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Bioactive Umbelliferone and Its Derivatives: an Update

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Bioactive Umbelliferone and Its Derivatives: an Update Journal of Pharmacognosy and Phytochemistry 2019; 8(1): 59-66 E-ISSN: 2278-4136 P-ISSN: 2349-8234 JPP 2019; 8(1): 59-66 Bioactive Umbelliferone and its derivatives: An Received: 27-11-2018 Accepted: 29-12-2018 update Radha GV GITAM Institute of pharmacy, Radha GV, Sadhana B, Trideva Sastri K and Ganapaty S GITAM Deemed to be University, Rushikonda, Abstract Visakhapatnam, Andhra Umbelliferone (UMB) is 7-hydroxycoumarin which is a natural constituent of the coumarins family Pradesh, India which synthesized and is regarded as the basis of a synthetic procedure (synthon) for a wider variety of Sadhana B coumarin-heterocycles and is also synthesized in E. coli. UMB has broadly circulated inside the Rutaceae GITAM Institute of pharmacy, and Apiaceae (Umbelliferae) families and is extracted utilizing methanol. It is widely used as anti- GITAM Deemed to be bacterial and anti-fungal, for the treatment of diabetes, cancer, hepatocellular carcinoma, has antioxidant University, Rushikonda, property, in the treatment of cerebral ischemia, Parkinson ’s disease, in the treatment of bronchial Visakhapatnam, Andhra asthma. UMB is incorporated into biodegradable polymers to form SLNS and phytosomes and deliver Pradesh, India the drug easily into the body. UMB having the capacity to be a defender against the adverse effects of anti-inflammatory agents. Trideva Sastri K GITAM Institute of pharmacy, Keywords: Umbelliferone, solid lipid nanoparticles, PLGA, neuroprotective, antioxidant GITAM Deemed to be University, Rushikonda, Visakhapatnam, Andhra Introduction Pradesh, India UMB otherwise called as skimmetine, hydrangine, 7-hydroxycoumarin, and beta-UMB a benzopyrone compound (fig.1) which is a natural constituent of the coumarins family which is Ganapaty S largely present in plants. The coumarins name came from 'Coumarou', the common name for GITAM Institute of pharmacy, the Tonka bean (Dipteryxodorata Wild, Fabaceae), from which coumarins were separated [1]. GITAM Deemed to be University, Rushikonda, The name UMB, on the other hand, was taken from the plants those come under the family [1] Visakhapatnam, Andhra Umbelliferae . Pradesh, India UMB has been appeared to show different pharmacological activities [2, 3] including conditions relating to pro-oxidants and receptive oxygen species, for example, degenerative diseases, inflammation, tumour cells, and microbial contaminations. Fig 1: Structure of UMB Physical characteristics Properties Its molecular formula is C9H6O3. It is a yellowish-white needle-like crystal that has a slight solubility in hot water, but high solubility in ethanol, dioxane [4]. It has a molecular weight of 162.144g/mol, melting point: 230-233ᶿC, log P value: 1.58. It absorbs ultraviolet light strongly at several wavelengths. The absorbance maximum in acid is 325 nm while in alkaline solution it shifts to 365 nm. The fluorescence excitation maxima in acid and alkali solutions are 330nm and 370 nm respectively, while the emission maxima is 460 nm [5]. The IR spectra of UMB demonstrates bands at 3165 (Ar-OH), 1715–1690 and 1628–1603 (lactone), 1575, 1109 and 835 (CH) cm1. At the point when UMB form solid interactions with [6-8] hydroxypropyl-ά-cyclodextrin the IR bands move to higher wavenumbers . Sources and Extraction Correspondence UMB has broadly circulated inside the Rutaceae and Apiaceae (Umbelliferae) families and is Radha GV extracted utilizing methanol. Additionally, present in garden angelica, coriander, carrot and in GITAM Institute of pharmacy, GITAM Deemed to be addition in plants from different families (Table1), for example, the huge leaf (Hydrangea University, Rushikonda, macrophylla, Hydrangeaceae, under the name hydrangine) or the mouse-ear hawkweed Visakhapatnam, Andhra (Hieracium pilosella, Asteraceae). Pradesh, India ~ 59 ~ Journal of Pharmacognosy and Phytochemistry Table 1: Sources of UMB Source Part of plant Family Extracting solvent References Acacia nilotica Bark Mimosaceae MeOH [12] Coriandrum sativum Aerial Umbelliferae MeOH [13] Ferula communis Peduncles Umbelliferae MeOH [14] Ferula asafoetida Rhizomes Umbelliferae MeOH [15] Glycyrrhiza glabra Rhizomes Fabaceae MeOH [16] Ipomoea mauritiana Tuber Convolvulaceae MeOH [11] Platanusacerifolia Stem Planataceae EtOH [17] Extraction dioxygenase chemical that was recognized from UMB has been reported from the CHCl3, ethyl acetate and Rutagraveolens and catalyzed the hydroxylation of the active methanol crude extracts and the hexane soluble fraction of the 4-coumaryl-CoA 11 to produce 2, 4-dihydroxycinnamate that methanol extract. The ideal proportion of plant matter (in immediately forms UMB [26]. grams) to solvent volume was 1:15 [9]. Successful divisions were accounted for utilizing high-speed counter-current Biological activities of UMB chromatography solvent system n-hexane/ dethyl acetate/ Anti-bacterial and anti-fungal activities methanol/ water [10]. The high pressure liquid chromatography It is generally felt that some coumarins, including UMB and (HPLC), ultraviolet(UV) (254 nm) examination of UMB furano coumarins are phytoalexins that assume critical content in n-hexane/ethyl acetate division from the ethyl fungicidal roles in plants. The antimicrobial properties of acetate separate on octadecylsily C18 section utilizing UMB detached from Rhododendron lepidotum were analyzed acetonitrile-water linear gradient elution and the retention against various bacterial strains 0.5 McFarland standard. The time was accounted10.The Chrysantha edgeworthia UMB minimum inhibitory concentration (MIC) utilizing micro crude extract content was also determined [10]. UMB from the dilution strategies were against Staphylococcus aureusand tubers of Ipomoeamauritiana was evaluated by the HPLC Pseudomonas aeruginosa, while action against methicillin strategy utilizing water-acetonitrile mobile phase on C-18 resistant S. aureus (MRSA) and E. coli was appeared by MIC reverse phase (RP) column. In the high pressure thin layer estimation of 1000 lg/ml [27]. chromatography (HPTLC) technique, the mobile phase was Unadulterated UMB has demonstrated unobtrusive toluene, isopropanol and ammonia [11]. A retention time was antibacterial activities with inhibition zones of 1– 4 mm accounted for the HPLC analysis of UMB from grapefruit against E coli, P. aeruginosa and Staphylococcus epidermidis. (citrus heaven) on a C-18 RP column utilizing MeOH/H2O The coumarins were dormant against bacterial strains Bacillus mobile phase, 7-hydroxycoumarin and some of its methyl subtilis, Micrococcus luteus and S. aureus, and against subsidiaries are found in plants of the family Umbelliferae. parasitic strains Candida albicans, Saccharomyces cerevisiae and Aspergillus niger [28]. UMB was additionally surveyed Biosynthesis of Umb utilizing disc diffusion technique for action against plant The key steps in the biosynthesis of UMB coumarins are the pathogenic growths. It equally inhibited the development of cinnamic acid synthesis or para and ortho hydroxylation, Fusarium culmorum, and was inactive against trans-cis isomerisation of the double bond lastly lactonization. Heterobasidiumannosum, Botrytis cinerea, Phytophtora Cinnamic acid was derived from phenylalanine by the activity (Cactorum), Rhizoctonia solani and Rhizoctonia uni-nucleate of phenylalanine ammonia lyase (PAL), while para-hydroxy strain [28]. cinnamic acid (Para-coumaric acid) was derived from tyrosine UMB at low concentration couldn't restrain the development utilizing tyrosine amino lyase (TAL). The p-coumaric acid of the accompanying bacteria, Bacillus ceres, Sarcina lutea, S may likewise be derived specifically from cinnamic acid aureus SG8A, Streptococcus lactis, Alcalegenes faecalis utilizing a P540 dependent enzyme; 4-cinnamic acid B170, E. coli ML30, P. aeruginosa 111, hydroxylase (C4H). The para-hydroxylation is a pre-requisite Salmonellatyphimurim Tml, Serrala marcescens, and parasitic for ortho-hydroxylation as has been confirmed through tracer strains Zygosaccharomyces spp, Candida spp, Pichia chodati, tests including Melilotus officinalis and Lavandula Hansenulaanomala, Saccharomyces spp, Torulautilis, angustifolia which demonstrated that cinnamate was fused Hanseniasporamelligeri, Aspergilus spp, Penicillium into the coumarins and 7-hydroxycoumarin [18-21]. chrysogenum, Rhizopus senti, B. cinerea and Aliernara spp, The next step includes the ortho-hydroxylation of p-coumaric while Byssochlamys fulva development was successfully acid to form 2, 4-dihydroxycoumaric acid. The cinnamate restrained [29]. trans-double bond is stable and can't lactonize, thus it must isomerize to the cis form which is unstable. A proof was Diabetes displayed that demonstrates the part of glycosides Post-prandial hyperglycaemia is portrayed as the earliest development to impact the trans-cis isomerisation. The work symptom of diabetes consequently anti-hyperglycaemic detailed in vitro changes of trans-DGC (diglucoside of 2, 4- impacts of UMB were accounted. Diabetes has a long dihydroxycinnamic acid) to cis-DGC and the isolation and authentic record which first focuses up in the therapeutic identification skimmin (glucoside of UMB) from Hydragenea content of a few ancient methods. As indicated by the reports macrophylla leaf extracts. A compound that hydrolyzes to that, 135 million adults affected from the diabetes mellitus in yield UMB and two molecules of glucose has been accounted the year 1995 worldwide and the information will increment for from Hydragenea macrophylla [22]. to 300 million in coming years [30, 31]. Different
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