A Review Of The Important Chemical Constituents And .
A review of the important chemical constituents and medicinal uses of Vitex genus / Asian Journalof Traditional Medicines, 2011, 6 (2)ReviewsA review of the important chemical constituents andmedicinal uses of Vitex genusAjay Kumar Meena a *, U. S. Niranjan b, M. M. Rao a, M. M. Padhi c, Ramesh Babu ca. National Institute of Ayurvedic Pharmaceutical Research, Patiala–147001, Punjab, Indiab. School of Pharmaceutical Sciences, Shobhit University, Meerut, UP, Indiac. Central Council for Research in Ayurveda and Siddha, Janakpuri, Delhi-110058, India.AbstractPlants and their active constituents play an important role in the prevention of a variety of ailments. Most of the species of theGenus Vitex are used therapeutically in ancient Indian systems of medicine especially, Ayurveda and Siddha. The genus Vitexcontains about 270 species distributed around the world. These species contain a variety of potentially bioactive molecules, suchas iridoids, flavonoids, diterpenoids, derivatives, and phytosteroids. Most of these species possess analgesic, anti-inflammatory,antimicrobial, antioxidant, hepatoprotective, antihistamine, and antiasthmatic properties. This work reviews the pharmacologicalevidence for the effects of extracts of plants from the genus Vitex, giving an overview of the most widely studied biological effectsand the known phytochemical constituents.Key words: medicinal plants; pharmacology; phytochemistry; indian systems of medicine1. Introductionshrubs in tropical and sub-tropical regions, althougha few species are also found in temperate zones.In recent times, interest in plant research hasincreased all over the world owing to its potential usein traditional systems of medicine for treating a widevariety of diseases. Various medicinal plants havebeen identified and modern scientific approacheshave been used to study their authenticity, safetyand efficacy of their therapeutic use. The resultshighlight the great potential of medicinal plants inthe field of pharmacology. The genus Vitex includesapproximately 270 known species of trees and* Author to whom correspondence should be addressed. Address:National Institute of Ayurvedic Pharmaceutical Research, Patiala147001, Punjab, India; Tel.: 919779953364; E-mail: ajaysheera@gmail.comReceived: 2010-03-26Accepted: 2011-01-1554Vitex trifolia L. is a shrub or shrubby tree thatmay grow up to 6 meters in height. Its origin isunknown and several varieties have been describedin countries as are apart as India and Mexico. Vitexmollis, Vitex piramidata, Vitex pubescens, Vitexagnus-castus and. Vitex gaumeri are reported topossess antidysentery, analgesic, anti-inflammatoryand anti-tumor activities and they are used in folkmedicine for the treatment of scorpion stings andgastrointestinal disorders. In the Ayurveda and Unanisystems of medicine, the leaves [1] and seeds ofVitex negundo are widely used for the treatment ofrheumatism and inflammatory joint conditions. InIndia, the species Vitex glabrata, Vitex leucoxylon,Vitex penduncularis, Vitex pinnata, and Vitex trifoliaare found to have insecticidal properties. Vitex
A review of the important chemical constituents and medicinal uses of Vitex genus / Asian Journalof Traditional Medicines, 2011, 6 (2)negundo has larvicidal activity against the mosquitospecies Culex quinquefasciatus and Anophelesstephensi and is used as a mosquito deterrent againtAedes aegypti and Vitex rotundifolia also acts asdeterrent against Aedes aegypti. Several other Vitexspecies are currently being investigated for use inspecific pest control programs [2].dichloromethane, ethyl acetate and methanol) andthe oil. As expected, the total phenolics contentwas very high in this extract. The dichloromethaneextract has been found to be rich in flavonoids anda positive correlation has been found between theantioxidant activity potential and the total phenolicand flavonoid contents of the extracts [5].2. Species of the genus VitexFrom the fruits, one new diterpene, 6β,7β-diacetoxy-13-hydroxy-labda-8, 14-diene, as wellas two previously described diterpenes, rotundifuranand vitexilactone, have been isolated. All thediterpenoids obtained are of the labdane type.Structural determinations were mainly based on 1Dand 2D NMR spectra and MS data interpretation.The compounds, 6β, 7β-diacetoxy-13-hydroxylabda-8, 14-diene and rotundifuran, showed ahigh affinity for dopamine-D 2-receptors [6]. Thecompound vitexilactone was isolated from theleaves of Vitex cannabifolia and the fruits of Vitexrotundifolia Linn. All the physical and spectroscopicdata were identical to those of rotundifuran describedin the literature.2.1. Vitex agnus-castusVitex agnus-castus L. (Verbenaceae) is a smalltree or shrub which is widely distributed along theAnatolian coast line and is used in the treatmentof premenstrual problems and hyperprolactinemia.In Anatolian folk medicine, it is used as a diuretic,digestive, antifungal, and anxiolytic agent. Thisplant exhibits a number of activities such as anaction against P388 leukemia cells, inhibition ofprolactin synthesis and an inhibitor for dopamine D2and opiod receptors. The antiepileptic activity of thehydrophilic extract of the fruit has been evaluatedusing the kindling model of epilepsy. It containsiridoids flavonoids diterpenoids, essential oils andketosteroids [3]. The methanolic extract of theflowering stems of Vitex agnus-castus contains threenew iridoids: 6’-O-foliamenthoylmussaenosidic acid(agnucastoside A), 6’-O-(6, 7- dihydrofoliamenthoyl)mussaenosidic acid (agnucastoside B) and ganic acid(agnucastoside C) in addition to four known iridoids(aucubin, agnuside, mussaenosidic acid and 6’-O-phydroxybenzoylmussaenosidic acid) and one knownphenylbutanone glucoside (myzodendrone) [4]. Thedried ripe fruit of Vitex agnus-castus L. is widelyused for the treatment of premenstrual syndrome.Major components of the essential oil are 1,8-cineole, sabinene, a-pinene, a-terpinyl acetate and(Z)-β-farnesene. In all systems, the aqueous extractexhibited greater activity than other extracts (hexane,A novel labdane diterpene alkaloid, vitexlactamA, was isolated in the form of prisms from then-hexane extract of the fruits through normal andreverse phase column chromatography. Its structurewas shown to be 6β-acetoxy-9α-hydroxy-13(14)labden-16, 15-amide, based on chemical and spectralevidences, including 1D and 2D NMR spectra. Thestructure was confirmed by X-ray crystallographicanalysis. The compound, vitexlactam A, is the firstnaturally occurring labdane diterpenoid containingan α, β-unsaturated γ-lactam moiety [7].Four new flavonoids, luteolin 6-C-(4”-methyl-6”-O-trans-caffeoylglucoside), luteolin 6-C-(6”-Otrans-caffeoylglucoside), luteolin 6-C-(2”-O-trans-caffeoylglucoside), and luteolin 7-O-(6”-p-benzoylglucoside), together with four knownones 5, 4’-dihydroxy-3, 6, 7, 3-tetramethoxyflavone,55
A review of the important chemical constituents and medicinal uses of Vitex genus / Asian Journalof Traditional Medicines, 2011, 6 (2)luteolin, artemetin and isorhamnetin, have beenisolated from the root bark. Their structures wereelucidated using spectroscopic metheods [8].A methanol extract was tested for its abilityto displace radio-labeled estradiol from thebinding site of estrogen receptors alpha (ERα)and beta (ERβ). Progesterone receptors were upregulated in the Ishikawa endometrial cancer cellline. Bioassay-guided isolation, using ER bindingas a monitor, resulted in the isolation of linoleicacid as one possible estrogenic component of theextract. Linoleic acid also stimulated mRNA ER βexpression in T47D: A18 cells,and PR expression inIshikawa cells [9].Subjects who took mixed essential oil of vitexwith any form of progesterone supplementation(including progesterone cream) consistentlynoted breakthrough bleeding. Any woman whois concurrently taking any form of hormonereplacement therapy should be closely monitored bya health professional when vitex is started [10].The starting material for the isolation of singleconstituents was the extract which was obtainedby extracting finely ground seeds with aqueousethanol 70 % (v/v) and then drying gently in vacuo.The ethanol extract of the dried ripe fruit displayscytotoxic activity against some human cancer celllines resulting in the induction of apoptosis.The extract inhibits prolactin release which iscaused by selective stimulation of D2-type pituitarydopamine receptors. In clinical investigations anddouble-blind trials with preparations containingthis extract, a decrease in pathologically increasedprolactin levels and an effect on prolactin releasein healthy subjects have been demonstrated. Theextract appears effective and was well tolerated andfurther evaluation of this agent in the treatment ofcyclical mastalgia is warranted [11].562.2. Vitex trifolia LinnVitex trifolia Linn. is a tropical shrub widelydisibuted in Pacific-Asian countries, such as India,Sri Lanka, China, Philippines, Indonesia, NorthAustralia, New Caledonia and French Polynesia. Ithas also been reported in East Africa and introducedto many islands in the Central Pacific and Hawaii.The anti-inflammatory potential of an aqueous extractof Vitex trifolia leaves was evaluated by monitoringits effects on the modulation of cytokines, mediatorsof inflammation, as well as on the expression profilesof inducible nitric oxide synthase, which producesthe free radical nitric oxide. The leaves are usedinternally or externally in baths to cure Ciguaterafish poisoning-related pruritus. It is used as ananti-pyretic, anti-inflammatory, and nematicidalagent and to increase body weight and it has alsobeen reported to have anti-tumor activity [12]. Thepetroleum ether and ethanol extracts of Vitex trifolialeaves exhibited moderate inhibition of both Grampositive and Gram-negative bacteria [13].Biological assays of plant organic extracts haveshown a number of important activities. Hexanicand dichloromethanic extracts, when prepared fromstems and foliage, have proved to be very toxicagainst cultures of several cancer cell lines. Also,an important anti-feeding activity against the insectpest Spodoptera frugiperda has been recorded. Thehexanic extract of the leaves completely inhibited thegrowth of the fungal plant pathogen Fusarium sp.The essential oils of Vitex trifolia have been shownto having insecticidal activity [14]. An abietane-typediterpene, named vitetrifolin A, and two labdanetype diterpenes, named vitetrifolins B and vitetrifolinC, were isolated from the acetone extract of thefruits of Vitex trifolia Linn. along with three knownditerpenes, rotun-difuran, dihydrosolidagenone andabietatriene 3β-ol.2.3. Vitex cymosa
A review of the important chemical constituents and medicinal uses of Vitex genus / Asian Journalof Traditional Medicines, 2011, 6 (2)Vitex cymosa Bertero is a small tree widelydistributed in the Central and Amazon regions ofBrazil, where it is popularly known as Taruma-doIgapo and Taruma-do-alagado. A new ecdysteroid,26-hydroxypinnatasterone, together with20-hydroxyecdysone, have been isolated from thestem bark of Vitex cymosa [15].2.4. Vitex polygamaThe species Vitex polygama Cham. is foundmainly in the states of Bahia, Minas Gerais and Riode Janeiro and the bark and fruits of this plant aretraditionally used as emenagogues and diuretics.The compounds 20-hydroxyecdysone, ajugasteroneC, ajugasterone C monoacetonide and turkesteronehave been isolated from the branches of Vitexpolygama [16].2.5. Vitex canescensVitex canescens Kurz is a medium-sized treewidely distributed throughout Thailand. A numberof Vitex species have been investigated in a searchfor ecdysteroids. From the bark of Vitex canescens20-hydroxyecdysone and turkesterone, a newecdysteroid, canescensterone, have been isolatedalong with the teroid, 24-epi-abutasterone, from theroot. The compound 20-hydroxyecdysone, 24-epimakisterone A, shidasterone, calonysterone andturkesterone have also been isolated from this plantspecies [17] .2.6. Vitex negundo LinnVitex negundo Linn. Verbenaceae, known asNirgundi in Hindi, grows widely in wastelands andhas also been used as a hedge-plant. It is an erect,slender tree, 2–5 m in height, with quadrangularbranchlets growing throughout India. The leaveshave five leaflets in a palmate arrangement, whichare lanceolate, 4–10 cm long, with a hairy undersideand pointed at both ends. It has many bluish purpleflowers. The fruit is succulent, and black when ripe,rounded and about 4 mm in diameter. Phytochemicalstudies of Vitex negundo have afforded severaltypes of compounds, such as volatile oils, lignans,flavonoids, terpenes (triterpenes, diterpenes,sesquiterpenes) and steroids [18-19].The most common flavonoid glycosidesfrom an ethanolic extract of the leaves of Vitexnegundo are 5-hydroxy-3, 6, 7-trimethoxy-2-(3,4-dimtoxypheny)-4H-chrome-4-on and 5,7-dihydroxy-2-(3, 4-dihydroxyphenyl)-4H-chromen4-one. The methanolic extract also contains,Negundoside, Agnuside, and Vitegnoside. From barkof Vitex negundo Linn., p-hydroxybenzoic acid andβ-sitosterol have been isolated, and identified fromthe methanol and hexane extracts of Vitex negundo.In the acetoacetate fraction of the seeds , twophenylnaphtha-lene-typelignans have been- obtainedand identified as methyl-7-methoxy-3,4-dihydro-2-naphthaldehyde and vitedoamine A.It is used to treat dyspepsia, colic, rheumatism,worms, boils and leprosy. The roots contain afuranoeremophilane. Tyrosinase inhibitory ligninshave been found in the methanol extract of the rootsof Vitex negundo Linn [20].The hepatoprotective activity of the ethanolicexract of Vitex negundo leaves has been investigatedas a treatment of hepatotoxicity produced byadministering a combination of three anti-tuberculardrugs, isoniazid-7.5 mg/kg, rifampin-10 mg/kgand pyrazinamide-35 mg/kg. This plant containsmany polyphenolic compounds, terpenoids,glycosidic iridoids and alkaloids. Since polyphenoliccompounds have a high antioxidant potential,the antioxidant potency of Vitex negundo wasinvestigated using a variety of established invitro systems, such as 2, 20-azino-bis 3-ethylbenzothiazoline- 6-sulfuric acid/lipid peroxide/superoxide/hydroxyl radical scavenging and iron ion57
A review of the important chemical constituents and medicinal uses of Vitex genus / Asian Journalof Traditional Medicines, 2011, 6 (2)chelation.2.9. Vitex leucoxylon LinnIn Ayurvedic medicine and in various recentexperimental models, the oral administration ofthe plant leaves have been claimed to have antiinflammatory, analgesic, anti-hyperglycemic andanti-bacterial, anti-asthmatic and anti-implantationactivities [21].An ethanolic extract of the leaves was found toreduced spontaneous motor activity. In addition theethanolic extract produced significant inhibition ofgranulation tissue formation while a cold aqueousinfusion reduced total serum cholesterol. In acuteinflammation, a cold aqueous infusion as well asa mixture of flavonoids of Vitex leucoxylon Linnexhibited anti-inflammatory activity without anyeffect on chronic inflammation [24].The methanolic root extracts (Vitex negundo andEmblica officinalis) significantly antagonized thelethal action induced by Vipera russellii and Najakaouthia venom in both in vitro and in vivo studies.The petroleum ether extract of the leaves has beenevaluated in the laboratory for larvicidal activityagainst the larval stages of Culex tritaeniorhynchusThe crude aqueous extract of Vitex negundo Linn.leaves has been investigated for laxative activity. Anethanolic extract was tested for anthelmintic activityagainst the Indian earthworm Pheritima posthuma.2.7. Vitex peduncularis WallExtraction of the dried leaves yielded pachypodol,ursolic acid, 2α-hydroxyursolic acid, vitexin andpeduncularcin. In Orissa, a decoction of the leavesis taken as tea during the cold season. An infusionof leaves administered intramuscularly or orallyto rabbits increases the osmtic resistance of cellsand inhibits haemolysis produced by saponin ,cobravenom, bile salts, or saline solution [22] .2.8. Vitex pinnata LinnAn ecdysteroid, pinnatasterone, together with20-hydroxyecdysone and turkesterone has beenisolated from the bark of this plant. Pinnatasteroneexhibited weak biological activity in the pupariationtest using housefly larvae. The flavonoids, luteolin,iso-orientin, and vitexin, have been isolated from theflowers. In Brunei, the young leaf shoots are eatenraw to treat hypertension and fever. A root-tea istaken for backache, bodyache and fatigue [23].582.10. Vitex altissima Linn.This is a large tree with a grey, scaly, fibrousbark. The leaves are 3-foliolate; petiole angular orwinged; the leaflets are subsessile, elliptic-lanceolatewhile the flowers are bluish-white, terminalpaniculate cymes. The fruit is mostly used to treatstomatitis, cardiac diseases, anorexia, blindness,leprosy and worm infestation, heart-wood, leavesand bark contain the flavonoid–vitexin [25].2.11. Vitex mollisVitex mollis is a tree native to Mexico thatgrows up to 18 m high. It can be found in humid andtropical regions. The fruit is known as ‘uvalama’in Sinaloa. This fruit is a drupe with a fleshyedible part consisting of an epicarp and mesocarp,commonly known as peel and pulp, respectively.The fruit is eaten fresh, as a conserve, or as a boileddrink with milk and sugar. It has been reportedthat some indigenous cultures used this fruit aswell as other parts of the plant to treat diseases,such as fever, diarrhea, dysentery and abdominalcolic. It also has anti-inflammatory and analgesicproperties. In addition, uvalama has been suggestedfor the treatment of scorpion stings and to alleviatemenstrual pains. Fruits are important sources ofminerals, fiber and vitamins, and they provideessential dietary nutrients [26].
A review of the important chemical constituents and medicinal uses of Vitex genus / Asian Journalof Traditional Medicines, 2011, 6 (2)3. ConclusionThis review summarizes the main biologicalfindings and known phytochemical constituentsof the Vitex genus. The studies conducted to datehave demonstrated that the plants of the Vitexgenus contain many biologically active compoundswith antioxidant, anti-inflammatory, antimicrobial,hepatoprotective, analgesic antihistamine, antiimplantation, and antiasthmatic effects. Thus, theVitex genus deserves further evaluation as a sourceof hepatoprotective agents. Indeed, there is a currentneed for new plant-derived bioactive agents; thusgenus Vitex may be an important natural source forthe development of new drugs and may provide acost-effective means of treating heart problems andother important diseases in the developing world.AcknowledgementThe authors are very grateful to DirectorGeneral, CCRAS, New Delhi and Director ShobhitUniversity, Meerut for providing encouragementand help in carrying out this work. The authorsacknowledge the secretarial assistance rendered byMs. Rekha in preparation of the paper.References[1] Argueta A, Cano LM, Rodarte ME. Atlas de las Plantasde la Medicina Tradicional I y III. Instituto NacionalIndigenista, 1994, 537-538.[2] Rahman MS, Bhattacharya GN. Effects of leaf extractof Vitex negundo on Lathyrus satitus Linn. Used toprotect stored grains from insects. Curr Sci, 1982, 51(8): 434-435.[3] Saden-Krehula M, Kustrak D, Blazevic N. 4-3-Ketosteroidsin flowers and leaves of Vitex agnus-castus. PlantaMedica, 1990, 56: 547.[4] Kuruuzum A, Stroch K, Demirezer O. Glucosides fromVitex agnus-castus. Phytochemistry, 2003, 63: 959–964.[5] Sarikurkcu C, Arisoy K, Tepe B, Cakir A, Abali G.Studies on the antioxidant activity of essential oil anddifferent solvent extracts of Vitex agnus castus L. fruitsfrom Turkey. Food and Chemical Toxicology, 2009, 47:2479-2483.[6] Sticher O, Meier B, Orjala J, Hoberg E. Diterpenoidsfrom the fruits of Vitex agnus-castus, Phytochemistry,1999, 52: 1555-1558.[7] Sun HD, Farnsworth NR, Fong HS, Mesecar AD,Santarsi
55 A review of the important chemical constituents and medicinal uses of Vitex genus / Asian Journal of Traditional Medicines, 2011, 6 (2) negundo has larvicidal activity against the mosquito species Culex quinquefasciatus and Anopheles stephensi and is used as a mosquito deterrent againt Aedes aegypti and Vitex rotundifolia also acts as deterrent against Aedes aegypti.
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Le genou de Lucy. Odile Jacob. 1999. Coppens Y. Pré-textes. L’homme préhistorique en morceaux. Eds Odile Jacob. 2011. Costentin J., Delaveau P. Café, thé, chocolat, les bons effets sur le cerveau et pour le corps. Editions Odile Jacob. 2010. Crawford M., Marsh D. The driving force : food in human evolution and the future.
Le genou de Lucy. Odile Jacob. 1999. Coppens Y. Pré-textes. L’homme préhistorique en morceaux. Eds Odile Jacob. 2011. Costentin J., Delaveau P. Café, thé, chocolat, les bons effets sur le cerveau et pour le corps. Editions Odile Jacob. 2010. 3 Crawford M., Marsh D. The driving force : food in human evolution and the future.
