Review Article A Review on Medicinal Properties of Orientin

Review ArticleA Review on Medicinal Properties of Orientin

Kit Ying Lam1 Anna Pick Kiong Ling2 Rhun Yian Koh2

Ying Pei Wong2 and Yee How Say3

1School of Postgraduate Studies and Research International Medical University 57000 Kuala Lumpur Malaysia2Division of Biomedical Science and Biotechnology School of Health Sciences International Medical University57000 Kuala Lumpur Malaysia3Department of Biomedical Science Faculty of Science Universiti Tunku Abdul Rahman Perak Campus31900 Kampar Perak Malaysia

Correspondence should be addressed to Anna Pick Kiong Ling anna lingimuedumy

Received 17 November 2015 Revised 4 March 2016 Accepted 14 April 2016

Academic Editor Hansen Wang

Copyright copy 2016 Kit Ying Lam et al This is an open access article distributed under the Creative Commons Attribution Licensewhich permits unrestricted use distribution and reproduction in any medium provided the original work is properly cited

Medicinal plants continue to play an important role in modern medications and healthcare as consumers generally believe thatmost of them cause fewer or milder adverse effects than the conventional modern medicines In order to use the plants as a sourceof medicinal agents the bioactive compounds are usually extracted from plants Therefore the extraction of bioactive compoundsfrommedicinal plants is a crucial step in producing plant-derived drugs One of the bioactive compounds isolable frommedicinalplants orientin is often used in various bioactivity studies due to its extensive beneficial properties The extraction of orientinin different medicinal plants and its medicinal properties which include antioxidant antiaging antiviral antibacterial anti-inflammation vasodilatation and cardioprotective radiation protective neuroprotective antidepressant-like antiadipogenesis andantinociceptive effects are discussed in detail in this review

1 Introduction

Plants have been the key source of medicinal agents sinceancient times Based on fossil records the use of medicinalplants most likely began in the middle Paleolithic about60000 years ago [1] Over the years traditional medicinalplants have been widely used to treat andor to prevent dis-eases and even for daily consumption For example Camelliasinensis is an evergreen tree whose leaves and leaf buds areused to produce tea The hot water extract of the dried leafis taken orally as an antihypertensive tea in China but toincrease milk production for nursing mothers in MexicoIndians also use the powder or decoction of dried leaves onteeth to prevent tooth decay [2] The other example is Gingkobiloba which has traditionally been used to improvememoryThe Chinese take the oil from fruit pulp to treat pulmonarytuberculosis but consume the hot water extract of the leaforally as a vermifuge and also to treat asthma and senility[3] Besides that Koreans use the hot water extract of theGingko biloba seed to induce labour or as an abortifacient [3]

In addition the Ocimum sanctum Linn (holy basil) has beenused for the treatment of malaria dysentery skin diseasearthritis bronchitis asthma and verminosis in the ancientIndian system of medicine [4 5]

Traditionally all of or part of a therapeutic plant such asgarlic and cranberry is used as an herbal remedy Howeverthis has evolved in the recent drug discovery processes inwhich bioactive compounds were isolated from plants andused as drugs either in its original or in semisynthetic form[6] Normally semisynthesis of novel bioactive compoundswith higher therapeutic values and lower toxicity can bedone by modifying the structure of the existing bioactivecompounds [7] With this development medicinal plantsparticularly those with less toxic secondary metabolitescontinue to play an important role in the modernmedicationand healthcare According to Prasad and Tyagi about 61of 877 small-molecule drugs introduced worldwide between1981 and 2002 were derived from natural products [8] Somefamous examples of plant-derived modern medicines arethe cardiotonic drug (Digitoxin and Digoxin from Digitalis

Hindawi Publishing CorporationAdvances in Pharmacological SciencesVolume 2016 Article ID 4104595 9 pageshttpdxdoiorg10115520164104595

2 Advances in Pharmacological Sciences

O

OOH

OH

OH

OHOH

HO

HO

HO

O

H

Figure 1 Chemical structure of orientin

purpurea L) [6ndash8] the anti-inflammatory drug (Aescinfrom Aesculus hippocastanum L) [7] antitumour agent(Etoposide from Podophyllum peltatum L [7 8] Vincristineand Vinblastine from Catharanthus roseus [6 8] Irinotecanand Topotecan from Camptotheca acuminate [8] Paclitaxeland Abraxane from Taxus brevifolia [8] Solamargine fromSolanum dulcamara [8] Masoprocol from Larrea tridentata[8] Alitretinoin from Daucus carota [8]) antimalaria andantiarrhythmic agent (quinine and quinidine from Cinchonaspp) [6] muscle relaxant (atropine from Atropa belladonna)[6] and antinociceptive and cough suppressant drugs (mor-phine and codeine resp) from Papaver somniferum [6]

Considering the importance of bioactive compoundsextraction of these bioactive compounds from medicinalplants is a crucial step in producing plant-derived drugs Oneof the bioactive compounds isolable from medicinal plantsorientin is often used in the studies due to its extensivetherapeutic properties Orientin is a water-soluble flavonoidC-glycoside which is commonly extractable from somemedicinal plants such as Ocimum sanctum (holy basil)[9ndash11] Phyllostachys nigra (bamboo leaves) [12ndash18] Passifloraspecies (passion flower) [19 20] Trollius species (GoldenQueen) [21ndash24] Jatropha gossypifolia (Bellyache Bush) [25ndash28] Linum usitatissimum (flax) [29] Commelina communis(dayflower) [30] Euterpe oleracea Mart (Acai palm) [31]Ascarina lucida [32] Celtis africana (white stinkwood) [33]Croton zambesicus (Lavender croton) leaves [34] Cajanuscajan (Pigeon pea) leaves [35] andThlaspi arvense (Field Pen-nycress) [36]The extraction of orientin in differentmedicinalplants and its medicinal properties which include antioxi-dant antiaging antiviral antibacterial anti-inflammationvasodilatation and cardioprotective antiadipogenesisantinociceptive radiation protective neuroprotective andantidepressant-like effects are discussed in this review

2 Orientin

Orientin is a water-soluble flavonoid C-glycoside whichhas the IUPAC name of 2-(34-dihydroxyphenyl)-57-dihy-drox-y-8-[(2S3R4R5S6R)-345-trihydroxy-6-(hydroxym-ethyl)oxan-2-yl]chromen-4-one It has a molecular formulaof C21H20O11

and a molecular weight of 4483769 gmol[38] The chemical structure of orientin (Figure 1) shows that

it consists of mostly phenol groups with two ether groupsand one ketone group Therefore a polar solvent such asmethanol ethanol or water is required to extract orientinfrom the medicinal plants

3 From Plants to Orientin

Orientin has been isolated from various medicinal plantssuch as Ocimum sanctum Phyllostachys species (bambooleaves) Passiflora species (passion flowers) Trollius species(Golden Queen) and Jatropha gossypifolia (Bellyache Bush)

Ocimum sanctum (also known as Indian holy basil orTulsi in Sanskrit) was planted in India and it is well known forits medicinal values The Ayurveda (Indian ancient system ofmedicines) uses different parts of Ocimum sanctum to treatcough common cold malarial fever skin diseases and snakebites [39] Nair et al successfully isolated orientin from theleaves of O sanctum alongside with other flavonoids suchas apigenin apigenin-7-O-glucuronide molludistin luteolinand luteolin-7-O-glucuronide [10] Similarly Uma Devi etal isolated orientin from the same plant parts for in vivoradioprotective effect studies [11]

Bamboo leaves have been an essential resource in Chinafor years and Phyllostachys pubescens Mazel ex H de Lehaieis the most abundant species among the bamboo leaves inChina due to its high yield high growth rate and extensiveuse [12] Yong et al isolated orientin and other compoundssuch as isoorientin vitexin isovitexin caffeic acid and ferulicacid by immersing different cultivars of P pubescens in70 methanol [16] Besides that Zhang et al have isolated49mg of orientin from the antioxidant of bamboo leaves(AOB) concentrated solution initially from the 65 g ofcrude column chromatography fraction [17] In additionorientin has been separated from the three bamboo speciesPhyllostachys pubescens Mazel ex H de Lehaie PhyllostachysglaucaMcClure and Pleioblastus yixingensis by Sun et al withnewly proposed high-performance thin-layer chromatogra-phy (HPTLC) method [18] With this simple method 644782 and 492 (ww) of orientin were produced from Ppubescens P glauca and P yixingensis respectively [18]

Orientin has also been isolated from the Passifloraspecies Passiflora was originally named in Spanish meaningldquothe flower with the five woundsrdquo in the 17th Century bySpanish priests in South America Up to now there areabout 400 Passiflora species that have been recognised Itwas suggested that Passiflora incarnata is used as a mildcalming agent while other species were reported to possessmedicinal properties [19] In isolating orientin Grundmannet al managed to obtain 336mg of orientin per gram of driedP incarnata [19] while de Paris et al isolated orientin fromwater extract of P edulis dried leaves [20]

In Traditional ChineseMedicineTrollius chinensis Bungehas been used to treat pharyngitis respiratory infectionsbronchitis and tonsillitis for years The dried flowers ofother Trollius species were also discovered to possess variousmedicinal properties [37] Liu et al used HPLC method toisolate orientin from Trollius chinensis with the detectionwavelength of 340 nm [21] Besides that 5mg of orientin hasbeen eluted from 15 kg of dried flowers of Trollius ledebouri

Advances in Pharmacological Sciences 3

Table 1 Isolation of orientin from different medicinal plants

Medicinal plants Solvents Separation and analysismethods Amount of orientin extracted References

Ocimum sanctum Water (i) Chromatography(ii) NMR mdash [10ndash12]

Phyllostachys species Methanol or ethanol

(i) Chromatography(silica gel column orAB-8 resin column)(ii) HPLC(iii) HPTLC

(i) 49mg of orientin from the AOBconcentrated solution(ii) 644 782 and 492 (ww)of orientin were produced from Ppubescens P glauca and Pyixingensis respectively by HPTLC

[15ndash19]

Passiflora species Ethanol or water (i) TLC(ii) HPLC

(i) 336mg of orientin per gram ofdried P incarnata extract [21 37]

Trollius species Ethanol

(i) HPLC(ii) Columnchromatography(iii) HSCCC(iv) UPLC-ESI-MSMS

(i) 5mg of orientin from 15 kg of Tledebouri dried flowers(ii) 958mg of orientin from 500mgof the crude extract of T ledebouri(iii) Able to measure minimum515 120583g of orientin per gram of plantmaterial by UPLC-ESI-MSMSmethod

[25ndash27]

Jatropha gossypifolia

Waterdichloromethaneethyl acetate

n-butanol or residualaqueous

(i) TLC(ii) HPLC

(i) The retention factor of orientin is052 for TLC analysis(ii) Solve the problem ofoverlapping of the isomers (orientinand homorientin) chromatographicbands in HPLC

[30ndash33]

[22] In addition Zhou et al successfully isolated 958mg oforientin from 500mg of the crude extract ofTrollius ledebouriwith high-speed countercurrent chromatography (HSCCC)and semipreparative HPLC methods [23] An ultraperfor-mance liquid chromatography-electrospray ionization tan-dem mass spectrometric (UPLC-ESI-MSMS) method hasbeen developed by Li et al in order to study the activecompounds in Trollius ledebouri flower qualitatively andquantitatively It was found that the smallest quantity oforientin that could be measured by this method was 515 120583gper gram of plant material [24]

Jatropha gossypifolia from Euphorbiaceae family is a tallshrub with plentiful fascicled bristles originally from Brazilbut now can be found in all parts of India The different partsof the plant are believed to have different medicinal valuesFor instance the leaves are used as an insecticidal andwoundsor ulcer healing agent and the roots together with the leavesare used to treat anaemia dysentery fistula and biliousnesswhile the seeds are used as aphrodisiacs laxatives andanthelmintic agents [40] The seed oil is also a traditionalmedication for skin diseases such as itch eczema andherpes [40] Orientin was isolated from the dried leaves ofJ gossypifoliawith the retention factor of 052 in TLC analysis[25ndash27] Besides that Pilon et al used the crude leaf extractsof J gossypifolia to improve the chromatographic resolutionof HPLC-UV-diode-array detector (DAD) experiments toresolve the overlapping problem of chromatographic bandsin HPLC between orientin and its isomer homorientin [28]

Apart from the few plants mentioned above there aresome other medicinal plants that also contain orientin and

yet are not as well studied Orientin in the leaves and stemsof Linum usitatissimum (flax) was first isolated togetherwith some other compounds such as isoorientin vitexinisovitexin vicenin-1 and vicenin-2 [29] The natural herbthat is used to treat type 2 diabetes Commelina communis(dayflower) was found to contain orientin as well The invitro studies show that orientin has been one of the majorantioxidants in this plant [30] In addition Gallori et al haveidentified the presence of orientin in Euterpe oleracea Mart(Acai palm) fruit by using HPLC-DAD-UV-Vis and HPLC-MS analysis [31] Soltis and Bohm also successfully obtainedorientin and some other flavonoids from the methanolextract of Ascarina lucida leaves [32] Besides that orientinwas also isolated from Celtis africana (white stinkwood) [33]Croton zambesicus (Lavender croton) leaves [34] Cajanuscajan (Pigeon pea) leaves [35] and Thlaspi arvense (FieldPennycress) [36]

Table 1 summarises the extraction methods and amountof orientin extracted in each main medicinal plant discussedabove

4 Medicinal Properties of Orientin

41 Antioxidant and Antiaging Orientin has been widelystudied for its antioxidant property The antioxidant prop-erty of orientin can be explained through the study of itselectron affinity electronegativity electrophilic index andadiabatic ionization potential of its high radical scavengingactivity which is the ability to donate electrons [41] Theeffect of orientin on hydrogen peroxide- (H

2O2-) induced


120573-galactosidase activity also shows the antioxidant prop-erty of orientin Orientin reduced the H

2O2-induced 120573-

galactosidase activity when compared to the increase ofenzyme activity in H

2O2treatment alone [42] Besides that

orientin significantly enhanced the survival ofEscherichia colimutants DSH56 andDSH19 [42] Nayak et al also stated thatthe treatment of orientin highly reduced the mortality of themutant cells which is due to oxidation of macromolecules[42]

The antioxidant activity of orientin has also been shownin animal models The D-galactose-treated aged mice wereadministrated with orientin for 8 weeks An et al foundthat orientin significantly increased the mice brain weightsand general health status The orientin-treated age micealso have increased levels of catalase glutathione peroxidasesuperoxide dismutase in serum brain liver and kidneyswhile the levels ofmalondialdehyde (a biomarker of oxidativestress) in the brain liver and kidneys as well as the levels oflipofuscin (an age pigment) were significantly decreased [43]In addition orientin also improves the structure of neuronalcell injuries in D-galactose-aged mice [43]

42 Antiviral and Antibacterial The antiviral and antibac-terial activities of orientin are beneficial for the futureantibiotics development Lin et al [44] and Li et al [45] havedemonstrated that orientin has moderate or potent antiviralactivity against Para 3 virus Besides that the flavonoidsmixture (orientin rutin quercetin and kaempferol) at themaximum nontoxic dose of 0048120583gmL fully inhibitedHerpes Simplex Virus Type 2 (HSV-2) of different viraltitre (1 10 100 TCID

50) on Hep-2 cells [46] This is a great

breakthrough in the medical field as HSV infection has beenknown to be a life-threatening disease Apart from antiviraleffects orientin also expresses antibacterial effects The studyshows that the combination of flavonoids from Ocimumsanctum orientin and vicenin synergistically inhibited thegrowth of Escherichia coli Staphylococcus aureus Staphylo-coccus cohnii Klebsiella pneumoniae and Proteus while theindividual flavonoids were found to be less effective thanthe combined flavonoids [47] The total flavonoids of Trolliuschinensis include orientin and vitexin also showed evidenceof antibacterial [44]

43 Anti-Inflammatory Inflammation is a biological defencemechanism of tissue to injury or infection Inflammation ischaracterized into acute and chronic phase in which they aredifferentiated by the presence of neutrophilic and monocyticleucocytes during the acute phase whereas there are inci-dences of macrophages and lymphocytes during the chronicphase [48 49] It is well studied that the development ofatherosclerosis is strongly related to vascular inflammationtherefore there is an urge to develop an anti-inflammationmedication which benefits vascular inflammation [50] Thebiomarkers of vascular inflammation high mobility groupbox-1 (HMGB1) protein and endothelial cell protein Creceptor (EPCR) have been investigated after the treatmentof orientin Orientin has been shown to inhibit the HMGB1level in lipopolysaccharide- (LPS-) induced umbilical vein

endothelial cells (HUVECs) as well as the HMGB1-mediatedcytoskeletal rearrangements [51] In addition in the humanendothelial cell lines orientin suppressed LPS-inducedmem-brane disruption migration of monocytes expression ofcell adhesion molecules (CAMs) and LPS-induced EPCRdetaching [52] Furthermore in vivo assessments showedthat orientin inhibited HMGB1-mediated and LPS-inducedhyperpermeability CLP-induced release of HMGB1 levelleukocyte migration LPS-induced tumour necrosis factor-120572(TNF-120572) level interleukin-6 (IL-6) level nuclear factor-120581B(NF-120581B) level extracellular regulated kinases (ERK) 12 leveland lethality of mice [52] Besides that diabetes mellitus isthe main complication in the progression of atherosclerosisby vascular inflammation Ku et al have also found thatpretreatment of orientin inhibited the high glucose-inducedCAMs reactive oxygen species (ROS) and NF-120581B levels inHUVECs and mice [53]

44 Vasodilatation andCardioprotective Effect Presently oneof the most frequent cardiovascular diseases is hypertensionwhich increases the risk factor for congestive heart failureNevertheless the maximum efficacy of the antihypertensivedrugs is only 60 and typically two or more drugs from thecategories of diuretics calcium channel blockers angiotensinconverting enzyme or receptor blockers adrenergic drugsand vasodilators have to be combined to attain high efficacyon patients [54]Therefore vasorelaxant is an essential medi-cation for hypertensive patients to reduce their elevated bloodpressure and to protect the patients from cardiovasculardiseases [54 55]

Orientin has been identified to have vasodilatation effectson removed thoracic aortic rings from the New Zealand rab-bit It was found that orientin with an IC

50value of 228120583M

and 727120583M relaxed phenylephrine-induced contractionsin the endothelium-intact and endothelium-isolated aorticrings respectively [56] The possible pathway that orientinacts as a vasorelaxant on thoracic aortic rings is by the nitric-oxide-cGMP pathway while in the vascular smooth muscleit relaxes the muscle via activation of voltage-dependentcalcium channels [56]

Besides that orientin has been massively studied for itsin vivo cardioprotective effect Orientin was demonstratedto reduce myocardium apoptosis of rat heart with ischemia-reperfusion The apoptosis of rat cardiomyocytes that wereinjured by hypoxiareoxygenation also decreased upon pre-treatment with orientin at 3 10 and 30 120583mol Lminus1 [57] Studiesalso showed that the protein levels of Bax cytochrome cand caspase-3 were reduced whereas the level of bcl-2 wasincreased This shows that orientin has antiapoptotic effecton ischemia-reperfusion and hypoxiareoxygenation-treatedheart and cardiomyocytes by deactivating the cytochromec-caspase-3 mitochondrial apoptotic pathway [57] On theother hand Liu et al showed that the myocardial struc-tures ventricular remodeling electrocardiogram and hemo-dynamic index of myocardial infarction rats have beenimproved after the treatment of orientin [58]

In addition the cardioprotective effect of orientin hasalso been shown in dogs Orientin increased endogenous


antioxidase activity and reduced the oxygen-free radicalformation by inhibiting the serum creatine phosphokinaseand lactic dehydrogenase activities as well as enhancingsuperoxide dismutase activity in acute myocardial infarctiondogs while reducing the myocardial infarction sizes [59]In addition the cardiac function upon orientin treatmenthas been observed in anesthetized open-chest dogs Resultsshowed that orientin was able to diminish maximal rising ordropping rate of intraventricular pressure (plusmn119889119901119889119905max) andleft ventricular end dilation pressure and myocardial oxygenconsumption but enhance cardiac output and coronary bloodflow to boost up cardiac function in anesthetized dogs[60] Moreover orientin has been revealed to reduce arachi-donic acid-induced blood platelet aggregation in rabbits andimprove coronal flow in the removed heart of guinea pigs[61] However the in vitro study on the cardioprotective effectof orientin demonstrated the repolarization of mitochondrialmembrane potential reduced generation of reactive oxygenspecies inhibition of mitochondrial cytochrome c and theassociation with the PI3KAkt signaling pathway by orientinon the H9c2 cardiomyocytes cells [62]

45 Radioprotective Effect The radiation protective com-pounds have been widely studied recently due to the highlydamaging power of ionizing radiation on human tissuesThe damage of DNA and proteins by radiation can result inapoptosis necrosis mitotic death or cell cycle interruptionon the normal tissues [63] Therefore the search of radiopro-tective compounds is vital to protect human against radiationTwo flavonoids isolated from the leaves of Ocimum sanctumorientin and vicenin have been frequently examined fortheir radioprotective effectThe pretreatment of optimal doseat 50 120583gkg body weight of orientin or vicenin 30 minuteson mice before being exposed to 11 Gy of gamma radiationshowed protection against fatality but the posttreatment oforientin or vicenin was not as effective as pretreatment [11]The possible mechanisms of action of this protective effectwere then determined Both flavonoids have given protectionagainst whole-body 3Gy of gamma radiation-induced lipidperoxidation in mouse liver and also scavenged free radicalactivities include diphenylpicrylhydrazyl (DPPH) and 221015840-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) invitro [64]Therefore the antioxidant activity of the flavonoidsmight be the possible pathway of the radiation protectiveeffect

Additionally in the Micronucleus (MN) assay the treat-ment of orientin or vicenin at the optimum concentrationof 175 120583M decreased the radiation-induced MN frequencywhich indicates reduced chromosome damage in the humanperipheral lymphocytes [65] Besides that the radiationprotective effect of orientin and vicenin was demonstratedin mouse bone marrow as well The intraperitoneal injectionof orientin or vicenin significantly diminished the radiation-induced chromosomal aberrant cells and enhanced thenumber of exogenous spleen colonies (CFU-S) [66] Theex vivo irradiated mouse splenocytes also showed a fasterrepairing effect and less radiation-induced DNA damage byorientin or vicenin [67] The clonogenic survival of repair

proficient cells was also elevated [9] Furthermore the com-bination treatment of orientin and vicenin together with twosynthetic compounds WR-2721 and 2-mercaptopropionylglycine (MPG) demonstrated reduced chromosomal aberra-tion cells in bonemarrow and significant drop in the percent-age of aberrant metaphases [67] These studies propose thepotential of orientin and vicenin in protecting the normal tis-sues during the radiotherapy in cancer patients and the pro-tection of radiation-related job workers such as radiologists

46 Neuroprotective or Antidepressant-Like Effect Neurode-generative diseases are the incurable and weakening con-ditions where there are aggregation and deposition of mis-folded intracellular and extracellular proteins which lead toprogressive central nervous system diseases [68 69] Theyhave been emphasised among aging diseases because of theinadequate effective treatment incurability and associatedeconomic and social burdens [70]Therefore there is an urgefor the development of preventive or curative neuroprotectivemedications for the patients A previous study using 3-(45-dimethylthiazol-2-yl)-25-diphenyltetrazolium bromide(MTT) assay reported that orientin at the concentration ofless than 20120583Mwas not cytotoxic to SH-SY5Yneuroblastomacells [71] In this study the percentage of apoptotic cellswas significantly decreased compared to the cells treatedwith 150120583M H

2O2alone Law et al concluded that this

antiapoptotic effect of orientin could have been attributed tothe inactivation of caspases 37 and caspase-9 activities basedon the caspase assays [71]

The neuroprotective effect has also been demonstratedin Amyloid 120573-Protein- (A120573

1ndash42-) induced mitochondrialdysfunction oxidative-stressed (Alzheimerrsquos disease AD)mice Orientin was found to improve cognitive impair-ment of the AD mice and significantly reduced the levelsof the oxidative stress biomarkers 3-nitrotyrosine (3-NT)4-hydroxynonenal (4-HNE) 8-hydroxy-21015840-deoxyguanosine(8-OHdG) and ROS [72]Themitochondrial apoptotic path-way was attenuated by reducing mitochondrial dysfunctionby orientin The possible pathway that orientin protects ADmice was found to be Nrf2HO-1 redox signaling pathway asthe expression of HO-1 was increased during the study [72]

Besides that orientin also showed antidepressant-likeeffect The chronic unpredictable mild stress (CUMS) miceshowed enhanced central oxidative stress amplified sero-tonin and norepinephrine levels as well as less CUMS-induced depression-like behaviours upon oral treatment oforientin for 3 weeks [73]

47 Antiadipogenesis Effects Adipogenesis is the processby which undifferentiated precursor cells differentiate intofat cells and further leads to the increasing prevalence ofobesity among the society Orientin together with someother flavonoids has been reported to exhibit potent antiadi-pogenesis activity The orientin isolated from the ethanolextract of Spirodela polyrhiza exerts antiadipogenesis on lipidaccumulation in 3T3-L1 cells [74] In this study Kim et aldiscovered that the butanol soluble fraction had the high-est adipogenesis and intracellular triglyceride accumulation


inhibitory effect by inhibiting the protein expressions ofCEBP120572 and PPAR120574 [74] CEBP120572 and PPAR120574 are the essen-tial transcription factors during adipogenesis and participatein a single pathway of fat cell development with PPAR beingthe proximal effector of adipogenesis [75] Considering theantiadipogenesis mechanism of orientin it could be one ofthe useful therapeutic agents for obesity and type 2 diabetespatients

48 Antinociceptive Effects Pain is one of themost frequentlyobserved symptoms of different pathologies The principaltargets of effective pain management are to ameliorate noci-ception to reduce the threshold of pain sensation and toimprove quality of life [76]Thepain relieved effect of orientinhas been demonstrated in models of pain in mice Orientinwith the ID

50of 65mgkg was able to reduce acetic acid-

induced writhing and capsaicin- and glutamate-induced painin mice [77] Surprisingly Da Silva et al also discovered thatorientin was 20-fold more potent than the typical painkilleracetylsalicylic acid (aspirin) and 35-foldmore dynamic thanthe common anti-inflammatory drug indomethacin [77]Thus orientin can be an alternative antinociceptive treatmentto the patients

5 Concluding Remarks

The extensive studies of orientin on the medicinal proper-ties of antioxidant antiaging antiviral anti-inflammationvasodilatation and cardioprotective radioprotective neuro-protective antiadipogenesis and antinociceptive effects canlead to promising therapeutic effect of orientin in themedicalfield Yet the underlying mechanisms of these therapeuticproperties are not well studied and remain indecisive Besidesthat orientin was found to have difficulty in crossing theblood-brain-barrier due to its hydrophilicity [78] In addi-tion at this stage most of the biological studies of orientincomprise only in vitro and preclinical investigations Clinicaldata are yet to be available to support the use of orientin inpatients Therefore the future research on orientin should befocused on the underlying pathways the pharmacokineticsand the tissue distribution in the human body in order todevelop a highly effective drug which causes less adverseeffects to patients

Abbreviations

AOB Antioxidant of bamboo leavesHPLC High-performance liquid

chromatographyTLC Thin-layer chromatographyUPLC-ESI-MSMS Ultraperformance liquid

chromatography-electrosprayionization tandem massspectrometric

HSCCC High-speed countercurrentchromatography

H2O2 Hydrogen peroxide

HSV-2 Herpes Simplex Virus Type 2

TCID50 Median tissue culture infective dose

HMGB1 Mobility group box-1EPCR Endothelial cell protein C receptorLPS LipopolysaccharideHUVECs Umbilical vein endothelial cellsCAMs Cell adhesion moleculesTNF-120572 Tumour necrosis factor-120572IL-6 Interleukin-6NF-120581B Nuclear factor-120581BERK Extracellular regulated kinasesROS Reactive oxygen speciesIC50 Half maximal inhibitory concentration

DPPH DiphenylpicrylhydrazylABTS 221015840-azino-bis(3-ethylbenzothiazoline-6-

sulfonic acid)MN MicronucleusCFU-S Exogenous spleen colonyMPG 2-Mercaptopropionyl glycineMTT 3- (4 5-Dimethylthiazol-2-yl)-25-diphen-

yltetrazolium bromide assayA120573 Amyloid 120573-ProteinCUMS Chronic unpredictable mild stressID50 Half maximal inhibitory dose

Competing Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

The study is funded by the Ministry of Higher EducationMalaysia under the Fundamental Research Grant Scheme(FRGS) (FRGS12013SKK07IMU033) Acknowledgmentis due to Henry Ling of Columbia University New York forhis editorial comments

References

[1] R Solecki ldquoShanidar IV a neanderthal flower burial in northernIraqrdquo Science vol 190 no 4217 pp 880ndash881 1975

[2] I A Ross Medicinal Plants of the World Volume 3 ChemicalConstituents Traditional and Modern Medicinal Uses HumanaPress 2005


[4] P Pattanayak P Behera D Das and S K Panda ldquoOcimumsanctum Linn A reservoir plant for therapeutic applicationsan overviewrdquo Pharmacognosy Reviews vol 4 no 7 pp 95ndash1052010

[5] S K Das and D M Vasudevan ldquoTulsi the Indian holy powerplantrdquo Indian Journal of Natural Products and Resources vol 5no 4 pp 279ndash283 2006

[6] S M K Rates ldquoPlants as source of drugsrdquo Toxicon vol 39 no5 pp 603ndash613 2001

[7] D S Fabricant and N R Farnsworth ldquoThe value of plantsused in traditional medicine for drug discoveryrdquo EnvironmentalHealth Perspectives vol 109 supplement 1 pp 69ndash75 2001


[8] S Prasad and A K Tyagi ldquoTraditional medicine the goldminefor modern drugsrdquoAdvanced Techniques in Biology ampMedicinevol 3 no 1 article 1 2015

[9] M Satyamitra S Mantena C K K Nair et al ldquoThe antioxidantflavonoids orientin and vicenin enhance repair of radiation-induced damagerdquo Scholarena Journal of Pharmacy and Pharma-cology vol 1 no 1 article 105 2014

[10] A G R Nair R Gunasegaran and S Joshi ldquoChemical investi-gation of some South Indian plantsrdquo Indian Journal of ChemistryB vol 21 p 979 1982

[11] P Uma Devi A Ganasoundari B S S Rao and K KSrinivasan ldquoIn Vivo radioprotection by Ocimum flavonoidssurvival of micerdquo Radiation Research vol 151 no 1 pp 74ndash781999

[12] Y-X Zhang and C-H He ldquoProcess for extracting and sepa-rating total flavonoids from leaves of phyllostachys pubescensrdquoJournal of Chemical Engineering of Chinese Universities vol 20no 5 pp 690ndash695 2006

[13] B Y Lu X Q Wu J Y Shi Y J Dong and Y ZhangldquoToxicology and safety of antioxidant of bamboo leaves Part 2developmental toxicity test in rats with antioxidant of bambooleavesrdquo Food and Chemical Toxicology vol 44 no 10 pp 1739ndash1743 2006

[14] W X Sun X Li N Li and D L Meng ldquoChemical constituentsof the extraction of bamboo leaves from Phyllostachys nigra(Loddex Lindl) Munro varhenonis (Mitf) Stepfex RendlerdquoJournal of Shenyang Pharmaceutical University vol 25 no 1 pp39ndash43 2008

[15] J Xie P P Zhou X Y Zhu X J Liu R E Chen and PWang ldquoStudy on extraction of bamboo leaves flavonoids byhomogenate extraction technique and its antioxidant activityrdquoFood Science and Technology vol 2010 no 5 pp 194ndash198 2010

[16] C J Yong L L Hua and Y Ke ldquoSimultaneous determination ofseven effective constituents in the leaves of bamboo by reversedphase high performance liquid chromatography (RP-HPLC)rdquoJournal of Medicinal Plant Research vol 5 no 23 pp 5630ndash5635 2011

[17] Y Zhang J Jiao C Liu X Wu and Y Zhang ldquoIsolation andpurification of four flavone C-glycosides from antioxidant ofbamboo leaves by macroporous resin column chromatogra-phy and preparative high-performance liquid chromatographyrdquoFood Chemistry vol 107 no 3 pp 1326ndash1336 2008

[18] J Sun Y Yue F Tang and X Guo ldquoSimultaneous HPTLCanalysis of flavonoids in the leaves of three different species ofbamboordquo Journal of PlanarChromatographymdashModernTLC vol23 no 1 pp 40ndash45 2010

[19] O Grundmann J Wang G P McGregor and V ButterweckldquoAnxiolytic activity of a phytochemically characterized Passi-flora incarnata extract is mediated via the GABAergic systemrdquoPlanta Medica vol 74 no 15 pp 1769ndash1773 2008

[20] F de Paris RD Petry FH Reginatto et al ldquoPharmacochemicalstudy of aqueous extracts of Passiflora alata Dryander andPassiflora edulis Simsrdquo Acta Farmaceutica Bonaerense vol 21no 1 pp 5ndash8 2002

[21] Z Liu L Wang W Li Y Huang and Z-C Xu ldquoDeterminationof orientin and vitexin inTrollius chinesispreparation byHPLCrdquoChina Journal of Chinese Materia Medica vol 29 no 11 pp1049ndash1051 2004

[22] L-Z Wu H-F Wu X-D Xu and J-S Yang ldquoTwo newflavone C-glycosides from Trollius ledebourirdquo Chemical andPharmaceutical Bulletin vol 59 no 11 pp 1393ndash1395 2011

[23] X Zhou J Y Peng G R Fan and Y T Wu ldquoIsolationand purification of flavonoid glycosides from Trollius ledebouriusing high-speed counter-current chromatography by stepwiseincreasing the flow-rate of the mobile phaserdquo Journal of Chro-matography A vol 1092 no 2 pp 216ndash221 2005

[24] X Li Z Xiong X Ying L CuiW Zhu and F Li ldquoA rapid ultra-performance liquid chromatography-electrospray ionizationtandem mass spectrometric method for the qualitative andquantitative analysis of the constituents of the flower of Trolliusledibouri Reichbrdquo Analytica Chimica Acta vol 580 no 2 pp170ndash180 2006

[25] J Felix-Silva T Souza Y A S Menezes et al ldquoAqueous leafextract of Jatropha gossypiifolia L (Euphorbiaceae) inhibitsenzymatic and biological actions of Bothrops jararaca snakevenomrdquo PLoS ONE vol 9 no 8 Article ID e104952 2014

[26] J Felix-Silva T Souza R B A G Camara et al ldquoIn vitroanticoagulant and antioxidant activities of Jatropha gossypiifoliaL (Euphorbiaceae) leaves aiming therapeutical applicationsrdquoBMC Complementary and Alternative Medicine vol 14 article405 2014

[27] J Felix-Silva J A S Gomes L M De Quadros Barbosa etal ldquoSystemic and local anti-inflammatory activity of aqueousleaf extract from Jatropha gossypiifolia L (Euphorbiaceae)rdquoInternational Journal of Pharmacy and Pharmaceutical Sciencesvol 6 no 6 pp 142ndash145 2014

[28] A C Pilon R L Carneiro F S Carnevale Neto V Bolzaniand I Castro-Gamboa ldquoInterval multivariate curve resolutionin the dereplication of HPLC-DAD data from Jatropha gossypi-foliardquo Phytochemical Analysis vol 24 no 4 pp 401ndash406 2013

[29] J Dubois and T J Mabry ldquoThe C-glycosylflavonoids of flaxLinum usitatissimumrdquo Phytochemistry vol 10 no 11 pp 2839ndash2840 1971

[30] M ShibanoKKakutaniMTaniguchiMYasuda andK BabaldquoAntioxidant constituents in the dayflower (Commelina commu-nis L) and their 120572-glucosidase-inhibitory activityrdquo Journal ofNatural Medicines vol 62 no 3 pp 349ndash353 2008

[31] S Gallori A R Bilia M C Bergonzi W L R Barbosa and FF Vincieri ldquoPolyphenolic constituents of fruit pulp of EuterpeoleraceaMart (Acai palm)rdquo Chromatographia vol 59 no 11-12pp 739ndash743 2004

[32] D E Soltis and B A Bohm ldquoFlavonoids of Ascarina lucidardquoJournal of Natural Products vol 45 no 4 pp 415ndash417 1982

[33] S Perveen A M El-Shafae A Al-Taweel et al ldquoAntioxi-dant and urease inhibitory C-glycosylflavonoids from Celtisafricanardquo Journal of AsianNatural Products Research vol 13 no9 pp 799ndash804 2011

[34] HWagner LHorhammer and I CKiraly ldquoFlavon-c-glykosidein Croton zambezicusrdquo Phytochemistry vol 9 no 4 p 897 1970

[35] D Pal P Mishra N Sachan and A K Ghosh ldquoBiologicalactivities andmedicinal properties ofCajanus cajan (L)MillsprdquoJournal of Advanced Pharmaceutical Technology and Researchvol 2 no 4 pp 207ndash214 2011

[36] S Pang Y Ge L S Wang X Liu C W Lin and H YangldquoIsolation and purification of orientin and isovitexin fromThlaspi arvense linnrdquo Advanced Materials Research vol 781ndash784 pp 615ndash618 2013

[37] R-F Wang X-W Yang C-M Ma et al ldquoTrollioside a newcompound from the flowers of Trollius chinensisrdquo Journal ofAsianNatural Products Research vol 6 no 2 pp 139ndash144 2004

[38] B Koeppen and D Roux ldquoC-gylcosylflavonoids the chemistryof orientin and iso-orientinrdquo Biochemical Journal vol 97 no 2pp 444ndash448 1965


[39] P Uma Devi ldquoRadioprotective anticarcinogenic and antiox-idant properties of the Indian Holy Basil Ocimum sanctum(Tulasi)rdquo Indian Journal of Experimental Biology vol 39 no 3pp 185ndash190 2001

[40] M DanielMedicinal Plants Chemistry and Properties SciencePublishers 2006

[41] R Praveena K Sadasivam V Deepha and R SivakumarldquoAntioxidant potential of orientin a combined experimentaland DFT approachrdquo Journal of Molecular Structure vol 1061no 1 pp 114ndash123 2014

[42] V Nayak H Nishioka and P Uma Devi ldquoAntioxidant andradioprotective effects of Ocimum flavonoids orientin andvicenin in Escherichia colirdquo Defence Science Journal vol 56 no2 pp 179ndash187 2006

[43] F An G D Yang J M Tian and S H Wang ldquoAntioxidanteffects of the orientin and vitexin in Trollius chinensis Bungein D-galactose-aged micerdquo Neural Regeneration Research vol7 no 33 pp 2565ndash2575 2012

[44] Q F Lin S Q Feng Y Z Cen Y T Yang and L Y WangldquoStudy on the antibacterial and antiviral activity compositionsof Trollium chinensis Bungerdquo Journal of Zhejiang UniversitySCIENCE B vol 31 no 4 pp 412ndash415 2004

[45] Y-L Li S-C Ma Y-T Yang S-M Ye and P P-H ButldquoAntiviral activities of flavonoids and organic acid from Trolliuschinensis Bungerdquo Journal of Ethnopharmacology vol 79 no 3pp 365ndash368 2002

[46] S P Boominathan G Sarangan S Srikakelapu S Rajesh CDuraipandian and P Srikanth ldquoAntiviral activity of bioassayguided fractionation of Plumbago zeylanica roots against Her-pes Simplex Virus Type 2rdquo World Journal of PharmaceuticalSciences vol 3 no 12 pp 1003ndash1017 2014

[47] H Ali and S Dixit ldquoIn vitro antimicrobial activity of flavanoidsof Ocimum sanctum with synergistic effect of their combinedformrdquo Asian Pacific Journal of Tropical Disease vol 2 no 1 ppS396ndashS398 2012

[48] C A Feghali and TMWright ldquoCytokines in acute and chronicinflammationrdquo Frontiers in Bioscience vol 2 pp d12ndashd26 1997

[49] C Gabay ldquoInterleukin-6 and chronic inflammationrdquo ArthritisResearch andTherapy vol 8 supplement 2 p S3 2006

[50] A R Brasier A Recinos III M S Eledrisi and M S RungeldquoVascular inflammation and the renin-angiotensin systemrdquoArteriosclerosis Thrombosis and Vascular Biology vol 22 no8 pp 1257ndash1266 2002

[51] H Y Yoo S-K Ku T H Lee and J-S Bae ldquoOrientin inhibitsHMGB1-induced inflammatory responses in HUVECs and inmurine polymicrobial sepsisrdquo Inflammation vol 37 no 5 pp1705ndash1717 2014

[52] W H Lee S-K Ku and J-S Bae ldquoVascular barrier protectiveeffects of orientin and isoorientin in LPS-induced inflammationin vitro and in vivordquo Vascular Pharmacology vol 62 no 1 pp3ndash14 2014

[53] S-K Ku S Y Kwak and J-S Bae ldquoOrientin inhibits highglucose-induced vascular inflammation in vitro and in vivordquoInflammation vol 37 no 6 pp 2164ndash2173 2014

[54] T Sun R Liu and Y-X Cao ldquoVasorelaxant and antihyperten-sive effects of formononetin through endothelium-dependentand -independent mechanismsrdquo Acta Pharmacologica Sinicavol 32 no 8 pp 1009ndash1018 2011

[55] T Ogihara M Matsuzaki H Matsuoka et al ldquoThe combina-tion therapy of hypertension to prevent cardiovascular events(COPE) trial rationale and designrdquoHypertension Research vol28 pp 331ndash338 2005

[56] X-C Fu M-W Wang S-P Li Y Zhang and H-L WangldquoVasodilatation produced by orientin and itsmechanism studyrdquoBiological and Pharmaceutical Bulletin vol 28 no 1 pp 37ndash412005

[57] X-C FuM-WWang S-P Li andH-LWang ldquoAnti-apoptoticeffect and the mechanism of orientin on ischaemicreperfusedmyocardiumrdquo Journal of Asian Natural Products Research vol8 no 3 pp 265ndash272 2006

[58] L Y Liu Q Q Ma J Y Li et al ldquoThe therapeutic effect oforientin on myocardial infarction ratsrdquo Lishizhen Medicine andMateria Medica Research vol 2013 no 8 pp 1807ndash1810 2013

[59] X C Fu Z X Huang Y W Cai and Q H Yang ldquoProtectiveeffects of orientin on experimental myocardial infarction indogsrdquo Herald of Medicine vol 25 no 7 pp 621ndash623 2006

[60] X C Fu Q H Yang Z X Huang and S P Li ldquoEffects of ori-entin on cardiac function and hemodynamics in anesthetizeddogsrdquo West China Journal of Pharmaceutical Sciences vol 22no 3 pp 289ndash291 2007

[61] X-C Fu X Wang H Zheng and L-P Ma ldquoProtective effectsof orientin on myocardial ischemia and hypoxia in animalmodelsrdquo Journal of Southern Medical University vol 27 no 8pp 1173ndash1175 2007

[62] N Lu Y Sun and X Zheng ldquoOrientin-induced cardiopro-tection against reperfusion is associated with attenuation ofmitochondrial permeability transitionrdquo Planta Medica vol 77no 10 pp 984ndash991 2011

[63] C K K Nair D K Parida and T Nomura ldquoRadioprotectors inradiotherapyrdquo Journal of Radiation Research vol 42 no 1 pp21ndash37 2001

[64] P Uma Devi A Ganasoundari B Vrinda K K SrinivasanandM K Unnikrishnan ldquoRadiation protection by theOcimumflavonoids orientin and vicenin mechanisms of actionrdquo Radia-tion Research vol 154 no 4 pp 455ndash460 2000

[65] B Vrinda and P Uma Devi ldquoRadiation protection of humanlymphocyte chromosomes in vitro by orientin and viceninrdquoMutation ResearchGenetic Toxicology and EnvironmentalMutagenesis vol 498 no 1-2 pp 39ndash46 2001

[66] Nayak and P Uma Devi ldquoProtection of mouse bone marrowagainst radiation-induced chromosome damage and stem celldeath by the Ocimum flavonoids orientin and viceninrdquo Radia-tion Research vol 163 no 2 pp 165ndash171 2005

[67] P Uma Devi K S Bisht and M Vinitha ldquoA comparativestudy of radioprotection by Ocimum favonoids and syntheticaminothiol protectors in the mouserdquo British Journal of Radiol-ogy vol 71 no 847 pp 782ndash784 1998

[68] C A Ross andMA Poirier ldquoProtein aggregation and neurode-generative diseaserdquo Nature Medicine vol 10 pp S10ndashS17 2004

[69] D M Skovronsky V M-Y Lee and J Q Trojanowski ldquoNeu-rodegenerative diseases new concepts of pathogenesis and theirtherapeutic implicationsrdquoAnnual Review of Pathology vol 1 pp151ndash170 2006

[70] C-W Hung Y-C Chen W-L Hsieh S-H Chiou and C-LKao ldquoAgeing and neurodegenerative diseasesrdquo Ageing ResearchReviews vol 9 supplement pp S36ndashS46 2010

[71] B N T Law A P K Ling R Y Koh S M Chye andY P Wong ldquoNeuroprotective effects of orientin on hydro-gen peroxide-induced apoptosis in SH-SY5Y cellsrdquo MolecularMedicine Reports vol 9 no 3 pp 947ndash954 2014

[72] L Yu S Wang X Chen et al ldquoOrientin alleviates cognitivedeficits and oxidative stress in A120573

1ndash42-induced mouse model ofAlzheimerrsquos diseaserdquo Life Sciences vol 121 pp 104ndash109 2015


[73] Y Liu N Lan J Ren et al ldquoOrientin improves depression-like behavior and BDNF in chronic stressed micerdquo MolecularNutrition amp Food Research vol 59 no 6 pp 1130ndash1142 2015

[74] J Kim I Lee J Seo et al ldquoVitexin orientin and other flavonoidsfrom Spirodela polyrhiza inhibit adipogenesis in 3T3-L1 cellsrdquoPhytotherapy Research vol 24 no 10 pp 1543ndash1548 2010

[75] E D Rosen C-H Hsu X Wang et al ldquoCEBP120572 inducesadipogenesis through PPAR120574 a unified pathwayrdquo Genes andDevelopment vol 16 no 1 pp 22ndash26 2002

[76] F S Kilic B Sirmagul E Yildirim S Oner and K ErolldquoAntinociceptive effects of gabapentin and its mechanism ofaction in experimental animal studiesrdquo Indian Journal of Medi-cal Research vol 135 no 5 pp 630ndash635 2012

[77] R Z Da Silva R A Yunes MM De Souza F DMonache andV Cechinel-Filho ldquoAntinociceptive properties of conocarpanand orientin obtained from Piper solmsianum C DC varsolmsianum (Piperaceae)rdquo Journal of Natural Medicines vol 64no 4 pp 402ndash408 2010

[78] DQ Li QWang Z F Yuan et al ldquoPharmacokinetics and tissuedistribution study of orientin in rat by liquid chromatographyrdquoJournal of Pharmaceutical and Biomedical Analysis vol 47 no2 pp 429ndash434 2008

Submit your manuscripts athttpwwwhindawicom

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Hindawi Publishing Corporationhttpwwwhindawicom

Volume 2014

ToxinsJournal of

VaccinesJournal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

AntibioticsInternational Journal of

ToxicologyJournal of


StrokeResearch and TreatmentHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Drug DeliveryJournal of



Advances in Pharmacological Sciences

Tropical MedicineJournal of


Medicinal ChemistryInternational Journal of


AddictionJournal of



BioMed Research International

Emergency Medicine InternationalHindawi Publishing Corporationhttpwwwhindawicom Volume 2014


Autoimmune Diseases


Anesthesiology Research and Practice

ScientificaHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of


Pharmaceutics


MEDIATORSINFLAMMATION

of


O

OOH

OH

OH

OHOH

HO

HO

HO

O

H

Figure 1 Chemical structure of orientin

purpurea L) [6ndash8] the anti-inflammatory drug (Aescinfrom Aesculus hippocastanum L) [7] antitumour agent(Etoposide from Podophyllum peltatum L [7 8] Vincristineand Vinblastine from Catharanthus roseus [6 8] Irinotecanand Topotecan from Camptotheca acuminate [8] Paclitaxeland Abraxane from Taxus brevifolia [8] Solamargine fromSolanum dulcamara [8] Masoprocol from Larrea tridentata[8] Alitretinoin from Daucus carota [8]) antimalaria andantiarrhythmic agent (quinine and quinidine from Cinchonaspp) [6] muscle relaxant (atropine from Atropa belladonna)[6] and antinociceptive and cough suppressant drugs (mor-phine and codeine resp) from Papaver somniferum [6]

Considering the importance of bioactive compoundsextraction of these bioactive compounds from medicinalplants is a crucial step in producing plant-derived drugs Oneof the bioactive compounds isolable from medicinal plantsorientin is often used in the studies due to its extensivetherapeutic properties Orientin is a water-soluble flavonoidC-glycoside which is commonly extractable from somemedicinal plants such as Ocimum sanctum (holy basil)[9ndash11] Phyllostachys nigra (bamboo leaves) [12ndash18] Passifloraspecies (passion flower) [19 20] Trollius species (GoldenQueen) [21ndash24] Jatropha gossypifolia (Bellyache Bush) [25ndash28] Linum usitatissimum (flax) [29] Commelina communis(dayflower) [30] Euterpe oleracea Mart (Acai palm) [31]Ascarina lucida [32] Celtis africana (white stinkwood) [33]Croton zambesicus (Lavender croton) leaves [34] Cajanuscajan (Pigeon pea) leaves [35] andThlaspi arvense (Field Pen-nycress) [36]The extraction of orientin in differentmedicinalplants and its medicinal properties which include antioxi-dant antiaging antiviral antibacterial anti-inflammationvasodilatation and cardioprotective antiadipogenesisantinociceptive radiation protective neuroprotective andantidepressant-like effects are discussed in this review

2 Orientin

Orientin is a water-soluble flavonoid C-glycoside whichhas the IUPAC name of 2-(34-dihydroxyphenyl)-57-dihy-drox-y-8-[(2S3R4R5S6R)-345-trihydroxy-6-(hydroxym-ethyl)oxan-2-yl]chromen-4-one It has a molecular formulaof C21H20O11

and a molecular weight of 4483769 gmol[38] The chemical structure of orientin (Figure 1) shows that

it consists of mostly phenol groups with two ether groupsand one ketone group Therefore a polar solvent such asmethanol ethanol or water is required to extract orientinfrom the medicinal plants

3 From Plants to Orientin

Orientin has been isolated from various medicinal plantssuch as Ocimum sanctum Phyllostachys species (bambooleaves) Passiflora species (passion flowers) Trollius species(Golden Queen) and Jatropha gossypifolia (Bellyache Bush)

Ocimum sanctum (also known as Indian holy basil orTulsi in Sanskrit) was planted in India and it is well known forits medicinal values The Ayurveda (Indian ancient system ofmedicines) uses different parts of Ocimum sanctum to treatcough common cold malarial fever skin diseases and snakebites [39] Nair et al successfully isolated orientin from theleaves of O sanctum alongside with other flavonoids suchas apigenin apigenin-7-O-glucuronide molludistin luteolinand luteolin-7-O-glucuronide [10] Similarly Uma Devi etal isolated orientin from the same plant parts for in vivoradioprotective effect studies [11]

Bamboo leaves have been an essential resource in Chinafor years and Phyllostachys pubescens Mazel ex H de Lehaieis the most abundant species among the bamboo leaves inChina due to its high yield high growth rate and extensiveuse [12] Yong et al isolated orientin and other compoundssuch as isoorientin vitexin isovitexin caffeic acid and ferulicacid by immersing different cultivars of P pubescens in70 methanol [16] Besides that Zhang et al have isolated49mg of orientin from the antioxidant of bamboo leaves(AOB) concentrated solution initially from the 65 g ofcrude column chromatography fraction [17] In additionorientin has been separated from the three bamboo speciesPhyllostachys pubescens Mazel ex H de Lehaie PhyllostachysglaucaMcClure and Pleioblastus yixingensis by Sun et al withnewly proposed high-performance thin-layer chromatogra-phy (HPTLC) method [18] With this simple method 644782 and 492 (ww) of orientin were produced from Ppubescens P glauca and P yixingensis respectively [18]

Orientin has also been isolated from the Passifloraspecies Passiflora was originally named in Spanish meaningldquothe flower with the five woundsrdquo in the 17th Century bySpanish priests in South America Up to now there areabout 400 Passiflora species that have been recognised Itwas suggested that Passiflora incarnata is used as a mildcalming agent while other species were reported to possessmedicinal properties [19] In isolating orientin Grundmannet al managed to obtain 336mg of orientin per gram of driedP incarnata [19] while de Paris et al isolated orientin fromwater extract of P edulis dried leaves [20]

In Traditional ChineseMedicineTrollius chinensis Bungehas been used to treat pharyngitis respiratory infectionsbronchitis and tonsillitis for years The dried flowers ofother Trollius species were also discovered to possess variousmedicinal properties [37] Liu et al used HPLC method toisolate orientin from Trollius chinensis with the detectionwavelength of 340 nm [21] Besides that 5mg of orientin hasbeen eluted from 15 kg of dried flowers of Trollius ledebouri








[15ndash19]






[25ndash27]




(i) TLC(ii) HPLC


[30ndash33]








2O2-) induced



2O2-induced 120573-












50value of 228120583M























Abbreviations












Competing Interests


Acknowledgments


References























































































Volume 2014

ToxinsJournal of

VaccinesJournal of















AddictionJournal of






Autoimmune Diseases




Journal of


Pharmaceutics



of








[15ndash19]






[25ndash27]




(i) TLC(ii) HPLC


[30ndash33]








2O2-) induced



2O2-induced 120573-












50value of 228120583M























Abbreviations












Competing Interests


Acknowledgments


References























































































Volume 2014

ToxinsJournal of

VaccinesJournal of















AddictionJournal of






Autoimmune Diseases




Journal of


Pharmaceutics



of



2O2-induced 120573-












50value of 228120583M























Abbreviations












Competing Interests


Acknowledgments


References























































































Volume 2014

ToxinsJournal of

VaccinesJournal of















AddictionJournal of






Autoimmune Diseases




Journal of


Pharmaceutics



of




















Abbreviations












Competing Interests


Acknowledgments


References























































































Volume 2014

ToxinsJournal of

VaccinesJournal of















AddictionJournal of






Autoimmune Diseases




Journal of


Pharmaceutics



of
















































































Volume 2014

ToxinsJournal of

VaccinesJournal of















AddictionJournal of






Autoimmune Diseases




Journal of


Pharmaceutics



of

Review Article A Review on Medicinal Properties of Orientin

Documents

Transcript of Review Article A Review on Medicinal Properties of Orientin