 281.60 1.596
2 225.20 3.109
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TLC PROFILE
Sample detail : 6-Gingerol
Adsorbant : Precoated silicagel (Al - Sheet)
Solvent system : n Hexane : Ether 40 : 60
Sample preparation : 10 mg of 6-Gingerol was dissolved in 1 ml ofmethanol. 10µl of this solution was appliedon the TLC plate.
Solvent front run upto : 9 cms
Detection : Vanillin sulphuric acid reagent. (Fig.22)
Scanning : Densitometer 280 nm (Fig. 23)
Application : CAMAG Linomat IV
Fig. 23 Fig. 24
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Zingiber officinale
FTIR SPECTRUM
Fig. 25 - FTIR SPECTRUM OF LIQUID FILM IN KBr DISK
FTIR SPECTRUM MATCHES WITH THE PEAK POSITION PROVIDED IN D.W. CONNELL, AUST. J.CHEM., 1969; 22 : 1040-1041
3400s(br), 2930s, 1710s, 1603, 1515s, 1465, 1453, 1430, 1370s, 1275s, 1240s, 1210s, 1151s, 1123s, 1090,1033s, 935w, 850w, 813, 793, 723 cm-1
NMR SPECTRUM
Fig. 26- NMR SPECTRUM IN CDCl3
NMR SPECTRUM MATCHES WITH THE DETAILS PROVIDED IN D.W. CONNELL, AUST. J.CHEM., 1969; 22 : 10416.35 to 6.75 (3H, multiplet), 3.7(3H, s), 2.6(4H, s), 2.4(2H, d, j6 c/s), 1.25 (8-9H, 0.87 p.p.m(3H).
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HPLC PROFILE USING PDA-DETECTOR
CHROMATOGRAM PDA SPECTRUM
Fig. 27 Fig. 28
CHROMATOGRAM IN 3D VIEWFig. 29
PEAK TABLE
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HPLC PROFILE USING UV-DETECTOR
CHROMATOGRAM
Fig. 30 Fig. 31
PEAK TABLE
MASS SPECTRUM
Fig. 32
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Zingiber officinale
ANALYTICAL SPECIFICATION
OF 8-GINGEROL
(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-hexanone
8-Gingerol is another important pungent and active principle isolated from the rhizome of Zingiberofficinale Roscoe. Normally obtained as yellow oil.
2
+�&2
+2
2+
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Mol. Formula: C 19H30O4 Mol. Wt. 322.7
TESTS RESULTSDescription Yellow oily liquid
Solubility Sparingly soluble in petroleum ether, soluble in alcohol,chloroform, ether and almost insoluble in water.
Identification (by Spectroscopy & Chromatography)
TLC & HPTLC Gives a single spot
FTIR Characteristic of 8-Gingerol
NMR Characteristic of 8-Gingerol
HPLC (using PDA detector)
UV spectra of the principal peak matches with the 8-Gingerol
MASS SPECTRUM Characteristic of 8-Gingerol
Moisture content < 0.5%w/w
Purity > 96%w/w
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TLC PROFILE
Sample detail : 8-Gingerol
Adsorbant : Precoated silicagel (Al - Sheet)
Solvent system : n Hexane : Ether 40 : 60
Sample preparation : 10 mg of 8-Gingerol was dissolved in 1 ml ofmethanol. 10µl of this solution was appliedon the TLC plate.
Solvent front run upto : 9 cms
Detection : Vanillin sulphuric acid reagent. (Fig.33)
Scanning : Densitometer 280 nm (Fig. 34)
Application : CAMAG Linomat IV
Fig. 33 Fig. 34
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Zingiber officinale
FTIR SPECTRUM
FTIR SPECTRUM OF LIQUID FILM IN KBr DISKFig. 35
NMR SPECTRUM
NMR SPECTRUM IN CDCl 3
Fig. 36MASS SPECTRUM
Fig. 37
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Zingiber officinale
HPLC PROFILE USING PDA-DETECTOR
CHROMATOGRAM PDA SPECTRUM
Fig. 38 Fig. 39
CHROMATOGRAM IN 3D VIEWFig. 40
** Peak Report ** GINGE28.K02 99/09/28 19:38:24
PKNO ChNO TIME AREA HEIGHT CONC NAME1 1 10.463 2308591 100744 100.0000 8-Gingerol TOTAL 2308591 100744 100.0000
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Zingiber officinale
ANALYTICAL SPECIFICATION
OF 6-SHOGAOL
6-Shogaol is another important pungent and active principle isolated from the rhizome of Zingiberofficinale Roscoe. Normally obtained as yellow oil.
CH3O
O
( )n
[6] Shogaol 4 C 17H24O3 276.3
HO
[8] Sh l 6 C H O 304 4
n3
TESTS RESULTSDescription Yellow oily liquid
Solubility Sparingly soluble in petroleum ether, soluble in alcohol,chloroform, ether and almost insoluble in water.
Identification (by Spectroscopy & Chromatography)
TLC & HPTLC Gives a single spot
FTIR1 Characteristic of 6-Shogaol
NMR1 Characteristic of 6-Shogaol
HPLC (using PDA detector)
UV spectra of the principal peak matches with the 6-Shogaol
MASS SPECTRUM Characteristic of 6-Shogaol
Moisture content < 0.5%w/w
Purity > 96%w/w
References:
1. D.W. Connell et al., Aust. J. Chem., 1969; 22 : 1033-1043
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Zingiber officinale
TLC PROFILE
Sample detail : 6-Shogaol
Adsorbant : Precoated silicagel (Al - Sheet)
Solvent system : n-Hexane : Ether 40 : 60
Sample preparation : 10 mg of 6-Shogaol was dissolved in 1 ml ofmethanol. 10µl of this solution was appliedon the TLC plate.
Solvent front run upto : 9 cms
Detection : Vanillin sulphuric acid reagent. (Fig.41)
Scanning : Densitometer 280 nm (Fig. 42)
Application : CAMAG Linomat IV
Fig. 41 Fig. 42
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Zingiber officinale
FTIR SPECTRUM
FTIR SPECTRUM OF LIQUID FILM IN KBr DISKFig. 43
NMR SPECTRUM
Fig. 44MASS SPECTRUM
Fig. 45
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Zingiber officinale
HPLC PROFILE USING PDA-DETECTOR
CHROMATOGRAM PDA SPECTRUM
Fig. 46 Fig. 47
CHROMATOGRAM IN 3D VIEWFig. 48
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Zingiber officinale
References:
Botanical Description
1. Schauenberg P & Paris F, Guide to Medicinal Plants, Keats Publishing,New Canaan CT,1977
Geographical Distribution
1. Kokate C.K, et.al, Pharmacognosy, Nirali Prakashan, 4th edition, 1996
Traditional Use
1. Misra B, Bhavaprakasha Nighantu , 5th edition,1969, p.14
2. Sharma P.V. Dravyagunavigna, Part II, Chowkamba Publications, 1993, p. 331
3. Indian Medicinal Plants, A Compendium of 500 species, Part V, by Orient Longman Publications, 1997,p. 431.
4. Nadakarni, Indian Materia Medica, Vol. I, 1993, p. 1308.
Anatomy of the Rhizome
1. British Herbal Pharmacopoeia, B.H.M.A., 1983, 239-240
2. Wallis T.E., Textbook of Pharmacognosy, C.B.S. Publishers, 5th edition, 1985
Pharmacology and Clinical Studies, Toxicity and Adverse Reactions
1. Chang, H.M et al, “Pharmacology and Applications of Chinese Materia Medica.” World Scientific,Singapore, 1987
2. Mowrey, D.B, et al, “ Motion Sickness, Ginger, and Psychophysics” Lancet, 1982, 1(8273); 655-657
3. Kawai, T, et al, “Anti-emetic principles of Magnolia obovata Bark and Zingiber officinale Rhizome”,Planta Medica, 1994, 60; 17-20
4. Blumberger, W, et al, “The Physiology of Spices and Condiments. The Action of Ginger on the Amountand Condition of the Saliva” , Nutritio et Dieta (European Review of Nutrition and Dietetics), 1965,7(3); 222-237
5. Yamahara, J, et al, “Cholagogic Effect of Ginger and its Active Constituents”, Journal ofEthnopharmacology, 1985, 13(2); 217-225
6. Thompson, E.H, et al, “Ginger Rhizome : A New Source of Proteolytic Enzyme”, Journal of FoodScience, 1973, 38; 652-655
7. Suekawa, M, et al, “Pharmacological Action of Pungent Constituents, (6)-Gingerol and (6)-Shogaol”,Journal of Pharmacobio-Dynamics”, 1984, 7(11), 836-848
8. Desai, H.G, et al, “Effect of Ginger and Garlic on DNA Content of Gastric Aspirate”, Indian Journal ofMedical Research, 1990, 92; 139-141
1$785$/ 5(0(',(6 ² 5(6($5&+ &(175( 0'?=2?����� 30
Zingiber officinale
9. Yamahara, J, et al, “The Anti-ulcer Effect in Rats of Ginger Constituents”, Journal ofEthnopharmacology, 1988, 23(2-3); 299-304
10. al-Yahya, M.A, et al, “Gastroprotective Activity of Ginger (Zingiber officinale Rose.) in Albino Rats”,American Journal of Chinese Medicine, 1989, 17(1-2); 51-56
11. Srivastava, K.C, “Effects of Aqueous Extracts of Onion, Garlic and Ginger on Platelet Aggregation andMetabolism of Arachidonic Acid in the Blood Vascular System; In vitro Study”, ProstaglandinsLeukotrienes and Medicine, 1984, 13(2); 227-235
12. Srivastava, K.C, “Aqueous Extracts of Onion, Garlic and Ginger Inhibit Platelet Aggregation and AlterArachidonic Acid Metabolism”, Biomedica, Biochimica Acta, 1984, 43(8-9); S335-346
13. Srivastava, K.C, “Isolation and Effects of Some Ginger Components of Platelet Aggregation andEicosanoid Biosynthesis”, Prostaglandins Leukotrienes and Medicine, 1986, 25(2-3); 187-198
14. Guh, J.H, et al, “Antiplatelet Effect of Gingerol Isolated from Zingiber officinale”, Journal of Pharmacyand Pharmacology”, 1995, 47(4); 329-332
15. Mascolo, N, et al, “Ethnopharmacologic Investigation of Ginger (Zingiber officinale)”, Journal ofEthnopharmacology, 1989, 27; 129-140
16. Sharma, J.N, et al, “Suppressive Effects of Eugenol and Ginger Oil on Arthritic Rats”, Pharmacology,1984, 49(5), 314-318.
17. Flynn, D.L, et al, “ Inhibition of Neutrophil 5-Lipoxygenase Activity by Gingerdione, Shogaol,Capsaicin and Related Pungent Compounds”, Prostaglandins Leukotrienes and Medicine, 1986, 24(226),195-198
18. Kiuchi, F, et al, “Inhibitors of Prostaglandin Biosynthesis from Ginger”, Chemical and PharmaceuticalBulletin, 1982,(30(2); 754-757
19. Iwakmi, S, et al, “Inhibition of Arachidonate 5-Lipoxygenase by Phenolic Compounds”, Chemical andPharmaceutical Bulletin, 1986, 34(9); 3960-3963
20. Kiuchi, F, et al, “Inhibition of Prostaglandin and Leukotriene Biosynthesis by Gingerols andDiarylheptanoides”, Chemical and Pharmaceutical Bulletin, 1992, 40(2); 387-391
21. Suekawa, N, et al, “Pharmacological Studies on Ginger IV. Effect of (6)-Shogaol on the ArachidonicCascade”, Nippon Yakurigakuzasshi (Folia Pharmacologica Japonica), 1986, 88(4); 263-269 (InJapanese)
22. Farnsworth, N.R, et al, Bunyapraphatsara, N, eds Thai Medicinal Plants. Medicinal Plant InformationCentre, Bangkok, 1992.
23. Shoji, N, et al, “Cardiotonic Principles of Ginger (Zingiber officinale Roscoe.)”, Journal ofPharmaceutical Sciences, 1982, 71(10), 1174-1175
24. Kobayashi, M, et al, “Cardiotonic Action of (8)-Gingerol, An Activator of Ca2+ pumping AdenosineTriphosphatase of Sarcoplasmic Reticulum in Guinea Pig Atrial Muscle”, Journal of Pharmacology andExperimental Therapeutics”, 1988, 246(2), 667-673
25. Govindarajan, V.S, “Ginger- Chemistry, Technology and Quality evaluation; Parts 1 & 2”, CRC CriticalReviews in Food, Science and Nutrition, 1982, 17(1); 1-96: 1982, 17(3), 189-258
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Zingiber officinale
26. Hikino, H, et al, “Anti-hepatotoxic Actions of Gingerols and Diarylhepanoids”, Journal ofEthnopharmacology, 1985, 14; 31-39
27. Naora, K, et al, “Pharmacokinetics of (6)-Gingerol after Intravenous Administration in Rats with AcuteRenal or Hepatic Failure” Chemical and Pharmaceutical Bulletin, 1992, 40(5); 1295-1298
28. Monge, P, et al, “ The Metabolism of Zingeronem, a Pungent Principle of Ginger”, Xenobiotica, 1976,6(7); 411-423
29. Mahmoud, I, et al, “Mutagenic andToxic Activities of Several Spices and Some Jordanian MedicianlPlants”, International Journal of Pharmacognosy, 1992,30(2); 81-85
30. Nakamurah, H, et al, “Mutagen and Anti-mutagen in Ginger, Zingiber officinale”, Mutation Research,1982, 103; 119-126
31. Qian, D.S, et al, “Pharmacologic Studies of Antimotion Sickness Actions of Ginger”, Chung-kuochunghsii chieh ho tsa chih, 1992, 12(2); 70, 95-98
32. Qureshi, A, et al, “ Studies on Herbal Aphrodisisacs Used in Arab System of Medicine” AmericanJournal of Chinese Medicine, 1989, 17(1-2); 57-63
33. Futrell, J.M, et al, “Spice Allergy Evaluated by Results of Patch Tests”, Cutis, 1993, 52(5); 288-290
Phytochemistry
1 Kiuchi F, et al ,Chem Pharm Bull, !982,30,754
2 Wagner H, et al, Plant Drug Analysis, Spinger, 1996, 300
3 British Pharmacopoeia, 305
4 Akhila A & Tewari, CROMAP,1984,6(3),143-156
Analytical Specifications
1. Merck Index. 12th edn., 1996
2. Wagner H, et al, Plant Drug Analysis, Spinger, 1996, 300
3. D.W. Connell et al., Aust. J. Chem., 1969; 22 : 1033-1043
4. British Pharmacopoeia, 305
5. Indian Standard Specification for Ginger Oleoresin, 1st Revision, Bureau of Indian Standards, IS: 7826 –1984.
6. Indian Standard Specification for Oil of Ginger, 1st Revision, Bureau of Indian Standards, IS: 761 –1988.