Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
권호 표지
DOI QR코드

DOI QR Code

Ergosterol peroxides from the fruit body of Sparassis crispa

꽃송이버섯(Sparassis crispa) 자실체로부터 ergosteol peroxide의 분리 및 동정

  • Lee, Yeong-Geun (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Thi, Nhan Nguyen (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Kim, Hyoung-Geun (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Lee, Dae Young (Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, RDA) ;
  • Lee, Seung-Eun (Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, RDA) ;
  • Kim, Geum-Soog (Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, RDA) ;
  • Baek, Nam-In (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University)
  • Received : 2016.07.09
  • Accepted : 2016.08.08
  • Published : 2016.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

Sparassis crispa fruits were extracted in 80 % MeOH, and the concentrated extract was partitioned into EtOAc, n-butyl alcohol, and water fractions. The repeated octadecyl $SiO_2$ and silica gel ($SiO_2$) column chromatographies for the EtOAc and nbutyl alcohol fractions led to isolation of two ergosterol peroxides. There chemical structures were determined as ($3{\beta}$,$5{\alpha}$,$8{\alpha}$,22E)-5,8-Epidioxyergosta-6,22-dien-3-ol (ergosterol peroxide) (1) and 3-O-${\beta}$-D-glucopyranosyl ergosterol peroxide (2) based on spectroscopic data analyses including nuclear magnetic resonance, infrared spectrometry, and mass spectrometry (MS). Compounds 1 and 2 were for the first time isolated from S. crispa in this study.

꽃송이 버섯(S. crispa)을 80 % MeOH 수용액으로 추출하고, 추출물을 EtOAc, n-butyl alcohol 및 물 분획으로 나누었다. EtOAc 분획과 n-BuOH 분획에 대해 $SiO_2$ 및 ODS column chromatography를 반복적으로 실시하여 2종의 ergosterol peroxide를 분리, 정제하였다. infrared spectrometry, nuclear magnetic resonance 및 FAB-MS data를 해석, 화합물 1과 2를 ergosterol peroxide와 3-O-${\beta}$-D-glucopyranosyl ergosterol peroxide로 각각 구조동정 하였다. 두 화합물 모두 꽃송이 버섯으로부터는 이번 실험에서 처음으로 분리되었다.

Keywords

References

  1. Akihisa T, Franzblau SG, Tokuda H, Tagata M, Ukiya M, Matsuzawa T, Metori K, Kimura Y, Suzuki T, Yasukawa K (2005) Antitubercular activity and inhibitory effect on Epstein-Barr virus activation of sterols and polyisoprenepolyols from an edible mushroom, Hypsizigus marmoreus. Biol Pharm Bull 28: 1117-1119 https://doi.org/10.1248/bpb.28.1117
  2. Bok JW, Leonard L, Jeff C, Hans GK, Neil T (1999) Antitumer sterols from the mycelia of Cordyceps sinensis. Phytochem 51: 891-898 https://doi.org/10.1016/S0031-9422(99)00128-4
  3. Kang JH, Jang JE, Mishra SK, Lee HJ, Nho CW, Shin D, Jin M, Kim MK, Choi C, Oh SH (2015) Ergosterol peroxide from Chaga mushroom (Inonotus obliquus) exhibits anti-cancer activity by down-regulation of the ${\beta}$-catenin pathway in colorectal cancer. Ethnopharmacol 173: 303-312 https://doi.org/10.1016/j.jep.2015.07.030
  4. Kazuko Y, Naoki K, Toshihiro H, Kyosuke Y, Toshiaki I, Takashi K (2010) Novel phthalide compounds from Sparassis crispa (hanabiratake), hanabiratakelide A-C, exhibiting anti-cancer related activity. Biol Pharm Bull 33: 1355-1359 https://doi.org/10.1248/bpb.33.1355
  5. Kim DS, Baek, NI, Oh SR, Jung KY, Lee IS, Kim JH, Lee HK (1997) Anticomplementary activity of ergosterol peroxide from Naematoloma fasciculare and reassignment of NMR data. Arch Pharm Res 20: 201-205 https://doi.org/10.1007/BF02976145
  6. Kim EJ, Yoo KH, Kim YS, Seok SJ, Kim JH (2015) Biological activities of wild Sparassis crispa extracts. Mycobiol 43: 40-46
  7. Kim KH, Choi SU, Noh HJ, Zee O, Lee KR (2014) Cytotoxic ergosterol derivatives from the mushroom Naematoloma fasciculare. Nat Pro Sci 20: 76-79
  8. Kim MS, Lee KT, Jeon SM, Ka KH (2010) The quantities of methyl orsellinate and sparassol of Sparassis latifolia by host plants. Korean J Mycol 41: 130-712
  9. Kim SW, Park SS, Min TJ, Yu KH (1999) Antioxidant activity of ergosterol peroxide ($5,8-epidioxy-5{\alpha},8-{\alpha}-ergosta-6,22E-dien-3{\beta}-ol$) in Armillariella mellea. Bull Korean Chem Soc 20: 819-823
  10. Lee MA (2010) Lipolytic effect of Sparassis crispa extract in differentiated 3T3-L1 cells and diet-induced obesity mice. Dissertation, KyungHee University
  11. Lee YG, Seo KH, Hong EK, Kim DM, Kim YE, Baek NI (2016) Diels-Alder type adducts from the fruits of Morus alba L. J Appl Biol Chem 59: 91-94 https://doi.org/10.3839/jabc.2016.016
  12. Nguyen TT, To DC, Tran MH, Lee JH, Woo MH, Choi JS, JW Kim, SH Ryu, BS Min (2013) Inhibitory effect on NO production of triterpenes from the fruiting bodies of Ganoderma lucidum. Bioorg Med Chem Lett 23: 1428-1432 https://doi.org/10.1016/j.bmcl.2012.12.066
  13. Rui T, Toshie H, Noriko N, Yoshiyuki A, Mitsuhiro N, Tochiro Y, Naohito O (2007) NMR characterization of the structure of a ${\beta}-(1{\rightarrow}3)$-D-glucan isolate from cultured fruit bodies of Sparassis crispa. Carbohyd Res 342: 2611-2618 https://doi.org/10.1016/j.carres.2007.08.016
  14. Shina K, Kanako H, Mamiko H, Takashi K, Munehiko D, Hirokazu K (2009) New sesquiterpenoid from the mushroom Sparassis crispa. Biosci Biotechnol Biochem 73: 228-229 https://doi.org/10.1271/bbb.80595
  15. Wang SJ, Kim HS, Wi AJ, Yoon BS, Park WS, Park HH, DS Oh (2014) Optimal medium composition of cauliflower mushroom (Sparassis latifolia) cultivation using douglas fir wood chip and comparison of the $\^{a}$-glucan contents of the fruiting body. J Korean Wood Sci Technol 42: 428-438 https://doi.org/10.5658/WOOD.2014.42.4.428
  16. Yoshihisa T, Minoru U, Takashi O, Kimiko N, Koutarou M, Toshiaki T (1991) Glycosides of ergosterol derivatives from Hericum erinacens. Phytochem 30: 4117-4120 https://doi.org/10.1016/0031-9422(91)83478-4
  17. Zhang Y, Pei L, Gao L, Huang Q, Qi J (2011) A neuritogenic compound from Tremella fuciformis. China J Chinese Mater Med 36: 2358-2360

Cited by

  1. Effects of Sparassis crispa in Medical Therapeutics: A Systematic Review and Meta-Analysis of Randomized Controlled Trials vol.19, pp.5, 2018, https://doi.org/10.3390/ijms19051487
  2. Rapid Characterization of Chemical Components in Edible Mushroom Sparassis crispa by UPLC-Orbitrap MS Analysis and Potential Inhibitory Effects on Allergic Rhinitis vol.24, pp.16, 2019, https://doi.org/10.3390/molecules24163014