gingerol from ginger extract

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INTRODUCTION LITERATURE REVIEW OBJECTIVE OF CURRENT WORK METHODS OF EXTRACTION RESULTS AND DISCUSSION CONCLUSION REFERENCES

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Page 1: Gingerol From Ginger Extract

• INTRODUCTION

• LITERATURE REVIEW

• OBJECTIVE OF CURRENT WORK

• METHODS OF EXTRACTION

• RESULTS AND DISCUSSION

• CONCLUSION

• REFERENCES

Page 2: Gingerol From Ginger Extract

• Ginger (Zingiber officinale) has copious medicinal properties

• Characteristic odour and flavour of ginger from Zingerone,

Shogaols and Gingerols.

• Composition of ginger :

Component Weight Percent

Starch 45.09 %

Sesquiterpene Hydrocarbons 15 %

Proteins 14.6 %

Crude Fiber 10.3 %

Ash 6.5 %

Fatty Acids 4.5 %

Oleoresin 4 %

Page 3: Gingerol From Ginger Extract

• 6-Gingerol inhibits cell adhesion, invasion, motility and activities of

MMP-2 and MMP-9 in MDA-MB-231 human breast cancer cell lines

• Possesses antioxidant and anti-inflammatory properties, to suppress

cytokine formation and to promote angiogenesis

• Reported to be an active inhibitor of M. avium and M.tuberculosis in

vitro

• 6-gingerol is shown to have analgesic, antipyretic, and cardiotonic

properties

Page 4: Gingerol From Ginger Extract

• 6-Gingerol is a heat sensitive compound and gets reversibly de-hydrated to 6-Shogaol.

• Steam Distillation cannot be used as a means of separation.

Page 5: Gingerol From Ginger Extract

•Yoshio Yonei, Hajime Ohinata, Ryuichi Yoshida, Yukio Shimizu and Chiaki

Yokoyama supercritically extracted 6-gingerol using a semi-batch type apparatus,

found the pressure of 4.5 MPa and temperature of 303 K as optimum.

•S. Balachandran, S.E. Kentish, R. Mawson, and M. Ashokkumar found that in

the presence of ultrasound during the extraction of pungent compounds from a

ginger with supercritical CO2 both the extraction rate and the yield increased.

•Gingerols were stable in ethanolic solution over a 5-month period when stored at

4 °C. Shogaols are not native constituents of fresh ginger was reported by Hans

Wohlmuth, David. N. Leach, Mike. K. Smith and Stephen P. Myers.

Page 6: Gingerol From Ginger Extract

• Investigate of the potential of solvent extraction and determination of the

most efficient solvent for the extraction of 6- gingerol

• Effect of temperature on extraction

• Optimum solvent to ginger sample ratio

• For a semi-batch process, the effect of flow rate on extraction

Page 7: Gingerol From Ginger Extract

• A paste was made of a weighted of peeled ginger sample with the

help of a mortar.

• The paste was then transferred to the batch reactor, 100ml volume

of solvent is poured into the reactor.

• The reactor is placed in the constant temperature bath setup and

contents are stirred for a period of 1 hour.

• The solids are then allowed to settle and the liquid phase is

centrifuged and analyzed by HPLC.

Page 8: Gingerol From Ginger Extract
Page 9: Gingerol From Ginger Extract
Page 10: Gingerol From Ginger Extract

• Ginger shredded to a length of 3mm and thickness of 2mm

• Glass column of height 51cm, diameter 2cm and with a maximum

volume of 100ml

• Column bottom outlet was plugged with cotton and glass beads up to a

height of 5 cm

• Shredded ginger constituted the column bed, bed height of 20 cm

• Solvent poured from top inlet from an aspirator, flow rate controlled by

pinch cock

• Keeping the bed height fixed, three different flow rates studied, samples

collected at regular time intervals

• Samples analyzed by HPLC

Page 11: Gingerol From Ginger Extract

•The liquid phase extract after centrifugation is analyzed by HPLC ( Perkin Elmer Series 200 UV/Vis Detector) by injecting 30µL of extract

The operating conditions were:

•Column: C-18 & UV visual detector type

•Stationary Phase: Carbon 18

•Mobile Phase: Acetonitrile : Water (9:1)

•Flow Rate: 1.0 ml/min

•Detector(wave length): 282 nm

•Column Temp: 28°C

•Run Time: 9 minutes

Page 12: Gingerol From Ginger Extract

• Standard dried ginger extract powder procurred from Salem, Tamil

Nadu

• 5gm of standard centrifuged with 10ml of the respective solvent

• Centrifuged for a period of 30 minutes at a r.p.m of 2000.

• The liquid phase was analyzed by HPLC

• For calibration curve above procedure was repeated for 4,3,2,1 gm of

standard powder with a resulting r2 = 0.984

Page 13: Gingerol From Ginger Extract

← Solvent Peak

Step 1: Solvent peak identified by HPLC

Page 14: Gingerol From Ginger Extract

Solvent peak →← Pure 6-gingerol peak with area Apure

Step 2: 6-gingerol peak identified using the pure sample procured

Page 15: Gingerol From Ginger Extract

Solvent Peak → ←6-gingerol peak in extract

with area Aextract

Step 3: area of 6-gingerol peak used to quantify amount of 6-gingerol extracted

Page 16: Gingerol From Ginger Extract

Percentage extraction = A extract X 100 A pure

A pure quantifies the amount of 6-gingerol originally present in the raw ginger sample.

A extract quantifies the amount of 6-gingerol that has been extracted by the process.

Step 4: Percentage extraction is calculated

Page 17: Gingerol From Ginger Extract

Solvent Selection: Organic Solvents

Maximum extraction by Ethanol 19.48% followed by Iso Propanol with 14.08%.

Page 18: Gingerol From Ginger Extract

Solvent Selection: Edible Oils

Maximum extraction by Sunflower oil 58.73 % followed by Ricebran oil with 51.13%

Page 19: Gingerol From Ginger Extract

Effect of temperature on extraction by Sunflower OilConstant Parameters: Ginger weight =20 gm, Solvent volume = 100 ml, r.p.m = 700

Maximum extraction of 68.74% was obtained at 10°C

Page 20: Gingerol From Ginger Extract

Effect of variation of Solvent (Sunflower Oil) to Sample ratio (ml/gm)Constant Parameter: Temperature = 10 ºC, r.p.m = 700

Page 21: Gingerol From Ginger Extract

Height of ginger bed = 20 cm, Solvent : Sunflower oil, Flow rate = 2 ml/min

Maximum extraction value of 59.62 % after 105 minutes, bed begins to get exhausted after 105 minutes

Page 22: Gingerol From Ginger Extract

Height of ginger bed = 20 cm, Solvent : Sunflower oil, Flow rate = 5 ml/min

Maximum percentage extraction 37.70%, lower than for 2 ml/min but arrives earlier, after 90 minutes

Page 23: Gingerol From Ginger Extract

Height of ginger bed = 20 cm, Solvent : Sunflower oil, Flow rate = 10 ml/min

Maximum percentage extraction of 30.81% after 60 minutes, bed begins to get exhausted faster

Page 24: Gingerol From Ginger Extract
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• Sunflower Oil showed best extraction characteristics among the

various edible oils and organic solvents studied.

• Temperature of 10°C gave good extraction results, as temperature is

raised the extraction of 6-gingerol drops due to thermal degradation of

the compound to its dehydrate form 6-shogaol.

• On varying the solvent to ginger sample ratio extraction curve shows

an optimum ratio of near to 2.0 (ml/gm).

• Solvent flow rate of 2 ml/min gave higher extraction but at the

expense of longer duration.

Page 26: Gingerol From Ginger Extract

P. N. Ravindran, K. Nirmal Babu. (2004). “Ginger: the genus Zingiber”, CRC Press, 88. Harvey A. Schwertner, Deborah C. Rios. (2007). “High-performance liquid chromatographic analysis of 6-gingerol, 8-gingerol, 10-gingerol and 6-shogaol in ginger-containing dietary supplements, spices, teas, and beverages.” Journal of Chromatography B, (856), 41–47. Yoshio Yonei and Hajime Ohinata. (1995). “Extraction of Ginger Flavor with Liquid or Supercritical Carbon Dioxide.” The Journal of Supercritical Fluids, 8, 156-161. R. D. Hiserodt, S. G. Franzblau, and R. T. Rosen. (1998). “Isolation of 6-, 8-, and 10-Gingerol from Ginger Rhizome by HPLC and Preliminary Evaluation of Inhibition of Mycobacterium avium and Mycobacterium tuberculosis.” Journal of Agricultural and Food Chemistry, 46, 2504-2508.

F. Kjuchi, M. Shibuya, U. Sankawa. (1992). “Inhibition of Prostaglandin and Leukotriene Biosynthesis by Gingerols and Diarylheptanoids,” Chemical & Pharmaceutical Bulletin, (Tokyo), 40 387.

 

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Hyun Sook Leea, Eun Young Seob, Nam E Kangc, Woo Kyung Kimb. (2008) “6-gingerol inhibits metastasis of MDA-MB-231 human breast cancer cells.” Journal of Nutritional Biochemistry, 19, 313–319. D.J. Harvey. (1981) “Gas chromatographic and mass spectrometric studies of ginger constituents: Identification of gingerdiones and new hexahydrocurcumin analogues,” Journal of Chromatography, 212, 75.

C.C. Chen, C.T. Ho. (1986) “Chromatographic analyses of isomeric shogaol compounds derived from isolated gingerol compounds of ginger (zingiber officinale roscoe),” Journal of Chromatography, 360, 175. X. He, M.W. Bernart, L. Lian, L. Lin. (1998). “High-performance liquid chromatography–electrospray mass spectrometric analysis of pungent constituents of ginger,” Journal of Chromatography, 796, 327. N. Shogi, A. Iwasa, T. Takemoto, Y. Ishida, Y. Ohizumi. (1982) “Cardiotonic principles of ginger (Zingiber officinale Roscoe),” Journal of Pharmaceutical Sciences. 711, 174.

F. Borrelli, R. Capasso, G.Aviello, M.H. Pittler, A.A. Izzo. (2005), “Effectiveness and safety of ginger in the treatment of pregnancy-induced nausea and vomiting,” Obstetrics & Gynecology, 105 849.

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