DOCSLIB.ORG

Antileishmanial Activity of Prenylated Coumarins Isolated from Ferulago Angulata and Prangos Asperula

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Antileishmanial Activity of Prenylated Coumarins Isolated from Ferulago Angulata and Prangos Asperula Research in Pharmaceutical Sciences, July 2016; 11(4): 324-331 School of Pharmacy & Pharmaceutical Sciences Received: Nov 2015 Isfahan University of Medical Sciences Accepted: Jan 2016 Original Article Antileishmanial activity of prenylated coumarins isolated from Ferulago angulata and Prangos asperula Seyed Ebrahim Sajjadi1,*, Abbas-Ali Eskandarian2, Yalda Shokoohinia3, Hosein-Ali Yousefi2, Marjan Mansourian4, Hasan Asgarian-Nasab5, and Negar Mohseni5 1Department of Pharmacognosy and Isfahan Pharmaceutical Sciences Research Center , School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, I.R. Iran. 2Department of Parasitology and Mycology, School of Medicine, Isfahan University of Medical Sciences, Isfahan, I.R. Iran. 3Pharmaceutical Sciences Research Center, School of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, I.R. Iran. 4Department of Biostatistics, Faculty of Health Sciences, Isfahan University of Medical Sciences, Isfahan, I.R. Iran. 5Isfahan Pharmaceutical Sciences Research Center, Isfahan University of Medical Sciences, Isfahan, I.R. Iran. Abstract Leishmaniasis has a wide spectrum of signs and symptoms due to infection to numbers of Leishmania species and makes enormous mortality and morbidity. There are clues of antileishmanial effects of prenylated coumarins. Apiaceae family is one of the most important sources of coumarins. Air-dried aerial parts of Ferulago angulata and fruits of Prangos asperula were extracted with n-hexane, using a soxhlet apparatus. The solvents were evaporated under reduced pressure. Column chromatography and crystallization process resulted to isolation of three prenylated coumarins. 1H-nuclear magnetic resonance, electron ionization Mass and Infrared spectra were used for elucidation of isolated compounds. Leishmanicidal activity of isolated coumarins was assessed on Leishmania major strain (MRHO/IR/75/ER) for the first time. Suberosin epoxide and suberosin were isolated from aerial parts of F. angulata and osthol was extracted from grounded fruits of P. asperula. Osthol showed a significant antileishmanial effect on promastigotes in early hours of exposure with IC50 of 14.40 µg/mL but suberosin epoxide showed only a weak antileishmanial activity. IC50 of osthol and suberosin epoxide after 48 h were 10.79 and 54.0 µg/mL, respectively. Suberosin showed no remarkable effect in these concentrations. This is the first report on the pharmacological activity of suberosin epoxide. Substantial difference between efficacies of two isomers, osthol and suberosin remarks the importance of prenyl substituent location on C-8. Keywords: Leishmania; Prenylated coumarins; Osthol; Suberosin epoxide; Suberosin INTRODUCTION Afghanistan, Brazil, Iran, Peru, Saudi Arabia, and Syria (2). Leishmaniasis includes a spectrum of Leishmaniasis can be classified in different infectious diseases caused by Leishmania clinical forms as cutaneous, mucocutaneous species. Many people in many countries and visceral forms of which cutaneous form is are affected by the parasite with high mortality the most prevalent. L. tropica, L. major and L. and morbidity and high endemicity aethiopica are the old species which cause in developing countries (1). According to cutaneous leishmaniasis (1). L. major, a World Health Organization (WHO) report, unicellular protozoan parasite is the cause of leishmaniasis is threatening lives of about 350 an acute infection with a period of 3 to 6 million men, women and children in 88 months (3). L. major is endemic in rural, arid countries all over the world. As many as 12 or desert regions of the Mediterranean littoral, million people are believed to be currently Middle East, North Africa, Central Asia and infected, with about 1–2 million estimated new cases occurring yearly. About ninety percent of cutaneous leishmaniasis cases occur in *Corresponding Author: S. E. Sajjadi Tel: 0098 31 37927125, Fax: 0098 31 36680011 Email: [email protected] Antileishmanial activity of three prenylated coumarins Middle East, North Africa, Central Asia and osthol, suberosin and suberosin epoxide were India. Although variable, human lesions tend investigated. Suberosin, suberosin epoxide and to be relatively large and wet, with overlaying osthol have been previously isolated from exudates. Desert rodents are the reservoirs. Ferulago angulata and Prangos asperula Phlebotomus papatasi and other Phlebotomus respectively. F. angulata (Apiaceae) is an spp. serve as vectors. L. major has also been a aromatic endemic plant (22) with wide use as major problem for rural settlers in Iran (1). food seasoning and antidiabetic agent in south- Plants derived compounds are proposed to western (Kohgiluyeh-Boirahmad) and oil provide new sources for alternative drugs. flavor and antioxidant in western of Iran Natural constituents such as alkaloids (4,5), (Kermanshah). The essential oil of the plant benzophenones (6), coumarins (7,8), and also possesses antimicrobial activity (23). P. terpenoids are proved to have antileishmanial asperula is also belongs to Apiaceae family effects (9,10). and used as provender for mutton. The fruits Coumarins are the lactones of ortho of some other Prangos species are used as hydroxycinnamic acid which is widely found emollient, carminative and tonic in Iranian in nature (11). Coumarins exist in plants in traditional medicine and proved to exert free or glycoside forms (12). Coumarin different pharmacological activities (24-26). derivatives have been reported to have numerous therapeutic applications including MATERIALS AND METHODS anti-inflammatory, antioxidant (13) and anti- HIV effects (14), and some are also active as General instrumental procedures neuroprotective (15) and cancer preventive 1H (500 MHz) and 13C (125 MHz) nuclear agents (16). Therefore, coumarins are excellent magnetic resonance (NMR) spectra were potential pharmaceutical agents. Several measured on a Bruker spectrometer (USA), coumarins have rendered leishmanicidal using CDCl3 as solvent and TMS as internal effects (7,8), among them auraptene and standard (Merck, Germany). Mass spectra umbelliprenin (Fig. 1), the prenylated were obtained using a Hewlett-Packard 7890A coumarins, have shown significant mass spectrometer (USA). Infrared spectra antileishmanial effects (17,18). Investigations were also recorded using an FTIR indicate that prenyl moieties (3-methyl-2- spectrometer (WQF-510, Rayleigh, China). buten-1-yl; bolded side chain in Fig. 1) in the Open column chromatography was performed terpenoid coumarins have an important role in using silica gel (70–230 mesh) and analytical biological activities of this group of natural grade solvents (Merck, Germany). Separations compounds (19,20). It is considered that the were monitored by thin layer chromatography prenyl moiety facilitate attachment of the on Merck 60 F254 (0.25 mm) plates and were bioactive molecules to cysteine residues of visualized by UV inspection (Camag, intercellular proteins (21). Switzerland) and/or staining with Cerium In the present study the antileishmanial Sulphate/ molibdate (Merck, Germany) properties of three other prenylated coumarins: proceeding by heating. O O O O O O Auraptene Umbelliprenin Fig. 1. Chemical structures of aurapten and umbelliprenin where prenyl substitution is highlighted. 325 Sajjadi et al. / RPS 2016; 11(4): 324-331 Plant material crystals; 1HNMR (CDCl3, 500 MHz, J in Hz): Aerial parts of F. angulata and the fruits of δ 7.66 (1H, d, J = 9.5, H-4), δ 7.33 (1H, s, H- P. asperula were collected from Dena 5), δ 6.82 (1H, H-8), δ 6.28 (1H, d, J = 9.5, H- Mountains, west of Iran, in June and July 2011 3), δ 3.93 (1H, H-16), δ 3.00 (2H, m, H-11), δ respectively. The plant materials were 2.77 (1H, dd, H-12), δ 1.42 (3H, s, H-14), δ identified by Department of Botany, Yasouj 1.36 (3H, s, H-15). University and voucher specimens were 13CNMR (CDCl3, 125 MHz): δ 161.7 (C- deposited at the Herbarium of School of 2), δ 161.1 (C-7), δ 155.3 (C-10), δ 143.9 (C- Pharmacy and Pharmaceutical Sciences, 4), δ 128.9 (C-5), δ 124.5 (C-6), δ 113.5 (C-3), Isfahan, Iran (No. 1972 and 1126). δ 112.5 (C-9), δ 99.2 (C-8), δ 63.6 (C-12), δ 59.3 (C-16), δ 56.4 (C-13), δ 29.6 (C-11), δ Extraction and isolation of prenylated 25.2 (C-14), δ 19.4 (C-15). coumarins Mass m/z 260 [M]+, 189 [M- + Air-dried aerial parts of F. angulata (200 g) ((CH3)2CHCO)] . Calculated for: C15H16O4. were extracted with n-hexane, using a soxhlet Fourier transform infrared spectroscopy apparatus (Duran, Germany) for 6 h. The (FT-IR) (KBr): νmax = 3001, 2962, 2848, 1716, solvent was evaporated under reduced pressure 1620, 1138, 1209, 831. to 50 mL and was cooled to 4 °C for several days to render a semi pure white to pale Compound 2 yellow crystals. For further purification, they Suberosin; 7-methoxy-6-(3-methyl-2- were washed with chilled n-haxane for several butenyl)-1-benzopyran-2-one; Colorless times. Later, the sample was subjected for re- crystals; 1HNMR (CDCl3, 500 MHz, J in Hz): crystallization process until resulted pure δ 7.61(1H, d, J = 9.5, H-4), δ 7.17 (1H, s, H- crystals of compound 1 (suberosin epoxide). 5), δ 6.74 (1H, s, H-8), δ 6.20 (1H, d, J = 9.5, The mother liquor was fractionated on an H-3), δ 5.28 (1H, t, J = 6.21, H-12), δ 3.84 open silica column using a mixture of heptane (3H, s, H-16), δ 3.29 (2H, d, J = 6.21, H-11), δ and ethyl acetate to render a lump of crystals 1.76 (3H, s, H-14), δ 1.70 (3H, s, H-15). which were further purified through a 13CNMR (CDCl3, 125 MHz): δ 161.91 (C- recrystallization process to get compound 2 2), δ 161.05 (C-7), δ 154.86 (C-10), δ 144.08 (suberosin). (C-4), δ 134.00 (C-12), δ 127.87 (C-5), δ Compound 3 (osthol) was also isolated 127.83 (C-6), δ 121.78 (C-13), δ 113.31 (C-3), from fruits of P asperula according to the δ 112.29 (C-9), δ 98.86 (C-8), δ 56.25 (C-16), method which we have previously described δ 28.19 (C-11), δ 26.20 (C-14), δ 18.15 (25).
Load more

Recommended publications
  • Suspect and Target Screening of Natural Toxins in the Ter River Catchment Area in NE Spain and Prioritisation by Their Toxicity
    toxins Article Suspect and Target Screening of Natural Toxins in the Ter River Catchment Area in NE Spain and Prioritisation by Their Toxicity Massimo Picardo 1 , Oscar Núñez 2,3 and Marinella Farré 1,* 1 Department of Environmental Chemistry, IDAEA-CSIC, 08034 Barcelona, Spain; [email protected] 2 Department of Chemical Engineering and Analytical Chemistry, University of Barcelona, 08034 Barcelona, Spain; [email protected] 3 Serra Húnter Professor, Generalitat de Catalunya, 08034 Barcelona, Spain * Correspondence: [email protected] Received: 5 October 2020; Accepted: 26 November 2020; Published: 28 November 2020 Abstract: This study presents the application of a suspect screening approach to screen a wide range of natural toxins, including mycotoxins, bacterial toxins, and plant toxins, in surface waters. The method is based on a generic solid-phase extraction procedure, using three sorbent phases in two cartridges that are connected in series, hence covering a wide range of polarities, followed by liquid chromatography coupled to high-resolution mass spectrometry. The acquisition was performed in the full-scan and data-dependent modes while working under positive and negative ionisation conditions. This method was applied in order to assess the natural toxins in the Ter River water reservoirs, which are used to produce drinking water for Barcelona city (Spain). The study was carried out during a period of seven months, covering the expected prior, during, and post-peak blooming periods of the natural toxins. Fifty-three (53) compounds were tentatively identified, and nine of these were confirmed and quantified. Phytotoxins were identified as the most frequent group of natural toxins in the water, particularly the alkaloids group.
    [Show full text]
  • Natural Compounds, Fraxin and Chemicals Structurally Related to Fraxin Protect Cells from Oxidative Stress
    EXPERIMENTAL and MOLECULAR MEDICINE, Vol. 37, No. 5, 436-446, October 2005 Natural compounds, fraxin and chemicals structurally related to fraxin protect cells from oxidative stress Wan Kyunn Whang1, Hyung Soon Park2, genes expressed differentially by fraxin and to InHye Ham1, Mihyun Oh1, compare antioxidative effect of fraxin with its struc- Hong Namkoong3, Hyun Kee Kim3, turally related chemicals. Of the coumarins, protective 2 4 effects of fraxin against cytotoxicity induced by H2O2 Dong Whi Hwang , Soo Young Hur , were examined in human umbilical vein endothelial 4 5 Tae Eung Kim , Yong Gyu Park , cells (HUVECs). Fraxin showed free radical scavenging Jae-Ryong Kim6 and Jin Woo Kim3,4,7 effect at high concentration (0.5 mM) and cell protective effect against H2O2-mediated oxidative stress. Fraxin 1 College of Pharmacy, Chung-Ang University recovered viability of HUVECs damaged by H2O2- 221, Heukseok-dong, Dongjak-gu treatment and reduced the lipid peroxidation and the Seoul 156-861, Korea internal reactive oxygen species level elevated by H2O2 2KeyGene Life Science Institute treatment. Differential display reverse transcrip- KeyGene Science, Corp. tion-PCR revealed that fraxin upregulated antiapo- Ansan, Gyeonggido 425-791, Korea ptotic genes (clusterin and apoptosis inhibitor 5) and 3Molecular Genetic Laboratory tumor suppressor gene (ST13). Based on structural Research Institute of Medical Science similarity comparing with fraxin, seven chemicals, 4Department of Obstetrics and Gynecology fraxidin methyl ether (29.4% enhancement of viability), 5Department of Biostatistics prenyletin (26.4%), methoxsalen (20.8 %), diffratic acid College of Medicine (19.9%), rutoside (19.1%), xanthyletin (18.4%), and The Catholic University of Korea kuhlmannin (18.2%), enhanced more potent cell via- Seoul 137-040, Korea bility in the order in comparison with fraxin, which 6Department of Biochemistry and Molecular Biology showed only 9.3% enhancement of cell viability.
    [Show full text]
  • Esculetin) - an Antirheumatoid Arthritic Compound: an Update
    Online - 2455-3891 Vol 11, Special issue 4, 2018 Print - 0974-2441 Research Article COUMARIN (ESCULETIN) - AN ANTIRHEUMATOID ARTHRITIC COMPOUND: AN UPDATE JAYA KUMARI S*, ANANDHI N, MOUNISHA B, MOHAMED SAMEER MH Department of Pharmacognosy, School of Pharmaceutical Sciences, Vels Institute of Science Technology and Advanced Studies, Pallavaram, Chennai, Tamil Nadu, India. Email: [email protected] Received: 11 October 2018, Revised and Accepted: 15 December 2018 ABSTRACT Context: Esculetin is a natural polyphenolic compound. It is chemically 6,7-dihydroxycoumarin and one of the ingredients of Cortex fraxini, a Chinese traditional medicine. It is used as a dietary supplement and found as non-toxic. Recently, there are many research works evaluated on esculetin in arthritis with supported molecular mechanisms. Objectives: Esculetin becoming more attractive prodrug for arthritis. Hence, the present minireview will consolidate the targeted site of esculetin in the treatment of arthritis over the past decade. Results: The most important molecular mechanism of esculetin is an antioxidant activities with decreased level of reactive oxygen species/reactive nitrogen species. It also inhibited lipoxygenase 5, lipoxygenase 12, and tyrosinase enzymes. It reduces the inflammation by modulating the key inflammatory enzyme matrix metalloproteinase-1 activity. It also lowers the nitrous oxide and prostaglandin E2 level in synovial fluid. Esculetin derivatives such as 5-methoxy esculetin inhibited the activity of nitrogen-activated protein kinases. The updated data also reveal that esculetin suppresses the leukotriene B4 level in plasma of adjuvant-induced arthritis tested animals. Conclusion: The presented update showed that esculetin may be useful as a tool in regulating the mechanism and physiological functions of the inflammatory mediators and enzyme.
    [Show full text]
  • The Nonvolatile and Volatile Metabolites of Prangos Ferulacea and Their Biological Properties*
    Published online: 2019-03-20 Reviews The Nonvolatile and Volatile Metabolites of Prangos ferulacea and Their Biological Properties* Authors Maurizio Bruno 1, Vincenzo Ilardi2, Giulio Lupidi 2, Luana Quassinti 3, Massimo Bramucci 3, Dennis Fiorini 4, Alessandro Venditti5,FilippoMaggi3 Affiliations Correspondence 1 Department of Biological, Chemical and Pharmaceutical Prof. Maurizio Bruno Sciences and Technologies (STEBICEF), University of Department of Biological, Chemical and Pharmaceutical ʼ Palermo, Viale delle Scienze, Parco d Orleans II, Palermo, Sciences and Technologies (STEBICEF), University of Palermo Italy Viale delle Scienze Ed. 17, Parco dʼOrleans II, 90128 Palermo, 2 Department of Earth and Marine Sciences (DISTeM), Italy University of Palermo, Palermo, Italy Phone:+3909123897531 3 School of Pharmacy, University of Camerino, Camerino, [email protected] Italy 4 School of Science and Technologies, University of ABSTRACT Camerino, Camerino, Italy Prangos ferulacea (L.) Lindl. (Fam. Apiaceae), an orophilous 5 DepartmentofChemistry,UniversityofRome species of eastern Mediterranean and western Asia, possesses “La Sapienza”, Rome, Italy a number of biological properties that are worthy of exploita- tion in different fields. Phytochemical investigations revealed Key words the presence of coumarins, prenyl-coumarins, and furano- Prangos ferulacea, Apiaceae, coumarins, prenyl‑coumarins, coumarins as the main constituents of this species, as well as furano‑coumarins, essential oil several flavonoids. Among prenyl-coumarins, osthol is a promising apoptotic agent quite selective toward cancer cells. received December 18, 2018 In addition, the essential oils have been extensively investi- revised March 1, 2019 gated, and several chemotypes have been identified. This accepted March 5, 2019 work reviews the literature on this species published between Bibliography 1965 and 2018, describes its volatile and nonvolatile metabo- DOI https://doi.org/10.1055/a-0873-8622 lites, and outlines its pharmacological effects.
    [Show full text]
  • Ce-Rtaif., a Studr of THE',Erzatiolism Sqa3i Itstratocrouc 001APOUNIA
    Ce-rtaif., A sTuDr OF THE',ErzATIOLISM SQA3i itstratocrouc 001APOUNIA. PARTICULARLY CaLTZARIN AND rrAT..E., y VIURRi KAIGHEN Wag a thesis presented in accordanee with the lipaatiees awr*rning the award of the Degree or for of Philosophy in the University* of Lord ion. 1961. Department of3 3odt a St. .4ary's Hospi hedieal Helm% 'Landon, 2. Abstract of Thesis., 34140Poumaria has been synthesised. 7Zabbite dosed with the labelled oorapound (50 mg./kg.) excreted nearly all the radioactivity ii the urine within 0 hours; in rats (100 og./kg.) the activity was allost equally distributed between urine and faeces. The metabolites in rabbits, armoured by isotope dilution were: mumarin (0.5. an acid-labile eourrerin precursor (15.gl, 3-ftramnrcounr-rin Olin 9 4,-hYdrawocoumarin (0.4), 5.hydroxycoumarin (0.V), 6-hydravooumarin (3.4n. 7-hYdroXY" Ocularin 8-bydrovootrarin 0.91, o-hydroxyphenylacetic acid (2Q), and e-hydroxdphenyllactic acid. (3"). The hydroxycoumarins were mainkr, o-lwL'.roxypherkylacetic acid partly, in conjugated form. Moss ortsbolites accounted for nearly 95, of the excreted radioactivity, 7C of which vas in the form of compounds containing the intact coularia ring, and :Was compounds in which the heterocyclic rind had been opened. Rats re qbolise ooursarin by ring opening to a greater extent than rabbits: only 3 of hydroxycoumarins were found as metabolites in the rat, whereas the amounts of hydroxyaoids foraed mere similar to those in rabbits. No 140 vas found in the expired air of rabbits or rata. 3-ilydroxyommarin is excreted by rabbits zcinly as conjugates, but also as o-hydrmrphmlyineetic and -.Untie acids; in rats it le excreted nairay as the ktrdrcavacids.
    [Show full text]
  • (12) Patent Application Publication (10) Pub. No.: US 2009/0269772 A1 Califano Et Al
    US 20090269772A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0269772 A1 Califano et al. (43) Pub. Date: Oct. 29, 2009 (54) SYSTEMS AND METHODS FOR Publication Classification IDENTIFYING COMBINATIONS OF (51) Int. Cl. COMPOUNDS OF THERAPEUTIC INTEREST CI2O I/68 (2006.01) CI2O 1/02 (2006.01) (76) Inventors: Andrea Califano, New York, NY G06N 5/02 (2006.01) (US); Riccardo Dalla-Favera, New (52) U.S. Cl. ........... 435/6: 435/29: 706/54; 707/E17.014 York, NY (US); Owen A. (57) ABSTRACT O'Connor, New York, NY (US) Systems, methods, and apparatus for searching for a combi nation of compounds of therapeutic interest are provided. Correspondence Address: Cell-based assays are performed, each cell-based assay JONES DAY exposing a different sample of cells to a different compound 222 EAST 41ST ST in a plurality of compounds. From the cell-based assays, a NEW YORK, NY 10017 (US) Subset of the tested compounds is selected. For each respec tive compound in the Subset, a molecular abundance profile from cells exposed to the respective compound is measured. (21) Appl. No.: 12/432,579 Targets of transcription factors and post-translational modu lators of transcription factor activity are inferred from the (22) Filed: Apr. 29, 2009 molecular abundance profile data using information theoretic measures. This data is used to construct an interaction net Related U.S. Application Data work. Variances in edges in the interaction network are used to determine the drug activity profile of compounds in the (60) Provisional application No. 61/048.875, filed on Apr.
    [Show full text]
  • Skin Care in Atopic Dermatitis
    MAVI Nature and Technology in daily hair and skin care to Cleanse • Re-hydrate • Protect MAVI Oil 1AVI QiJ J r---oi1oshampoo Bodylotion MAVIQ-i/ 1w/t1rotfkO . BodywaStl d1oltN MAYI () MAVI (Jtf oe.owmµoo ""11'''* .a rBodylot mn .. .. ... '~'~·-···-­ ' ..... ...__ .... """'-" --- · ~ ~-­ l ·' tf H &.~ I......< t it ]O t ~,_,~ ... tor oily skin and hair o.... o tor dry skin and hair N ·e: tor sensitive skin and hair Ì5 LI.. ci ~ ~ innovaLazio200 ~ "~lJ l [f 1. I [/ www.mavicosmetics.it ~ Ì r: .~I r1( · -~ I /"r I_ [email protected] (.'.) lllJ ~ mav1 ~ MAVI sud srl -V.le dell'lndustria,1 -Aprilia (LT) - ltaly - Fax. +39.06.9281523 clinical/y correct cosmetic oodUICljS SOld ,.... 3SS3018 .._ 3SS3019 J\ oo !we4s •3SS30l9 wa1q0Jd pio uo o, uo!,n1os 'lfB!J alfl SSO/ J!Dl/ JO 1uaw1oaJ1 al/I JO:I oodWDlfS• .iuawa1ddns .ia!a• ® Clinical studies demonstrated Bioesse efficacy to treat mild 111 121 131 to moderate hair loss in the frontal parietal scalp ' ' 111 12 3 lncreases hair mass and number in a short period ' J,( l BIOESSE MEAN PERCENTAGE VARIATION OF TOTAL HAIR MASS PER cm2 OF PATIENTS WITH ANOROGENETIC ALOPECIA TREATEO BY GELATIN·CYSTINE ANO SERENOA REPENS TOPICAL ANO /OR BY ORAL ROUTE n • 60 10~~~~~~~~~~--.~~~~~~~~~~~~~~~--. ~-r-~~-r-~----:::::t;;;;;;;oiiiiiiii-f-lliiiiiiiiiiiii... iiiiiii---i: 60% 50 1 ~ I I I • • ,:Ie 71?1 I2 I ~ 1ncrease 1n i 10 hair mass '#. ·10 -20 -+-Placobo (Lollon) O Placo bo (Dlet) ....._. Activo Lollon "'*" Actlvo Olot All p v•luea ue hlghly algnlflc• nt (p < 0.005) H ba1elln• valu• •• to group1 ~~~~~~~--' MEAN PERCENTAGE VARIATION OF HAIR NUMBER PER cm 2 OF PATIENTS WITH ANOROGENETIC ALOPEC IA TREATEO BY GELATIN· CYSTIN E ANO SERENOA REPEN S TOPICA L ANO/OR BY ORAL ROUTE n • 60 40..--~~~~~.,..-~~~~~...--~~~~~...--~~~~--.~~~~~--.
    [Show full text]
  • Flavonoids: a Review Application. Parti For
    J. Appl. Cosmetol. 25, 93-709 (July/September 2007) FLAVONOIDS: A REVIEW FOR COSMETIC APPLICATION. PARTI Mrs.ir. Elzbieta E.Brand-Garnys ', Dr. Horst Denzer ', Dr. Hamke Meijer ', Dr.ir. Hans M.Brand ' ' ELZBIETA COSMETICS B.V., Nieuwerkerk a/d IJssel - The Netherlands ' KAO CHEMICALS GmbH, Emmerich - Germany Received: March, 2007. Key words: Bio-active substances; Biologico/ extracts; Enzyme monipulation; Enzyme cofoctor; Summary Flavonoids are now recognised as essential dietary components, although their functions are just on the brink of understanding. Dietary requirements have been establi shed. Their significance is proba­ bly equal to vitamins. Approximately 5000 flavonoids have been identified, and the list is quickly expanding. The functionality of flavonoids is frequently "multi-purpose", contrary to vitamins, enzy­ mes and (to a lesser extent) hormones. Riassunto I flavonoidi sono riconosciuti come componenti essenziali delle diete, anche se non sono state anco­ ra comprese appieno le loro funzioni. Comunque ne è stato riconosciuto il loro ruolo dietetico che dovrebbe essere simile a quello delle vitamine. Circa 5000 sono i flavonoidi già identificati ed il loro numero si incrementa di continuo. Al contra­ rio delle vitamine, degli enzimi e degli ormoni, l'attività di questi composti naturali è più complessa e serve a molteplici scopi. 93 Flavonoids: a Review far Cosmetic App/ication INTRODUCTION noi. The corresponding flavonoids may be for­ med from the chalcones via oxidative ring closu­ The Greek word "flava" means yellow. re. Also flavonoids are known that are formed by Flavonoids represent a broad variation of aroma­ reduction of the carbonyl group on the 4-posi­ tic compounds occurring in higher plants, fre­ tion.
    [Show full text]
  • Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer
    cancers Review Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer Esra Küpeli Akkol 1,* , Yasin Genç 2, Bü¸sraKarpuz 1, Eduardo Sobarzo-Sánchez 3,4 and Raffaele Capasso 5,* 1 Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Etiler 06330, Ankara, Turkey; [email protected] 2 Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Sıhhiye 06100, Ankara, Turkey; [email protected] 3 Instituto de Investigación e Innovación en Salud, Facultad de Ciencias de la Salud, Universidad Central de Chile, 8330507 Santiago, Chile; [email protected] 4 Department of Organic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain 5 Department of Agricultural Sciences, University of Naples Federico II, 80055 Portici (Naples), Italy * Correspondence: [email protected] (E.K.A.); [email protected] (R.C.); Tel.: +90-312-2023185 (E.K.A); +39-081-678664 (R.C.) Received: 3 July 2020; Accepted: 17 July 2020; Published: 19 July 2020 Abstract: Cancer is one of the most common causes of disease-related deaths worldwide. Despite the discovery of many chemotherapeutic drugs that inhibit uncontrolled cell division processes for the treatment of various cancers, serious side effects of these drugs are a crucial disadvantage. In addition, multi-drug resistance is another important problem in anticancer treatment. Due to problems such as cytotoxicity and drug resistance, many investigations are being conducted to discover and develop effective anticancer drugs. In recent years, researchers have focused on the anticancer activity coumarins, due to their high biological activity and low toxicity. Coumarins are commonly used in the treatment of prostate cancer, renal cell carcinoma and leukemia, and they also have the ability to counteract the side effects caused by radiotherapy.
    [Show full text]
  • Chemistry and Health Effects of Furanocoumarins in Grapefruit
    journal of food and drug analysis xxx (2016) 1e13 Available online at www.sciencedirect.com ScienceDirect journal homepage: www.jfda-online.com Review Article Chemistry and health effects of furanocoumarins in grapefruit * Wei-Lun Hung, Joon Hyuk Suh, Yu Wang Citrus Research and Education Center, Department of Food Science and Human Nutrition, University of Florida, Lake Alfred, FL, USA article info abstract Article history: Furanocoumarins are a specific group of secondary metabolites that commonly present in Received 1 September 2016 higher plants, such as citrus plants. The major furanocoumarins found in grapefruits 0 0 Received in revised form (Citrus paradisi) include bergamottin, epoxybergamottin, and 6 ,7 -dihydroxybergamottin. 2 November 2016 During biosynthesis of these furanocoumarins, coumarins undergo biochemical modifi- Accepted 3 November 2016 cations corresponding to a prenylation reaction catalyzed by the cytochrome P450 enzymes Available online xxx with the subsequent formation of furan rings. Because of undesirable interactions with several medications, many studies have developed methods for grapefruit furanocoumarin Keywords: quantification that include high-performance liquid chromatography coupled with UV anticancer activity detector or mass spectrometry. The distribution of furanocoumarins in grapefruits is bergamottin affected by several environmental conditions, such as processing techniques, storage bone health temperature, and packing materials. In the past few years, grapefruit furanocoumarins furanocoumarins have been demonstrated to exhibit several biological activities including antioxidative, grapefruit -inflammatory, and -cancer activities as well as bone health promotion both in vitro and in vivo. Notably, furanocoumarins potently exerted antiproliferative activities against cancer cell growth through modulation of several molecular pathways, such as regulation of the signal transducer and activator of transcription 3, nuclear factor-kB, phosphatidy- linositol-3-kinase/AKT, and mitogen-activated protein kinase expression.
    [Show full text]
  • Download Presentation (PDF)
    Characterization of the Oxygen Heterocyclic Compounds (Coumarins, Psoralens, and Polymethoxylated Flavones) in Food Products Mariosimone Zoccali1, Adriana Arigò1, Marina Russo2, Francesca Rigano3, Paola Dugo1,2,3 and Luigi Mondello1,2,3 1Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, University of Messina, Italy 2University Campus Bio-Medico of Rome, Italy 3Chromaleont s.r.l. University of Messina, Italy Italy Universityof Messina, [email protected] Focus on the Oxygenated Heterocyclic Compounds secondary metabolites commonly found in all citrus plants Furocoumarin or Coumarin psoralen Polymethoxyflavone Beneficial effect on humans: Harmful effect on humans: ➢Anticancer ➢Phototoxic ➢Antioxidant ➢Inhibitor of intestinal and liver drug Italy Universityof Messina, ➢Antibacterial metabolism ➢Anti-inflammatory Development of high sensitive analytical methods Isolation of pure compounds Citrus essential oils Citrus bergamia Risso Food industry Cosmetic industry University of Messina, Italy Universityof Messina, Flavour and fragrance industry Opinion on Coumarin in Food products The Panel considered the toxicity studies and the studies on the metabolism of coumarin in humans with CYP2A6 polymorphism that have become available since the last opinion of 2004, as well as clinical studies, and concluded to maintain the TDI of 0.1 mg coumarin/kg bw allocated in the 2004 opinion. University of Messina, Italy Universityof Messina, Furocoumarins in Food products Furocoumarins are a class of photoactive compounds found in
    [Show full text]
  • Reference Substances 2018/2019
    Reference Substances 2018 / 2019 Reference Substances Reference 2018/2019 Contents | 3 Contents Page Welcome 4 Our Services 5 Reference Substances 6 Index I: Alphabetical List of Reference Substances and Synonyms 156 Index II: Plant-specific Marker Compounds 176 Index III: CAS Registry Numbers 214 Index IV: Substance Classification 224 Our Reference Substance Team 234 Order Information 237 Order Form 238 Prices insert 4 | Welcome Welcome to our new 2018 / 2019 catalogue! PhytoLab proudly presents the new you will also be able to view exemplary Index I contains an alphabetical list of all 2018 / 2019 catalogue of phyproof® certificates of analysis and download substances and their synonyms. It pro- Reference Substances. The seventh edition material safety data sheets (MSDS). vides information which name of a refer- of our catalogue now contains well over ence substance is used in this catalogue 1300 phytochemicals. As part of our We very much hope that our product and guides you directly to the correct mission to be your leading supplier of portfolio meets your expectations. The list page. herbal reference substances PhytoLab of substances will be expanded even has characterized them as primary further in the future, based upon current If you are a planning to analyse a specific reference substances and will supply regulatory requirements and new scientific plant please look for the botanical them together with the comprehensive developments. The most recent information name in Index II. It will inform you about certificates of analysis you are familiar will always be available on our web site. common marker compounds for this herb. with.
    [Show full text]