GC-MS analysis and in silico activity prediction of phytocompounds in the roots of Chrysopogon zizanioides (L.) Roberty
DOI:
https://doi.org/10.14719/pst.2021.8.1.1008Keywords:
Chrysopogon zizanioides, methanolic extract, root, GC-MS, Swiss ADMEAbstract
Chrysopogon zizanioides (L.) Roberty (Poaceae) commonly known as Ramachamis an aromatic, vigorous growing perennial grass with medicinal properties. The plant is tolerant to extreme soil and climatic conditions and is known for its cooling properties. Roots of the plant are widely used as body scrubber and is suggested for skin diseases in Ayurveda. The present work aims to identify the components in the crude methanolic root extract of C. zizanioides using GC-MS and also to predict the pharmacokinetic behaviour of selected compounds in silico using Swiss ADME online server . 41 compounds were identified of which sesquiterpenes formed the major group. Sesquiterpene Vetivenic acid was the compound with a maximum peak area of 38.9%. Components identified is reported to possess a range of biological activities like anti oxidant, antibacterial, anti cancer, anti inflammatory, anti ulcer, analgesic and insecticidal activities. Compounds with higher peak area like Vetivenic acid, beta vatirenene, beta.-Cedren-9-.alpha.-ol, D Viridiflorol, Gamma muurolene, (Z,E)-alpha-farnesene, Nootkatone, Aromadendrene oxide-(2), 7-Acetyl-2-hydroxy-2methyl-5isopropylbicyclo[4.3.0] nonane, Rosifoliol, 9,10-dehydro isolongifolene, Ylangenol, 4,7,10,13,16,19-Docosahexaenoic acid methyl ester, Carbonic acid, propargyl 2,2,2-tri chloroethyl ester, Oxacyclotetradeca-4,11-diyne, beta eudesmol and longifolene were evaluated in silico. All these compounds proved to obey Lipinski's rule-of-five and were water soluble. Vetivenic acid showed a good bioavailability score of 85% while the others showed 55%. None of the compounds were substrates to P glycoprotein. The values predicted may be used for preliminary evaluation of pharmacological properties of C. zizanioides and also as monographs for the development of potential semisynthetic or synthetic drugs.
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References
Lim TK. Chrysopogon zizanioides. In: Edible Medicinal and Non-Medicinal Plants. Springer, Cham. 2016;197-227. https://doi.org/10.1007/978-3-319-26062-4_16
Warrier PK, Nambiar VPK. Indian Medicinal Plants: A Compendium of 500 Species. 5th vol. Chennai: Orient Longman Private Limited;2005;
Sehgal VN, Srivastava G. Traditional/ayurvedic pharmacotherapy of skin diseases. Skinmed. 2010;8(5):282-84.
Ali B, Al-Wabel NA, Shams S, Ahamad A, Khan SA, Anwar F. Essential oils used in aromatherapy: A systemic review. Asian Pacific Journal of Tropical Biomedicine. 2015;5(8):601-11. https://doi.org/10.1016/j.apjtb.2015.05.007
Aburjai T, Natsheh FM. Plants used in cosmetics. Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives. 2003;17(9):987-1000. https://doi.org/10.1002/ptr.1363
Aswad M, Rayan M, Abu-Lafi S, Falah M, Raiyn J, Abdallah Z, Rayan A, et al. Nature is the best source of anti-inflammatory drugs: Indexing natural products for their anti-inflammatory bioactivity. Inflammation Research. 2018;67(1):67-75. https://doi.org/10.1007/s00011-017-1096-5
Lucas AJ, Sproston JL, Barton P, Riley RJ. Estimating human ADME properties, pharmacokinetic parameters and likely clinical dose in drug discovery. Expert opinion on drug discovery. 2019;14(12):1313-27. https://doi.org/10.1080/17460441.2019.1660642
Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports. 2017;7:42717. https://doi.org/10.1038/srep42717
Gomathi D, Kalaiselvi M, Ravikumar G, Devaki K, Uma C. GC-MS analysis of bioactive compounds from the whole plant ethanolic extract of Evolvulusalsinoides (L.) L. Journal of Food Science and Technology. 2015;52(2):1212-27. https://doi.org/10.1007/s13197-013-1105-9
Kannappan A, Gowrishankar S, Srinivasan R, Pandian SK, Ravi AV. Antibiofilm activity of Vetiveria zizanioides root extract against methicillin-resistant Staphylococcus aureus. Microbial Pathogenesis. 2017;110:313-24. https://doi.org/10.1016/j.micpath.2017.07.016
Chahal KK, Kaushal S, Sandhu AK. Chemical composition and biological properties of Chrysopogon zizanioides (L.) Roberty syn. Vetiveria zizanioides (L.) Nash-A Review. Indian Journal of Natural Products and Resources (IJNPR)[Formerly Natural Product Radiance (NPR)]. 2015;6(4):251-60.
Lima GM, Quintans-Júnior LJ, Thomazzi SM, Almeida EM, Melo MS, Serafini MR, Cavalcanti SC, Gelain DP, Santos JP, Blank AF, Alves PB, et al. Phytochemical screening, antinociceptive and anti-inflammatory activities of Chrysopogon zizanioides essential oil. Revistabrasileira de Farmacognosia. 2012;22(2):443-50. https://doi.org/10.1590/S0102-695X2012005000002.
David A, Wang F, Sun X, Li H, Lin J, Li P, Deng G. Chemical composition, antioxidant and antimicrobial activities of Vetiveria zizanioides (L.) Nash Essential Oil Extracted by Carbon Dioxide Expanded Ethanol. Molecules. 2019;24(10):1897. https://doi.org/10.3390/molecules24101897
Bos JD, Meinardi MM. The 500 Dalton rule for the skin penetration of chemical compounds and drugs. Experimental Dermatology: Viewpoint. 2000;9(3):165-69. https://doi.org/10.1034/j.1600-0625.2000.009003165.x
Savjani KT, Gajjar AK, Savjani JK. Drug solubility: importance and enhancement techniques. ISRN pharmaceutics; 2012. https://doi.org/10.5402/2012/195727
Arnott JA, Planey SL. The influence of lipophilicity in drug discovery and design. Expert opinion on drug discovery. 2012;7(10):863-75.https://doi.org/10.1517/17460441.2012.714363
Leopoldo M, Nardulli P, Contino M, Leonetti F, Luurtsema G, Colabufo NA. An updated patent review on P-glycoprotein inhibitors (2011-2018). Expert Opinion on Therapeutic Patents. 2019;29(6):455-61. https://doi.org/10.1080/13543776.2019.1618273
Duke J, Bogenschutz MJ. Dr. Duke's phytochemical and ethnobotanical databases. USDA, Agricultural Research Service; 1994.
Lee SK, Kim SD, Lee HY, Baek SH, Ko MJ, Son BG, Park S, Choi YW, Bae YS, et al. ?-Iso-cubebene, a natural compound isolated from Schisandra chinensis fruit, has therapeutic benefit against polymicrobial sepsis. Biochemical and Biophysical Research Communications. 2012 Sep 21;426(2):226-31. https://doi.org/10.1016/j.bbrc.2012.08.070.
Rocha NF, Rios ER, Carvalho AM, Cerqueira GS, de Araújo Lopes A, Leal LK, Dias ML, de Sousa DP, de Sousa FC, et al. Anti-nociceptive and anti-inflammatory activities of (?)-?-bisabolol in rodents. Naunyn-Schmiedeberg's Archives of Pharmacology. 2011;384(6):525-33. https://doi.org/10.1007/s00210-011-0679-x
do Nascimento KF, Moreira FM, Santos JA, Kassuya CA, Croda JH, Cardoso CA, do Carmo Vieira M, Ruiz AL, Foglio MA, de Carvalho JE, Formagio AS, et al. Antioxidant, anti-inflammatory, antiproliferative and antimycobacterial activities of the essential oil of Psidium guineense Sw. and spathulenol. Journal of Ethnopharmacology. 2018 Jan 10;210:351-58. https://doi.org/10.1016/j.jep.2017.08.030.
Trevizan LN, do Nascimento KF, Santos JA, Kassuya CA, Cardoso CA, do Carmo Vieira M, Moreira FM, Croda J, Formagio AS, et al., Anti-inflammatory, antioxidant and anti-Mycobacterium tuberculosis activity of viridiflorol: The major constituent of Allophylus edulis (A. St.-Hil., A. Juss. & Cambess.) Radlk. Journal of Ethnopharmacology. 2016;192:510-5. https://doi.org/10.1016/j.jep.2016.08.053
Chavan MJ, Wakte PS, Shinde DB. Analgesic and anti-inflammatory activity of Caryophyllene oxide from Annona squamosa L. bark. Phytomedicine. 2010;17(2):149-51. https://doi.org/10.1016/j.phymed.2009.05.016
Koo S, Thomas HR, Comolli JC, Rearden P, Baden LR, Marty FM, Inventors; Charles Stark Draper Laboratory Inc, Brigham, Women's Hospital, Assignee. Diagnosis and treatment of invasive aspergillosis. United States patent US 10,031,125. 2018 Jul 24.
Kishimoto K, Matsui K, Ozawa R, Takabayashi J. Volatile C6-aldehydes and allo-ocimene activate defense genes and induce resistance against Botrytis cinerea in Arabidopsis thaliana. Plant and Cell Physiology. 2005;46(7):1093-102. https://doi.org/10.1093/pcp/pci122
Tarek N, Hassan HM, AbdelGhani SM, Radwan IA, Hammouda O, El-Gendy AO. Comparative chemical and antimicrobial study of nine essential oils obtained from medicinal plants growing in Egypt. Beni-Suef University Journal of Basic and Applied Sciences. 2014;3(2):149-56. https://doi.org/10.1016/j.bjbas.2014.05.009
Forrer M, Kulik EM, Filippi A, Waltimo T. The antimicrobial activity of alpha-bisabolol and tea tree oil against Solobacterium moorei, a Gram-positive bacterium associated with halitosis. Archives of Oral Biology. 2013;58(1):10-16. https://doi.org/10.1016/j.archoralbio.2012.08.001
Dwivedi GR, Gupta S, Roy S, Kalani K, Pal A, Thakur JP, Saikia D, Sharma A, Darmwal NS, Darokar MP, Srivastava SK, et al. Tricyclic sesquiterpenes from Vetiveria zizanoides (L.) Nash as antimycobacterial agents. Chemical Biology & Drug Design. 2013 Nov;82(5):587-94. https://doi.org/10.1111/cbdd.12188
Hudak ES, Mercer BD, Wotiz JH. Fungistatic, bacteriostatic, and amebicidal studies on the isomeric normal nonynoic acids. Journal of the American Pharmaceutical Association. 1956;45(5):327-30. https://doi.org/10.1002/jps.3030450516
Rangasamy K, Namasivayam E. In vitro antioxidant and free radical scavenging activity of isolongifolene. Asian J Biol Sci. 2014;7(1):13-23.
Pavithra PS, Mehta A, Verma, R. S. Aromadendrene oxide 2, induces apoptosis in skin epidermoid cancer cells through ROS mediated mitochondrial pathway. Life Sciences. 2018;197:19-29. https://doi.org/10.1016/j.lfs.2018.01.029
Gu JL, Li ZJ, Zhang HX, Du ZZ. Fragrant volatile sesquiterpenoids isolated from the essential oil of Laggeraptera odonta by using olfactory?guided fractionation. Chemistry & Biodiversity. 2014;11(9):1398-405. https://doi.org/10.1002/cbdv.201400051
Rowan DD, Allen JM, Fielder S, Spicer JA, Brimble MA. Identification of conjugated triene oxidation products of alpha-farnesene in apple skin. Journal of Agricultural and Food Chemistry. 1995;43(8):2040-45. https://doi.org/10.1021/jf00056a016
Leonhardt RH, Berger RG. Nootkatone. In: Biotechnology of Isoprenoids Springer, Cham; 2014.391-404.
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