J Crit Rev, Vol 4, Issue 4, 9-13Review Article


BEEPROPOLIS (BEE’S GLUE): A PHYTOCHEMISTRY REVIEW

ADIL F. WALI1, AHLAM MUSHTAQ2, MUNEEB U REHMAN3, SEEMA AKBAR4, MUBASHIR HUSSAIN MASOODI5*

1Department of Pharmaceutical Chemistry, RAKCOPS, RAK Medical and Health Sciences University, RAS Al-Khaimah 11172, U. A. E., 2Department of Biochemistry, University of Kashmir, Srinagar, Jammu and Kashmir 190006, India, 3Department of Biochemistry, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir, Jammu and Kashmir 190006, India, 4Research Institute of Unani Medicine, University of Kashmir Campus, Srinagar, Jammu and Kashmir 190006, India, 5Department of Pharmaceutical Sciences, University of Kashmir, Srinagar, Jammu and Kashmir 190006, India
Email: mubashir@kashmiruniversity.ac.in

Received: 22 May 2017 Revised and Accepted: 22 Jul 2017


ABSTRACT

Propolis, also called ‘Bee glue’, is resinous material collected by Bees from flowers, buds, and exudates of plants. Literature survey were conducted using different electronic databases, like PubMed, Scifinder, and Indian scientific database. The phytoconstituents composition in the BeePropolis varies and depends upon the flora in the location; more than 500 compounds have been isolated and identified till now. They belong to such assorted chemical classes as polyphenols like, phenylpropanoids, chalcone, terpenenes, lignans, coumarins, aromatic acids and their esters. This current review is an attempt to compile data, which will give information of constituents present in Propolis.

Keywords: Propolis, Pinobanksin 3-acetate, Phytochemistry, Mummifying corpses


INTRODUCTION

The term ‘’Propolis’’emanates from the Greek word coined by Aristotle, pro (before) and polis (city), meaning, Before the City, or Defender of the City[1].BeePropolis (Bee’s glue) is a resinous, gummy and balsamic material collected from flora by honeyBees (Apis mellifera L.belongs to Apidae family, genus Apis) used as construction and insulating material their hive. It is not only used as a construction material but also to protect thehive from microbial growth (fungi and bacteria) [2].The composition of BeePropolis varies on its botanical original and ithasbeen reported that BeePropolis helps to maintain homeostasis, reduce vibration, keep air flow in check, prevent hive against squatter and prevent putrefaction [3].

Description

Most of the BeePropolisare opaque shiny irregular in shape and is solid at room temperature and become sticky above room temperature. It is dark green or brown in color having asweet taste but can be bitter too. The composition, aroma and color of the BeePropolis vary from hive to hive, season to season, Bee species, botanical source and geographical conditions prevailing at the location from where the resin is collected by honey Bees[4].

Traditional uses

Propolis has been known fromat least 300 BC for its medicinal values in the world. For the Egyptians, the Bee was holy and they used Propolis to theart of mummifying corpses and as anantibiotic [5]. The Romans, seeing the Bee as God Jupiter convert the lady Mellisa into a Bee and useto cure some lesions of the skin.Propolis has been anciently known to Greeks for healing qualities. It also was used in the Boer war for tissue regeneration and wound healing [6].In the Balkan States it’s still used for the treatment of wounds and burns, sore throat, stomach ulcer[7]Traditionally ethanol extract of Propolis, has been known for anti-inflammatory effect for centuries [8].BeePropolis has been used pragmatic for centuries as an immunomodulatory agent [9].It has been reported that from 12th centuryBeePropolis was using asremediesin themouth, throat infections, and dental caries [10].

Phytochemistry

BeePropolis is official in the United States Pharmacopeia and natural health product monograph Canada [11, 12]. Now days engross has been ascending about its phytochemistry and pharmacological property. The phytoconstituents composition in the bee propolisvaries and depends upon the flora in the location; more than 500 compounds have been isolated and identified till now. The main phytoconstituents reported to have been isolated and identified from the BeePropolis are polyphenolics, Chalcone, triterpenes, aromatic acids and their esters [13-17].

The chemical analysis of red-type Cuban Propolis revealed the presence of 11 isoflavonoids long with gallic acid, isoliquiritigenin, and (-)-liquiritigenin [18].It has been reported that the main phytoconstituents in the BeePropolis are flavonoids and their aglycones moiety [19, 20].The main phenolics compounds flavonoids with an unsubstituted ring are pinobanksin, pinocembrin-7-methylether, pinobanksin 3-acetate, pinocembrin, chrysin, galangin, tectochrysin, apigenin, kaempferol andquercetin and the flavonescomponents areeupatorin, hispidulin, 5-hydroxy-6,7,3′,4′-tetra methoxy flavone are also present [21-23].

The other phenolics compounds isolated are3-prenyl-4-hydroxy-cinnamic acid,2,2-dimethyl-6-carboxyethenyl-2H-1-benzopyrane,3,5-diprenyl-4-hydroxycinnamic acid,2,2-dimethyl-6-carboxy-ethenyl-8-prenyl-2H-1-benzopyran [24]. A prenylated cinnamic acid derivative and prenylated tetrahydroxystilbenes were also reported from the ethyl acetate extract of Propolisfrom Kangaroo Island [25].Anthraquinones mainly emodin and chrysophanol also havebeen reported in the ethanolic extract of BeePropolis[26].Cinnamic acid derivatives also havebeen reported p-coumaric acid, artepillin C, drupanin, baccharin [27, 28].A novel prenylated flavonoid was isolated from the Egyptian Propolisisonymphaeol-D, along with isonymphaeol-B and nymphaeol-B [29].During the phytochemical investigation of methanolic extract of the Thai Propolis isolation of a new phenylallylflavanone, (7″S)-8-[1-(4'-hydroxy-3'-methoxy-phenyl) prop-2-en-1-yl]-(2S) pinocembrin and (E)-cinnamyl-(E)-cinnamylidenate were reported along with flavonoids and phenolic esters [30].

Presence of two new benzofuran derivatives in the methanolic extract of Brazilian Propoliswas reported Propolis-benzofurans A and B along with isoprenylated compounds (E)-3-[2, 3-dihydro-2-(1-methylethenyl)-7-prenyl-5-benzofuranyl]-2-propen oic acid and (E)-3-4-hydroxy-3-[(E)-4-(2, 3-dihydrocinnamoyloxy)-3-methyl-2-butenyl]-5-prenylphenyl-2-propen oic acid[31].During the chemical analysis of water extract from Brazilian Propolis a new compound, propol (3-[4-hydroxy-3-(3-oxo-but-1-enyl)-phenyl]-acrylic acid) were isolated [32].

During the chemical investigation of red-type Mexican Propolis three new molecules has Been isolated, 1-(3',4'-dihydroxy-2'-methoxyphenyl)-3-(phenyl)propane, (Z)-1-(2'-methoxy-4',5'-dihydroxyphenyl)-2-(3-phenyl)propene and 3-hydroxy-5,6-dimethoxy-flavone, along withknown flavanones, isoflavones, and pterocarpans. Isoflavonoids, 1,3-diarylpropane and 1,3-diarylpropene carbon skeleton was first time found in Mexican Propolis [33].

Glycerol esters derivativeshas Been reportedfrom methanolic extract of Wuhan Propolis are 2-acetyl-1-coumaroyl-3-cinnamoylglycerol, (+)-2-acetyl-1-feruloyl-3-cinnamoylglycerol, (-)-2-acetyl-1-feruloyl-3-cinnamoylglycerol, 2-acetyl-1,3-dicinnamoylglycerol, and (-)-2-acetyl-1-(E)-feruloyl-3-(3″(ζ),16″)-dihydroxy-palmitoylglycerol[34, 35].The new esters haveBeen isolated from Egyptian Propolis are 4-methoxy-hydrocinnamic acid, hydro-ferulic acid, ferulic acid and 2,6-bis-(pentanyloxy)-4-pentanylphenoxyethanol, were present in asignificant amountabout 27% [36].

Isolation of Viscidone, vanillin, 3', 4’-(methylendioxy) acetophenone, cinnamic acid, 3-ethoxy-4-methoxybenzaldehyde and 3-methoxy-4-hydroxymethyl ester were first time reported from the Chilean matorral hives [37].

During the phytochemical screening Propolis collected from Jeju Island contained chalcon and coumarin compounds (±)-(E)-4'-methoxy-4,2'-dihydroxy-3'-(2″,3″-dihydroxy-3″-methylbutyl)-chalcone, (E,E,E)-4,2',4'-trihydroxy-3'-(7″-hydroxy-3″,7″-dimethyloct-2″,5″-dienyl)-chalcone,(±)-(E,E)-4,2',4'-trihydroxy-3'-(5″-hydroxy-3″,7″-di-methyl-oct-2″,6″-dienyl)-chalcone, (±)-(E)-4'-methoxy-4,3″,4″-tri-hydroxy-2″,2″-dimethyl- dihydropyrano-(2',3')-chalcone,(±)-(E)-4'-methoxy-4,3″-dihydroxy-2″-(1″'-hydroxyisopropyl)-dihydrofurano-(2',3')-chalcone,(-)-(E)-4,4'-dihydroxy-2″-(1″'-hydroxy-1″',5″'-dimethylhex-4″'-enyl)-dihydrofurano-(2',3')-chalcone,(+)-(E)-4,2'-dihydroxy-2″-methyl-2″-(3″',4″'-dihydroxy-4″'-methylpentanyl)-2H-pyrano-(3',4')-chalcone and (-)-(E)-4,2'-dihydroxy-2″-methyl-2″-(3″',4″'-dihydroxy-4″'-methylpentanyl)-2H-pyrano-(3',4')-chalcone [37]2',3',4'-trimethoxychalcone, 2'-hydroxy-3',4'-dimethoxy-chalcone, 2',4'-dihydroxy-3'-methoxy-chalcone [38].

From the Argentinean Propolis 2',4'-dihydroxy-3'-methoxychalcone, 2',4'-dihydroxychalcone, 2',4',4-trihydroxy-6'-methoxychalcone, 5-hydroxy-4',7-dimethoxyflavone, 4',5-dihydroxy-3,7,8-trimethoxyflavone and 7-hydroxy-5,8-dimethoxyflavone were also been isolated [39].From the Mexican Propolis methanolic extract phenylallylflavanones (2R, 3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl) prop-2-en-1-yl] pinobanksin and (2R, 3R)-6-[1-(4'-hydroxy-3'-methoxyphenyl) prop-2-en-1-yl] pino-banksin 3-acetate were isolated [39, 40].

From Chinese Propolisnewcomponents 3-O-[(S)-2-methyl-butyroyl]pinobanksin and 6-cinnamylchrysin were reported from ethyl acetate fraction of themethanolic extract [41]. A novel cinnamate ester derivative benzyl caffeate along with flavonoids 7-O-methylchrysin, genkwanin andrhamnazin were reported from Liaoxi Propolis [42].

Another chemical component which hasbeen isolated from the BeePropolis is terpenes, from the methanolic extract of Propolisbicyclic diterpenoids havebeen isolated and identified as ent-17-hydroxy-3, 13Z-clerodadien-15-oic acid, 15-oxo-3, 13Z-kolavadien-17-oic acid and itd E-isomer kolavadien-17-oic acid [43].The other derivative compounds reported are isocupressic, communic, imbricatoloic, acetoxy-isocupressic acid and 8(17), 13E-labdadien-15, 19-dioic acid and its methyl ester[44].Besides this may other prominent compounds were isolated from BeePropolis were the monoterpene α-pinene, the sesquiterpenes β-caryophyllene, α-cubebene, α-muurolene, γ-muurolene, γ-cadinene, germacrene-D,elemol, diterpenes manool and totarol[45].

In recently phytochemical investigation more compounds were reported diterpenes: 14,15-dinor-13-oxo-8(17)-labden-19-oic acid and a mixture of labda-8(17),13E-dien-19-carboxy-15-yl oleate and palmitate, triterpenes, 3,4-seco-cycloart-12-hydroxy-4(28),24-dien-3-oic acid and cycloart-3,7-dihydroxy-24-en-28-oic acid [46].

In amethanolic extract of Jordanian Propolisa new lanostane triterpenoid, 24(Z)-1β-3β-dihydroxyeupha-7,24-dien-26-oic acid, have been isolated 47]. From Indonesian Propolis collected East Java, four alk(en)ylresorcinols were reported for thefirst time from Propolis, along with four prenylflavanonesand three cycloartane-type triterpenes [48].

From the Methanolic extract of Myanmar Propolis thirteen cycloartane-type tritepenes in which two of them is novel (22Z,24E)-3-oxocycloart-22,24-dien-26-oic acid and (24E)-3-oxo-27,28-dihydroxycycloart-24-en-26-oic acidandknown four prenylated flavanones were isolated [49, 50]. Isolation of diterpene glycosides ent-8(17)-labden-15-O-alpha-L-rhamnoside and ent-8(17)-labden-15-O-(3'-O-acetyl)-alpha-L-rhamnoside were first reported from the El Salvador Propolis[38].From the Brazilian Propolis a novel triterpenoid melliferoneand moronic acid, anwuweizonic acid, and betulonic acid were isolated along with aromatic compounds [51]. Isolation of novel compounds 2, 2-dimethyl-8-prenyl-6-vinylchromene and 2, 6-diprenyl-4-vinylphenol werereported from the essential oil of Brazilian Propolis apart from terpenoids and aromatic components [52, 53].

From the aqueous Propolis extract many compounds has been isolation mainly caffeoyl quinic acid derivatives such asmethyl 3,4-di-O-caffeoyl quinate,3,4-di-O-caffeoyl quinic acid,methyl 4,5-di-O-caffeoyl quinate, 3,5-di-O-caffeoyl quinic acid [54] and 3,4-di-caffeoylquinic Acid, is a major component[55-58].

Other compounds reported namely, acetophenones: 2-[1-methyl]-vinyl-5-acetylcumarane 2-[1-hydroxymethyl]-vinyl-6-acetyl-5-hydroxy-cumarane and 2-[1-acetoxymethyl]-vinyl-6-acetyl-5-hydroxycumarane.

Lignans: 1-(4-hydroxy-3-methoxyphenyl)1,2-bis{4-[(E)-3-acetoxy-propen-1-yl]-2 methoxyphenoxy}-propan-3-ol acetate, 1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-acetoxypropen-1-yl]-2-methoxyphenoxy}propan-1,3-diol 3-acetate (erythro-and treo), 3-acetoxymethyl-5-[(E)-2-formylethen-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran, sesamin, aschantin, sesartenin,yangambin [58]. Recently two new unknownarylnaphtalene lignans hasbeen isolated, tetrahydrojusticidin B and 6-methoxydiphyllin [59].Isolation of three novel lignans from Chilean Propolis was identified trimeric coniferyl alcohol acetate, diastereomer of the dimeric coniferyl alcohol acetate, dihydrobenzofuran lignan aldehyde with two known lignans [60].

Sugars and sugar alcohols: xylose, galactose,mannose, glucuronic acid,lactose, maltose, melibiose,erytritol, xylitol,inositol also have been reported isolated from the BeePropolis[61].From the ethanolic extract of Brazilian green Propolis, flavonoids were isolated and purified baccharin, beturetol, kaempferide, isosakuranetin, dihydrokaempferideand drupanin [62, 63]. A prenylated benzophenonewas identified from the hexane fraction of Brazilian Propolis type 6hyperibone A [64], hyperibone B, garcinielliptoneIalong withpropolones B, C and Dwas isolated from Cuban Propolis [65]. From the ethanolic extract of Cuban Propolis a novel polyisoprenylated benzophenonewas isolated [66].

Isolation of new prenylated flavonoid, prokinawan were isolated from Propolis collected from Okinawa Japan along with known compounds [67].It hasbeen reported from Taiwanese Propolisisolation of six propolins, A-F and a new propolin G was found which is identical to the Nymphaeol C compound [68]. Isolation of novel compound propolinH from Taiwanese Propolis has been reported [69]. Two new prenylflavanones havebeen isolated from the TaiwanesePropolis are propolin A and B [70].

A new Chalcone together with 10 novel open chain neoflavonoids was isolated from the methanolic extract of Nepalese Propolis [71].

A Recent investigation carried out by using atomic absorption spectroscopy revealed that the presenceof mineral elements in Bee Propolis, Ca, Mg, K, Na, Fe and Zn were observed in Macedonian samples [72]and in ethanolic extracts of Cuban samples [73].

Structure of some molecules isolated fromPropolis

Artepillin C Drupanin
Hyperibone B Hyperibone A
Baccharin Isoliquiritigenin
(-)-liquiritigenin Pinobanksin

(All structures were draw using ChemDraw ultra-software)

CONCLUSION

Propolis has been known at least 300 BC for its traditional medicinal values around the globe. In this review, article data has beenthorough collected from various data base study, to sum up the chemical composition of Propolis till date.The composition, aroma and color of the BeePropolis vary from hive to hive, season to season, Bee species, botanical source and geographical conditions prevailing at the location from where the resin is collected by honeyBees. Around 500 compounds have been identified till date and the major chemical composition present on Propolis are flavonoids, terpenoids, phenolic and their ester. Besides that polyphenols like phenylpropanoids, chalcone, terpenenes, lignans, coumarins, aromatic acids and their esters were also identified and reported from the Propolis. However, the other secondary metabolites like as alkaloids, iridoids have not been isolated and identified from Propolistill date.

ACKNOWLEDGEMENT

Mubashir H. Masoodi would like to present his gratitude to University Grants Commission (UGC) Govt. of India for financial support on this research project F. No 42-861/2013 (SR).

CONFLICTS OF INTERESTS

There are no conflicts of interest

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How to cite this article

  • Adil F Wali, Ahlam Mushtaq, Muneeb U Rehman, Seema Akbar, Mubashir Hussain Masoodi. Beepropolis (Bee’s glue): a phytochemistry review. J Crit Rev 2017;4(4):9-13.



About this article

Title

BEE PROPOLIS (BEE’S GLUE): A PHYTOCHEMISTRY REVIEW

Keywords

Propolis, Pinobanksin 3-acetate, Phytochemistry, Mummifying corpses

DOI

10.22159/10.22159/jcr.2017v4i4.20135

Date

01-08-2017

Additional Links

Manuscript Submission

Journal

Journal of Critical Reviews
Vol 4, Issue 4 (July-Aug), 2017 Page: 9-13

Online ISSN

2394-5125

Authors & Affiliations

Adil F. Wali
Department of Pharmaceutical Chemistry, RAKCOPS, RAK Medical and Health Sciences University, RAS Al-Khaimah 11172, U.A.E
India

Ahlam Mushtaq
Department of Biochemistry, University of Kashmir, Srinagar, Jammu and Kashmir 190006, India
India

Muneeb U. Rehman
Department of Biochemistry, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir, Jammu and Kashmir 190006, India
India

Seema Akbar
Research Institute of Unani Medicine, University of Kashmir Campus, Srinagar, Jammu and Kashmir 190006, India
India

Mubashir Hussain Masoodi
Department of Pharmaceutical Sciences, University of Kashmir, Srinagar, Jammu and Kashmir 190006, India
India


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