Abstract
The degranulation of basophils stimulated by antigen is one of the allergic mechanisms of immediate hypersensitivity reactions. In a previous study, the β-hexosaminidase release of rat basophilic leukemia (RBL-2H3) cells stimulated by IgE cross-linking was specifically inhibited by ethanol extract of olive milled waste (OMW). OMW is a potential source of triterpenes, which show several biological activities. However, little is known about the effect of triterpenes in OMW on β-hexosaminidase release. Here we investigated anti-allergic triterpenes from the ethanol extract of OMW, and we discuss the structure–activity relationship. We subjected ethanol extract of OMW to activity-guided fractionation; this led to the isolation of five known triterpenes, i.e., maslinic acid (1), oleanolic acid (2), punicanolic acid (3), 2-O-acetylmaslinic acid (4), and epimaslinic acid (5) as well as one new triterpene, 11-oxo-maslinic acid (6). An anti-allergic assay revealed that 2-O-acetylmaslinic acid (4) and 11-oxo-maslinic acid (6) showed anti-allergic activity. Considering the structure–activity relationship of these triterpenes, it appears that the existence of a ketone group at C-11 or an acetyl group at C-2 would influence the anti-allergic activity.
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Abbreviations
- RBL-2H3:
-
Rat basophilic leukemia cell line
- OMW:
-
Olive milled waste
- MPLC:
-
Medium pressure liquid chromatography
- HPLC:
-
High-performance liquid chromatography
- MTT:
-
3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide
- DNP-BSA:
-
Albumin from bovine serum, 2,4-Dinitrophenylated
- DMSO:
-
Dimethyl sulfoxide
- Hex:
-
n-Hexane
- EtOAc:
-
Ethyl acetate
- MeOH:
-
Methanol
- CD3OD:
-
Deuterated methanol
- DMSO-d 6 :
-
Deuterated dimethyl sulfoxide
- HR-ESI–MS:
-
High-resolution electrospray ionization mass spectrometry
- NMR:
-
Nuclear magnetic resonance
- HSQC:
-
Heteronuclear single quantum coherence
- HMBC:
-
Heteronuclear multiple bond correlation
- NOESY:
-
Nuclear Overhauser effect spectroscopy
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Acknowledgements
This work was greatly supported by JSPS KAKENHI Grant Number JP16J09727. Also, we are grateful for the support by the JICA-JST Science and Technology Research Partnership for Sustainable Development (SATREPS 2) Project: “Valorization of Bioresources in Semi-Arid and Arid Land for Regional Development for New Industry”. We would like to express our deep gratitude to Dr. Tomofumi Miyamoto in Team Natural Products Chemistry, Graduate School of Pharmaceutical Sciences, Kyushu University for his help with polarimeter. The author is much obliged to Ms. Noriko Yazawa for measurement of Bruker AVANCE III 600 MHz CryoProbes spectra. We would like to thank Research and Education Support Center of the faculty of Agriculture, Kyushu University for supporting facilitates for LC-IT-TOF–MS analysis. The NMR analyses were performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices”.
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Kishikawa, A., Amen, Y. & Shimizu, K. Anti-allergic triterpenes isolated from olive milled waste. Cytotechnology 69, 307–315 (2017). https://doi.org/10.1007/s10616-016-0058-z
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DOI: https://doi.org/10.1007/s10616-016-0058-z