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Background and Fitness for Purpose for Ginger

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Background and Fitness for Purpose for Ginger AOAC Stakeholder Panel on Dietary Supplements: Background and Fitness for Purpose for Ginger Anton Bzhelyansky AOAC 2016 Annual Meeting – Dallas, TX, USA SPDS September 16, 2016 Ginger Plant The ginger plant is a herbaceous perennial grown as an annual crop. The plant is erect, has many fibrous roots, aerial shoots (pseudostem) with leaves, and the underground stem (rhizome). Ginger (Zingiber officinale Roscoe) is a sterile, reed-like plant with a pungenttd and aromati tihic rhizome on whi hihitlifch it relies for vege ttitative propagation. The plant is a cultigen, that is, it is only known from cultivation. Its wild origins are not known with certainty but are believed to be India or South-East Asia. Ginger rhizome, known as Rhizoma Zingiberis in pharmacy is used in several traditional systems of medicine, including Traditional Chinese Medicine, Ayurveda and Western herbal medicine. Its traditional uses cover a great variety of complaints including dyspepsia, flatulence and colic, nausea and vomiting, colds and flu, migraine, as well as muscular and rheumatic disorders. Wohlmuth, H 2008, 'Phytochemistry and pharmacology of plants from the ginger family, Zingiberaceae', PhD thesis, Southern Cross University, Lismore, NSW. Ginger Rhizome Production, Processing and Chemical Composition Ginger Production* Ginger is one of the earliest important species grown in the Western hemisphere reported to be a native of Southeast Asia. Gingqger requires a warm tem perature (29-35 degree Celsius) and a humid climate for growth. It also requires a distinctive pattern of rainfall of at least 150 to 200 cm during the growing period and no rainfall a month prior to harvest. In 2013, world production of ginger was reported to be 2.14 ton; the major producers, India and China, accounting for hlffthhalf of the wor ld’s ou tpu t. Indonesia, Nepal, Nigeria and Thailand account for additional 36%. The United States’ production of ginger amounts to about 0.04%, or 774 tons. *Data from FAOSTAT, retrieved Tue Sep 06 01:34:37 CEST 2016 Ginger Processing Ginger is harvested when stalks exhibit yellowing and withering, about nine (9) months after planting. Maximum oil and oleoresin content is typically reached between 150 and 170 days. POST HARVEST HANDLING A. Washing – Rhizomes are washed, cleaned from debris, shoots and roots. B. “Killing” – 10-min. immersion in boiling water, to terminate enzymatic processes. C.Drying to 8-10% moisture. D.Dry storage at 10-15 ⁰C. E. Solvent extraction is conducted preferably on unpeeled ginger. Dried powdered rhizomes extracted by percolation, and the extract Is then distilled at 45-55 ⁰C. Typical extraction solvents: ethyl acetate, hexane, or supercritical CO2. FAO: Ginger: Post-Production Management for Improved Market Access Two-Stage Extraction of Ginger Two-Stage Extraction: Ginger is ground and first steam distilled to obtain the volatile oil. This oil represents the aroma of the spice. The de-oiled spice is then subjected to solvent extraction to recover the nonvolatile taste principles. The aroma and taste fractions are proportionately blended to give the oleoresin of the spice. Since the aroma and pungency fractions are isolated individually, their relative percentages in the end product can be adjusted at will. Acetone, methanol, isopropanol, methylene chloride, ethyyyl acetate, and ethyl alcohol are popular extraction solvents for ginger. Ethylene dichloride is an efficient extractant; however, its use is restricted due to alleged carcinogenicity. Ginger Chemical Composition Ginger Constituents (WHO) Major constituents The rhizome contains 1–4% essential oil and an oleoresin. The composition of the essential oil varies as a function of geographical origin, but the chief constituent sesquiterpene hydrocarbons (responsible for the aroma) seem to remain constant. These compounds include (-)-zingiberene, (+)-ar-curcumene, (-)-β- sesquiphellandrene, and β-bisabolene. Monoterpene aldehydes and alcohols are also present. The constituents responsible for the pungent taste of the drug and possibly part of its anti-emetic properties have been identified as 1-(3- methoxy-4-hydroxyphenyl)-5-hydroxyalkan-3-ones, known as [3–6]-, [8]-, [10]-, and [12]-gingerols (having a side-chain with 7–10, 12, 14, or 16 carbon atoms, respectively) and their corresponding dehydration products, which are known as shogaols. Gingerols O OH Gingerols are homologues of 1-(3- H3CO 2 4 1 3 5 methoxy-4-hydroxyphenyl)-3-keto-5- CH3 [6]-Gingerol hhdydroxyh exane and iildthbnclude the subgroup HO methylgingerols. O OH Universally acknowledged as major H3CO CH3 constituents of ginger “pungent principles”. (5S)-[8]-Gingerol Gingerols are thermally labile and undergo HO chemical changes during processing and O OH storage. H3CO CH3 (5R)-[8]-Gingerol HO O OH H3CO CH3 [10]-Gingerol HO Shogaols O Shogaols are dehydration products of the H3CO CH3 gingerols. [6]-Shogaol HO Sometimes considered the degradation O products of gingerols, shogaols, in fact were found to readily interconvert into H3CO CH3 gingerols at specific conditions. [8]-Shogaol HO Shogaols are strong contributors to ginger O “pungent principles”. Thermal treatment of H3CO ginger rhizome is commonly undertaken to CH3 enhance content of shogaols . [6]-Shogaol [10]-Shogaol HO is considered a more “pungent” constituent relative to [6]-gingerol, and in numerous bioactivity studies was shown to outperform the latter. Content of shogaols increases significantly in ginger extracts. Paradols O Paradols are β-ketone hydroxyl H3CO CH3 deoxygenation products of gggingerols. [6]-Paradol HO Paradols represent another subclass of O ginger ‘pungent principles’, and possess H3CO marked bioactivity. CH3 [8]-Paradol HO The content of paradols is more pronounced in ginger extracts as opposed to the fresh O plant material. H3CO CH3 [10]-Paradol HO Gingerdiols and Gingerdiones OH OH O O H3CO H3CO CH3 CH3 (3R,5S)-[6]-Gingerdiol [6]-Gingerdione HO HO OH OH O O H3CO H3CO CH3 CH3 (3S,5S)-[6]-Gingerdiol [8]-Gingerdione HO HO OH OH O O H CO H3CO 3 CH CH3 3 [10]-Gingerdione (3R,5S)-[10]-Gingerdiol HO HO OH OH O O H3CO H CO CH 3 3 (CH2)nCH3 (3S,5S)-[10]-Gingerdiol 1-Dehydro-gingerdiones HO HO Gingerdiols are ketone reduction products Gingerdiones are β-ketone hydroxyl dehydrogenation products of gingerols; of gingerols. include the subgroup of 1-dehydroginger- diones. Major Ginger Sesquiterpenes Sesquiterpenes are primarily contained in ggginger volatile oil, but also in the oleoresin. The six major ginger sesquiterpenes are shown here. Zerumbone is the constituent of recent intense interest, with a number of investigations regarding its bioactivity publis he d. Zingerone (Vanillylacetone) Zingerone is absent in fresh ginger but cooking or heating transforms gingerol to zingerone. Zingerone has antiinflammatory, antidiabetic, antilipolytic, antidiarrhoeic, and antispasmodic properties. Besides, it enhances growth and stimulate immune system. It behaves as appetite stimulant, anxiolytic, antithrombotic, radiation protective, and antimicrobial. Pungent Principles as a Function of Ginger Cultivar Ginger Pungent Principles as a Function of the Extraction Solvent Ginger in Pharmacopeial and Related Texts The Pharmacopœia of the United States of America, 6th Edition, 1882 The United States Homeopathic Pharmacopœia, 1878 British Pharmacopoeia 16th Edition, 2016 Ginger (Ph. Eur. monograph 1522) Content: Minimum 15 mL/kg of essential oil (anhydrous drug). Identification: Macroscopic, microscopic, TLC Tests: Water (NMT 100 mL/kg), Total Ash (NMT 6.0%) Assay: Essential oil (NLT 15 mL/kg) Use 20.0 g of the freshly, coarsely powdered herbal drug, a 1000 mL round-bottomed flask, 10 drops of liquid paraffin R or other antifoam, 500 mL of water R as distillation liquid and 0.5 mL of xylene R in the graduated tube. Distil at a rate of 2-3 mL/min for 4 h. Strong Ginger Tincture Tests: Ethanol content (80 – 88%), Dry residue (2.0 – 3.0%), Relative density (0.832 – 0.846) Weak Ginger Tincture Tests: Ethanol content (86 – 90%), Dry residue (NLT 0.4%), Relative density (0.825 – 0.835) European Pharmacopoeia 9th Edition, 2017 Ginger (Zingiberis rhizoma) Content: Minimum 15 mL/kg of essential oil (anhydrous drug). Identification: Macroscopic, microscopic, TLC (against citral and resorcinol) Tests: Water (NMT 100 mL/kg), Total Ash (NMT 6.0%) Assay: Essential oil (NLT 15 mL/kg) Use 20.0 g of the freshly, coarsely powdered herbal drug, a 1000 mL round-bottomed flask, 10 drops of liquid paraffin R or other antifoam, 500 mL of water R as distillation liquid and 0.5 mL of xylene R in the graduated tube. Distil at a rate of 2-3 mL/min for 4 h. Japanese Pharmacopoeia 16th Edition, 2011 GgeGinger (Zingbegiberis s Rhizomaoa) Description: Macroscopy, microscopy, organoleptic Identification: TLC against [6]-gingerol Purity: Heavy metals (NMT 10 ppm), Arsenic (NMT 5 ppm), Total ash (NMT 8.0%) Powdered Ginger (Zingiberis Rhizoma Pulveratum) Description: Macroscopy, microscopy, organoleptic Identification: TLC against [6]- gingerol Purity: Heavy metals (NMT 10 ppm), Arsenic (NMT 5 ppm), Total ash (NMT 8.0%) Processed Ginger (Zingiberis Processum Rhizoma) Description: Macroscopy, microscopy, organoleptic Identification: TLC against [6]- shogaol Purity: Arsenic (NMT 5 ppm), LOD (NMT 15.0%), Total ash (NMT 6.5%), Acid- insoluble ash (NMT 1.5%), Ethanol extractive (NLT 8.0%) The Korean Pharmacopoeia, 10th Edition, 2012 Ginger (Zingiberis Rhizoma) – Description: Macroscopic, microscopic, organoleptic – Identification: TLC against [6]-gingerol – Purity:
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