Skip to main content
Top
Published in: BMC Complementary Medicine and Therapies 1/2019

Open Access 01-12-2019 | Human Immunodeficiency Virus | Research article

Anti-HIV-1 protease activity of the crude extracts and isolated compounds from Auricularia polytricha

Authors: Chanin Sillapachaiyaporn, Sunita Nilkhet, Alison T. Ung, Siriporn Chuchawankul

Published in: BMC Complementary Medicine and Therapies | Issue 1/2019

Login to get access

Abstract

Background

Acquired immunodeficiency syndrome (AIDS) is caused by the Human immunodeficiency virus type-1 (HIV-1). HIV-1 protease (HIV-1 PR) is an essential enzyme for the HIV replication, and therefore, it is an important target for antiretroviral drugs development, particularly from natural products. Auricularia polytricha (AP) is an edible mushroom with several important therapeutic properties. These properties will be investigated as HIV-1 PR inhibitors.

Methods

The sequential hexane (APH), ethanol (APE) and water (APW) extracts from AP were screened for inhibitory activity against HIV-1 PR. The extract that consistently showed the strong HIV-1 PR inhibition was further investigated for its phytochemical constituents. The compounds were purified by column chromatography. The isolated compounds were structurally elucidated using 1D and 2D NMR, HRMS, FTIR, and GC/MS techniques. Each compound was screened against HIV-1 PR to determine its inhibitory activity and to provide an explanation for the activity found in the extract.

Results

Hexane crude extract of AP (APH) exhibited significant inhibition on HIV-1 PR activity. Four major compounds isolated from APH fraction were identified to be two triacylglycerols, linoleic acid and ergosterol. Moreover, all four compounds showed significant inhibition of HIV-1 PR activity.

Conclusion

The findings from this study suggest that AP is a good source of fatty esters, fatty acids and ergosterol. These natural products exhibit anti-HIV-1 properties by blocking HIV-1 PR. These important biological results warrant further development of AP as an alternative antiretroviral drug.
Appendix
Available only for authorised users
Literature
1.
go back to reference Smith T, Srinivasan A, Schochetman G, Marcus M, Myers G. The phylogenetic history of immunodeficiency viruses. Nature. 1988;333(6173):573.CrossRef Smith T, Srinivasan A, Schochetman G, Marcus M, Myers G. The phylogenetic history of immunodeficiency viruses. Nature. 1988;333(6173):573.CrossRef
2.
go back to reference Barré-Sinoussi F, Ross AL, Delfraissy J-F. Past, present and future: 30 years of HIV research. Nat Rev Microbiol. 2013;11(12):877.CrossRef Barré-Sinoussi F, Ross AL, Delfraissy J-F. Past, present and future: 30 years of HIV research. Nat Rev Microbiol. 2013;11(12):877.CrossRef
3.
go back to reference Carr A, Cooper DA. Adverse effects of antiretroviral therapy. Lancet. 2000;356(9239):1423–30.CrossRef Carr A, Cooper DA. Adverse effects of antiretroviral therapy. Lancet. 2000;356(9239):1423–30.CrossRef
4.
go back to reference Montessori V, Press N, Harris M, Akagi L, Montaner JS. Adverse effects of antiretroviral therapy for HIV infection. Can Med Assoc J. 2004;170(2):229–38. Montessori V, Press N, Harris M, Akagi L, Montaner JS. Adverse effects of antiretroviral therapy for HIV infection. Can Med Assoc J. 2004;170(2):229–38.
5.
go back to reference Apisarnthanarak A, Jirayasethpong T, Sa-nguansilp C, Thongprapai H, Kittihanukul C, Kamudamas A, et al. Antiretroviral drug resistance among antiretroviral-naïve persons with recent HIV infection in Thailand. HIV Med. 2008;9(5):322–5.CrossRef Apisarnthanarak A, Jirayasethpong T, Sa-nguansilp C, Thongprapai H, Kittihanukul C, Kamudamas A, et al. Antiretroviral drug resistance among antiretroviral-naïve persons with recent HIV infection in Thailand. HIV Med. 2008;9(5):322–5.CrossRef
6.
go back to reference Yu J, Sun R, Zhao Z, Wang Y. Auricularia polytricha polysaccharides induce cell cycle arrest and apoptosis in human lung cancer A549 cells. Int J Biol Macromol. 2014;68:67–71.CrossRef Yu J, Sun R, Zhao Z, Wang Y. Auricularia polytricha polysaccharides induce cell cycle arrest and apoptosis in human lung cancer A549 cells. Int J Biol Macromol. 2014;68:67–71.CrossRef
7.
go back to reference Park KM, Kwon KM, Lee SH. Evaluation of the antioxidant activities and tyrosinase inhibitory property from mycelium culture extracts. Evid Based Complement Alternat Med. 2015;2015:616298. Park KM, Kwon KM, Lee SH. Evaluation of the antioxidant activities and tyrosinase inhibitory property from mycelium culture extracts. Evid Based Complement Alternat Med. 2015;2015:616298.
8.
go back to reference Chen Y, Xue Y. Purification, chemical characterization and antioxidant activities of a novel polysaccharide from Auricularia polytricha. Int J Biol Macromol. 2018;120:1087–92.CrossRef Chen Y, Xue Y. Purification, chemical characterization and antioxidant activities of a novel polysaccharide from Auricularia polytricha. Int J Biol Macromol. 2018;120:1087–92.CrossRef
9.
go back to reference Wu N-J, Chiou F-J, Weng Y-M, Yu Z-R, Wang B-J. In vitro hypoglycemic effects of hot water extract from Auricularia polytricha (wood ear mushroom). Int J Food Sci Nutr. 2014;65(4):502–6.CrossRef Wu N-J, Chiou F-J, Weng Y-M, Yu Z-R, Wang B-J. In vitro hypoglycemic effects of hot water extract from Auricularia polytricha (wood ear mushroom). Int J Food Sci Nutr. 2014;65(4):502–6.CrossRef
10.
go back to reference Hossen M, Billah Prince M, Tanvir E, Chowdhury M, Rahman M, Alam F, et al. Ganoderma lucidum and Auricularia polytricha mushrooms protect against Carbofuran-induced toxicity in rats. Evid Based Complement Alternat Med. 2018;2018:6254929. Hossen M, Billah Prince M, Tanvir E, Chowdhury M, Rahman M, Alam F, et al. Ganoderma lucidum and Auricularia polytricha mushrooms protect against Carbofuran-induced toxicity in rats. Evid Based Complement Alternat Med. 2018;2018:6254929.
11.
go back to reference Koyama K, Akiba M, Imaizumi T, Kinoshita K, Takahashi K, Suzuki A, et al. Antinociceptive constituents of Auricularia polytricha. Planta Med. 2002;68(03):284–5.CrossRef Koyama K, Akiba M, Imaizumi T, Kinoshita K, Takahashi K, Suzuki A, et al. Antinociceptive constituents of Auricularia polytricha. Planta Med. 2002;68(03):284–5.CrossRef
12.
go back to reference Mengoni F, Lichtner M, Battinelli L, Marzi M, Mastroianni CM, Vullo V, et al. In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells. Planta Med. 2002;68(02):111–4.CrossRef Mengoni F, Lichtner M, Battinelli L, Marzi M, Mastroianni CM, Vullo V, et al. In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells. Planta Med. 2002;68(02):111–4.CrossRef
13.
go back to reference Min BS, Jung HJ, Lee JS, Kim YH, Bok SH, Ma CM, et al. Inhibitory effect of triterpenes from Crataegus pinatifida on HIV-I protease. Planta Med. 1999;65(04):374–5.CrossRef Min BS, Jung HJ, Lee JS, Kim YH, Bok SH, Ma CM, et al. Inhibitory effect of triterpenes from Crataegus pinatifida on HIV-I protease. Planta Med. 1999;65(04):374–5.CrossRef
14.
go back to reference Xu H-X, Zeng F-Q, Wan M, Sim K-Y. Anti-HIV triterpene acids from Geum japonicum. J Nat Prod. 1996;59(7):643–5.CrossRef Xu H-X, Zeng F-Q, Wan M, Sim K-Y. Anti-HIV triterpene acids from Geum japonicum. J Nat Prod. 1996;59(7):643–5.CrossRef
15.
go back to reference Pornpakakul S, Suwancharoen S, Petsom A, Roengsumran S, Muangsin N, Chaichit N, et al. A new sesquiterpenoid metabolite from Psilocybe samuiensis. J Asian Nat Prod Res. 2009;11(1):12–7.CrossRef Pornpakakul S, Suwancharoen S, Petsom A, Roengsumran S, Muangsin N, Chaichit N, et al. A new sesquiterpenoid metabolite from Psilocybe samuiensis. J Asian Nat Prod Res. 2009;11(1):12–7.CrossRef
16.
go back to reference Luangsuphabool T, Piapukiew J, Parnmen S, Nelsen MP, Lumbsch HT, Sangvichien EJTL. Diversity of the Trypethelium eluteriae group in Thailand (Ascomycota, Trypetheliales). Lichenologist. 2016;48(1):53–60.CrossRef Luangsuphabool T, Piapukiew J, Parnmen S, Nelsen MP, Lumbsch HT, Sangvichien EJTL. Diversity of the Trypethelium eluteriae group in Thailand (Ascomycota, Trypetheliales). Lichenologist. 2016;48(1):53–60.CrossRef
17.
go back to reference Lim Y, San Ryu J, Shi S, Noh W, Kim E, Vang Le Q, et al. Isolation of bacteria associated with the king oyster mushroom, Pleurotus eryngii. Mycobiology. 2008;36(1):13–8.CrossRef Lim Y, San Ryu J, Shi S, Noh W, Kim E, Vang Le Q, et al. Isolation of bacteria associated with the king oyster mushroom, Pleurotus eryngii. Mycobiology. 2008;36(1):13–8.CrossRef
18.
go back to reference Chira N-A, Todasca M-C, Nicolescu A, Rosu A, Nicolae M, Rosca S-I. Evaluation of the computational methods for determining vegetable oils composition using 1H-NMR spectroscopy. Rev Chim. 2011;1:42–6. Chira N-A, Todasca M-C, Nicolescu A, Rosu A, Nicolae M, Rosca S-I. Evaluation of the computational methods for determining vegetable oils composition using 1H-NMR spectroscopy. Rev Chim. 2011;1:42–6.
19.
go back to reference Tao R, Wang C-Z, Kong Z-W. Antibacterial/antifungal activity and synergistic interactions between polyprenols and other lipids isolated from Ginkgo Biloba L. leaves. Molecules. 2013;18(2):2166–82.CrossRef Tao R, Wang C-Z, Kong Z-W. Antibacterial/antifungal activity and synergistic interactions between polyprenols and other lipids isolated from Ginkgo Biloba L. leaves. Molecules. 2013;18(2):2166–82.CrossRef
20.
go back to reference El-Mekkawy S, Meselhy MR, Nakamura N, Tezuka Y, Hattori M, Kakiuchi N, et al. Anti-HIV-1 and anti-HIV-1-protease substances from Ganoderma lucidum. Phytochemistry. 1998;49(6):1651–7.CrossRef El-Mekkawy S, Meselhy MR, Nakamura N, Tezuka Y, Hattori M, Kakiuchi N, et al. Anti-HIV-1 and anti-HIV-1-protease substances from Ganoderma lucidum. Phytochemistry. 1998;49(6):1651–7.CrossRef
22.
go back to reference Van Etten JL, Gottlieb D. Biochemical changes during the growth of fungi II. Ergosterol and fatty acids in Penicillium atrovenetum. J Bacteriol. 1965;89(2):409–14.PubMedCentral Van Etten JL, Gottlieb D. Biochemical changes during the growth of fungi II. Ergosterol and fatty acids in Penicillium atrovenetum. J Bacteriol. 1965;89(2):409–14.PubMedCentral
23.
go back to reference Ruess L, Häggblom MM, Zapata EJG, Dighton J. Fatty acids of fungi and nematodes—possible biomarkers in the soil food chain? Soil Biol Biochem. 2002;34(6):745–56.CrossRef Ruess L, Häggblom MM, Zapata EJG, Dighton J. Fatty acids of fungi and nematodes—possible biomarkers in the soil food chain? Soil Biol Biochem. 2002;34(6):745–56.CrossRef
25.
go back to reference Lee DY-W, Lin X, Paskaleva EE, Liu Y, Puttamadappa SS, Thornber C, et al. Palmitic acid is a novel CD4 fusion inhibitor that blocks HIV entry and infection. AIDS Res Hum Retrovir. 2009;25(12):1231–41.CrossRef Lee DY-W, Lin X, Paskaleva EE, Liu Y, Puttamadappa SS, Thornber C, et al. Palmitic acid is a novel CD4 fusion inhibitor that blocks HIV entry and infection. AIDS Res Hum Retrovir. 2009;25(12):1231–41.CrossRef
26.
go back to reference Lee DY-W, Canki M. Methods and compositions for the use of Sargassum fusiforme for the inhibition of hiv-1 infection. Google Patents; 2010. Lee DY-W, Canki M. Methods and compositions for the use of Sargassum fusiforme for the inhibition of hiv-1 infection. Google Patents; 2010.
Metadata
Title
Anti-HIV-1 protease activity of the crude extracts and isolated compounds from Auricularia polytricha
Authors
Chanin Sillapachaiyaporn
Sunita Nilkhet
Alison T. Ung
Siriporn Chuchawankul
Publication date
01-12-2019
Publisher
BioMed Central
Published in
BMC Complementary Medicine and Therapies / Issue 1/2019
Electronic ISSN: 2662-7671
DOI
https://doi.org/10.1186/s12906-019-2766-3

Other articles of this Issue 1/2019

BMC Complementary Medicine and Therapies 1/2019 Go to the issue