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<strong>International</strong> <strong>Journal</strong> <strong>of</strong> <strong>Research</strong> in Pharmaceutical and Biomedical Sciences ISSN: 2229-3701<br />
__________________________________________Review Article<br />
<strong>Eugenia</strong> <strong>caryophyllata</strong> <strong>Thunberg</strong> (Family Myrtaceae): A Review<br />
Jitender Singh*, Anupama Baghotia and SP Goel<br />
Sachdeva College <strong>of</strong> Pharmacy, Gharuan, Mohali, Punjab, India.<br />
__________________________________________________________________________________<br />
ABSTRACT<br />
<strong>Eugenia</strong> <strong>caryophyllata</strong> <strong>Thunberg</strong>, belongs to family Myrtaceae, commonly known as clove, is an aromatic tree,<br />
native to Indonesia and used as a spice in cuisines in many parts <strong>of</strong> the world. Clove has been traditionally used<br />
from ancient times in the treatment <strong>of</strong> roundworms and tapeworms, asthma, toothache, soar throat, dental,<br />
respiratory disorders, digestive system ailments, dyspepsia, gastritis, diarrhea, as antipyretic, aphrodisiac,<br />
carminative, appetizer, expectorant, antiemetic, anxiolytic, myorelaxant, analgesic, decongestant, antiinflammatory,<br />
hypnotic, vermifuge, antibacterial agent etc. Clove is widely used in Indian Ayurvedic<br />
medicines, Chinese medicines, Unani medicines <strong>of</strong> Asian countries and Western herbal medicines. <strong>Research</strong> on<br />
clove has been done on a larger level in many parts <strong>of</strong> the world. Eugenol is the main constituent in essential<br />
oil <strong>of</strong> clove, which is responsible for its medicinal properties to larger extent. In view <strong>of</strong> its importance, it is<br />
worthwhile to compile a review article, which serves the needs <strong>of</strong> scientists and others involved in the<br />
medicinal plant research.<br />
Key Words: Clove, <strong>Eugenia</strong> <strong>caryophyllata</strong>, Myrtaceae, Eugenol.<br />
INTRODUCTION<br />
The genus <strong>Eugenia</strong> is one <strong>of</strong> 75 genera (~3000<br />
species) belonging to the family Myrtaceae which<br />
is native in the tropics, particularly in tropical<br />
America as well as Australia and plants <strong>of</strong> this<br />
family are known to be rich in volatile oils which<br />
are reported for their medicinal importance. Genus<br />
<strong>Eugenia</strong> has properties like anti-inflammatory,<br />
analgesic, antipyretic 1,2 , antifungal 3 and used in<br />
peptic ulcer treatment 4 .<br />
Syzygium aromaticum (Linn.) Merr. & L.M. Perry<br />
(Syn. <strong>Eugenia</strong> aromatica) Kuntze, <strong>Eugenia</strong><br />
<strong>caryophyllata</strong> <strong>Thunberg</strong>, belongs to family<br />
Myrtaceae, commonly known as clove, is an<br />
aromatic tree, native to Indonesia and used as a<br />
spice in cuisines in many parts <strong>of</strong> the world 5,6,7 . It is<br />
grown naturally in Moluku Islands <strong>of</strong> Indonesia<br />
and cultivated in many parts <strong>of</strong> the world like<br />
Tanzania, Madagascar, Sri Lanka, India, China,<br />
Indonesia, Malaysia, Brazil, Malagasy Republic,<br />
Jamaica and Guinea 8,9 . It is an ever-green plant <strong>of</strong><br />
10 to 20 m in height with spear-shaped leaves and<br />
racemiferous yellowish flowers, has a strong<br />
phenolic smell and sharp acrid taste, whereas,<br />
essential oil <strong>of</strong> clove is a colorless or light<br />
yellowish fluid extracted from dried flower buds.<br />
Flower buds collected twice a year, in the months<br />
<strong>of</strong> October and February when they change color<br />
from green to crimson, dried carefully and<br />
separated from their peduncles. Clove is broadly<br />
used in cooking (biryanis, salads, pickles and<br />
garam masala), pharmacy, perfumery and<br />
cosmetics.<br />
Vernacular Names<br />
Arabic: Kabsh qarunfil, Kabsh quaranful;<br />
Bulgarian: Karamfil; Chinese: Ding xiang; Danish:<br />
Nellike; French: Gir<strong>of</strong>lier; German: Nelke; Greek:<br />
Garifalo; Georgian: Mikhaki, Mixaki; Indian:<br />
Laung, Clove; Indonesian: Cengke; Italian: Chiodo<br />
di garifano; Japanese: Garifla, Choji, Kurobu;<br />
Korean: Jeonghyang; Nepalis: Lewaang;<br />
Portuguese: Cravo de India; Persian: Mikhak;<br />
Pasto: Kala; Russian: Gvosdika, Shambala;<br />
Spanish: Clovo, Clovo de olor; Swedish:<br />
Kryddnejlika, Nejlikor; Turkish: Caranfil; Thai:<br />
Khan plu, Garn ploo; Vienamese: Ding huong 10 .<br />
Description<br />
The <strong>Eugenia</strong> <strong>caryophyllata</strong> tree is an evergreen<br />
tree, which grows to a height ranging from 10-20<br />
m. Flower buds are first <strong>of</strong> a pale color and<br />
gradually become green after which they develop<br />
into dark brown or dusty red. Flower buds are<br />
generally 10-17.5 mm in length and consist <strong>of</strong> a<br />
sub-cylindrical, slightly flattened, four sided<br />
hypanthium. Upper portion <strong>of</strong> hypanthium consists<br />
<strong>of</strong> two celled inferior ovary with numerous ovules<br />
attached to an axile placenta, surmounted by four<br />
thick, divergent sepals and covered by unopened<br />
corolla consisting <strong>of</strong> four membranous imbricate<br />
petals, frequently detached, enclosing numerous<br />
incurved stamens, odor, strongly aromatic; taste,<br />
pungent, aromatic followed by slight tingling <strong>of</strong> the<br />
tongue 11 .<br />
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<strong>International</strong> <strong>Journal</strong> <strong>of</strong> <strong>Research</strong> in Pharmaceutical and Biomedical Sciences ISSN: 2229-3701<br />
Identity, Purity and Strength<br />
The Ayurvedic Pharmacopoeia <strong>of</strong> India listed the<br />
standards <strong>of</strong> clove as Foreign matter Not more than<br />
2 per cent, Total ash Not more than 7 per cent,<br />
Acid-insoluble ash Not more than 1 per cent,<br />
Alcohol-soluble extractive Not less than 3 per cent,<br />
Water-soluble extractive Not less than 9 per cent,<br />
Volatile oil Not less than 15 percent 11 .<br />
ETHANOPHARMACOLOGY<br />
In British Columbia, Flower <strong>of</strong> Clove is widely<br />
used in the treatment <strong>of</strong> roundworms and<br />
tapeworms in pets and pigs 12 whereas, flower bud<br />
<strong>of</strong> E. <strong>caryophyllata</strong> has been used as traditional<br />
medicine for the treatment <strong>of</strong> asthma and various<br />
allergic disorders; as vermifuge, antibacterial agent<br />
and in toothache in China, Japan and Korea 13,14 .<br />
The flower bud is a well known food flavor for<br />
exotic food preparations and a popular remedy for<br />
headache, soar throat, dental and respiratory<br />
disorders, digestive system ailments, in traditional<br />
medicines <strong>of</strong> Australia and Asian countries 8,13,15,16 .<br />
In addition, the clove is widely used as traditional<br />
medicine for treatment <strong>of</strong> dyspepsia, gastritis and<br />
diarrhea; as antipyretic, aphrodisiac, appetizer,<br />
expectorant, antiemetic, anxiolytic, myorelaxant,<br />
analgesic, decongestant, anti-inflammatory and<br />
hypnotic 17,18,19,20 . Clove is widely used in Indian<br />
Ayurvedic medicines, Chinese medicines, Unani<br />
medicines <strong>of</strong> Asian countries and Western herbal<br />
medicines and considered as warm, aromatic, to<br />
fortify the kidney yang (hypochlorhydria),<br />
carminative, in toothache, as aphrodisiac and in the<br />
treatment <strong>of</strong> male sexual disorders 15,21,22 .<br />
Clove oil has been used to improve peristalsis, as<br />
anodyne, in anaesthesia and is said to be a natural<br />
anthelmintic 23,24,25,26 . Due to its frequent use in<br />
teeth problems, it is widely used as an ingredient in<br />
popular toothpastes and mouth fresheners in<br />
India 27 . Clove is broadly used in cooking, food<br />
processing, pharmacy, perfumery and cosmetics.<br />
PHARMACOLOGICAL UPDATE<br />
Several studies have been reported on clove as a<br />
potent antifungal 28,29,30,31,32,33,34,35,36 , antiviral (such<br />
as Herpex simplex, Hepatitis C virus) 37,38,39 ,<br />
antiseptic and antibacterial effect against several<br />
bacteria including Escherichia coli, Helicobacter<br />
pylori, Staphylococcus aureus etc.<br />
25,30,40,41,42,43,44,45,46,47,48 .<br />
Mishra and Singh has demonstrated the biphasic<br />
nature <strong>of</strong> hexane extract <strong>of</strong> flower buds on testis.<br />
The lower dose (15 mg/kg) increased testosterone<br />
production, while higher doses (30 and 60 mg/kg)<br />
caused reduction in testosterone production thereby<br />
perturbation in spermatogenesis <strong>of</strong> mice 49 . In<br />
addition, the clove is antimutagenic 50 , antiinflammatory<br />
13 , antiulcerogenic 42,45 ,<br />
antithrombotic 5 and antiparasitic 51 .<br />
The essential oil <strong>of</strong> this plant has been proved<br />
efficacious repellency on the mosquitoes Ades<br />
aegypti, Culex quinquefasciatus and Anopheles<br />
dirus 52 , insecticidal activity on Pediculus capitis 51<br />
as well as acaricidal activity against<br />
Dermatophagoides farinae and D. pteronyssinus 14 .<br />
It is also effective against Psoroptes cuniculi, a<br />
mange mite 53 and possesses anti-inflammatory,<br />
cytotoxic, anesthetic and antimicrobial properties.<br />
It is commonly associated with dental caries and<br />
periodontal disease 25,39 .<br />
Sesquiterpenes, found in clove, were investigated<br />
as potent anticarcinogenic agents 9 . Eugenol, the<br />
major aromatic constituent <strong>of</strong> clove oil, has been<br />
reported to have a variety <strong>of</strong> different applications,<br />
e.g. as an antioxidant 54,55,56,57,58,59 , antimycotic 60,61 ,<br />
antibacterial 62,63 , antifungal 64 , participates in<br />
photochemical reactions 65 , as insecticidal 66 , in<br />
photocytotoxicity 67 and also as an additive used in<br />
certain cigarettes 68,69 .<br />
It has been reported that eugenol at low<br />
concentration acts as an antioxidant and antiinflammatory<br />
agent, whereas its higher<br />
concentrations act as a pro-oxidant resulting from<br />
the enhanced generation <strong>of</strong> tissue-damaging free<br />
radicals 70,71 and it induced apoptosis <strong>of</strong> human<br />
cancer cells 72 . It also prevents the transmission <strong>of</strong><br />
HSV-2 in a mouse model <strong>of</strong> intra vaginal HSV-2<br />
challenge and was found to give protection in<br />
guinea pig model <strong>of</strong> HSV 73 . It has been reported<br />
that the essential oil <strong>of</strong> clove has anticonvulsive<br />
effect in tonic seizures but not in colonic seizures<br />
in mice 74 and produces a sustained increase in the<br />
mounting frequency <strong>of</strong> normal male rats and<br />
mice 21,75 . On the other hand, Eugenol, a chief<br />
constituent <strong>of</strong> clove oil, causes desquamation <strong>of</strong> the<br />
inner secretory columnar cell layer and exerts<br />
adverse effects on secretory activity <strong>of</strong> seminal<br />
vesicle 76 , spermicidal activity on ejaculated human<br />
spermatozoa 77 and possesses significant antiinflammatory<br />
activity at 0.025 mL/kg 78 .<br />
It has been reported that eugenol at various<br />
concentrations 5, 10, 50 and 100 µM exhibited a<br />
remarkable DPPH free radical scavenging potential<br />
and showed the cytotoxic effect. The IC50 values<br />
<strong>of</strong> eugenol were reported to be 700 µM in HepG2<br />
cells; 1000 µM in Caco-2 cells and 700 µM in<br />
VH10 cells. The terpenes, beta-caryophyllene,<br />
beta-caryophyllene oxide, alpha-humulene, alphahumulene<br />
epoxide I and eugenol isolated from<br />
essential oil <strong>of</strong> <strong>Eugenia</strong> <strong>caryophyllata</strong> induce<br />
glutathione S-transferase enzyme which plays a<br />
vital role in detoxification in liver and intestines 79 .<br />
It is stated that induction <strong>of</strong> glutathione Stransferase<br />
inhibits chemical carcinogens, hence<br />
these terpenes are promising anticarcinogens 9 .<br />
However, clove oil is toxic to human cells 26 . If<br />
ingested or injected in large quantity, it has been<br />
shown to cause life threatening complications,<br />
including Acute Respiratory Distress Syndrome,<br />
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<strong>International</strong> <strong>Journal</strong> <strong>of</strong> <strong>Research</strong> in Pharmaceutical and Biomedical Sciences ISSN: 2229-3701<br />
Fulminant Hepatic Failure and Central Nervous<br />
System disorder. The lethal oral dose <strong>of</strong> clove has<br />
been reported as 3.752 g/Kg body weight 80,81 and<br />
the median lethal dose <strong>of</strong> <strong>Eugenia</strong> <strong>caryophyllata</strong><br />
and its etheric oil were reported as 0.613 mL/kg<br />
and 0.863 mL/kg in mice respectively 82 .<br />
PHYTOCHEMISTRY<br />
Many <strong>Eugenia</strong> species were reported as a good<br />
source <strong>of</strong> polyphenols, gallic and ellagic acid<br />
derivatives 83,84 , tannins 85,86 and flavonol<br />
glycosides 1,2,86,87,88 .<br />
<strong>Eugenia</strong> <strong>caryophyllata</strong> is a rich source <strong>of</strong> essential<br />
oil. It contains 15-20% essential oil, 13% tannins,<br />
10% fixed oil and 6-12% non-essential ether<br />
extract. Essential oil <strong>of</strong> clove is a colorless or light<br />
yellowish fluid, a distillate <strong>of</strong> dried flowers, stalks<br />
and leaves 7,89 . Several constituents <strong>of</strong> clove oil<br />
have been identified but eugenol (C10H12O2),<br />
eugenyl acetate and β-caryophyllene represent the<br />
major components <strong>of</strong> the oil. Eugenol (4-allyl-2methoxyphenol),<br />
makes up 70 to 90% by<br />
weight 90,91 , eugenol acetate (> 17%) and cari<strong>of</strong>ilen<br />
(> 12%), β-caryophyllene (9%), 1,8-Cineole<br />
(0.1%), Linalool (0.2%), α-Copaene (1.2%), α-<br />
Humulene (3.5%), β-Cadinene (0.5%),<br />
Epizonarene (0.1%), α -Muurolene (0.1%),<br />
Eugenyl acetate (4.2%), δ-Cadinene (3.6%), αcopaen<br />
(1.0%), methoxy benzaldehyde, benzyl<br />
alcohol, benzaldehyde, carvacrol, 2-heptanone,<br />
methyl salicylate, isoeugenol, methyl eugenol,<br />
phenyl propanoides, dehydrodieugenol, transconfireryl<br />
aldehyde, biflorin, kaempferol,<br />
rhamnocitrin, myricetin, gallic acid, ellagic acid,<br />
oleanolic acid, thymol, cinnamaldehyde, acetyl<br />
salicylate, vanillin, and crategolic acid. It has been<br />
reported that clove also contains tannins<br />
(gallotannic acid), flavonoids (eugenin, rhamnetin,<br />
and eugenitin), triterpenoids (oleanolic acid,<br />
stigmasterol and campesterol) 6,7,9,25,39,51,53,78,92,93 .<br />
The characteristic smell and taste <strong>of</strong> clove oil is due<br />
to the presence <strong>of</strong> a wide range terpene<br />
compounds 94,95 .<br />
CONCLUSION<br />
Clove is a medicinally important drug, reported to<br />
have a variety <strong>of</strong> different applications like<br />
antioxidant, antifungal, antiviral, antibacterial, antiinflammatory,<br />
antithrombic, antipyretic, analgesic,<br />
anticonvulsant, antimycotic, insecticidal,<br />
antimutagenic, antiulcerogenic etc. Eugenol is the<br />
main constituent reported to be responsible for<br />
these activities. There is a great scope for<br />
researchers to develop efficacious formulations<br />
using clove or eugenol. This review will be helpful<br />
to the future researchers for the up-to-date<br />
information on clove.<br />
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