Isolation and Identification of (-)-Usnic Acid Compound from Lichen Usnea sp. and Its Cytotoxic Activity on Murine Leukemia P388 Cell

  • MAULIDIYAH MAULIDIYAH UNIVERSITAS HALU OLEO
  • THAMRIN AZIS UNIVERSITAS HALU OLEO
  • SITTI HADIJAH SABARWATI UNIVERSITAS HALU OLEO
  • MUHAMMAD NURDIN UNIVERSITAS HALU OLEO

Abstract

Lichen is a symbiotic organism composed by algae and fungi that already known produces spesific secondary metabolites having bioactivities. The aim of this study were to isolate and determine the structure of secondary metabolites of Lichen Usnea sp. and to examine the cytotoxic activity against murine leukemia P388 cells. Isolation was carried out by utilizing colom chromatography using silica gel 60 stationary phase with eluent mixtures of n-hexane and ethyl acetate in a gradient elution. Isolates compounds were identified using UV-Vis spectroscopy, IR, 1H-NMR and 13C-NMR. The identification result obtained was (-)-usnic acid compound with molecular weight (MW) of 344 g/mol, needle-shaped yellow crystals. Test results cytotoxic compound of (-)-usnic acid against murine leukemia P388 cells were derived IC50 5.738 ± 0.61  µg/mL.

References

1. Mitrovic T, Stamenkovic S, Cvetkovic V, Nikolic M, Tosic S, Stojicic D. Lichens as source of versatile bioactive compounds. Biologica Nyssana. 2011. 2(1):1-6.
2. Lauterwein M, Oethinger M, Belsner K, Peters T, Marre R. In vitro activities of the Lichen secondary metabolites vulvinic acid, (+)-usnic acid, and (-)-usnic acid against aerobic and anaerobic microorganism. Antimicrob Agents Chemother 2013. 39:2541-3.
3. Mitrovic T, Stamenkovic S, Cvetkovic V, Tosic S, Stankovic M, Radojevic I, Stefanovic O, Comic L, DacicD, Curcic M and Markovic S. Antioxidant, antimicrobial and antiproliferative activities of five Lichen species. Int J Mol Sci. 2011.12:5428-48.
4. Brisdelli F, Perilli M, Sellitri D, Piovano M,Garbarino JA, Nicoletti M, Bozzi A, Amicosante G, Celenza G. Cytotoxic activity and antioxidant capacity of purified Lichen metabolites: An in vitro study. Phytotherapy Research. 2012. X:XXX (DOI: 10.1002/ptr.4739).
5. Emadi SN, Bhatt SM, M’Imunya JM, Suleh AJ, Raeeskarami SR, Rezai MS, Navaeifar MR. Cutaneous manifestation in children with HIV/AIDS. J Pediatr Rev. 2014.2(1):17-28.
6. Kato MA, Hegab DS, Sweilam MAER, Gaffar ESAE. Serum levels of tumor necrosis factor-α in patients with lichen planus. Egypt J Dermatol Venereol. 2014.34:102-6.
7. Ismail SB, Kumar SKS, Zain RB. Oral Lichen planus and lichenoid reactions: etiopathogenesis, diagnosis, management and malignant transformation. Journal of Oral Science. 2007. 49(2):86-106.
8. Emst-Russel MA, Elix JA, Chai CLL, Williams AC, Hamada N, Nash TH. Hybocarpone, a novel cytotoxic naphtazarin derivatives from mycobiont cultures of the Lichen Lecanora hybocarpa. Tetrahedron Lett. 2009.40:6321-4.
9. Karagoz A, Dogruoz N, Zeybek Z, Aslan A. Antibacterial activity of some Lichen extracts. Journal of Medicinal Plants Research. 2009.3(12):1034-9.
10. Sinon SH, Rich AM, Firth and Seymour GJ. Qualitative and quantitative assessment of immune cells in Oral Mucosal Lichen Planus (OMLP). Sains Malaysiana. 2013.42(1):65-71.
11. Rawstron AC, Kennedy B, Evans PA, Davies FE, Richards SJ, Haynes AP, Russell NH, Hale G, Morgan GJ, Jack AS, Hillmen P. Quantitation of minimal disease levels in chronic lymphocytic leukemia using a sensitive flow cytometric assay improves the prediction of outcome and can be used to optimize therapy. Blood 2001. 98:29–35.
12. Paudel B, Bhattarai HD, Pandey PD, Hur JS, Hong SG, Kim II-C,Yim JH. Antioxidant, antibacterial activity and brine shrimp toxitytes of some mountainous Lichens from Nepal. Biol Res. 2012.45:387-91.
13. Ernawati T, Anita Y, Lotulung DP , Hanafi M. Synthesis of methyl 2-cinnamamido-3-hydroxy propanoate having activity against P388 leukimia cells. Journal of Applied Pharmaceutical Science. 2014. 4(3):092-5.
14. Waud WR, Parker WB, Gilbert KS, Secrist JA. Isolation and characterization of a murine P388 leukimia line resistant to thiarabine. Nucleosides Nucleotides Nucleic Acids. 2012. 31(1):14-27.
15. Rankovic B, Kosanic M, Stanojkovic T, Vasiljevic P, Manojlovic N. Biological activities of Tonimia candida and Usnea barbata together with their norshiclic acid and usnic acid constituents. Int J Mol Sci. 2012.13:14707-22.
16. Maulidiyah, Cahyana HA, Suwarso WP. A new phenolic compound from acetone extract of Lichen Usnea flexuosa Tayl. Indo J Chem. 2011.11(3):290-4.
17. Sahid A, Pandiangan D, Siahaan P, Ummondor M. Uji sitotoksisitas ekstrak metanol daun sisik naga (Drymoglossum piloselloides Presl) terhadap sel leukemia P388. Jurnal MIPA UNSRAT. 2013. 2(2):94-9.
18. Ito C, Itoigawa M, Takakura T, Ruangrungsi N, Enjo F, Tokuda H, Nishino H, Furukawa H. Chemical constituents of Garcinia fusca: Structure elucidation of night new anthones and their cancer chemopreventive activity. J Nat Prod. 2003. 66:200-5.
Published
2015-04-30
How to Cite
MAULIDIYAH, MAULIDIYAH et al. Isolation and Identification of (-)-Usnic Acid Compound from Lichen Usnea sp. and Its Cytotoxic Activity on Murine Leukemia P388 Cell. JURNAL ILMU KEFARMASIAN INDONESIA, [S.l.], v. 13, n. 1, p. 40-44, apr. 2015. ISSN 2614-6495. Available at: <http://jifi.farmasi.univpancasila.ac.id/index.php/jifi/article/view/121>. Date accessed: 30 dec. 2024.
Section
Articles