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Computational Studies Reveal Piperine, the Predominant Oleoresin of Black Pepper (Piper Nigrum) As a Potential Inhibitor of SARS-Cov-2 (COVID-19)
RESEARCH ARTICLES Computational studies reveal piperine, the predominant oleoresin of black pepper (Piper nigrum) as a potential inhibitor of SARS-CoV-2 (COVID-19) Prassan Choudhary1, Hillol Chakdar1,*, Dikchha Singh1, Chandrabose Selvaraj2, Sanjeev Kumar Singh2, Sunil Kumar3 and Anil Kumar Saxena1 1ICAR-National Bureau of Agriculturally Important Microorganisms, Kushmaur, Mau 275 103, India 2Department of Bioinformatics, Alagappa University, Karaikudi 630 003, India 3Centre for Agricultural Bioinformatics, ICAR-Indian Agricultural Statistics Research Institute, New Delhi 110 002, India receptor binding conformations8. Inhibitors of protease In this study, we screened 26 bioactive compounds have the risk of causing severe side effects as they can in- present in various spices for activity against SARS- 9 CoV-2 using molecular docking. Results showed that hibit the cellular homologous proteases non-specifically . piperine, present in black pepper had a high binding Whole genome sequencing (WGS) has played a crucial affinity (–7.0 kCal/mol) than adenosine monophos- role in paving the way for exploration of novel drug phate (–6.4 kCal/mol) towards the RNA-binding pock- targets10. The GISAID database has undertaken a global et of the nucleocapsid. Molecular dynamics simulation initiative and currently holds WGS of approximately of the docked complexes confirmed the stability of 9300 different isolates of SARS-CoV-2, characterizing piperine docked to nucleocapsid protein as a potential the epidemiology and functional annotation of this virus inhibitor of the RNA-binding site. Therefore, piperine genome (https://www.gisaid.org/). seems to be potential candidate to inhibit the packag- Nucleocapsid (NC) is a highly conserved zinc finger ing of RNA in the nucleocapsid and thereby inhibiting structural protein which plays a crucial role in viral repli- the viral proliferation. -
Steroidal Glycoside Compounds As Core 2 Glcnac-T Inhibitors
(19) TZZ_ZZ _T (11) EP 1 909 802 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 31/704 (2006.01) A61K 31/7048 (2006.01) 21.05.2014 Bulletin 2014/21 A61K 31/706 (2006.01) A61P 1/04 (2006.01) A61P 1/06 (2006.01) A61P 1/16 (2006.01) (2006.01) (2006.01) (21) Application number: 06755733.0 A61P 3/10 A61P 7/02 A61P 9/10 (2006.01) A61P 11/00 (2006.01) A61P 11/06 (2006.01) A61P 13/12 (2006.01) (22) Date of filing: 06.07.2006 A61P 17/06 (2006.01) A61P 31/18 (2006.01) A61P 19/02 (2006.01) (86) International application number: PCT/GB2006/002518 (87) International publication number: WO 2007/003957 (11.01.2007 Gazette 2007/02) (54) Steroidal glycoside compounds as core 2 GlcNAc-T inhibitors Steroidale Glycosid-Verbindungen als core 2 GlcNAc-T-Hemmer Glycosides steroïdiens en tant qu’inhibiteurs du core 2 GlcNAc-T (84) Designated Contracting States: WO-A-2004/062675 WO-A-2005/060977 AT BE BG CH CY CZ DE DK EE ES FI FR GB GR WO-A-2005/120535 WO-A2-01/32679 HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI WO-A2-02/069980 CN-A- 1 415 625 SK TR US-A- 4 602 003 US-A- 5 104 856 US-A1- 2003 148 962 (30) Priority: 06.07.2005 GB 0513881 • DATABASE WPI 7 January 2004 (2004-01-07), (43) Date of publication of application: Derwent Publications Ltd., London, GB; Class 16.04.2008 Bulletin 2008/16 042,page 3, AN 2004-239758 XP002409228 HUANG H, LIU Z: "Medicine composition for (60) Divisional application: treating myocardial ischemia, angina pectoris 11163561.1 / 2 382 979 and cardiac infarction" -
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PEER-REVIEWED ARTICLE bioresources.com GC-MS Characterisation of Sapogenins from Sisal Waste and a Method to Isolate Pure Hecogenin Jener David G. Santos * and Alexsandro Branco ** Five steroidal sapogenins (tigogenin, neotigogenina, hecogenin, gloriogenin, and dehydrohecogenin) were characterised by gas chromatography coupled with mass spectrometry (GC-MS) from a hydrolysed extract of sisal waste. In addition, pure hecogenin, an important raw material for the pharmaceutical industry, was obtained from this waste by selective liquid-liquid extraction of saponins with only hecogenin as aglycone, followed by acid hydrolysis. The yield of pure hecogenin was 460 mg.Kg-1 of sisal waste. Keywords: Agave sisalana; Sisal waste; Extraction; Steroids; Hecogenin Contact information: Laboratory of Phytochemistry, State University of Feira de Santana, 44.036-900 Feira de Santana, Bahia, Brazil; Corresponding authors: *[email protected], **[email protected] INTRODUCTION Steroidal sapogenins are a glycone non-sugar portion of the saponin molecule used for the semi-synthesis of bioactive compounds. Example compounds used in this application include the following: smilagenin, sarsasapogenin, diosgenin, yamogenin, tigogenin, neotigogenin, gloriogenin, gentrogenin, hecogenin, sisalagenin, 9-dehydro- hecogenin, and gitogenin (Agrawal et al. 1985). Among these steroidal sapogenins, diosgenin, sarsasapogenin, and hecogenin are particularly important. The usefulness of hecogenin (Fig. 1) as a synthetic starting material is due to the presence of an oxygen atom in the C-12 position that can be moved to the C-11 position. This makes it possible to introduce the 9-11 double bond required for the syntheses of corticosteroids (Beauvoir 1976). Fig. 1. Chemical structural of hecogenin In the 1940s, steroidal sapogenins achieved great economic importance because of their transformation into pharmaceutically valuable derivatives such as corticosteroids (prednisone, dexamethasone, betamethasone, triamcinolone, and others), sexual hormones, and steroid diuretics (Fernández-Herrera et al. -
Naturally Occurring Saponins: Chemistry and Biology
Journal of Poisonous and Medicinal Plant Research Vol. 1(1), pp. 001-006, May, 2013 Available online at http://www.apexjournal.org ISSN 2315-8834© 2013 Apex Journal International Review Naturally occurring saponins: Chemistry and biology J. S. Negi 1*, P. S. Negi 2, G. J. Pant 2, M. S. M. Rawat 2, S. K. Negi 3 1Herbal Research and Development Institute, Mandal, Gopeshwar (Chamoli) - 246 401, Uttarakhand, India. 2Department of Chemistry, HNB Garhwal University, Srinagar (Garhwal)- 246 174, Uttarakhand, India. 3Department of Botany, HNB Garhwal University, Srinagar (Garhwal) - 246 174, Uttarakhand, India. Accepted 2 April, 2013 Naturally occurring saponins are glycosides of steroids, alkaloids and triterpenoids. They are widely distributed in nature and reported to be present in 500 genera of plants. A wide variety of plants belonging to family Liliaceae, Dioscoreaceae, Solanaceae, Sapindaceae and Agavaceae are the major source of saponins. They are amorphous substances having high molecular weight and are soluble in water and alcohol to produce foam but organic solvents inhibit their foaming property. Plants saponins are generally extracted into butanol through liquid-liquid partition and separated through column chromatography using silica gel as adsorbent and chloroform: methanol as mobile phase. HPLC, GC, Sephadex LH-20 Chromatography, DCCC, preparative paper chromatography and TLC were also used for the separation and isolation of saponins. The structures of saponins were determined by several spectroscopic techniques, viz., UV, IR, 1H NMR, 13 C NMR and Mass spectroscopy. Saponins possess several biological activities such as antioxidant, immunostimulant, antihepatotoxic, antibacterial, anticarcinogenic, antidiarrheal, antiulcerogenic, antioxytoxic, antihypoglycemic, anticytotoxic and antimolluscicidal. Saponins are biologically synthesized by C5 isoprene units through cytosolic mevalonate pathway. -
Phytochemical and Biological Investigations of Asparagus Adscendens and Trillium Govanianum
Phytochemical and Biological Investigations of Asparagus adscendens and Trillium govanianum By Kashif Maqbool Khan CIIT/FA12-R60-004/ATD PhD Thesis In Pharmacy COMSATS University Islamabad, Abbottabad Campus - Pakistan Fall, 2018 COMSATS University Islamabad Phytochemical and Biological Investigations of Asparagus adscendens and Trillium govanianum A Thesis Presented to COMSATS University Islamabad, Abbottabad Campus In partial fulfillment of the requirement for the degree of PhD (Pharmacy) By Kashif Maqbool Khan CIIT/FA12-R60-004/ATD Fall, 2018 ii Phytochemical and Biological Investigations of Asparagus adscendens and Trillium govanianum A Post Graduate Thesis submitted to the Department of Pharmacy as partial fulfillment of the requirement for the award of Degree of Ph.D in Pharmacy. Name Registration Number Kashif Maqbool Khan CIIT/FA12-R60-004/ATD Supervisor Dr. Abdul Manann Associate Professor Department of Pharmacy COMSATS University Islamabad, Abbottabad Campus Co-Supervisor Dr. Muhammad Arfan Associate Professor Department of Chemistry, School of Natural Sciences (SNS) National University of Sciences & Technology (NUST), Islamabad iii iv v vi vii DEDICATION Dedicated to my family and friends who were the pillars of support during my PhD study viii ACKNOWLEDGEMENTS I bow my head before Almighty Allah, The omnipotent, The omnipresent, The merciful, The most gracious, The compassionate, The beneficent, who is the entire and only source of every knowledge and wisdom endowed to mankind and who blessed me with the ability to do this work. It is the blessing of Almighty Allah and His Prophet Hazrat Muhammad (Sallallaho Alaihe Wasallam) which enabled me to achieve this goal. I would like to take this opportunity to convey my cordial gratitude and appreciation to my worthy, reverently and zealot supervisor Dr. -
Yamogenin 3-O-β- <Emphasis Type="Smallcaps">D
J. Chem. Sci., Vol. 116, No. 2, March 2004, pp. 79–82. © Indian Academy of Sciences. Yamogenin 3–O–b–D-glucopyranosyl (1 ® 4)–O–a–D-xylopyranoside from the seeds of Trigonella foenum-graecum V K SAXENA* and ALBERT SHALEM Department of Chemistry, Dr H S Gour University, Sagar 470 003, India e-mail: [email protected] MS received 17 March 2003; revised 10 June 2003 Abstract. Trigonella foenum-graecum (NO – Leguminosae) is cultivated in many parts of India. It has been found to possess significant medicinal value. Its leaves are used both internally and externally to re- duce swelling, prevent falling of hair and in treating burns. Its seeds are carminative, antipyretic, anthelmintic and diuretic, and are also useful in treatment of dropsy, chronic cough, heart diseases, bron- chitis, piles and small pox. This plant also possesses antidiabetic property. The present communication deals with the isolation and identification of steroidal saponin SA-III, characterised as yamogenin 3–O–b–D-glucopyranosyl (1 ® 4)–O–a–D-xylopyranoside, which was iso- lated from the seeds of Trigonella foenum-graecum. Keywords. Trigonella foenum-graecum; Leguminosae; steroidal saponin; yamogenin 3–O–b–D-gluco- pyranosyl (1 ® 4)–O–a–D-xylopyranoside. 1. Introduction trum of SA-III shows the spiroketal nature of SA- III. It shows all characteristic colour reactions of Trigonella foenum–graecum1–3 (NO – Leguminosae) steroidal saponin9,10 and also gives positive Molisch and is cultivated in many parts of India. It has been test for glycoside. found to possess significant medicinal value. Its Compound SA-III on acid hydrolysis yielded SA- leaves are used both internally and externally to re- III (A), C27H42O3, m.pt. -
Piperine : a Bioenhancer
International Journal of Pharmacy Research and Technology 2011, Volume 1, Issue 1, 01-05. ISSN xxxx-xxxx Review article Piperine : A Bioenhancer * Amar Singh , Amar Deep *Smt. Tarawati Institute of Bio-Medical & Allied Sciences, Roorkee-Dehradun Road, Saliyar, Roorkee, Dist. Haridwar- 247667, *Corresponding author: E-mail: [email protected] Received: 16/07/2011, Revised: 18/08/2011, Accepted: 12/09/2011 ABSTRACT Piperine is a major alkaloid of Pepper fruits belonging to family Piperaceae which has a number of medicinal proper- ties. Pepper fruits are one of them which have been established as bioenhancer for some selected drugs. In Ayureveda since centuries it is called as “Yogvahi”. Black pepper fruits are the supporting evidence where piperine was one of the ingredients of “Trikatu”. Black pepper fruits are used in different food, drink, dessert, perfume as a brandy flavors and preservative of pickles. It is well known as “King of Spices”. Piperine enhances the bioavailability of structurally and therapeutically differ- ent drugs, either by increasing the absorption or by delaying the metabolism of the drug or by a combination of both processes. It is evident that black pepper fruits have been used as bio-enhancer in allopathic system of medicine. Piperine has been used as bioenhancer for certain antibacterial- antibiotics with promising results. The interaction of piperine with drug- metabolizing enzymes is responsible for oxidation, hydroxylation and glucuronidation. Piperine appears to top in the list of bioenhancers as it has been used as bioenhancer for Allopathic, Ayurvedic and Unani drugs. Piperine enhances Cmax of different drugs significantly. KEY WORDS: Black Pepper, Bio-enhancer, Trikatu, Piper nigrum, Piperine. -
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View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Indonesian Journal of Cancer Chemoprevention Indonesian Journal of Cancer Chemoprevention, June 2011 ISSN: 2088–0197 e-ISSN: 2355-8989 Activity of Trigonella foenum-graecum on Some Cell Lines Kurnia Agustini*, Wahono Sumaryono, and R. Micho Widyanto Center for Pharmaceuticals and Medical Technology Laboratory for Development of Industrial Agro and Biomedical Technology Agency for the Assessment and Application of Technology (BPPT) Kawasan PUSPIPTEK, Serpong – Indonesia Abstract Trigonella foenum-graecum (TFG) is one of medicinal plants contains some steroidal sapogenin such as diosgenin, yamogenin, gitogenin, tigogenin and trigoneoside, also alkaloid trigonellin, which is have many activity as antidiabetic, estrogenic and also as anti cancer. This experiment was done to explore the activity of some extract of TFG on some cell lines such as MCF7 (Human Breast Cancer Cell-line), T47D (Human Breast Cancer Cell-line), PC3 (Human Prostate Cell-line) and SKOV (Human Ovarian Carcinoma Cell-line). This assay was done using MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium) methods. Results showed that ethyl acetate fraction gives the lowest IC50 than another extracts. IC50 for PC3 is 66.24 ppm, IC50 for MCF7 is 41.81 ppm, IC50 for T47D is 58.63 ppm. These datas can be used for further research to isolate the active compound from TFG. Keywords: Trigonella foenum-graecum, MCF-7, T47D, SKOV, PC3. INTRODUCTION Empirically fenugreek was use as aphrodisiac, carminative, diuretic, emmenagogue, emollient, Fenugreek seed or Foenigraeci semen is galactogogue and tonic. Many researches, dried seed from Trigonella foenum-graecum L., preclinically and clinically, showed that fenugreek Leguminosae, (Anonim, 1979).Geographical have activity for diabetic disease (Annida and distribution of Fenugreek is indigenous to the Stanley 2004).Fenugreek also have estrogenic Mediterranean region, China, India and Indonesia. -
Identification and Characterization of Piperine Synthase from Black
ARTICLE https://doi.org/10.1038/s42003-021-01967-9 OPEN Identification and characterization of piperine synthase from black pepper, Piper nigrum L. Arianne Schnabel 1, Benedikt Athmer1, Kerstin Manke1, Frank Schumacher2, Fernando Cotinguiba 3 & ✉ Thomas Vogt 1 Black pepper (Piper nigrum L.) is the world’s most popular spice and is also used as an ingredient in traditional medicine. Its pungent perception is due to the interaction of its major compound, piperine (1-piperoyl-piperidine) with the human TRPV-1 or vanilloid receptor. We now identify the hitherto concealed enzymatic formation of piperine from piperoyl coenzyme A and piperidine based on a differential RNA-Seq approach from developing black pepper 1234567890():,; fruits. This enzyme is described as piperine synthase (piperoyl-CoA:piperidine piperoyl transferase) and is a member of the BAHD-type of acyltransferases encoded by a gene that is preferentially expressed in immature fruits. A second BAHD-type enzyme, also highly expressed in immature black pepper fruits, has a rather promiscuous substrate specificity, combining diverse CoA-esters with aliphatic and aromatic amines with similar efficiencies, and was termed piperamide synthase. Recombinant piperine and piperamide synthases are members of a small gene family in black pepper. They can be used to facilitate the microbial production of a broad range of medicinally relevant aliphatic and aromatic piperamides based on a wide array of CoA-donors and amine-derived acceptors, offering widespread applications. 1 Leibniz Institute of Plant Biochemistry, Dept. Cell and Metabolic Biology, Halle (Saale), Germany. 2 Core Facility Vienna Botanical Gardens, Vienna, Austria. ✉ 3 Instituto de Pesquisas de Produtos Naturais (IPPN), Universidade Federal do Rio de Janeiro (UFRJ), Rio de Janeiro/RJ, Brasil. -
ICP TRM 002 E Eng.Pdf (6.079Mb)
ICP /TFYJ 002-E 10 Oc tober 1986 ENGLl SH ONLY REPORT ~IENTIFIC GROUP ON HERBAL MEDICINE RESEARCH ~ Convened by the REGIONAL OFFICE FOR THE WESTERN PACIFIC OF THE WORLD HEALTH ORGANIZATION Tokyo, Japan, 10-12 March 1986 Not for sale Printed and Distributed by the Regional Office for the Western Pacific of the World Health Organization Manila, Philippines October 1986 'Wh0/ A4aoila, l)jJiLij.);)L.... ..; "OtE The vie~. expressed in thi. repott are those of the participants in the meeting of the Scientific Gtoup ott Herbal Medicine Research and do not necessarily teflect the policit. of the organization. This report has been prep"rteo ty the Regional Ottice for the liestern Pacific of the World Health organization for the governn,ents of ~len.ber States in the Region and for the participants in the meeting of the Scientific Group on Herbal Meaicine Research which was held in Tokyo, Japan, fron, 10 to 12 March 1980. - ii - CONTENTS 1. INTRODUCTION . ,. .. ,. ............................... ,. ...... 1 1.1 Background ... ..•.. .•...... ••. ..•. .... ..•. .••..•••..• 1 1.2 Objectives of the Scientific Group •••••••••••••••••• 1 2. ORGANIZATION OF THE SCIENTIFIC GROUP •••••••••••••••••••• 2 2.1 Participants .......•....•.• ,........................ 2 2.2 Opening address ...................................... 2 2.3 Selection of officers ••••••••••••••••••••••••••.•..• 2 2.4 Agenda •••...••.....•...••.•....•...•..••...•.••..... 2 2.5 Working documents ..•....••••...••.•••.•.•..•••••.••. 2 2.6 Closing session..................................... -
Piperine-Type Amides: Review of the Chemical and Biological Characteristics
International Journal of Chemistry; Vol. 5, No. 3; 2013 ISSN 1916-9698 E-ISSN 1916-9701 Published by Canadian Center of Science and Education Piperine-Type Amides: Review of the Chemical and Biological Characteristics Simon Koma Okwute1 & Henry Omoregie Egharevba2 1 Department of Chemistry, Faculty of Science, University of Abuja, Gwagwalada, F. C. T., Nigeria 2 National Institute for Pharmaceutical Research and Development (NIPRD), Idu, Industrial Layout, Garki, Abuja, Nigeria Correspondence: Simon Koma Okwute, Department of Chemistry, Faculty of Science, University of Abuja, P.M.B. 117, Gwagwalada, F. C. T., Abuja, Nigeria. Tel: 234-803-595-3929. E-mail: [email protected] Received: June 13, 2013 Accepted: July 20, 2013 Online Published: July 28, 2013 doi:10.5539/ijc.v5n3p99 URL: http://dx.doi.org/10.5539/ijc.v5n3p99 Abstract A new group of alkaloids emerged in 1819 following the isolation of piperine from the fruits of Piper nigrum. Since then, a large number of these compounds now referred to as piperine-type alkaloids or alkamides or piperamides have been isolated commonly from species belonging to the genus piper (piperaceae) which have worldwide geographical distribution. As a result of the traditional uses of piper species as spices in foods and in phytomedicines globally a number of their extractives and indeed the constituent amides have been screened for pharmacological properties. The biogenesis of the amides has been investigated and a number of synthetic pathways have been developed to make them readily available for biological studies. It has now been established that piperine and its analogues are potential pesticides and possess a number of medicinal properties. -
"Saponins," In: Ullmann's Encyclopedia of Industrial Chemistry
Article No : a23_485 Saponins MICHAEL W. SCHWARZ, E. Merck OHG, Darmstadt, Federal Republic of Germany 1. Introduction......................... 177 3.2. Glycoalkaloids ...................... 183 1.1. General Properties.................... 178 3.3. Triterpene Saponins................... 184 1.2. Distribution ......................... 178 4. Animal Saponins ..................... 188 1.3. Isolation ............................ 178 4.1. Asterosaponins....................... 188 1.4. Structure Elucidation.................. 179 4.2. Holothurins ......................... 189 1.5. Analysis ............................ 179 References .......................... 189 2. Pharmacology ....................... 179 3. Plant Saponins ....................... 180 3.1. Steroid Saponins ..................... 180 Abbreviations galA: b-D-galacturonic acid glc: b-D-glucose api: b-D-apiose glcA: b-D-glucuronic acid ara: a-L-arabinose 0 qui: b-D-quinovose drib: b-D-2 -deoxyribose rha: a- -rhamnose f: furanoside L xyl: b-D-xylose fuc: b-D-fucose fru: b-D-fructose gal: b-D-galactose 1. Introduction Saponins are categorized according to the structure of the aglycone moiety (sapogenin) and Saponins are glycosides (see ! Carbohydrates: the number of linked sugar chains. Aglycones Occurrence, Structures and Chemistry) occur- can be divided into triterpenoid and steroid ring primarily in plants but also in starfish sapogenins. Steroid saponins with basic proper- (Asteroidea) and sea cucumbers (Holothuridea). ties are termed glycoalkaloids. Properties generally considered to be shared by Hexoses common in all saponins are b-D- this group of natural products are surfactant glucose (glc), b-D-galactose (gal), and a-L- activity, hemolytic action, steroid- complexing rhamnose (rha); pentoses are a-L-arabinose ability, and biocidal capability. (ara) and b-D-xylose (xyl). Pentoses occur The characteristic soapy lather formed when primarily as pyranosides, less frequently as saponin- containing plant extracts are agitated in furanosides (f).