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Fractional Extraction, Isolation and Identification of Biologically Active Compounds from Anamirta Cocculus

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Fractional Extraction, Isolation and Identification of Biologically Active Compounds from Anamirta Cocculus Journal of Communicable Diseases Volume 52, Issue 3 - 2020, Pg. No. 53-57 Peer Reviewed & Open Access Journal Research Article Fractional Extraction, Isolation and Identification of Biologically Active Compounds from Anamirta cocculus (L.) Wight & Arn to Control Culex quinquefasciatus Say and Aedes albopictus Skuse Anju Viswan K1, E Pushapalatha2, S Arivudainambi3, T Selvamuthukumaran4 1,2Biopesticides & Toxicology Laboratory, Department of Zoology, University of Calicut, Malappuram, Kerala, India. 3,4Department of Entomology, Faculty of Agriculture, Annamalai University, Chidambaram, Tamil Nadu, India. DOI: https://doi.org/10.24321/0019.5138.202031 INFO ABSTRACT Corresponding Author: Background & Objectives: Development of resistance towards synthetic Anju Viswan K, Department of Zoology, University insecticides is one of the major problems in vector control programmes of Calicut, Malappuram, Kerala, India. and it can be reduced to an extent by the alternate use of botanical or bio E-mail Id: insecticides. The present study aims to find out the larvicidal activities of [email protected] Anamirta cocculus (L.) Wight and Arn against Culex quinqueafsciatus Say Orcid Id: and Aedes albopictus Skuse and to isolate the most active compounds https://orcid.org/0000-0001-7926-5826 present in the active fraction of the plant extract. How to cite this article: Methods: Cold extracts of A. cocculus seeds were taken using methanol Anju Viswan K, Pushapalatha E, Arivudainambi as solvent and fractionation was done using the solvents n-hexane, ethyl S, Selvamuthukumaran T. Fractional Extraction, acetate and acetone by column chromatographic method. Bioassays Isolation and Identification of Biologically Active were conducted using all these extracts and LC were calculated using Compounds from Anamirta cocculus (L.) Wight 50 the probit analysis developed by Finney. The structural elucidation of the & Arn to Control Culex quinquefasciatus Say and compounds of most active fraction isolated from chromatographic studies Aedes albopictus Skuse. J Commun Dis 2020; after bioassay was done by Liquid chromatography–mass spectrometry 52(3): 53-57. (LCMS) and Nuclear magnetic resonance (NMR) spectroscopy. Date of Submission: 2020-03-12 Result: A. cocculus treated larvae exhibited more restlessness, Date of Acceptance: 2020-05-16 convulsions and sluggishness, and the restless activity is more in Ae. albopictus than in Cx. quinquefasciatus. The activity of column fractions of A. cocculus was in the order Hexane (H) > Acetone (A) > H:EA (3:1) >H:EA (2:1)> H:EA (1:1): Ethyl acetate (EA): H:EA (1:2) >H:EA (1:3). The compounds present in the most active fractions were Picrotin and Menispermine respectively. Interpretation & Conclusion: From the results it has been proved that the plant is having potential larvicidal activity. Keywords: Anamirta Cocculus, Aedes albopictus, Culex quinquefasciatus, Larvicidal Activity, NMR, LCMS Journal of Communicable Diseases (P-ISSN: 0019-5138 & E-ISSN: 2581-351X) Copyright (c) 2020: Advanced Research Publications Anju Viswan K et al. Special Issue on XIII Annual Conference of ISMOCD J. Commun. Dis. 2020; 52(3) Introduction with non-absorbent cotton, wrapped with aluminium foil The pharmacological and insecticidal properties of herbs and paraffin wax paper and secured using rubber band. have been well established by researchers all around Whenever needed methanol was added to the content. the world, especially in India where the climate is highly After 48 hours, the extracts obtained from the conical flasks were filtered through Whatman No. 40 filter paper. conducive for such pesticidal plants. Utilization of plant Then the collected extracts were reduced in Vacuum rotary derived products in the management of insect pests/ evaporator and collected miscella were transferred to amber vectors are not a new concept but renewed recent past coloured bottle, tightly covered, labelled and stored in a due to the development of wide resistance of pests against deep freezer at -200C. chemical/ synthetic insecticides. The ill effects of synthetic insecticides could be reduced to an extent by the use of Fractionation of A. cocculus Extracts 1 botanical insecticides. Fractionation of miscella was done by following column Plants are the reservoirs of complex phyto-chemicals chromatography techniques. A glass column of 50cm length like alkaloids, flavonoid, saponins and tannins, which are was used. Silica gel powder (60/ 120 mesh) was packed known to possess medicinal and pesticide properties.2 in the column and loaded with 5g of miscella. Then the The plant derived metabolites, such as saponine, steroids, miscella was eluted with different solvents (HPLC grades) isoflavonoids, essential oils, alkaloids and tannins were and solvent systems such as n-heaxane, EA and acetone and proved as potent mosquito larvicidal compounds by many combination of solvents at different ratio viz., n-hexane, researchers in their earlier studies. In addition to natural EA, hexane: EA (1:1), hexane: EA (1:2), hexane: EA (1:3), secondary metabolites, synthetic derivatives also provide hexane: EA (3:1), hexane: EA (2:1) and acetone. alternative source for the management of mosquitoes.3 Bioassay Bioactive organic compounds exerted by plants have a Conducted using the protocol of WHO (1981).6 LC were complex mode of action such as growth and oviposition 50 inhibitory, repellent activity, toxic and deterrence.4,5 calculated using a Probit programme developed by Finney (1971).7 In this study, Anamirta cocculus (L.) Wight and Arn., was Identification of Compounds tested for its efficacy against Aedes albopictus Skuse and Culex quinquefasciatus Say. A. cocculus is large woody The structural elucidation of the compounds isolated climbing shrub with vertically furrowed ash coloured bark from chromatographic studies done by LCMS and NMR and glabrous young parts. Leaves large, simple, alternate, spectroscopy. long petiole, petioles thickened at the base and apex broadly Result ovate, subcoriaceous, cordate or truncate at the base, tufts of hairs in the axils of the nerves except the basal ones, The different column fractions ofA. cocculus eluted using flowers greenish in long panicles, drooping from the nodes column chromatographic techniques were tested against of the old wood, fruits druped kidney shaped turning red III instar larvae of Cx. quinquefasciatus and Ae. albopictus on ripening. (tables 1 & 2). The data on 24h LC50 (ppm) of the eight different fractions of A. cocculus tested against III instar Materials and Methods larvae of Cx. quinquefasciatus were provided in the table Test Organism 2. The 24 h LC50 values ranged from 10.1 ppm to 28.86 ppm for the different column fractions viz; hexane, EA, The mosquito species Aedes albopictus Skuse and Culex hexane : EA (3:1), hexane : EA (2:1), hexane : EA (1:1), quinquefasciatus Say were used for the study. hexane : EA (1:2), hexane : EA (1:3) and acetone. 24 hr Plant Used in the Study LC50 and LC90 (ppm) values obtained after the treatment of Anamirta cocculus (L.) Wight and Arn. (Family: the eight column fractions of A. cocculus with III instar of Menispermaceae). Ae. albopictus is provided in table 3. As in the case of Cx. quinquefasciatus the activity of A. cocculus was same as Cold Extraction Method that for Ae. albopictus. The 24 h LC50 values for the different Powder of A. cocculus packed as 20 g packets using column fractions ranged between 9.81 ppm and 24.22 ppm Whatman No. 40 filter paper and held by stapler pin. The for all the eight column fractions. thimbles were placed carefully in to one litre conical flask NMR and LCMS Analysis thus leaving three packets per flask. Five such conical flasks were kept. Then methanol added to conical flask The hexane fraction of A. cocculus shown more activity in such a way that the packets were submerged in the against III instar larvae of both Ae. albopictus and Cx. solvent. The mouth of the conical flasks was tightly plugged quinquefasciatus. This fraction was subjected to NMR and LCMS analyzes. ISSN: 0019-5138 DOI: https://doi.org/10.24321/0019.5138.202031 54 Anju Viswan K et al. Special Issue on XIII Annual Conference of ISMOCD J. Commun. Dis. 2020; 52(3) LCMS and NMR Data of A. cocculus Discussion Fraction I The A. cocculus treated larvae exhibited more restlessness, The fraction I was subjected to1 H and 13C NMR and LCMS convulsions and sluggishness and the restless activity is Ae. albopictus Cx. quinquefasciatus analysis. The 1H and 13C NMR as well as LCMS data are given more in than in . The in Plate 1A, 1B and 1C. sluggish and peculiar coiling movement in treated larvae might be due to the neuronal or muscular disturbances Compound 1 caused by active ingredients released by the extracts in It is interesting to note that the structure isolated resembles to the water. After exposure to A. cocculus extracts, the the structure of 4, 6a-dihydroxy-1a1-methyl-2-oxo-5-(prop- larvae showed abnormal motions, tremors and convulsions 1-en-2-yl)octahydro-1a1H-oxireno[2’,3’:1,2]indeno[7,1-bc] followed by paralysis and finally settle at the bottom of the furan-6-carbo- xylic acid. International Union of Pure and container. The result is in corroboration with the reports of Applied Chemistry (IUPAC) Name: 4, 6a-dihydroxy-1a1- Sagar and Seghal against Cx. quinquefasciatus.8 methyl-2-oxo-5-(prop-1-en-2-yl) octahydro-1a1H- oxireno The column fractions of methanol extracts were taken using [2’,3’:1,2]indeno[7,1-bc]furan-6-carboxylic acid, Chemical the column chromatography and analyzed their larvicidal rd Formula: C15H18O7. activity against 3 instar larvae of both Cx. quinquefasciatus 1 and Ae. albopictus. The mortality rates were recorded H NMR (400 MHz, CDCl3), δ (ppm): 1.18 (s, 3H, H(31), H(32) and H(33). 1.54 (d, 1H, H(24) J=1, 7 Hz). 1.95 (d, 1H, and the LC50 values were calculated. The calculated values H(23), J=1.5Hz).
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