Phytochemical study of ethyl acetate fraction from lichen Stereocaulon massartianum Hue. and antibacterial activity assay with TLC-bioautography method

Article Sidebar

JSFK 7(2) Agustus 2020
PDF (Bahasa Indonesia)
Published: Aug 31, 2020
DOI: https://doi.org/10.25077/jsfk.7.2.164-171.2020
Keywords:
antibacterial, lichen, TLC-bioautography, Stereocaulon massartianum

Main Article Content

Friardi Ismed
Laboratorium Biota Sumatera dan Fakultas Farmasi, Universitas Andalas, Padang, 25163
https://orcid.org/0000-0002-6200-7502
Nadhifa Putri
Fakultas Farmasi, Universitas Andalas, Padang, 25163
Deddi Prima Putra
Laboratorium Biota Sumatera dan Fakultas Farmasi, Universitas Andalas, Padang, 25163
https://orcid.org/0000-0002-0930-3150

Abstract

This research is a continuation study in the inventory of lichens of the genus Stereocaulon which is currently focused on the Stereocaulon massartianum Hue collected in the rocks of Diatas Lake, West Sumatera, Indonesia. Reports on phytochemical studies and pharmacological activities of this species are still limited, based on literature studies that have been carried out. This research was conducted to determine their secondary metabolites and potential antibacterial activity. The air-dried thallus of lichen S. massartianum was macerated successively using n-hexane, ethyl acetate and methanol solvents. The compounds were separated by chromatography and recrystallization methods, then analyzed by spectroscopy (UV-Vis, FTIR, 1H and 13C-NMR). Furthermore, the antibacterial activity assay was performed by agar diffusion method on ethyl acetate extract, and TLC-Bioautography for the isolated compound. Three compounds have been isolated from ethyl acetate extract, i.e. atranorin (1), stictic acid (2) and norstictic acid (3). The results of antibacterial assay from the extract showed antagonistic activity against pathogenic bacteria S. aureus, E. faecalis, E. coli, and P. aeruginosa at concentrations of 10 and 20%, while TLC-bioautography of compound 3 exhibited growth inhibition area in all test bacteria.

Article Details

How to Cite
Ismed, F., Putri, N., & Putra, D. P. (2020). Phytochemical study of ethyl acetate fraction from lichen Stereocaulon massartianum Hue. and antibacterial activity assay with TLC-bioautography method. Jurnal Sains Farmasi & Klinis, 7(2), 164–171. https://doi.org/10.25077/jsfk.7.2.164-171.2020
Issue
Vol. 7 No. 2 (2020): J Sains Farm Klin 7(2), Agustus 2020
Section
Research Articles
Creative Commons License

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

The authors retain the copyright and grant the journal the right of first publication simultaneously under the Creative Commons Attribution License. This license allows others to share the work with proper acknowledgment of authorship and initial publication in this journal. Authors are permitted and encouraged to deposit their articles in institutional repositories, on their personal websites, or in other online repositories after the article has been published in JSFK.

Author Biographies

Friardi Ismed, Laboratorium Biota Sumatera dan Fakultas Farmasi, Universitas Andalas, Padang, 25163

Laboratorium Biota Sumatera dan Fakultas Farmasi, Universitas Andalas, Padang, 25163

Nadhifa Putri, Fakultas Farmasi, Universitas Andalas, Padang, 25163

Fakultas Farmasi, Universitas Andalas, Padang, 25163

Deddi Prima Putra, Laboratorium Biota Sumatera dan Fakultas Farmasi, Universitas Andalas, Padang, 25163

Laboratorium Biota Sumatera dan Fakultas Farmasi, Universitas Andalas, Padang, 25163

References

Kirk P, Cannon P, Minter D, Stalpers J, editors. Ainsworth & Bisby’s Dictionary of the Fungi. Wallingford: CABI; 2008. 771 p. https://doi.org/10.1079/9780851998268.0000

Lamb I. On the morphology, phylogeny, and taxonomy of the lichen genus Stereocaulon. Can J Bot. 1951;29(27):522–84. https://doi.org/10.1139/b51-045

Ismed F, Lohézic-Le Dévéhat F, Guiller A, Corlay N, Bakhtiar A, Boustie J. Phytochemical review of the lichen genus Stereocaulon (Fam. Stereocaulaceae) and related pharmacological activities highlighted by a focus on nine species. Phytochem Rev. 2018;17(5):1165–78. https://doi.org/10.1007/s11101-018-9576-y

Nylander J. Synopsis methodica lichenum. Paris; 1860.

Riddle LW. The North American species of Stereocaulon. Bot Gaz. 1910;50(4):285–304. https://doi.org/10.1086/330363

Magnusson A. Studies on boreal Stereocaula. K Vet O Vitterh Samh Handl. 1926;30(7):1–89.

Dodge C. A synopsis of Stereocaulon with notes on some exotic species. Ann Cryptog Exot. 1929;2(2):93–153.

Johnson GT. The Taxonomic Importance and Phylogenetic Significance of the Cephalodia of Stereocaulon. Ann Missouri Bot Gard. 1938;25(3):729–68. https://doi.org/10.2307/2394275

Duvigneaud P. Les Stereocaulons des hautes montagnes du Kivu. Rev Bot. 1955;14:1–141.

Lamb M. A conspectus of the lichen genus Stereocaulon (SCHREB.) HOFFM. J Hattori Bot Lab. 1977;43:191–355.

Lamb M. Keys to the species of the lichen genus Stereocaulon (SCHREB.) HOFFM. J Hattori Bot Lab. 1978;44:209–50.

Boekhout T. Studies on Colombia cryptogams XVIII. the genus Stereocaulon (SCHREBER)HOFFMAN (Lichenes). J Hattori Bot Lab. 1982;53:483–511.

McCarthy P. Checklist of the lichens of Australia and its island territories [Internet]. Aust Biol Resour Study. 2012. Available from: https://www.anbg.gov.au/abrs/lichenlist/introduction.html

Duvigneaud P. Contribution à l’étude systématique et chimique du genre Stereocaulon. Biol Jaarb “Dodonaea.†1942;25:80–98.

Ismed F. Phytochimie de lichens du genre Stereocaulon : étude particulière de S. Halei Lamb et S. montagneanum Lamb, deux lichens recoltés en Indonésie [Internet]. Universite de Rennes 1; 2012. Available from: https://www.theses.fr/2012REN1S053

Vu TH. Etude des acides gras du genre Stereocaulon etude phytochimique du lichen S. evolutum Graewe. Université de Rennes1; 2014.

Ismed F, Farhan A, Bakhtiar A, Zaini E, Nugraha YP, Dwichandra Putra O, et al. Crystal structure of olivetolic acid: a natural product from Cetrelia sanguinea (Schaer.). Acta Crystallogr Sect E Crystallogr Commun. 2016;72(11):1587–9. https://doi.org/10.1107/S2056989016016273

Zaini E, Khairun Nisak R, Dwi Utami R, Fitriani L, Ismed F. Effect of Milling on Physicochemical Properties of Usnic Acid Isolated from Usnea sp. Orient J Chem. 2017;33(6):3031–6. https://doi.org/10.13005/ojc/330641

Ismed F, Lohezic-Le Devehat F, Delalande O, Sinbandhit S, Bakhtiar A, Boustie J. Lobarin from the Sumatran lichen, Stereocaulon halei. Fitoterapia. 2012;83(8). https://doi.org/10.1016/j.fitote.2012.09.025

Ismed F, Dévéhat FL-L, Rouaud I, Ferron S, Bakhtiar A, Boustie J. NMR reassignment of stictic acid isolated from a Sumatran lichen Stereocaulon montagneanum (Stereocaulaceae) with superoxide anion scavenging activities. Z Naturforsch C Bio Sci. 2017;72(1–2). https://doi.org/10.1515/znc-2016-0148

Ismed F, Arifa N, Zaini E, Bakhtiar A, Umeda D, Putra OD, et al. Ethyl Haematommate from Stereocaulon graminosum Schaer.: Isolation and Crystal Structure. Nat Prod Sci. 2018;24(2):115. https://doi.org/10.20307/nps.2018.24.2.115

Huneck S, Yoshimura I. Identification of lichen substances [Internet]. Berlin, Heidelberg: Springer Berlin Heidelberg; 1996. 493 p. https://doi.org/10.1007/978-3-642-85243-5

Dewanjee S, Gangopadhyay M, Bhattacharya N, Khanra R, Dua TK. Bioautography and its scope in the field of natural product chemistry. J Pharm Anal. 2015;5(2):75–84. https://doi.org/10.1016/j.jpha.2014.06.002

Hylands PJ, Ingolfsdottir K. The isolation of methyl β-orsellinate from Stereocaulon alpinum and comments on the isolation of 4,6-dihydroxy-2- methoxy-3-methylacetophenone from Stereocaulon species. Phytochemistry. 1985;24(1):127–9. https://doi.org/10.1016/S0031-9422(00)80821-3

Huneck S, Schmidt J, Tabacchi R. Thermal decomposition of lichen depsides. Z Naturforsch C Bio Sci. 1989;44(10):1283. https://doi.org/10.1515/znb-1989-1023

Bolognese A, Chioccara F, Scherillo G. Isolation and characterization of atranorin and 4,6 dihydroxy-2-methoxy-3-methylacetophenone from Stereocaulon vesuvianum. Phytochemistry. 1974;13(9):1989–90. https://doi.org/https://doi.org/10.1016/0031-9422(74)85131-9

Bachelor F, Cheriyan U, Wong J. Cleavage of depsides by tert-butyl alcohol. Phytochemistry. 1979;18:487–8. https://doi.org/10.1016/s0031-9422(00)81895-6

Man-Rong H. Noteworthy species of Stereocaulon from China. Mycosystema. 2008;27(1):85–90.

Putra HE. Analisis Profil Metabolit Sekunder Dan Penetapan Kadar Atranorin Pada Lichen Sumatera Genus Stereocaulon Dengan Metode Klt-Densitometeri. Universitas Andalas; 2016.

Santiago K, Borricano J, Canal J, Marcelo D, Perez M, Cruz T. Antibacterial activities of fructicose lichens collected from selected sites in Luzon Island, Philippines. Philipp Sci Lett. 2010;3:18–29.

Jesionek W, Majer-Dziedzic B, Horváth G, Móricz ÃM, Choma IM. Screening of antibacterial compounds in Salvia officinalis L. tincture using thin-layer chromatography—direct bioautography and liquid chromatography—tandem mass spectrometry techniques. JPC - J Planar Chromatogr - Mod TLC. 2017;30(5):357–62. https://doi.org/10.1556/1006.2017.30.5.4

Jóźwiak GW, Majer-Dziedzic B, Jesionek W, Zieliński W, Waksmundzka-Hajnos M. Thin-layer chromatography: Direct bioautography as a method of examination of antimicrobial activity of selected Potentilla species. J Liq Chromatogr Relat Technol. 2016;39(5–6):281–5. https://doi.org/10.1080/10826076.2016.1163466

Botz L. BIOASSAYS | Bioautography. In: Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Elsevier; 2013. https://doi.org/10.1016/B978-0-12-409547-2.00035-4

Arifa N. Isolasi dan Elusidasi Struktur Senyawa Metabolit Sekunder dari Lichen Sumatera Stereocaulon graminosum serta Pengujian Aktivitas Antibakteri. Universitas Andalas; 2018.

Tay T, Türk AÖ, Yılmaz M, Türk H, Kıvanç M. Evaluation of the Antimicrobial Activity of the Acetone Extract of the Lichen Ramalina farinacea and its (+)-Usnic Acid, Norstictic Acid, and Protocetraric Acid Constituents. Zeitschrift für Naturforsch C. 2004;59(5–6):384–8. https://doi.org/10.1515/znc-2004-5-617.