A REVIEW ON NATURAL CHALCONES AN UPDATE

A REVIEW ON NATURAL CHALCONES AN UPDATE

Ramya Kuber Banoth ^* and Ashwini Thatikonda

Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam (Women’s University), Tirupati - 517502, Andhra Pradesh, India.

ABSTRACT: Plants are a valuable source of secondary metabolites. Many phytochemicals are obtained from the plant sources that are used as valuable medicinal agents. Chalcones are one of the important secondary metabolites obtained from many edible plants like foods, vegetables, tea, spices and natural foodstuffs. Chalcones considered as obligate intermediated in flavonoid biosynthesis but they do not accumulate to an appreciable degree in most plants. Chalcones are a group of plant-derived polyphenolic compounds belonging to the flavonoids family that possess a wide variety of cytoprotective and modulatory functions, which may have therapeutic potential for multiple diseases. The largest number of natural chalcones has been isolated from species of the Leguminosae, Asteraceae and Moraceae families. Chalcone accumulating plants have often been used in traditional medicine and These chalcones and their derivatives have shown important antimicrobial, antifungal, anti-mycobacterial, antimalarial, antiviral, anti-inflammatory, antioxidant, anti-tumor, antileishmanial, anticancer properties. The purpose of this review is to summarize the various naturally occurring chalcone compounds which have been isolated from different plants and to describe the recent efforts of scientists in a pharmacological screening of chalcones, studying importance of chalcones and their biological activities.

Chalcones, Secondary metabolites, Cytoprotective, Natural products, Modulatory, Pharmacological screening

INTRODUCTION: Chalcones are a group of phenolic or flavonoid compounds widely distributed in plant kingdom ¹. They are both intermediates and end products in flavonoid synthesis, act as defensive compounds, participated in pathogens interactions and contribute to the medicinal value of herbs ². Naturally occurring chalcones and their synthetic derivatives show a wide spectrum of biological activities ³. For these reasons, chalcones are an object of continuously growing interest amongst scientists ⁴.

Chalcones are belonged to the largest class of plant secondary metabolites and are considered to be precursors of flavonoids and isoflavonoids ⁵. They serving in plant defense mechanisms to counteract reactive oxygen species in order to survive and prevent molecular damage and attack by microorganisms, insects and animals ⁶. Chemically, chalcones or 1,3-diaryl-2-propen-1-one Fig. 1 consist of open chain flavonoids in which two aromatic benzene rings are joined by a three-carbon enone moiety, α, β- unsaturated carbonyl system ⁷.

FIG. 1: STRUCTURE OF CHALCONE

Synthetic Method of Preparing Chalcones: Although chalcones occur naturally, they could be available in larger amounts through an efficient synthesis method. Chalcones can be prepared by any two condensation reactions namely:

Claisen Schmidt Condensation: The most convenient method is the Claisen-Schmidt condensation of equimolar quantities of aryl methyl ketone (acetophenone) with aryl aldehyde (benzaldehyde) in the presence of alcoholic alkali (sodium hydroxide) as a catalyst.

SCHEME 1: REACTION OF CLAISEN SCHMIDT CONDENSATION

This method of reaction has been found without any solvent as a solid-state reaction. It can be used as an example of green chemistry synthesis in undergraduate education ⁸.

Aldol Condensation: Acetophenone and benzaldehyde are the starting materials for this reaction. First, acetophenone is treated with a base like KOH which converts it into the more active form, its enolate form.

It will then react with benzaldehyde to form intermediate. The intermediate will then lose water molecule by heat to form chalcone ⁹.

C₆H₅ CO-CH₃+O=CHC₆H₅→C₆H₅CO-CH=CHC₆H₅

Acetophenone   Benzaldehyde         Benzalacetophenone

SCHEME 2: REACTION OF ALDOL CONDENSATION

FIG. 2: PHENYLPROPANOID BIOSYNTHESIS PATHWAY

Biosynthesis of Chalcones: Chalcones or benzylideneacetophenone are the important constituents of natural products and have been reported to possess varied biological and pharmacological activity ¹⁰. In higher plants, chalcones are synthesized by the enzyme Chalcone synthase from one molecule of p-coumaril-CoA and three molecules of malonyl-CoA. The amino acid L-phenylalanine, which is formed in the shikimic acid pathway, is converted to p-coumaril-CoA through the phenylpropanoid pathway, resulting in the formation of the aromatic B-ring and the 3C bridge of chalcone (C₆-C₃-). The aromatic A-ring is formed after the condensation of three molecules of malonyl-CoA (-C₆).

Once synthesized, chalcone has three main destinations in plant metabolism. It can be used to produce aurones by the Aureusidin synthase; to form glycosyl conjugates, which are yellow flower pigments that accumulate in plants; and in most cases, it can be converted to naringenin by the action of Chalcone isomerase. Chalcone isomerase “type I”, broadly found in higher plants (except leguminous plants) produces the 5-hydroxyflavanone naringenin, which is the biosynthetic precursor of virtually all flavonoids (flavones, isoflavones, flavonols, condensed tannins, and anthocyanins) ¹¹.

Natural Occurrence of Chalcones: 2-hydroxyl-4,6-dimethoxy-3-methylchalcone and 2,4-dihydroxy- 5- methyl- 17, 6- methoxy chalcone, named aurentiacin A and aurentiacin B, respectively, were isolated from Dydimocarpus aurentica ¹². Triangularin-2′, 6′-dihydroxy- 4′-methoxy-3′-methylchalcone has been isolated from the exudate farina of the ceroptin chemotype of Pityrogramma triangularis ¹³. From the fruits of Myrica gale the isolation of 2′,6′-dihydroxy-4′-methoxy-3′,5′-dimethyldihydrochalcone, and 4,4,6-trimethyl- 2- (3-phenylpropionyl)-cyclohexane-1,3, 5-trione ¹⁴ . Rubone, a new chalcone isolated from Derris robusta seed shells ¹⁵. A new Bakuchalcone, dihydrofuranochalcone has been identified in seeds of Psoralea corylifolia ¹⁶. Several known chalcones, a new isoflavone, a dihydrochalcone and three chalcone derivatives lapathinol, lapathone, angelafolone, valafolone and melafolone were isolated from Polygonum lapathifolium ¹⁷. Brackenin, a new dimeric dihydrochalcone isolated from Brackenridgea zanguebarica ¹⁸. A new prenylated flavanone, oaxacacin, and its chalcone, mixtecacin have been isolated from roots of Tephrosia woodii ¹⁹. A complex mixture of chalcones and flavanones, 1, 3, 4- trimethoxy derivatives and dimethylallyl groups and methoxy derivatives were obtained from Helichrysum rugulosum ²⁰. Two dihydrochalcones, 2′, 6′-dihydroxy-4′-methoxydihydrochalcone and 2,4′,6′-trihydroxydihydrochalcone have been isolated from leaves of Lindera umbellate ²¹. Isoliquiritin and licuraside both of which are kinds of chalcones, identified from Glycyrrhizae radix ²².

Four new chalcones, xanthangelols B-E were isolated from roots of Angelica keiskei ²³. 2'-hydroxy- 4, 4'- dimethoxychalcone was isolated from green parts and flower heads of Bidens tripartitus ²⁴. Two new β-hydroxychalcones named ponganones I and II were isolated from the root bark of Pongamia pinnata.

The structures were characterized as 7-hydroxy-2'5'-dimethoxy-[6'', 6''-dimethylpyrano(2'', 3'': 4', 3')] chalcone for ponganone-I, and 7-hydroxy-2', 5'-dimethoxy-3, 4-methylenedioxy-[6'', 6''-dimethyl-pyrano (2'',3'',4',3')] chalcone for ponganone II ²⁵. A new diprenylated chalcone stipulin has been characterized from the roots of Dalbergia stipulacea ²⁶. A new dihydroxy chalcone 3, 3' -dihydroxychalcone, 3' -methoxyflavone and beta-sitosterol have been isolated for the first time from the whole plant of Primula macrophylla ²⁷. Spinochalcones A and B, flemistrictin A chalcones were isolated from roots of Tephrosia spinosa ²⁸.

Two new chalcones, calythropsin and dihydrocalythropsin isolated from the crude extract of Calythropsis aurea ²⁹. From the aerial parts of Boronia inconspicua two novel dihydrochalcones, 2',4, 4', 6'-tetrahydroxy-5-(E-3, 7-dimethylocta-2, 6-dienyl)-3-(3-methylbut-2-enyl) dihydrochalcone and 2',4,4',6'- tetrahydroxy-3,5-di(3-methylbut-2-enyl) dihydrochalcone have been isolated and identified ³⁰. Chalcone pedicin, two new condensed chalcones, fissistin and isofissistin were also obtained from ethyl acetate extract of Fissistigma lanuginosum ³¹. A new triterpene, methyl-3-epi-betulinate in its native form and 4′,6′-dihydroxy-2′-methoxy-3′,5′-dimethyl chalcone isolated from the aerial parts of Syzygium samarangense ³².

Munchiwarin, a chalcone with the 2, 2, 6-tri-isoprenyl-cyclohex-5-ene-1, 3-dione skeleton, was isolated from Crotalaria trifoliastrum ³³. Flavonoids, syzalterin, L-farrerol and L-liquiritigenin and the chalcone isoliquiritigenin were isolated from fresh flowering bulbs of Pancratium maritimum L. ³⁴ α-hydroxydihydro-chalcone (α,4,2′-trihydroxy-4′-O-geranyldihydro-chalcone), a new isoflavone norisojamicin have been isolated from the stem bark of Millettia usaramensis ³⁵. 2', 3'-Dihydroxy-4' 6'-dimethox-chalcone and the corresponding dihydrochalcone were isolated from the leaves of Uvaria dulcis ³⁶. Prorepensin was isolated from the extract of the dried powdered twigs of Dorstenia prorepens. Dorstenia zenkeri yielded p-hydroxybenzaldehyde, dorsmanin A, 4,2,4- trihydroxychalcone and 4,2,4-trihydroxy-3-prenylchalcone ³⁷. L-hydroxypandu-ratin A, panduratin A, sakuranetin, pinostrobin, pinocembrin and dihydro-5,6-dehydrokawain were isolated from red rhizome variety of Boesenbergia pandurate ³⁸.

A new prenylated chalcone Artoindonesianin J isolated from the root bark of Artocarpus bracteata Hook ³⁹. Pure lonchocarpin and derricin were isolated from Lonchocarpus sericeus Kunth ⁴⁰. Xanthoangelol, isobavachalcone, Xanthoangelol H, laserpitin, isolaserpitin, 3'-senecioyl khellacone, 4'-senecioyl khellactone, selinidin, pteryxin, (3' R)- 3'-hysroxycolumbianidin, mumdulea flavanone A, prostratol F, falcarindiol and 5- N- penta-decylresorcinol were isolated from the exudate of Angelica keiskei ⁴¹. Three sweet dihydrochalcone glucosides tribatin 2''-acetate, phloridzin and trilobatin from the leaves of Lithocarpus pachyphyllus (Kurz) ⁴².

Three novel chalcone derivatives, malloto-philippens C, D, and E were isolated from the fruits of Mallotus philippinensis ⁴³. Two new chalcone 2′, 6′-dihydroxy-4-isopenteniloxy-3, 4-(3′′,3′′-dimeth-ylpyrano) chalcone and 4,2′,6′-trihydroxy-3′,4′-metilenodioxo-3-isopentenilchalcone were isolated from the wood ethanolic extract of Beilschmiedia tovarensis ⁴⁴. 2′-hydroxy-4′, 6′-dimethoxy-3, 4-methylenedioxy chalcone was isolated from the leaves of Bauhinia variegata ⁴⁵. A new flavanone, 7-hydroxy-5,6-dimethoxyflavanone together with three other flavonoids, didymocarpin, 2',4'-dihydroxy- 5' 6'- dimethoxychalcone and isodidymocarpin had been isolated from the methanol extract of the tree bark of Cryptocarya costata ⁴⁶. Three new chalcones, xanthokeismins A, B and C in addition to a known chalcone, Xanthoangelol B from the stem of Angelica keiskei ⁴⁷. Garcinol, the antioxidant chalcone isolated from Garcinia indica Choisy ⁴⁸. Isocordoin and 2',4'-dihydroxy-3'-(dimethylallyl)-dihydrochalcone were isolated from the root of Lonchocarpus xuul ⁴⁹. The phytochemical analysis of the plant Bacopa monnierie reveals that it contains a chalcone type of compound 2, 4, 6-trihydroxy-5-(3,3-dimethyl propenyl)-3-(4-hydroxyphenyl) propiophenone ⁵⁰. Two new chalcone derivatives morachalcones B and C were isolated from the leaves of Mora alba L. ⁵¹

Hybrid flavan-chalcones, desmosflavans A and B, together with three known compounds, cardamonin, pinocembrin and crysin were isolated from leaves of Desmos cochinchinensis ⁵². Eight chalcone derivatives as the active principles, including licochalcone G, licochalcone A, echinantin, 5-prenylbutein, licochalcone D, isoliquiritigenin, licoagrochalcone A and kanzonol C from the Glycyrrhiza inflata ⁵³. Two new chalcone glycosides 4'-O-(6''-O-galloyl-β-d-glucopyranosyl)- 2',4-dihydroxychalcone and 4'-O-(6''-O-galloyl-β-d-glucopyranosyl)- 2'-hydroxy-4-methoxychalcone together with one known chalcone glycoside 4'-O-β-d-glucopyranosyl- 2'-hydroxy-4-methoxychalcone were isolated from the stems of Entada phaseoloides ⁵⁴. A new flavanone (mildbone) and a new chalcone (mildbenone) have been obtained from African Erythrina species, Erythrina mildbraedii of Cameroon ⁵⁵.

Four flavonoids were obtained and their structures were identified as 3- hydroxy- 4- methoxylon-chocarpin a new prenylated chalcone, 4-methoxylonchocarpin, isobavachromene and dorspoinsettifolin were isolated from the seeds of Millettia pachycarpa ⁵⁶. A new acetylated chalcone glycoside, trans-2' 6'-dihydroxy- 4'- O-(4''-acetyl-rhamnoside)- 4- methoxychalcone and a new biflavonoid glycosides, 5,3',5'', 4'''-tetrahydroxy-3''', 5'''dimethpxy- biflavone (4'→8'')- 7- O- ((2-rhamnoside) rhamnoside) were isolated from the ethyl acetate soluble fraction of the methanol extract obtained from Trigonosciadium brachytaenium ⁵⁷.

Three new chalcone dimers oxyfadichacones A, B and C along with four known chalcones, 2',4'-dihydroxychalcone, 2',4',4-trihydroxychalcone, 2'-hydroxy-4'-methoxychalcone and 2',4'-dihydroxy-4-methoxychalcone, were yielded and identified from Oxytropis falcata ⁵⁸. Bractelactone, a novel chalcone from Fissistigma bacteolatum ⁵⁹.

Nardokanshone A, a new type of sesquieterpenoid- chalcone hybrid isolated from Nardostachys chinensis ⁶⁰. Two new diprenylated dihydro-chalcones, elastichalcone A1 and elastichalcone B2 were isolated from the leaves of Artocarpus elasticus ⁶¹. Three new chalcones, 3, 2'-dihydroxy-4,3'-dimethoxychalcone-4'-glucoside, 4'-O-(2'''-O-caffeoyl)-2',3',3,4-tetrahydroxychalcone and 2',4',3-trihydroxy-3',4-dimethoxychalcone were isolated from Coreopsis lanceolate flowers ⁶².

Chalcone dimers Lophirone B and C compounds were isolated from Lophira alata ⁶³. A new prenylated chalcone xanthohumol-M, bichalcone humulusol and six known chalcones were found from Humulus lupulus ⁶⁴. Bis-dihydrochalcone diglucoside containing a cyclobutene ring, a methylene-bridged bischalconeglycoside, both probably dimers of the co-occuring isosalipur-poside, and seven known naringenin, apigenin, kaempferol and luteoline glucoside identified and isolated from extract of the air-dried aerial parts of Helicrysum zivojinii ⁶⁵. Cardamonin, a schistoso-micidal chalcone from Piper aduncum L. (Piperaceae) that inhibits Schistosoma mansoni ATP diphosphohydrolase ⁶⁶.

Six new flavonoids 2′,4′-dihydroxychalcone-6′-O-β-D-glucopyranoside, α, 3, 2′, 4′-tetrahydroxy-4-methoxy-dihydrochalcone-3′, -C-β-glucopyranosy-6′- O- β- D- glucopyranoside, 7- hydroxy- 5, 8′-dimethoxy- 6′α- L- rhamnopyranosyl- 8- (3-phenyl-trans-acryloyl)- 1- benzopyran- 2- one, 6′, 7-dihydroxy-5, 8- dimethoxy- 8 (3- phenyl- trans-acryloyl)- 1- benzopyran- 2- one, 9- hydroxy-3, 8-dimethoxy- 4- prenylpterocarpan and α, 4, 4′-trihydroxydihydrochalcone-2′-O-β-D-glucopyrano-side were isolated from bark of Eysenhardtia polystachya ⁶⁷. Two chalcones, sappanchalcone and 3-deoxysappanchalcone were isolated from the ethanolic extract obtained from Haematoxylum campechianum L. ⁶⁸ Two chalcone derivatives isolated from Finger root with nutraceutical potentials ⁶⁹. Flavokawain B, pinostrobin and pashanone chalcones were isolated from seeds of Persicaria lapathifolia ⁷⁰.

TABLE 1: LIST OF CHALCONES FROM MEDICINAL PLANTS

Importance of Chalcones: An interesting feature of chalcones pharmacophore is that they serve as starting materials for the synthesis of five and six-membered heterocyclic compounds such as Pyrimidines, Pyrazolines, Flavones, Flavonols, Flavonones, Aurones and Benzoylcoumarones as well as certain compounds like Deoxybenzoins and Hydantoins which are of some therapeutic application ⁷¹. Chalcones and their derivatives find application as artificial sweeteners, scintillators, polymerization catalysts, fluorescent whitening agents, organic brightening agents, stabilizers against heat, visible light, ultraviolet light and aging ⁸. Chalcone containing plants have also been used for a long time in traditional medical practice. The use of herbal medicines continues to expand rapidly across the world. As a result of pharmacological studies, several pure chalcones isolated from different plants have been approved for clinical trials for treatment of cancer, viral and cardiovascular disorders or have been included as ingredients in cosmetic preparations ^{72, 73}. Polyphenols represent one of the most prevalent classes of compounds found in our daily diet. Over the last ten years, increasing attention has been dedicated to chalcones because of their interesting biological activities. Indeed, chalcones constitute an important group of natural compounds that are especially abundant in fruits (e.g., citruses, apples), vegetables (e.g., tomatoes, shallots, bean sprouts, potatoes) and various plants and spices (e.g., licorice), many of which have been used for centuries in traditional herbal medicine. The majority of the content of chalcones in citrus fruits and various plants is mediated through the formation of 4,2′,4′,6′-tetrahydroxychalcone (also known as naringenin chalcone by chalcone synthase. Naringenin chalcone also plays an essential role in the flavonoid biosynthetic pathway and contributes significantly to the total amount of plant flavonoids ⁷⁴.

FIG. 3: PHARMACOLOGICAL ACTIVITIES OF CHALCONE

Pharmacological Activities of Chalcones: The biological effects of chalcones were found to be dependent on the presence, the number and position of functional groups such as methoxy, glycosides, hydroxyl, halogens in both A and B rings ⁷⁵. They present a broad spectrum of biological activities such as antifungal ⁷⁶, antifilarial, larvicidal, anticonvulsant ⁶⁶, anticancer ^{77, 78}, anti-inflammatory ⁷⁹, neuroprotective ⁷⁹, antimalarial ⁸⁰, antibacterial ⁸¹, antilipidemic ⁸², antihyperglycemic ⁸²,  antiviral ⁸³, antimycobacterial ⁸⁴, antiprotozoal (antileishmanial and antitrypanosoma) ⁸⁵, antiangiogenic ⁸⁶, antiplatelet ⁸⁷, anti-HIV ⁸⁸ and Two chalconoids from the desert plant Pulicaria incisa prevented cell death by inhibiting reactive oxygen species (ROS) ⁸⁹. The chalcones showed selective, reversible and potent MAO-B inhibition compared to MAO-A. Recent studies also showed that heteroaryl-based chalcones are potent MAO-A inhibitors ⁹⁰.

CONCLUSION: Chalcones are a common scaffold found in many naturally occurring compounds, especially plant-derived natural products. In addition, many chalcone derivatives are prepared due to their easy convenience for synthesis. Chalcone is regarded as a privileged structure of great practical interests because these natural and synthetic chalcone derivatives have shown numerous interesting biological activities with clinical potential against various diseases. Chalcones attracted considerable research interest in multiple disciplines ⁹¹.

ACKNOWLEDGEMENT: Financial support provided by the DST-SERB, New Delhi under the Empowerment and Equity opportunities for Excellence in Science is gratefully acknowledged.

CONFLICTS OF INTEREST: The authors confirm that this article content has no conflicts of interest.

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How to cite this article:

Banoth RK and Thatikonda A: A review on natural chalcones an update. Int J Pharm Sci & Res 2020; 11(3): 546-55. doi: 10.13040/ IJPSR.0975-8232.11(3).546-55.

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