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Anti-allergic triterpenes isolated from olive milled waste

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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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Authors and Affiliations

  1. Division of Systematic Forest and Forest Products Sciences, Department of Agro-Environmental Sciences, Graduate School of Bioresource and Bioenvironmental Science, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka, 812-8581, Japan

    Asuka Kishikawa, Yhiya Amen & Kuniyoshi Shimizu

  2. Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt

    Yhiya Amen

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  1. Asuka Kishikawa
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  2. Yhiya Amen
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  3. Kuniyoshi Shimizu
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Correspondence to Kuniyoshi Shimizu.

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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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