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SCIENTIFIC NAME:
Eugenia sp.
COMMON NAME:
clove
  Evidence for Efficacy (Human Data)
   Clinical Trials  (3)
   Observational Studies/Case Reports  (1)
   Ethnobotanical Use  (5)
 Warnings
   Adverse Effects & Toxicity   (35)
   Interactions   (0)
   Contraindications   (2)
  Methods of Preparation
   Contemporary Standardized Methods  (1)
   Folk Methods  (7)
 Formulas/Blends
   Contemporary Formulas   (5)
   Folk Blends   (0)
  Evidence of Activity
   Pharmacodynamics  (43)
   Animal Studies  (15)
   Analytical Chemistry  (20)
   Pharmacokinetics (ADME)  (0)
   Genetics & Molecular Biology  (3)
 Other Information
   Pictures & Distribution Maps   (3)
   Cultivation, Conservation & Ecology   (4)
   Related Links   (6)
  Dynamic Updates
   Live PubMed Searches  (14)
  History of Records
   History of Record (1)
EVIDENCE FOR EFFICACY (HUMAN DATA)
 
Clinical Trials
  Stimulation of human olfactory epithelium with clove oil produces depolarization of 12.3 mV Monti-Bloch 1991
  Sweetening spices studied on 70 adults found cinnamon, vanilla, spearmint & anise to be more comparable to sugar than nutmeg, ginger, cloves, bay, and salt Blank 1990
  Dry socket treated with a specially formulated collagen paste was more effective than a treaditional method of zinc oxide/oil of cloves, with less pain and reaction Mitchell 1986
Observational Studies/Case Reports
  Mosquito bite was not prevented at 5 or 10% concentration of oils of geranium, cedarwood, clove, peppermint or thyme. Thyme and clove oils were the most effective repellents Barnard 1999
Ethnobotanical Use
  "In pursuit of palliation: oil of cloves in the art of dentistry " (historical, no abstract) Curtis 1990
  Eugenia uniflora is widely used in Paraguayan folk medicine for treating gout. Xanthine oxidase is inhibited by the quercitrin, quercetin, myricitrin and myricetin of the leaves Schmeda-Hirschmann 1987
         Eugenia in "A Modern Herbal" by Mrs. M. Grieve (Botanical.com)
         Eugenia in Cornell Ethnobotanical Database (EthnobotDB)
         Eugenia in Native American Food Plants Database (FoodplantDB)
WARNINGS
 
Contraindications
  Of 29 patients allergic to balsam of Peru, 5 had positive patch test with cinnamon and 17 to clove Niinimaki 1995
  Sensitivity to clove oil was common among 22 patients with dermatitis from propolis Rudzki 1983
Adverse Effects & Toxicity
  "Link between clove cigarettes and urticaria? " (no abstract) Pallares 1999
  Keratitis or uveitis were induced by intrastromal injection of clove oil in rabbits Palmero 1999
  "Occupational allergic contact dermatitis from eugenol, oil of cinnamon and oil of cloves in a physiotherapist " (no abstract) Sanchez-Perez 1999
  A specific pattern of dental decay in 1160 male bus drivers in Indonesia grows with number of years of clove cigarette smoking to 89% after 15 years Soetiarto 1999
  Of 1000 dermatology patients, 5 had occupational (food handling) allergy to spices, including garlic, cinnamon, ginger, allspice and clove. Although rare, it should not be overlooked Kanerva 1996
  4 microliters eugenol, i.v., caused acute respiratory distress with hemorrhagic pulmonary edema in rats. Superoxide dismutase pretreatment decreased the protein content Wright 1995
  Zinc-eugenol root canal sealer is toxic to fibroblasts when fresh and not after setting for a day. Substituting eugenol with higher fatty acids & glycol reduced toxicity Araki 1994
  Among 55 contact dermatitis patients none were allergic to clove or basil Futrell 1993
  A case of coma and liver damage from ingesting oil of cloves, similar to paracetamol poisoning and treated likewise Hartnoll 1993
  Case of an infant with intravascular coagulation & hepatocellular necrosis, following ingestion of clove oil. Treatment with heparin,plasma coagulation factor and inhibitor concentrates Brown 1992
  Inflammation induced by clove oil or arachidonic acid was reduced by ibufenac, ibuprofen, and their hydroxyethoxy analogs in the rabbit eye Rao 1992
  Allergy to spices among 28 processing workers appears to be proportional to the pungency of the spice Uragoda 1992
  "American Academy of Pediatrics Committee on Substance Abuse: Hazards of clove cigarettes " (no abstract) AAP 1991
  "American Academy of Pediatrics Committee on Substance Abuse: Hazards of clove cigarettes " (no abstract) AAP 1991
  Case of an infant with CNS depression, urinary abnormalities and a large anion-gap acidosis after the accidental oral administration of clove oil Lane 1991
  Lung edema was caused by infusing eugenol (0.1 & 1.0 mM) into isolated rabbit lungs McDonald 1991
  "Non-cardiogenic pulmonary oedema due to the intravenous administration of clove oil " (no abstract) Kirsch 1990
  Allergy testing 32 dermatitis patients found sensitivity to nutmeg (28%), paprika (19%), or cloves (12%) van den Akker 1990
  Allergy testing 32 dermatitis patients found sensitivity to nutmeg (28%), paprika (19%), or cloves (12%) van den Akker 1990
  Yeast assays shows mutagenicity of safrole & eugenol while the Ames assay does not Schiestl 1989
  N2O can suppress chemotaxis of PMNs in the cornea of rabbits injured by clove oil Kripke 1987
  Some central nervous system activity in hippocratic screening when Eugenia uniflora is given i.p., but little to no acute or subacute toxicity up to 4200 mg/kg orally in mice. LD50 of the extract was 220 mg/kg i.p. in mice Schmeda-Hirschmann 1987
  Clove oil irritation of the eye is reduced by chromocarb diethylamine Lapalus 1986
  Clove, Jamaica pepper and cinnamon were the spices giving the most positive skin patch tests among 118 people allergic to balsam of Peru Niinimaki 1984
  "Contact dermatitis to lilly pilly (Eugenia Smithi): report of a case " (no abstract) Rosner 1984
  "Permanent local anaesthesia and anhidrosis after clove oil spillage " (no abstract) Isaacs 1983
  11,632 patch tests with eugenol containing products showed only two cases of hypersensitivity Rothenstein 1983
  Essential oils and safrole-like compounds had only slight and mixed evidence of mutagenicity in sensitive microbe reversion assays Sekizawa 1982
  Prednisolone reduces the uveitis induced by clove oil in rabbit eyes Bolliger 1980
  "Evaluation of possible mutagenicity of the condiment clove when administered alone or in combination with caffeine in Drosophila melanogaster " (no abstract) Abraham 1978
  Myeloperoxidase activity in rabbit eyes in response to clove oil Williams 1982
         Latest FDA Adverse Events Reports on eugenia OR cloves
         Toxicity of eugenol at NIEHS/NIH
         Carcinogenesis Studies of Eugenol; at NIEHS/NIH
         Toxicology and Carcinogenesis Studies of Methyleugenol; at NIEHS/NIH
Interactions
No Records
 
METHODS OF PREPARATION
 
Contemporary Standardized Methods
         Apparatus for processing whole dried cloves; US Patent 5,323,791
Folk Methods
  Radioactive 137-Cs was highest in clove and black pepper out of 38 food items in Brazil Venturini 1999
  The mixing behaviour of plant oils (ricebran, saffola & clove) with water in presence of amphiphiles (Triton X-100, Tween-60, oleate, ethanol & cinnamic alcohol). Urea further increased the monophasic extent whereas NaCl decreased it Mitra 1996
  Ethylene oxide, used for spice storage & disinfection, quickly vaporizes off but there is persistent 2-chloroethanol Chaigneau 1993
  "Decontamination of spices by ethylene oxide. The case of cloves (Eugenia caryophyllus Spreng.) and white pepper " (French, no abstract) Muraz 1985
  "Action of clove oil, eugenol, and zinc-oxide eugenol paste on the dental pulp within "in vitro" conditions " (Croatian, no abstract) Stojicevic 1980
  Analytical methods for the determination of components of seasonings Salzer 1977
  Extraction of light filth from whole, cracked, or flaked spices by solvents & flotation Glaze 1975
FORMULAS/BLENDS
 
Contemporary Formulas
         Reducing desire for tobacco by a mixture of oil of cloves, oil of wintergreen, monosodiumglutamate, extract of evodia fruit, and extract of Sichuan Lovage Rhizome applied to certain specific acupuncture points; US Patent 5,592,956
         Insecticide for beetles composed of 50-90% boric acid, 1-15% sugar and 1-15% cloves and corn starch; US Patent 5,223,270
         Mixture of dry alum powder and powdered cloves for the treatment of gum diseases; US Patent 4,495,171
  "Zinc oxide-oil of cloves or zinc oxide-eugenol? " (German, no abstract) Gulzow 1981
  Imperviousness comparison of the materials Dycal, guttapercha, Reocap and zince oxide-oil of cloves for teeth Mayer 1978
Folk Blends
No Records
 
EVIDENCE OF ACTIVITY
 
Analytical Chemistry
  Derivatizing alcohols and phenols of oil of cloves, lemon oil, rose absolut, and oil of peppermint with ferroceneoyl azide for electrospray-tandem mass spectrometry Quirke 2000
  Nutritional composition of Rumex sp., Amaranthus quitensis & Taraxacum officinale leaves; Morrenia, Passiflora & Eugenia fruits; and Typha domingensis pollen Rozycki 1997
  Eugenol determination by GC-FID Myint 1996
  Quercetin and myricetin 3-O-beta-D-xylopyranosyl(1-->2) alpha-L-rhamnopyranosides isolated from the leaves of Eugenia jambos Slowing 1994
  Glutathione S-transferase in mouse liver and small intestine induced by Beta-caryophyllene, beta-caryophyllene oxide, alpha-humulene, alpha-humulene epoxide and eugenol (sesquiterpenes from Eugenia caryophyllata (Clove) Zheng 1992
  Beta-caryophyllene, beta-caryophyllene oxide, alpha-humulene, alpha-humulene epoxide & eugenol (sesquiterpenes from Eugenia caryophyllata (Clove) which induce glutathione S-transferase in mouse liver & small intestine Zheng 1992
  "Volatile constituents of Eugenia uniflora leaf oil " (no abstract) Weyerstahl 1988
  Nutrient content of spices. Celery seed, cumin, coriander leaf, dill weed, cloves & parsley flakes--were very high in sodium (3 to 9 mg. per 2 gm) Murphy 1978
  Spectrophotometric assay of thyme and clove oils El-Sayed 1976
  "The isolation and structural characterization of 5-O-methyldesmethoxymatteucinof from Eugenia javanica " (no abstract) Mitscher 1973
  "Studies on the components of essential oil of clove " (Japanese, no abstract) Deyama 1971
  "Determination of eugenol in the essence of "Eugenia caryophyllata". Titration in non-aqueous solvent and comparison with other methods of analysis " (Italian, no abstract) Covello 1966
         Molecular structure of eugenol at ChemExper
         Properties of eugenol at NIEHS/NIH
         Molecular structure of eugenol at NIST Chemistry WebBook
         Genus : Eugenia in PhytochemDB
         Material Safety Data Sheet of eugenol at PulpDent.com
         Plant biosynthesis of eugenol and isoeugenol at Purdue University
         Molecular structure of eugenol at Sigma-Aldrich
         Molecular structure of eugenol at WebMolecules
Pharmacodynamics
  Of the spices tested only garlic and clove had antimicrobial activity Arora 1999
  Inhibition of Bacillus subtilis, E. coli & S. cerevisiae by clove, cinnamon, bishop's weed, chilli, horse raddish, cumin, tamarind, black cumin, pomegranate seeds, nutmeg, garlic, onion, tejpat, celery, cambodge for food preservation De 1999
  Helicobacter pylori inhibition by Coptidis japonica (rhizoma), Eugenia caryophyllata (flower), Rheum palmatum (rhizoma), Magnolia officinalis (cortex) and Rhus javanica Bae 1998
  Aeromonas hydrophila and Listeria monocytogenes are inhibited by eugenol (clove extract) and pimento extract Hao 1998
  Microbial inhibition with Pelargonium essential oils was comparable with that of commercial thyme, clove, geranium and coriander oils Lis-Balchin 1998
  Oils of bay, cinnamon, clove and thyme were the most antimicrobial (concentration under 0.075%) against Campylobacter, Salmonella, E coli, Staphylococcus aureus and Listeria Smith-Palmer 1998
  Gram negative Pseudomonas & Serratia and gram-positive Brochothrix, Carnobacterium, Lactobacillus & Lactobacillus bacteria are most inhibited by essential oils of clove, cinnamon, pimento, and rosemary Ouattara 1997
  Concentration-dependent relaxation of aorta rings pre-contracted with noradrenaline by Eugenia uniflora alcoholic extract, IC50 = 7 mg/L. Relaxation is inhibited by nitric oxide synthase inhibitors Wazlawik 1997
  Existing agar-cup or disc diffusion methods are not adequate to study the antibacterial activity of aromatic oils due to lack of ideal diffusion. Agar slant method found Thymus vulgaris more effective than Eugenia, Cinnamonum or Cuminum Agnihotri 1996
  Cinnamon and clove essential oils have strong activity against HEp-2 cells in vitro Saenz 1996
  Cinnamon and clove inhibited histamine production and histidine decarboxylase activity of Morganella morganii (bacteria in fish). Turmeric and cardamom had a moderate effect and pepper was ineffective Shakila 1996
  Aflatoxin production on lentils inhibited by Chinese cassia, cinnamon, clove and thyme El-Maraghy 1995
  Herpes and bacterial inhibition by Polynesian folk medicines, Scaevola sericea, Psychotria hawaiiensis, Pipturus albidus & Eugenia malaccensis Locher 1995
  Ginger, pepper, pippali and mustard increased the number of revertants in a sensitive Salmonella assay indicating their mutagenic potential. Garlic, Asafoetida, tumeric, curcumin & eugenol were protective Soudamini 1995
  Tobacco-induced mutagenicity is inhibited by eugenol, Anacyclus pyrethrum extract or Spilanthes calva extract Sukumaran 1995
  Staphlococcus aureus is inhibited by Eugenia caryophyllata flowers, Myristica fragans seeds, Theobroma cacao bark, Triticum fruit, Zea mays fruit and Piper nigrum ripe fruit Perez 1994
  Superoxide anion generation by XO and Fenton reaction are inhibited by curcumin and eugenol Reddy 1994
  Clove oil inhibited human platelet aggregation induced by arachidonic acid, platelet-activating factor or collagen Saeed 1994
  Local anesthetics such as cocaine, ethyl chloride spray, tropocaine and Nupercaine, are composed of an aromatic portion, intermediate chain and an amide portion Wicker 1994
  Anti-mold activity of cinnamaldehyde and clove oil Zhang 1994
  Aflatoxin and sterigmatocystin production by Aspergillus is inhibited by cumin, onion and clove oils Hasan 1993
  Superoxide radicals were inhibited by zingerone from ginger, linalool from coriander, eugenol and cumin but not by piperine nor tumeric Krishnakantha 1993
  Dermatophyte fungi were inhibited by the oils of Cinnamomum zeylanicum, Ocimum gratissimum, Cymbopogon citratus, Eugenia uniflora and Alpinia speciosa Lima 1993
  0.2% Agar suspension was sufficient to obtain a stable dispersion of oregano and clove essential oils in liquid media and was more toxic to microbes indicating that studies using solvent dispersion underestimate antibiotic activity Remmal 1993
  Leukemia virus reverse transcriptase is inhibited by 125 micrograms/ml of hot-water extracts of Eugenia caryophyllus, Phyllanthus urinaria, Terminalia belerica, Nelumbo nucifera, Psidium guajava and Lawsonia inermis Suthienkul 1993
  Adriamycin induced lipid peroxidation in liver and heart microsomes is inhibited by oleanolic acid from Eugenia jumbolana (49 and 21%) and ursolic acid from Ocimum sanctum (13 and 17%) Balanehru 1992
  Fungistatic effects of clove and peppermint oils el-Naghy 1992
  Polyunsaturated fatty acids (PUFA) oxidation by liver microsomes inhibited by zingerone from ginger at high concentrations (over 150 microM), curcumin (5-50 microM), turmeric & eugenol (25-150 microM), cloves and capsaicin (25-150 microM) Reddy 1992
  Lipid peroxidation induced by ascorbic acid, carbon tetrachloride or ADP/Iron in isolated rat liver microsomes is inhibited by ursolic acid from Ocimum sanctum (90%) and oleanolic acid from Eugenia jumbolana (60%) Balanehru 1991
  Pseudomonas aeruginosa culture is strongly inhibited by cinnamon; somewhat by anise, chloroform or rose; not by clove, dill or peppermint; and growth is enhanced by lemon Ibrahim 1991
  Apple pie spice, cinnamon, cloves, bay leaves, and turmeric increased insulin activity more than three-fold in the rat epididymal fat cell assay Khan 1990
  Germicidal effect against various bacteria and Candida albicans by essential oil of clove, dispersed (0.4% v/v) in a concentrated sugar solution Briozzo 1989
  Oral bacterial tests against Streptococcus, Actinomyces, Actinobacillus, Bacteroides, Capnocytophaga, Eikenella, Fusobacterium and Propionibacterium show inhibition by cinnamon bark oil, papua-mace and clove bud oil Saeki 1989
  Myeloperoxidase from human PMNs, catalyzed the oxidation of eugenol to a reactive intermediate, which is likely to be a quinone methide Thompson 1989
  Antimicrobial activity of Thymus vulgaris, Ocimum gratissimum, Eugenia caryophyllata, Melaleuca viridiflora, Helichrysum sp., Psiadia altissima Ramanoelina 1987
  Arachidonic acid induced platelet aggregation inhibition by clove oil is mediated by reduced formation of thromboxane Srivastava 1987
  8 yeasts are more sensitive to essential oils (allspice, cinnamon, clove, garlic, onion, oregano, savory, and thyme) after sub-lethal heat stress Conner 1984
  Cholagogue effect by acetone extract of clove and eugenol Yamahara 1983
  Aspergillis fungus growth is inhibited best by cinnamon and clove, weakly by mustard, caraway seed, or celery seed. Aflatoxin production is inhibited by thyme and oregeno Llewellyn 1981
  Aspergillus inhibition by 29 spices: cloves, star anise seeds and allspice completely inhibited fungal growth, whereas most others inhibited only toxin production. Eugenol (cloves) and thymol (thyme) completely inhibited growth at 0.4 mg/ml or less Hitokoto 1980
  Aflatoxin inhibition by black pepper, cinnamon, peppermint, cumin, ginger and clove Mabrouk 1980
  [The bacteriology of dry socket: the effect of zinc oxide and oil of cloves.] MacGregor 1970
         Search for eugenol at NIH
Pharmacokinetics (ADME)
No Records
 
Genetics & Molecular Biology
  16S rRNA gene sequences for Burkholderia, a bacterial disease of bananas and Pseudomonas syzygii, the cause of Sumatra disease of cloves Taghavi 1996
  Acetylcholine esterase inhibition by Eugenia caryophyllus water, saline and ethanol extracts Akinrimisi 1976
  Hydrolysis of acetylcholine by the esterase is inhibited by aqueous extract of Eugenia caryophyllus Akinrimisi 1975
Animal Studies
  Plasma glucose rise during oral glucose tolerance test in mice was inhibited by EtOH extracts of Eugenia uniflora leaves. Failure on i.p. test indicates inhibition of glucose absorption from the intestine Arai 1999
  Blood pressure of normotensive rats was decreased dose-dependently by aqueous crude extract of Eugenia uniflora. ED50=3.1 mg dried leaves/kg (yielding 17% w/w extract), believed due to a direct vasodilating activity Consolini 1999
  Co-administration of urethane with extracts vegetables (carrot, spinach and cabbage), spices (cinnamon, pepper, cumin, clove and cardamom), tea and coffee and effect on glutathione S-transferase (GST) activity Abraham 1998
  CCl4 induced hepatotoxicity in rats is reduced by eugenol. It also showed anti-peroxidative activity in addition to decrease in O2 formation Krishnaswamy 1998
  Curcumin from turmeric (30 mg/kg body weight) or eugenol from cloves (100 mg/kg body weight), for 10 days lowered the liver and serum lipid peroxide levels, serum ALAT, ASAT and LDH, induced by iron in rats Reddy 1996
  Increased gastrointestinal absorption of water by leaves of Psidium guajava, Polygonum punctatum, Eugenia uniflora (Surinam cherry) or Aster squamatus indicating antidiarrhoeal value Almeida 1995
  Superoxide and hydrogen peroxide release by macrophages is reduced by capsaicin or curcumin (10 microM), eugenol or piperine (500 microM). Capsaicin and curcumin fed rats had lower radical levels Joe 1994
  Anti-inflammatory effect when Eugenia uniflora infusion of fresh leaves was given p.o. to rats 1 h before carrageenin. The infusion increased pentobarbital sleeping time and had an effect on intestinal transit, without acute toxic effect Schapoval 1994
  Anti-inflammatory activity (both acute and chronic phases) by Eugenia jambos extracts equivalent to 12.5 g/kg of dried leaf material Slowing 1994
  Glutathione S-transferase, cytochrome b5 and sulfhydryl increased and cytochrome P-450 & malondialdehyde decreased in mice fed cloves at 0.5%, 1% and 2% Kumari 1991
  [Eugenia uniflora leaf extract and lipid metabolism in Cebus apella monkeys.] Ferro 1988
  Eugenol was more effective in reducing fever than acetaminophen in rabbits induced by IL-1 Feng 1987
  Tiger Balm Red (menthol, camphor, 5% clove, cajuput, 5% cassia oils) is more irritating than Tiger Balm White (no cassia oil and 2% clove oil) on rabbit skin Guppy 1982
  [Action of a hypoglycemic agent found in the young bark of Eugenia jambolania(Myrtacea) on induced hyperglycemia of the rabbit and continuation of its purification]. Ratsimamanga 1973
  [Hypoglycemic effects of Rotra (Eugenia jambolona Lamarck) on the rabbit with alloxan diabetes]. Randriamampandry 1972
OTHER INFORMATION
 
Pictures & Distribution Maps
         US distribution of genus Eugenia at BONAP
         Eugenia at TAMU-BWG Digital Library
         Picture of Eugenia uniflora at University of Hawaii
Cultivation, Conservation & Ecology
         Eugenia luschnathiana (Pitomba) at Purdue University
         Eugenia uniflora (Surinam Cherry)at Purdue University
         Description and cultivation of Eugenia brasiliensis at Purdue University
         Eugenia stipitata at Purdue University
Related Links
         Eugenia at Germplasm Resources Information Network (GRIN)
         Habitat information in Ecosys
         Clove at Herbs and Aromas
         Description, usage and cultivation at Plants For A Future
         Cloves at Symmetry Corporation
         Description and picture by L. Watson and M. J. Dallwitz at The Families of Flowering Plants
DYNAMIC UPDATES
 
Live PubMed Searches
  Eugenia and Analytical Chemistry
  Eugenia and Animal Studies
  Eugenia and Case Reports
  Eugenia and Clinical Trials
  Eugenia and Drug Interactions
  Eugenia and Ethnobotanical Use
  Eugenia and Genetics
  Eugenia and In Vitro Studies
  Eugenia and Pharmacokinetics
  Eugenia and Reference Standards
  Eugenia and Therapeutic Activity
  Eugenia and Tissue Culture
  Eugenia and Toxicology
  Eugenia Preparations and Formulary

HISTORY OF RECORD
RESEARCHED BY: Soaring Bear, Ph.D.    May 2000
EDITED BY: Michael C. Tims    May 2000
 
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