Aardraka-Ginger (Zingiber officinale) Part 4
Aardraka-Ginger (Zingiber officinale) Part 4
Aardraka-Ginger
(Zingiber officinale) contains many
bioactive phytochemicals. Here I describe in detail the pharmacology of some important phytochemicals.
Zingerone
Molecular Formula: C11H14O3
Structural Formula:
Zingerone,
also called vanillyl acetone, is a key component of pungency of Ginger (Zingiber officinale) that imparts the
“sweet”, agreeable flavor to Ginger (Zingiber
officinale). Zingerone is a member of methoxyphenol family. It is a
crystalline solid, sparingly soluble in water but soluble in ether. Synthetic,
zingerone is not pungent. This suggests that zingerone is more likely a
decomposition product of pungency rather than a direct source of pungency of
Ginger (Zingiber officinale).
Zingerone is the least pungent compound of Ginger (Zingiber officinale).
Fresh
Ginger (Zingiber officinale) does not
contain zingerone but is produced by cooking or drying ginger rhizomes, which
causes reverse aldol-reaction on gingerol.
The
chemical structure of zingerone is similar to that of vanillin and eugenol.
Zingerone is used as a flavor-additive in spices. It is also used in perfumery
to impart spicy aromas to oils.
Zingerone
was first isolated from Ginger (Zingiber
officinale) in 1917 by Hiroshi Nomura. He identified the empirical formula
in the laboratory of the Agicultural College where he was a professor of
chemistry. [205]
Pharmacokinetics
of Zingerone
On oral or intraperitoneal administration of zingerone, its
metabolites, mainly glucuronide and/ or sulphate conjugates were excreted in
urine within 24 hours. [206]
Anti-inflammatory activityof
Zingerone
Peroxisome
proliferator-activated receptors (PPAR) have been demonstrated to be involved
in the modulation of nuclear κB (NF- κB) transcription factors, which are key
regulators of immune and inflammatory responses. By suppressing activities of peroxisome
proliferator-activated receptors (PPAR) and nuclear factor- κB (NF- κB)
zingerone displays its anti-inflammatory activity. [207]
Another
study showed that by downregulating nuclear factor κB (NF- κB) activity and
interleukin1β signaling pathway zingerone displays its anti-inflammatory
activity. [208]
Nuclear
factor κB (NF- κB) is a pro-inflammatory pathway. When activated, it induces
various inflammations. A mitogen-activated protein kinase (MAPK) is a type of
protein kinase that regulates cellular responses to a diverse array of stimuli
such as osmotic shock, heat stroke and pro-inflammatory cytokines.
Mitogen-activated protein kinases (MAPKs) regulate cell survival and apoptosis.
Via inhibition of pro-inflammatory nuclear κB (NF- κB) expression and
interfering with mitogen-activated protein kinase (MAPK) pathway, zingerone
acts as an anti-inflammatory and antioxidant agent. [209]
Antioxidant activity of Zingerone
DPPH
(2,2-diphenyl-1-picryl-hydrazyl) is a chemical compound composed of free
radical molecules. DPPH is used for study on antioxidant assay. Depending upon
the dose administered, zingerone displays its antioxidant activity and protects
DNA. In one study, at a concentration of 500 μg/mL the DPPH radical scavenging activity
of zingerone was found to be 86.7 percent. Stannus chloride (SnCl2)
is another chemical used to induce oxidative stress in experimental studies. In
another study zingerone at concentrations of 500 and 750 μg/mL conferred
protection against Stannus chloride (SnCl2)-induced oxidative damage
to DNA. Zingerone also offered protection to DNA against ultra violet (UV) rays
and hydrogen peroxide (H2O2), a known reactive oxygen
species (ROS) generating system. [210]
Peroxynitrite
is sometimes called peroxonitrite. In the laboratory peroxynitrite can be
prepared by treating acidified hydrogen peroxide with a solution of sodium
nitrite. Peroxynitrite is a potent oxidizing agent. [211]
Peroxynitrite modifies proteins by
oxidizing them. These modifications of proteins can change physical and
chemical properties of proteins culminating in cellular and tissue damage. Peroxynitrite
is able to break DNA strand and it can react with DNA. A study revealed that
zingerone has scavenging effect against peroxynitrite formed from the reaction
of superoxide and nitric oxide inducing cellular and tissue damage. [212]
Immunomodulatory activity of Zingerone
Recently zingerone is reported to be
immunostimulant and immunity enhancer. [213]
In an experimental study on white shrimp (Litopaenaeus vannamei juveniles), the
animals were fed with diet enriched with zingerone at doses of 1, 2.5 and
5mg/kg body weight. After 56 days, shrimp (Litopaenaeus
vannamei juveniles) fed on
zingerone supplement had greater weight, had higher survival rates, increased
phenoloxidase levels and could resist the pathogen Vibrio alginolyticus, a Gram-negative marine bacterium. Researchers
feel, in shrimp (Litopaenaeus vannamei juveniles), the
use of zingerone as appetizer and immunostimulant is promising. [214]
Antibacterial
activity of Zingerone
Opportunistic pathogen Pseudomonas aeruginosa produces
surface-associated communities called biofilms, which protect the pathogen by
forming a complex permeability barrier for antibiotics and immune cells.
Biofilm formation results in persistent chronic infection caused by Pseudomonas aeruginosa. This compels
clinicians to use various antibiotics to treat this pathogen which culminated
in the emergence of multiple drug-resistant strains of Pseudomonas aeruginosa. A study showed that zingerone could inhibit
formation of biofilm and increase the susceptibility of the pathogen to
ciprofloxacin. This suggests that zingerone can be used as an adjunct to
antibiotic therapy. [215]
Escherichia
coli is the commonest organism causing
diarrhea in children. Its enterotoxin is more detrimental. Enterotoxin can
cause infant death. Both zingerone extracted from Ginger (Zingiber officinale) and chemically synthesized zingerone
derivatives can significantly suppress enterotoxigenic Escherichia coli diarrhea. [216]
Antiviral
activity of Zingerone
Anti-inflammatory and antioxidant
properties of zingerone can exhibit antiviral activity
Antifungal activity of Zingerone
Zingerone displays antifungal
activity against some pathogenic fungi such as Aspergillus flavus that produces afflatoxin, Aspergillus niger that rots peanuts, pistachios, hazelnuts, walnuts,
coconut and copra, cereals and oil seeds, onions, dried and smoked fish etc.;
and some candida species. [217]
Actions of Zingerone on
the skin
Nowadays X-rays, gamma rays, infrared rays, ultra violet rays are
used for diagnostic and therapeutic purposes. Radiation therapy leads to
oxidative stress in organs. Radiation causes formation of reactive oxygen
species (ROS) which damages organs. Via its strong antioxidant activity
zingerone has been found to neutralize radiation-induced reactive oxygen
species (ROS) and free radicals. Reactive oxygen species (ROS) activates Bax
protein that is responsible for radiation-induced apoptosis. [218], [219]
Actions of Zingerone on Hematopoetic System
Zingerone displayed
anti-platelet aggregation activity in mice. It reduced activated partial
thromboplastin time but did not prolong bleeding time in mice. [220]
Actions of Zingerone on Nervous
System
The
vanilloid receptor agonist compound zingerone from Ginger (Zingiber officinale) possessed anticonvulsant and analgesic
activity. [221]
The neuronal mitochondria succumb to
ischemia-reperfusion injury. Ischemia-reperfusion injury of the nervous system
releases huge amount of reactive oxygen species (ROS). This oxidative stress
induces programmed cell death (apoptosis) of neurons. To evaluate the effect of
zingerone on ischemia-reperfusion-induced oxidative stress and subsequent
neuronal cell death, brain infarct was created in rats by occluding right
middle cerebral artery (RMCA). The maximum infarct volume was 43.29% and
maximum mitochondrial damage was 56.99%. However, oral administration of
zingerone at 50 and 100mg/kg bodyweight twice a day at 5 and 12 hours from
initiation of middle cerebral artery ligation showed a significant reduction in
infarct volume and mitochondrial injury (<0 .001="" activity="" also="" and="" animals.="" antioxidant="" behavior="" biochemical="" by="" furthermore="" histological="" in="" mitigated="" neurons="" o:p="" of="" penumbral="" result="" salvaged="" significantly="" studies.="" subsequently="" supported="" the="" this="" was="" zingerone="" zone.="">
Anti-inflammatory and antioxidant
activities of zingerone can arrest or delay Alzheimer’s disease. [223]
Progressive degeneration of
dopaminergic neurons in the neurostrial system and dopamine depletion in the
striatum results in the development of Parkinson’s disease (PD). The
antioxidant, free radical scavenging activity of zingerone prevents the
development of Parkinson’s disease. [224]
In an experimental study human
neuroblstoma cell lines SH-SY5Y, BE (2) C and BE (2)-M17 were treated with
zingerone for 24 to 48 hours. The results showed that the growth of BE (2)-M17
cells was significantly reduced. This suggests zingerone can be a potentially
effective agent for the treatment of neuroblastoma. [225]
Actions of Zingerone on
Cardiovascular System
Recently,
a study on rats showed that by virtue of its antioxidant property, zingerone
protects the myocardium against the isoproterenol-induced myocardial
infarction. [226]
Zingerone
reduces the catalase activity, normalizes the angiotensin receptor1 expression.
Zingerone protects the heart from diabetes related inflammations. Zingerone
alleviates the delayed repolarization and AV conduction in diabetes. Zingerone
also protects the heart from diabetes induced cardiac fibrosis. [227]
Actions of Zingerone on Respiratory
System
Microparticles
(MP) are phospholipid vesicles. Upon activation or at apoptosis cells shed
microparticles. Monocyte-derived microparticles (MP) are involved in the
synthesis of pro-inflammatory mediators (cytokines) by lung epithelial cells. In
Vitro studies showed that zingerone inhibited cytokine expression induced
by lipopolysaccharide (LPS). Zingerone attenuated lipopolysaccharide (LPS)
induced pulmonary inflammation. Zingerone attenuated lipopolysaccharide (LPS)
induced pulmonary edema in murine acute lung injury model. [228]
Actions of Zingerone on Gastro-intestinal
System
Vomiting
is the major side effect which hampers chemotherapy in cancer patients. Apart
from newer synthetic antiemetics, phytochemicals from Ginger (Zingiber officinale) come for rescue.
They are potent natural antiemetic agents. Zingerone is one such antiemetic
agent. The anti-serotonin receptor effect of zingerone exerts antiemetic
effect. It acts as a noncompetitive antagonist to 5-hydroxytryptamine-3
(5-HT-3) receptors. [229]
Acute
diarrhea is a leading cause of mortality in pediatric patients and young adult
individuals particularly during epidemics. The important organism causing
enteric infection is Escherichia coli (E. coli). The organism releases
enterotoxins which cause motility disturbances in the intestinal tract. The
mechanisms involved in diarrhea are bacterial infection, inflammation of the
intestines, abnormalities of intestinal motilities, secretory abnormalities and
osmotic disturbances. Studies on mice have shown that zingerone has the ability
to inhibit enterotoxins released by Escherichia
coli (E. coli). Zingerone
corrects motility disorders of gastro-intestinal tract caused by Escherichia coli (E. coli) infection. [230], [231]
Interstitial
cells of Cajal (ICCs) are the pacemaker cells responsible for slow waves in the
gastrointestinal (GI) tract. Depending upon the dose and the concentration in
Ginger (Zingiber officinale) extract,
zingerone inhibited pacemaker potentials of interstitial cells of Cajal (ICCs).
This suggests that zingerone may have the potential for development as gastrointestinal
(GI) tract regulating agent. [232]
To
study the efficacy of various drugs for the treatment of colitis, by using 2,
4, 6-trinitrobenzenesulpfonic acid (TNBS) colitis is induced in mice. In one
study colitis was induced in mice. Subsequently the animals were treated with
Ginger (Zingiber officinale) extract
and zingerone. The results showed that Ginger (Zingiber officinale) extract and zingerone regulated cytokine
related pathways and ameliorated colitis. [233]
Actions of Zingerone on Liver
Alcoholic
liver disease is a direct result of hepatic insult. Moreover alcohol-induced
hepatotoxicity implies the ability of the organ for regeneration. A study on
rats showed that anti-inflammatory and antioxidant properties of zingerone
protected the liver from alcohol-induced liver injury. Some researchers believe
that zingerone can be useful for the treatment of alcoholic liver disease (ALD)
[234]
In
another study, researchers induced liver injury in mice by using
lipopolysaccharide (LPS). The animals were treated with zingerone. The results
showed that anti-inflammatory activity of zingerone was useful for the
treatment of lipopolysaccharide (LPS)-induced liver damage. [235]
Actions of Zingerone on Metabolism
A
study on ovariectomized (Ovx) rats showed that oral administration of 170 mg/kg
bodyweight of zingerone significantly reduced bodyweight. Zingerone also
increased norepinephrine-induced lypolysis in adipocytes. Zingerone also
prevented fat storage. [236]
Actions of Zingerone against
diabetes
I
rats, zingerone normalized the elevated blood sugar in streptozotocin
(STZ)-induced diabetes. [237]
Antitumor activity of Zingerone
Angiogenesis
is essential for tumor survival and tumor progression. Zingerone inhibits the
formation of microvessels inside tumors. In mice, by suppressing angiogenesis,
zingerone suppresses tumor growth and tumor progression. This suggests that
zingerone can be a potential therapeutic agent for the treatment of various
human cancers. [238]
[246]
et al, Zingerone (Ginger Extract): Antioxidant Potential for Efficacy in Gastrointestinal and Liver Disease, Gastrointestinal Tissue, Chapter 21, 2017, Pages 289-297
β-Bisabolene
Molecular
formula: C15H24
Structural
formula
[239]
Bisabolenes are a group
of compounds classified as sequiterpenes. They are present in essential oils of
a wide variety of plants. They are produced by several fungi. The role of
bisabolenes in fungi is unclear. Bisabolenes have balsamic odor. It is a
natural sweetener. It is approved in Europe as a food additive. [240]
β-Bisabolene and its
alcoholic analogue, α-bisabolol display cytotoxic activity for cancer cells of
mouse IC50 and human breast cancer cells IC50. In vitro and in vivo β-Bisabolene
and α-bisabolol induce apoptosis in breast cancer cells. [241]
During the experiments
investing the effects on CNS it was found that 100 and 200 mg/kg bodyweight of β-Bisabolene
showed anti-inflammatory effect both in
vitro and in vivo. [242]
Zingiberene
Molecular
formula: C15H24
Structural
formola:
Zingiberene is a
monocyclic sesquiterpene. This compound gives Ginger (Zingiber officinale) its characteristic flavoring and causes the
fragrance of the spice. [243]
The concentration of
zingiberine is highest in fresh Ginger (Zingiber
officinale) and decomposes on drying and storage. Hence it is preferred to
use fresh rhizome than its dried form, shunthee. [244]
Zingiberene displays
anti-inflammatory and antioxidant activities.
Zingiberene is a potent
anti-rheumatic agent.
Zingiberene shows
antibacterial activity. Zingiberene displays high virucidal activity against
acyclovir resistant herpes simplex virus-1. It protects against dangers caused
by radiation. For this it is used in cosmetic industry.
At 200 mg/kg
bodyweight, zingiberene displayed antiemetic, analgesic and antipyretic
activities.
When treated for twenty
one days, zingiberene restored the elevated blood sugar to normal in diabetic
rats.
After the treatment of
rats for twenty one days, zingiberene lowered the total serum cholesterol
levels from 136.46 to 109.46 mg/dl, elevated the levels of high density
lipoproteins from 41.82 to 65.42 mg/dl and decreased low density lipoprotein
and triglycerides.
Zingiberene inhibits
the viability of breast cancer.
By inhibiting
angiogenesis, zingiberene arrests the growth and proliferation of various cancer
cells.
Lipid peroxidation
causes food spoilage. By preventing lipid peroxidation, at concentration 20 to
100 μg /ml, zingiberene can be used as a natural preservative [245]
Paradol
Molecular
formula: C17H26O3
Structural
formula:
[6]-paradol is a
pungent vanilloid derived from the rhizome of Ginger (Zingiber officinale). This compound can be obtained from Ginger (Zingiber officinale) by dehydration and
hydrogenation. Paradol is responsible for the characteristic pungent taste of
Ginger (Zingiber officinale). Similar
to gingerol and shogaol, paradol has many analogs.
Pharmacology
of Paradol
By inhibiting
Cyclooxygenase-2 (COX-2), [8]-paradol shows anti-inflammatory activity.
Some of the paradols
possess broad spectrum antibacterial and antiviral activity.
In experimental studies
on mice, [6]-paradol displayed DNA protective and anti-cancer activity.
Furthermore paradols show anti-inflammatory, antioxidant, free radical
scavenging, immunomodulatory activities. Paradols suppress angiogenesis,
inhibit growth of tumor cells, spread of tumor cells and prevent formation of
metastases. Paradols are potent chemopreventive agents.
Bode et al reported
that [6]-paradol induced apoptosis in oral squamous cell carcinoma. Paradol and
its derivatives are effective in controlling the gastric, colorectal, ovarian
and prostate cancers. [247]
et al, Zingerone (Ginger Extract): Antioxidant Potential for Efficacy in Gastrointestinal and Liver Disease, Gastrointestinal Tissue, Chapter 21, 2017, Pages 289-297
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proliferator-activated receptor activation by a short-term feeding of zingerone
in aged rats, Journal of Medicinal Food, Volume 12, No. 2, pp. 345-350, 2009
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extract and zingerone ameliorated trinitrobenzene sulphonic acid-induced
colitis in mice via modulation of nuclear factor-κB activity and interleukin-1
β signaling pathway, Food Chemistry,
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protects against stannous chloride-induced and hydrogen peroxide-induced
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production of the flavoring agent Zingerone and both (R)- and (S)- Zingerols
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growth, non-specific immune response and resistance to Vibrio alginolyticus in
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formation and improve antibiofilm efficacy of ciprofloxacin against Pseudomonas aeruginosa PAO1,
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Radiomodifying and anticlastogenic effect of Zingerone on Swiss albino mice
exposed to whole body gamma radiation, Mutation Research/Genetic Toxicology and
Environmental Mutagenesis, vol. 677, no. 1-2, pp. 33-41, 2009
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oxygen species are required for hyperoxia-induced Bax activation and cell death
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[4-(4-hydroxy-3-methoxyphenyl)-2-butenone] and eugenol
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pungent constituents non-competitively inhibit serotonin currents on visceral
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no. 2 pp.149-153, 2014
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