Short Communication: Composition of terpenoid compounds in essential oils extracted from stems of eight Piper species and their role in taxonomic relationships
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Abstract. Nugroho LH, Lexinta EC, Priyono Y, Susandarini R. 2020. Short Communication: Composition of terpenoid compounds in essential oils extracted from stems of eight Piper species and their role in taxonomic relationships. Biodiversitas 21: 3438-3443. Piper is widely used as source of essential oils from which many bioactive compounds with medicinal properties were used in traditional medicine. The objectives of this study were to explore the chemical composition of essential oils of eight Piper species and to identify its role in determining taxonomic relationships. Chemical composition of essential oils was analyzed using GC-MS analysis on petroleum ether extracts from stems of eight Piper species, while taxonomic relationship was determined using cluster analysis and principal component analysis. Results showed that 21 terpenoid compounds were identified as constituents of the essential oils, consisted of 4 monoterpenes, 14 sesquiterpenes, and 3 diterpenes. The composition of essential oils varied between species. Cluster analysis and principal component analysis showed that differences in the composition of essential oil compounds determined the grouping of species into two clusters. Five compounds were identified as having major role in the grouping of species. These compounds were ?-selinene, ?-caryophyllene, ?-caryophyllene, farnesyl acetone, and ?-amorphene. The results of this study offer opportunities for the use of Piper stems as source of essential oils. This study also confirms the interspecies variability in composition of essential oils, and at the same time supports the use of essential oils in chemotaxonomic studies.
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References
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Alvarenga SAV, Ferreira MJP, Emerenciano VP, Cabrol-Bass D. 2001. Chemosystematic studies of natural compounds isolated from Asteraceae: characterization of tribes by principal component analysis. Chemometr. Intell. Lab. 56: 27-37.
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Bhargava VV, Patel SC, Desa KS. 2013. Importance of terpenoids and essential oils in chemotaxonomic approach. Int. J. Herb. Med. 1 (2): 14-21.
Câmara JS, Alves MA, Marques JC. 2006. Multivariate analysis for the classification and differentiation of Madeira wines according to main grape varieties. Talanta 68: 1512–1521. doi:10.1016/j.talanta.2005.08.012.
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Rassem HHA, Nour AH, Yunus RM. 2016. Techniques for extraction of essential oils from plants: A Review. Aust. J. Basic & Appl. Sci. 10 (16): 117-127.
Riani LR, Macedo AL, Chedier LM, Pimenta DS. 2017. Chemical Analysis of Essential Oil and Hydrolates of Leaves, Inflorescences and Stems of Piper chimonanthifolium Kunth. Rev. Virtual Quim., 2017, 9 (4), 1560-1569.
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Rukshana MS, Doss A, Kumari RPTP. 2017. Phytochemical screening and GC-MS analysis of leaf extract of Pergularia daemia (Forssk) Chiov. Asian J. Plant Sci. Res. 7(1): 9-15.
Salleh WMNHW, Ahmad F, Sirat MH, Yen KH. 2012. Chemical compositions and antibacterial activity of the leaf and stem oils of Piper porphyrophyllum (Lindl.) N.E. Br. EXCLI Journal 11: 399-406.
Sanjaya P, Lekha K. 2019. Preliminary phytochemical analysis, GC-MS studies and antioxidant activity of Majidea zangueberica J. Kirk leaf extracts. J. Med. Plants Stud. 7(2): 186-195.
Setyawan AD. 2002. Chemotaxonomic studies on the genus Amomum based on chemical components of volatile oils. Jurnal Hayati 9 (3): 71-79.
Setzer WN, Park G, Agius BR, Stokes SL, Walker TM, Haber WA. 2008. Chemical compositions and biological activities of leaf essential oils of twelve species of Piper from Monteverde, Costa Rica. Nat. Prod.Commun. 3 (8): 1367-1374.
Sharmila S, Nalli R, Ramya EK, Mownika S. 2019. GC-MS Analysis of bio-active components in petroleum ether extract of Lepidagathis scariosa (Nees.) – Acanthaceae. Int. J. Pharm. Sci. Rev. Res. 54(1): 56-63.
Singh R. 2016. Chemotaxonomy: A tool for plant classification. J. Med. Plants Stud. 4(2): 90-93.
Valadares ACF, Alves CCF, Alves JM, Deus IPBD, Filho JGDO, Santos TCLD, Dias HJ, Crotti AEM, Miranda MLD. 2018. Essential oils from Piper aduncum inflorescences and leaves: chemical composition and antifungal activity against Sclerotinia sclerotiorum. An. Acad. Bras. Cienc. 90 (3): 2691-2699. http://dx.doi.org/10.1590/0001-3765201820180285
Varughese T, Unnikrishnan PK, Deepak M, Balachandran I, Shree ABR. 2016. Chemical composition of the essential oils from stem, root, fruit and leaf of Piper longum Linn. J. Essent. Oil Bear. Plants 19:1, 52-58. doi: 10.1080/0972060X.2015.1119065.
Susandarini R, Rugayah, Nugroho LH, Subandiyah S. 2016. Chemotaxonomy of Indonesian Citrus maxima based on leaf essential oils. OnLine J. Biol. Sci. 16 (1): 26-33. doi: 10.3844/ojbsci.2016.26.33.
Zahira A, Thamilmani K, and .Mohamed RR. 2016. Phytochemical screening and GC- MS profiling of Piper nigrum L. World J. Pharm. Res. 5 (5): 798-807.
Adams RP. 2007. Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Espectroscopy, 4th ed. Allured Publishing Corporation, Carol Stream, Illinois.
Adams RP, Mao K, Liu J. 2013. The volatile leaf oil of Juniperus microsperma and its taxonomy. Phytologia 95 (1): 87-93.
Almeda F, Astorga L, Orellana A, Sampuel L, Sierra P, Gaitán I, Cáceres A. 2015. Piper genus: source of natural products with anti-tyrosinase activity favored in phytocosmetics. International Journal of Phytocosmetics and Natural Ingredients 2:6. doi:10.15171/ijpni.2015.06.
Alvarenga SAV, Ferreira MJP, Emerenciano VP, Cabrol-Bass D. 2001. Chemosystematic studies of natural compounds isolated from Asteraceae: characterization of tribes by principal component analysis. Chemometr. Intell. Lab. 56: 27-37.
Araujo CA de, Camara CAG da, Moraes MM de, Vasconcelos GJN de, Pereira MR,. Zartman CE. 2019. Chemical compositions of essential oil of Piper species from Atlantic Forest of Amazonia, Brazil. Rec. Nat. Prod. 13 (4): 324-332. http://doi.org/10.25135/rnp.110.18.09.904
Assis A, Brito V, Bittencourt M, Silva L, Oliveira F, Oliveira R. 2013. Essential oils composition of four Piper species from Brazil. J. Essent. Oil Res. 25:3, 203-209. doi: 10.1080/10412905.2013.767755
Bhargava VV, Patel SC, Desa KS. 2013. Importance of terpenoids and essential oils in chemotaxonomic approach. Int. J. Herb. Med. 1 (2): 14-21.
Câmara JS, Alves MA, Marques JC. 2006. Multivariate analysis for the classification and differentiation of Madeira wines according to main grape varieties. Talanta 68: 1512–1521. doi:10.1016/j.talanta.2005.08.012.
Chaveerach A, Mokkamul P, Sudmoon R, Tanee T. 2006. Ethnobotany of the genus Piper (Piperaceae) in Thailand. Ethnobot. Res. Appl. 4: 223-231.
Dyer LA, Richards J, Dodson CD. 2004. Isolation, Synthesis, and Evolutionary Ecology of Piper Amides. In: Dyer LA, Palmer ADN (Eds.). Piper: A Model Genus for Studies of Phytochemistry, Ecology, and Evolution. Kluwer Academic/Plenum Publishers, New York.
Gomathi D, Kalaiselvi M, Ravikumar G, Devaki K, Uma C. 2015. GC-MS analysis of bioactive compounds from the whole plant ethanolic extract of Evolvulus alsinoides (L.) L . J. Food Sci. Technol. 52(2): 1212-1217. doi: 10.1007/s13197-013-1105-9.
Hao CY , Fan R, Qin XW, Hu LS, Tan LH, Xu F, Wu BD. 2018. Characterization of volatile compounds in ten Piper species cultivated in Hainan Island, South China. Int. J. Food Prop. 21 (1): 633-644. doi: 10.1080/10942912.2018.1446147.
Hieu LD, Hoi TM, Thang TD, Ogunwande IA. 2015. Volatile Constituents of Three Piper Species from Vietnam. Natural Product Communications 10 (11): 1997-1998.
Hussain SZ, Maqbool K. 2014. GC-MS: Principle, technique and its application in food science. Int. J. Curr. Sci. 13: E 116-126.
Jaramillo MA, Callejas R. 2004. Current perspectives on the classification and phylogenetics of the genus Piper L. In: Dyer LA, Palmer ADN. (Eds.). Piper: A Model Genus for Studies of Phytochemistry, Ecology, and Evolution. Kluwer Academic/Plenum Publishers, New York.
Judzentiene A, Mockute D. 2010. Essential oil composition of two yarrow taxonomic forms. Cent. Eur. J. Biol. 5(3): 346–352. doi: 10.2478/s11535-010-0011-7.
Kanjikar AP, Londonkar RL. 2017. GC-MS analysis of bioactive compounds in petroleum ether extract of Ficus krishnae. Int. Res. J. Pharm. 2017, 8 (10): 178-181. doi: 10.7897/2230-8407.0810204.
Karak S, Acharya J, Begum S, Mazumdar I, Kundu R, De B. 2018. Essential oil of Piper betle L. leaves: Chemical composition, antiacetylcholinesterase, anti-?-glucuronidase and cytotoxic properties. J. Appl. Res. Med. Aroma. 10 (2018) 85–92.
Kilic O. 2013. Essential oil compounds of three Centaurea L. taxa from Turkey and their chemotaxonomy. J. Med. Plants Res. 7(19): 1344-1350. doi: 10.5897/JMPR12.1233.
Liu K, Abdullah AA, Huang M, Nishioka T, Altaf-Ul-Amin Md, Kanaya S. 2017. Novel approach to classify plants based on metabolite-content similarity. BioMed Res. Int. Volume 2017, Article ID 5296729, 12 pages. https://doi.org/10.1155/2017/5296729
Liu Y, Huang T, Ba WJ. 2015. Chemical composition of essential oils from Piper kadsura. Chem. Nat. Compd. 51 (3): 583-585. doi: 10.1007/S10600-015-1354-0
Nowicka P, Wojdy?o A, Laskowski P. 2019. Principal component analysis (PCA) of physicochemical compounds’ content in different cultivars of peach fruits, including qualification and quantification of sugars and organic acids by HPLC. European Food Research and Technology 245: 929-938. https://doi.org/10.1007/s00217-019-03233-z
Rassem HHA, Nour AH, Yunus RM. 2016. Techniques for extraction of essential oils from plants: A Review. Aust. J. Basic & Appl. Sci. 10 (16): 117-127.
Riani LR, Macedo AL, Chedier LM, Pimenta DS. 2017. Chemical Analysis of Essential Oil and Hydrolates of Leaves, Inflorescences and Stems of Piper chimonanthifolium Kunth. Rev. Virtual Quim., 2017, 9 (4), 1560-1569.
Rivera-Mondragón A, Bijttebier S, Tuenter E, Custers D, Ortíz OO, Pieters L, Caballero-George C, Apers S, Foubert K. 2019. Phytochemical characterization and comparative studies of four Cecropia species collected in Panama using multivariate data analysis. Sci. Rep. 9:1763. https://doi.org/10.1038/s41598-018-38334-4
Rocha DS, Silva JM da, Navarro DMAF, Camara CAG, Lira CS de, Ramos CS. 2016. Potential antimicrobial and chemical composition of essential oils from Piper caldense Tissues. J. Mex. Chem. Soc. 60(3): 148-151.
Rukshana MS, Doss A, Kumari RPTP. 2017. Phytochemical screening and GC-MS analysis of leaf extract of Pergularia daemia (Forssk) Chiov. Asian J. Plant Sci. Res. 7(1): 9-15.
Salleh WMNHW, Ahmad F, Sirat MH, Yen KH. 2012. Chemical compositions and antibacterial activity of the leaf and stem oils of Piper porphyrophyllum (Lindl.) N.E. Br. EXCLI Journal 11: 399-406.
Sanjaya P, Lekha K. 2019. Preliminary phytochemical analysis, GC-MS studies and antioxidant activity of Majidea zangueberica J. Kirk leaf extracts. J. Med. Plants Stud. 7(2): 186-195.
Setyawan AD. 2002. Chemotaxonomic studies on the genus Amomum based on chemical components of volatile oils. Jurnal Hayati 9 (3): 71-79.
Setzer WN, Park G, Agius BR, Stokes SL, Walker TM, Haber WA. 2008. Chemical compositions and biological activities of leaf essential oils of twelve species of Piper from Monteverde, Costa Rica. Nat. Prod.Commun. 3 (8): 1367-1374.
Sharmila S, Nalli R, Ramya EK, Mownika S. 2019. GC-MS Analysis of bio-active components in petroleum ether extract of Lepidagathis scariosa (Nees.) – Acanthaceae. Int. J. Pharm. Sci. Rev. Res. 54(1): 56-63.
Singh R. 2016. Chemotaxonomy: A tool for plant classification. J. Med. Plants Stud. 4(2): 90-93.
Valadares ACF, Alves CCF, Alves JM, Deus IPBD, Filho JGDO, Santos TCLD, Dias HJ, Crotti AEM, Miranda MLD. 2018. Essential oils from Piper aduncum inflorescences and leaves: chemical composition and antifungal activity against Sclerotinia sclerotiorum. An. Acad. Bras. Cienc. 90 (3): 2691-2699. http://dx.doi.org/10.1590/0001-3765201820180285
Varughese T, Unnikrishnan PK, Deepak M, Balachandran I, Shree ABR. 2016. Chemical composition of the essential oils from stem, root, fruit and leaf of Piper longum Linn. J. Essent. Oil Bear. Plants 19:1, 52-58. doi: 10.1080/0972060X.2015.1119065.
Susandarini R, Rugayah, Nugroho LH, Subandiyah S. 2016. Chemotaxonomy of Indonesian Citrus maxima based on leaf essential oils. OnLine J. Biol. Sci. 16 (1): 26-33. doi: 10.3844/ojbsci.2016.26.33.
Zahira A, Thamilmani K, and .Mohamed RR. 2016. Phytochemical screening and GC- MS profiling of Piper nigrum L. World J. Pharm. Res. 5 (5): 798-807.
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