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STUDY OF CHEMICAL COMPOSITION AND MEDICINAL PROPERTIES OF VOLATILE OIL FROM CLOVE BUDS (EUGENIA CARYOPHYLLUS)

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The aim of this study was to analyze the chemical composition of dried clove buds volatile oil in Bangladesh by Gas Chromatography-Mass Spectrometry (GC-MS) technique and also show their medicinal properties according to the characteristics of the constituents present in that essential oil. In this experiment the clove buds essential oil was extracted by hydro distillation method. The major constituents obtained from the oil includes 3-Allyl-6-methoxyphenol i.e. m-Eugenol (69.44%), Eugenol acetate (10.79%), 4-hydroxy-4-mehtylpentan-2-one i.e. Tyranton (7.78%) Caryophyllene (6.80%), 1,4,7-Cycloundecatriene, 1,5,9,9-tetramethyl-,Z,Z,Z-and trace amounts (<1%) of other constituents. Eugenol is present in concentration of 69.43% which is the major volatile constituent of clove bud essential oil. It has wide range of medicinal value such as antiseptic and anaesthetic analgesic, antioxidant, anti-inflamatory and antimicrobial activities. Clove oil is used in dental care and it can relieve toothache temporarily. So, from these chemical constituents it is clear that clove buds essential oil of Bangladesh has medicinal properties because of the medicinal characteristics of these constituents.
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Uddin et al., IJPSR, 2017; Vol. 8(2): 895-899. E-ISSN: 0975-8232; P-ISSN: 2320-5148
International Journal of Pharmaceutical Sciences and Research 895
IJPSR (2017), Vol. 8, Issue 2 (Research Article)
Received on 10 August, 2016; received in revised form, 19 October, 2016; accepted, 03 November, 2016; published 01 February, 2017
STUDY OF CHEMICAL COMPOSITION AND MEDICINAL PROPERTIES OF VOLATILE
OIL FROM CLOVE BUDS (EUGENIA CARYOPHYLLUS)
Md. Azir Uddin 1, Md. Shahinuzzaman * 2, Md. Sohel Rana 3 and Zahira Yaakob 2
Department of Chemical Engineering 1, Z. H. Sikder University of Science and Technology, Shariatpur,
Bangladesh.
Department of Chemical and Process Engineering 2, University Kebangsaan Malaysia, Bangi, Selangore,
Malaysia.
Department of Applied Chemistry and Chemical Technology 3, Islamic University, Kushtia, Bangladesh.
ABSTRACT: The aim of this study was to analyze the chemical
composition of dried clove buds volatile oil in Bangladesh by Gas
Chromatography-Mass Spectrometry (GC-MS) technique and also show
their medicinal properties according to the characteristics of the constituents
present in that essential oil. In this experiment the clove buds essential oil
was extracted by hydro distillation method. The major constituents obtained
from the oil includes 3-Allyl-6-methoxyphenol i.e. m-Eugenol (69.44%),
Eugenol acetate (10.79%), 4-hydroxy-4-mehtylpentan-2-one i.e. Tyranton
(7.78%) Caryophyllene (6.80%), 1,4,7-Cycloundecatriene, 1,5,9,9-
tetramethyl-,Z,Z,Z-and trace amounts (<1%) of other constituents. Eugenol
is present in concentration of 69.43% which is the major volatile constituent
of clove bud essential oil. It has wide range of medicinal value such as
antiseptic and anaesthetic analgesic, antioxidant, anti-inflamatory and
antimicrobial activities. Clove oil is used in dental care and it can relieve
toothache temporarily. So, from these chemical constituents it is clear that
clove buds essential oil of Bangladesh has medicinal properties because of
the medicinal characteristics of these constituents.
INTRODUCTION: Cloves are the aromatic
flower buds of a tree in the family Myrtaceae,
Eugenia caryophyllus. They are native to the
Maluku Islands in Indonesia, and it is mainly used
as a spice. Cloves are commercially harvested
primarily in India, Pakistan, Indonesia,
Madagascar, Zanzibar, Sri Lanka and Tanzania.
But, Indonesia and Madagascar are the main clove
buds oil producer 1.
QUICK RESPONSE CODE
DOI:
10.13040/IJPSR.0975-8232.8(2).895-99
Article can be accessed online on:
www.ijpsr.com
DOI link: http://dx.doi.org/10.13040/IJPSR.0975-8232.8 (2).895-99
There are three types of clove oil; bud oil, leaf oil
and stem oil. Bud oil is derived from the flower-
buds of Eugenia caryophyllus. It contains mainly of
60-90% eugenol, eugenyl acetate, caryophyllene
and other minor constituents. Leaf oil is derived
from the leaves of Eugenia caryophyllus. It consists
of 82-88% eugenol, little amount of eugenyl
acetate, and other minor constituents. Stem oils are
evolved from the twigs of Eugenia caryophyllus.
It consists of 90-95% eugenol, and some other
minor constituents. A major component of clove
taste is imparted by the chemical eugenol. Eugenol
is the component which is most responsible for
clove aroma and comprises 72-90% of the essential
oil extracted from cloves 2.
Keywords:
Clove buds,
Hydro distillation, Essential oil,
Eugenol, Medicinal properties
Correspondence to Author:
Md. Shahinuzzaman
Ph.D researcher
Universiti Kebangsaan Malaysia,
Bangi, Selangor, Malaysia.
E-mail: shahinchmiu@gmail.com
Uddin et al., IJPSR, 2017; Vol. 8(2): 895-899. E-ISSN: 0975-8232; P-ISSN: 2320-5148
International Journal of Pharmaceutical Sciences and Research 896
Other important essential oil constituents of clove
oil are acetyl eugenol, beta-caryophyllene and
vanillin, crategolic acid, tannins such as bicornin 3-
4, methyl salicylate (painkiller), gallotannic acid,
the flavonoidseugenin, rhamnetin, kaempferol, and
eugenitin, triterpenoids such as oleanolic acid,
campesterol and stigmasterol, and several
sesquiterpenes 5-8.
It is now believed to the FDA that there are not
enough evidence indicates clove oil or eugenol is
effective for toothache pain or other types of pain 9.
Studies to determine its effectiveness for fever
reduction, as a mosquito repellent, and to prevent
premature ejaculation have been inconclusive 9-10.
Clove may reduce blood sugar levels but it is not
proven yet and studies going on to determine this.
Furthermore, clove oil is used in preparation of
some Clovacaine solution, and toothpastes which
are the local anesthetic used in oral ulceration and
inflammation. Eugenoland zinc oxide are mixed
together to form a temporary tooth cavity filling.
Clove oil can be used to anesthetize of fish. It also
can be considered as a humane means of euthanasia
with higher doses and the recommended dose is
400 mg/l 11. Eugenol is a colorless or pale yellow
oily liquid which are extracted from different
essential oils especially from clove oil, nutmeg,
basil, cinnamon and bay leaf. In clove bud oil it is
present in concentrations of about 80-90% where
clove leaf contain 82-88% of eugenol. Eugenol is
used as the perfumeries, flavorings, essential oils
and also in the medicine as a local antiseptic and
anaesthetic 12.
Eugenol can be produce zinc oxide eugenol by
mixing with zinc oxide which is used in dentistry
as the restorative and prosthodontics application.
For root canal sealing, zinc oxide eugenol is used.
It is also used in some mousetraps and kills
particular human colon cancer cell lines in vivo and
in vitro 13. Eugenol may have potential therapeutic
effects against diseases characterized by excessive
osteoclast activity 14.
MATERIALS AND METHODS:
Plant materials: Healthy and mature buds of clove
(Eugenia caryophyllus) were purchased from local
market of Kushtia, Bangladesh. The cleaned and
dust free samples were dried in air and at 30°C in a
ventilated drying oven and stored in plastic bags at
ambient temperature. Then the samples were
ground by blender machine into a finely grounded
form (Fig. 1). Exposure to direct sunlight was
avoided to prevent the loss of active components.
FIG. 1: A. DRIED CLOVE BUD, B. GROUNDED CLOVE BUDS POWDER
Essential oil isolation: The dried and ground clove
buds (200 g) were taken in a 2-litre round bottom
flask. Then distilled water was added according to
the ratio 2:1 (400 ml distilled water for 200 g
Uddin et al., IJPSR, 2017; Vol. 8(2): 895-899. E-ISSN: 0975-8232; P-ISSN: 2320-5148
International Journal of Pharmaceutical Sciences and Research 897
ground clove buds) and subjected to hydro
distillation for 3 h using a modified Clevenger type
glass apparatus. The volatile distillate was collected
until no oil drop out. By using anhydrous Na2SO4
the oil was dried and stored in an air tight container
at 2 ºC before GC- MS analysis.
Gas Chromatography-Mass Spectroscopy (GC-
MS) analysis: Essential oil constituents from clove
buds were analyzed by GC-MS. The GC-MS was
carried out using total ion monitoring mode on a
Varian 3800 gas chromatograph interfaced to a
Varian Saturn ion trap 2200 GC-MS spectrometer.
The temperatures of transfer line and ion source
were 280°C and 275°C respectively. Ions were
obtained by electron ionization mode. The VF-5
capillary column (30 m length, 0.25 mm I.D. and
0.25 μm film thickness) was used. A 20% split
injection mode was selected with a solvent delay
time of 3 min with injection volume 0.2 μl.
The initial column temperature was started at 50°C
for 1 min, programmed at 8°C/min to 200°C and
heated until 280°C at 10°C/min. Injection port was
set at 250°C. Helium was used as the carrier gas at
a constant flow rate of 1.0 ml/min. Molecular ions
(mass range: 40-500 m/z) were monitored for
identification. The relative percentage of the oil
constituents was expressed as percentage by peak
area normalization. Identification of components of
the essential oil was based on their retention
indices, relative to a homologous series of n-alkane
(C8 - C20) on the VF-5 capillary column under the
same operating conditions and computer matching
with the GC-MS spectra from the Wiley 6.0 MS
data and literature data 15-16.
RESULTS AND DISCUSSION:
Chemical composition of the essential oil: The
GCMS analysis of clove buds (Eugenia
caryophyllus) essential oil led to identification of
13 different compounds (Fig. 2). The major
compounds are 3-Allyl-6-methoxyphenol; Eugenol
acetate; 2-Pentanone, 4-hydroxy-4-methyl and
Caryophyllene which given in Table 1. The minor
compounds are 1,4,7-Cycloundecatriene, 1,5,9,9-
tetramethyl-,Z,Z,Z-; Toluene; 2-Pentanone-3-
methylene; Copaene; alpha-Farnesene; 2,4,4,6-
Tetramethyl-4,5-dihydro-1,3-oxazine; m-Dioxan-4-
ol, 2,6-diethyl-5methyl acetate and m-Dioxan-4-ol,
2,6-diethyl-5methyl acetate.
FIG. 2: GCMS ANALYSIS OF CLOVE BUDS (EUGENIA CARYOPHYLLUS) ESSENTIAL OIL
TABLE 1.CHEMICAL COMPOSITION OF THE ESSENTIAL OIL OF BUDS FROM EUGENIA CARYOPHYLLUS
Peak no.
Retention time (min)
Name of the compound
Formula
1
3.589
Toluene
C7H8
2
4.134
2-Pentanone-3-methylene
C6H10O
3
4.899
2-Pentanone, 4-hydroxy-4-methyl
C6H12O2
4
5.647
m-Dioxan-4-ol, 2,6-diethyl-5methyl acetate
C11H20O4
5
6.937
2,4,4,6-Tetramethyl-4,5-dihydro-1,3-oxazine
C8H15NO
6
8.322
2,4,4,6-Tetramethyl-4,5-dihydro-1,3-oxazine
C8H15NO
Uddin et al., IJPSR, 2017; Vol. 8(2): 895-899. E-ISSN: 0975-8232; P-ISSN: 2320-5148
International Journal of Pharmaceutical Sciences and Research 898
7
13.675
3-Allyl-6-methoxyphenol
C10H12O2
8
13.973
Copaene
C15H24
9
14.63
Caryophyllene
C15H24
10
15.094
1,4,7-Cycloundecatriene, 1,5,9,9-tetramethyl-,Z,Z,Z-
C15H24
11
15.621
alpha-Farnesene
C15H24
12
15.903
Eugenol acetate
C12H14O3
13
16.823
Caryophyllene oxide
C15H24O
Determination of medicinal properties:
According to the chemical composition of the
essential oil of Eugenia caryophyllus given
in Table 1, it has been seen that thirteen major
constituents are present in that sample. For analysis
of medicinal values, the essential constituents are
m-Eugenol i.e. 3-Allyl-6-methoxyphenol (69.43%),
Eugenol acetate (10.78%), Caryophyllene (6.80%),
2-Pentanone (7.78%) etc. Eugenol is present in
concentration of 69.43% which is the major volatile
constituent of clove bud essential oil. It has wide
range of medicinal value such as antiseptic and
anaesthetic 12 analgesic, antioxidant, anti-
inflammatory and antimicrobial activities. Clove oil
is used in dental care. It can relieve toothache
temporarily 17. As an important ingredient, it is
used in manufacturing some toothpastes, mouth
wash and oral care medications. To relieve general
pain and skin problem clove oil is used. Clove oil is
also used in the treatment of fever, headache,
cough, asthma, indigestion, depression etc.
CONCLUSION: The chemical composition of
dried clove bud in Bangladesh was investigated.
The essential oil composition was identified by Gas
Chromatography- Mass Spectrometry (GC-MS)
technique and also showed their medicinal
properties according to the characteristics of the
constituents present in the essential oil. In this
experiment the clove buds essential oil was
extracted by hydro distillation method. The major
constituents obtained from the oil includes 3-Allyl-
6-methoxyphenol i.e. m-Eugenol (69.44%) and
Eugenol acetate (10.79%) which have wide range
of medicinal values such as antiseptic and
anaesthetic, analgesic, antioxidant, anti-inflamatory
and antimicrobial activities.
ACKNOWLEDGEMENT: We are grateful to the
Islamic University, Kushtia, Bangladesh and
BCSIR for providing research facilities. This study
also would not have been possible without the
cooperation of the researchers of Living lab, Kuala
pilah, UKM, Malaysia.
CONFLICT OF INTEREST: Authors have no
conflict of interest.
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How to cite this article:
Uddin MA, Shahinuzzaman M, Rana MS and Yaakob Z: Study of chemical composition and medicinal properties of volatile oil from
clove buds (Eugenia caryophyllus). Int J Pharm Sci Res 2017; 8(2): 895-99.doi: 10.13040/IJPSR.0975-8232.8(2).895-99.
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Chapter
Syzygium aromaticum (clove), a taxon of dicotyledonous plants, is a dried, unopened flower bud that belongs to the family Myrtaceae. It is one of the most valuable and second most crucial spice crops in world trade. Since ancient times, cloves have been used in the dental care system as an analgesic and antiseptic agent. The United States Food and Drug Administration listed clove oil as “Generally Regarded as Safe” for human consumption. Cloves essential oil can be obtained from buds, leaves, and plant stem, which differ in their color, flavor, and chemical composition. Good-quality clove essential oil is obtained from buds that are yellow and denser than water. The bud oil is dominated by eugenol, eugenol acetate, β-caryophyllene, and α-humulene. The composition of clove essential oil may vary depending upon genetic factors, climatic conditions, and cultivation techniques. Clove oil has various biological properties such as anti-inflammatory, anesthetic, antimicrobial, antifungal, antiviral, leishmanicidal, antioxidant, anticancer, nematicidal, herbicidal, acaricidal, and larvicidal. Hence, clove essential oil is considered the most valuable natural resource with immense medicinal properties and is considered one of Mother Nature’s exclusive gifts to humankind.
Chapter
Oleoresin is a mixture of volatile and nonvolatile components available in whole extract of natural herb or spice. It principally comprises essential oils and resin. Lemongrass oleoresins come from the Cymbopogon species, which grow in the tropical and subtropical regions of the world. Oleoresin of lemongrass is a dark green-colored viscous liquid having a characteristic lemon aroma and flavor and is mostly used as a flavoring ingredient. The lemon prefix in the lemongrass specifies the characteristic lemon-like odor, which is due to the availability of citral content (mixture of two isomeric aldehydes, geranial and neral). It has been utilized in synthesizing flavors, perfumes, cosmetics, detergents, and in the food and pharmaceutical industries. Different methods are used to extract the lemongrass essential oil, but steam distillation is the most suitable method as it doesn’t alter the quality of the obtained oil. The chemical composition of lemongrass oil varies depending on its extraction methods, genetic differences, harvest period, photoperiod, plant age, farming practices, and geographical origin. Lemongrass essential oil has shown several biological activities, including antimicrobial, antifungal, antiprotozoan, antioxidant, antidiarrheal, antimutagenic, antiinflammatory, antimalarial, antinociceptive, antihepatotoxic activities, etc. Lemongrass oil is a potent food preservative because of its extraordinary antifungal and antibacterial activities.
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Objective: To evaluate the antibacterial activity of essential oil from Trigonella foenum-graecum seeds powder, and identify the compounds from the extracted oil. Methods: The seeds powder of Trigonella foenum-graecum was subjected to Clevenger extractor. Seven strains of bacteria were used to test antibacterial activity of the extract. The activity against bacteria was tested by disk diffusion method using Whatman No. 1 filter paper. Gas chromatography mass spectrometry analysis was performed with an Agilent7890/5975B-gas chromatography/mass selective detector. Results: The hydrodistillation of seeds powder yielded 0.285% (v/w) of oil. Disk diffusion of the oil showed bactericidal activity against both Gram negative and Gram positive bacteria of tasted strains. The inhibition zone ranged from (8 ± 0) mm to (15.0 ± 0.7) mm depending on microbial strains. Gas chromatography mass spectrometry analysis showed 14 different compounds. The total compounds represented 80.96% of the oil. Conclusions: The antibacterial activity is due to the effects of different biological active compounds present in the extract. Identification of the compounds may help to develop new effective antimicrobial agent(s). Further researches on purification, characterization and toxicology of the active compounds are needed.
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Medicinal plants are generating an ever-increasing amount of interest due to the effectiveness, low cost and minimal side-effects associated with drugs derived from them. Clove (Syzygium aromaticum (L.) (Family Myrtaceae) is one of the most important herbs in traditional medicine, having a wide spectrum of biological activity. Phytoconstituents of clove comprise of various classes and groups of chemical compounds such as monoterpenes, sesquiterpenes, phenolics and hydrocarbon compounds. The major phytochemicals found in clove oil is mainly eugenol (70-85%) followed by eugenyl acetate (15%) and β-caryophyllene (512%). Their derivatives result in biological benefits such as antibacterial, antifungal, insecticidal, antioxidant, anticarcinogenic capacities. In addition to clove oil’s worldwide use as a food flavoring agent, it has also been employed for centuries as a topical analgesic in dentistry. This review presents an overview and details of the phytochemical and pharmacological investigations on the S. aromaticum.
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Though kitchen spices constitute an important source of dietary antioxidants, their consumption at a physiologically relevant dose is very often hampered by their unpleasant flavour characteristics. The present paper describes a novel approach to derive stable de-flavoured spice extracts with minimised taste and odour profiles which are suitable for impregnation into a variety of food and beverage matrices at physiologically relevant doses. A popular kitchen spice, clove bud (Syzygium aromaticum L), having strong flavour and pungency characteristics was selected in the present study to derive a de-flavoured extract with a standardised polyphenolic profile (Clovinol) and was incorporated into various foods. The antioxidant efficacy of Clovinol on healthy human volunteers who check and answer official emails involving responsibility was investigated by analysing their endogenous antioxidant enzymes and the extent of lipid peroxidation upon consumption of Clovinol either as capsules or in a different food/beverage at 250 mg per serving per day for 30 days. It was observed that Clovinol can be conveniently incorporated in various food matrices without flavour issues and the consumption of such food/beverage items may support an effective detoxification process with an average elevation of 33 ± 3% in catalase, 66 ± 8% in SOD, 56 ± 5% in GPx and 167 ± 21% in GSH levels, and 81 ± 11% attenuation in membrane lipid peroxidation level.
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Syzygium aromaticum essential oil is widely used in dental care, as an antiseptic and analgesic and is effective against a large number of bacteria. The major component of clove essential oils is usually considered to be eugenol, with β-caryophyllene and eugenyl acetate, being present although in lower concentrations. A review of published results reveals a great variability in the chemical composition of clove essential oils. The purpose of this study is to compare the chemical composition of Madagascar, Indonesia and Zanzibar bud, leaf and stem essential oils. 121 commercial essential oils isolated from bud, leaf and stem were used in this work. The oils were analyzed by GC and ten constituents were identified from the whole. The major constituent of Madagascar and Indonesia bud essential oils was eugenol (72.08 – 80.71% and 77.32 – 82.36% respectively). Out of this constituent which was common to Madagascar and Indonesia bud essential oils, significant difference was observed with respect to eugenyl acetate (11.68 – 21.32% vs 8.61 – 10.55% respectively) and β–caryophyllene (2.76 – 6.38% vs 5.34-8.64% respectively). Comparing chemical composition of leaf essential oils from Madagascar with those of Indonesia, variation in the contents of main constituent, eugenol (80.87 – 83.58% vs 75.04 – 77.54%), β-caryophyllene (11.65 – 15.02 vs 17.04 – 19.53%) and eugenyl acetate (0.29 – 1.45% vs 0-0.06%) was observed. The major constituents of Madagascar, Indonesia and Zanzibar stem essential oils were eugenol (91.81-96.65%, 88.76-89.28% and 87.52-89.47%, respectively) and β-caryophyllene (1.66-4.48%, 7.40-7.75% and 7.19-9.70%). For each plant material, variation in the percentage of the main constituents was observed according to the sample geographic origin.
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Clove (Syzygium aromaticum) is one of the most valuable spices that has been used for centuries as food preservative and for many medicinal purposes. Clove is native of Indonesia but nowadays is cultured in several parts of the world including Brazil in the state of Bahia. This plant represents one of the richest source of phenolic compounds such as eugenol, eugenol acetate and gallic acid and posses great potential for pharmaceutical, cosmetic, food and agricultural applications. This review includes the main studies reporting the biological activities of clove and eugenol. The antioxidant and antimicrobial activity of clove is higher than many fruits, vegetables and other spices and should deserve special attention. A new application of clove as larvicidal agent is an interesting strategy to combat dengue which is a serious health problem in Brazil and other tropical countries. Pharmacokinetics and toxicological studies were also mentioned. The different studies reviewed in this work confirm the traditional use of clove as food preservative and medicinal plant standing out the importance of this plant for different applications.
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This reference work provides a wealth of information regarding medicinal plants and phytochemicals. It is addressed both to researchers and teachers. The handbook describes phytochemicals, which, by the strictest definition, are chemicals that are produced by plants. During the last decades, more and more groups became actively involved in exploring plants for useful metabolites that lead to the identification of several useful curative agents and many promising molecules to fight and/or prevent diseases, including carcinogenesis and stroke. But when we talk about phytochemicals, there are also medicinal plants where not a single molecule is responsible for the observed properties. This reference work therefore reviews and compiles the information on both these aspects. The volumes contain contributions on phytochemicals and herbal extracts. A large number of natural products obtained from plants and microorganisms is used in cosmetic, drug, flavor and fragrance industries. For this compilation, a range of the most important medicinal herbs and phytochemicals were selected and are described by the recognized authors in the field. The present reference work encompasses the information about well established phytochemicals, biology and biotechnology of medicinal plants or their products, their biosynthesis, novel production strategies, demand and uses, metabolism and bioavailability. There is a surge of information published in recent years on herbal medicine and their pharmacologic effects with single books available on varied subjects. However, all this information is widespread and difficult to overview. Researchers who wish to keep a pace with the rapidly developing field of natural products can now consult this newly compiled handbook to find all information about bioactive molecules and medicinal plants thoroughly compiled in one place!
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Despite the various reports on the pharmacology of Clove bud [Syzygium aromaticum]-derived essential oil and its major component eugenol, systematic informations on the bioactivity of clove polyphenols is very much limited. Being one of the richest sources of dietary polyphenols with many traditional medicinal uses, the present contribution attempted to derive standardized polyphenol-rich extracts of clove buds (Clovinol) as water soluble free flowing powder suitable for functional food applications, without having the issues of characteristic pungency and aroma. The extract was characterized by electrospray ionization-time of flight mass spectrometry (ESI-TOF-MS), and investigated for in vivo antioxidant, anti-inflammatory and anti-ulcerogenic activities. Clovinol showed significant antioxidant and anti-inflammatory effects as measured by cellular antioxidant levels, and the ability to inhibit the carrageenan-induced paw swelling in mice. Further investigations revealed its significant anti-ulcerogenic activity (> 97% inhibition of ethanol-induced stomach ulcers in Wistar rats when orally administered at 100 mg kg- 1 b.w.) and up regulation of in vivo antioxidants such as superoxide dismutase (SOD), glutathione (GSH), and catalase (CAT). Clovinol also reduced the extent of lipid peroxidation among ulcer induced rats, indicating its usefulness in ameliorating the oxidative stress and gastrointestinal health, especially upon chronic alcohol consumption. The extract was also shown to be safe and suitable for further investigations and development upon acute toxicity studies at 5 g kg-1 body weight and 28-days of repeated dose toxicity studies at 2.5 g kg-1 b.w.
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Abstract Bone loss diseases are often associated with increased receptor activator of NF-κB ligand (RANKL)-induced osteoclast formation. Compounds that can attenuate RANKL-mediated osteoclast formation are of great biomedical interest. Eugenol, a phenolic constituent of clove oil possesses medicinal properties; however, its anti-osteoclastogenic potential is unexplored hitherto. Here, we found that eugenol dose-dependently inhibited the RANKL-induced multi-nucleated osteoclast formation and TRAP activity in RAW264.7 macrophages. The underlying molecular mechanisms included the attenuation of RANKL-mediated degradation of IκBα and subsequent activation of NF-κB pathway. Furthermore, increase in phosphorylation and activation of RANKL-induced mitogen-activated protein kinase pathways (MAPK) was perturbed by eugenol. RANKL-induced expression of osteoclast specific marker genes such as TRAP, cathepsin K (CtsK), and matrix metalloproteinase-9 (MMP-9) was remarkably downregulated by eugenol. These findings provide the first line of evidence that eugenol mediated attenuation of RANKL-induced NF-κB and MAPK pathways could synergistically contribute to the inhibition of osteoclast formation. Eugenol could be developed as therapeutic agent against diseases with excessive osteoclast activity.
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Eighteen hydrolysable tannins, including a new C-glucosidic tannin named aromatinin A (1), were isolated from an aqueous acetone extract of dried flower buds of Syzygium aromaticum Merr. et Perry. We determined that 1 had a gallic acid C-glucoside structure, based on the spectral data and synthesis from casuarinin (18) and gallic acid (20). This is a rare example of hydrolysable tannins with gallic acid C-glucoside structure. We also report the 1H nuclear magnetic resonance (NMR) spectral features of syzyginin A (2), bicornin (3), and platycaryanin A (4), which were also isolated from S. aromaticum, based on their structures with a tergalloyl group or its depsidone form. The remaining known compounds were identified as alunusnin A (5), rugosin C (6), 1,2,3-tri-O-galloyl-β-D-glucose (7), 1,2,3,6-tetra-O-galloyl-β-D- glucose (8), tellimagrandin II (9), casuarictin (10), heterophylliin D (11), rugosin D (12), rugosin F (13), euprostin A (14), 1,2-di-O-galloyl-3-O- digalloyl-4,6-O-(S)-hexahydroxydiphenoy- β-D-glucose (15), alienanin B (16), squarrosanin A (17), and 18. The antifungal effects of hydrolysable tannins, 9, 12, and 18 against Candida strains are also described.