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Antiallergic Phorbol Ester from the Seeds of Aquilaria malaccensis

Authors

Keywords:

Aquilaria malaccensis seeds, antiallergic, degranulation, phorbol ester, bioactivity-guided fractionation

Abstract

The Aquilaria malaccensis (Thymelaeaceae) tree is a source of precious fragrant resin, called agarwood, which is widely used in traditional medicines in East Asia against diseases such as asthma. In our continuous search for active natural products, A. malaccensis seeds ethanolic extract demonstrated antiallergic effect with an IC50 value less than 1 µg/mL. Therefore, the present research aimed to purify and identify the antiallergic principle of A. malaccensis through a bioactivity-guided fractionation approach. We found that phorbol ester-rich fraction was responsible for the antiallergic activity of A. malaccensis seeds. One new active phorbol ester, 12-O-(2Z,4E,6E)-tetradeca-2,4,6-trienoylphorbol-13-acetate, aquimavitalin (1) was isolated. The structure of 1 was assigned by means of 1D and 2D NMR data and high-resolution mass spectrometry (HR-MS). Aquimavitalin (1) showed strong inhibitory activity in A23187- and antigen-induced degranulation assay with IC50 values of 1.7 and 11 nM, respectively, with a therapeutic index up to 71,000. The antiallergic activities of A. malaccensis seeds and aquimavitalin (1) have never been revealed before. The results indicated that A. malaccensis seeds and the pure compound have the potential for use in the treatment of allergy. Keywords: Aquilaria malaccensis seeds, antiallergic, degranulation, phorbol ester, bioactivity-guided fractionation

Author Biographies

Michal Korinek, Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; [email protected] (M.K.); [email protected] (V.D.W.); [email protected] (I.-W.L.); [email protected] (Y.-M.H.); [email protected] (Y.-C.W.); [email protected] (Y.-B.C.)

Department of Biotechnology, College of Life Science, Kaohsiung Medical University, Kaohsiung 807, Taiwan

Bing-Hung Chen, Department of Biotechnology, College of Life Science, Kaohsiung Medical University, Kaohsiung 807, Taiwan

The Institute of Biomedical Sciences, National Sun Yat-Sen University, Kaohsiung 804, Taiwan

Yuan-Bin Cheng, Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; [email protected] (M.K.); [email protected] (V.D.W.); [email protected] (I.-W.L.); [email protected] (Y.-M.H.); [email protected] (Y.-C.W.); [email protected] (Y.-B.C.)

Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung 807, Taiwan

Yang-Chang Wu, Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; [email protected] (M.K.); [email protected] (V.D.W.); [email protected] (I.-W.L.); [email protected] (Y.-M.H.); [email protected] (Y.-C.W.); [email protected] (Y.-B.C.)

Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan

Tsong-Long Hwang, Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan; [email protected]

Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan

Fang-Rong Chang, Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; [email protected] (M.K.); [email protected] (V.D.W.); [email protected] (I.-W.L.); [email protected] (Y.-M.H.); [email protected] (Y.-C.W.); [email protected] (Y.-B.C.)

Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan

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