Two new tirucallane triterpenoids from the leaves of Aquilaria sinensis

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RESEARCH ARTICLE

Two new tirucallane triterpenoids from the leaves of Aquilaria sinensis Jin Tang Cheng • Ya Qiong Han • Juan He • Xing De Wu • Liao Bin Dong • Li Yan Peng • Yan Li • Qin Shi Zhao

Received: 30 November 2012 / Accepted: 11 March 2013 Ó The Pharmaceutical Society of Korea 2013

Abstract Two new tirucallane triterpenoids, aquilacallanes A–B (1–2), together with 15 known compounds (3–17) were isolated from the leaves of Aquilaria sinensis. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses. All compounds were evaluated for their cytotoxic activity against five human cancer cell lines. The known compounds, ursolic acid (7) and 5,7,40 -trimethoxyflavone (14), exhibited weak cytotoxic activity against some cells. Keywords Aquilaria sinensis  Tirucallane triterpenoids  Aquilacallanes A–B  Cytotoxic activity

Introduction Aquilaria sinensis (Lour) Gilg (Thymelaeaceae), a principal source of the expensive eaglewood, is distributed in the south China such as Hainan, Guangxi, Guangdong, Fujian, and Taiwan provinces. The resin of A. sinensis have been used as a traditional sedative, analgesic, and digestive medicine in East Asia (Feng et al. 2011), while the leaves of it is used in China for treatments of inflammation and anaphylaxis (Qi et al. 2009). Unlike the sesquiterpenes and 2-(2-phenylethyl) chromone derivatives isolated from

J. T. Cheng  J. He  X. De Wu  L. B. Dong  L. Y. Peng  Y. Li  Q. S. Zhao (&) State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People’s Republic of China e-mail: [email protected] Y. Q. Han College of Pharmacology, Kunming Medical University, Kunming 650031, People’s Republic of China

eaglewood of A. sinensis (Dai et al. 2010; Gao et al. 2012; Hashimoto et al. 1985; Jain and Bhattacharyya 1959; Maheshwari et al. 1963a, b; Nakanishi et al. 1981, 1984; Shimada et al. 1982; Varma et al. 1965; Yagura et al. 2005; Yang et al. 2012), flavonoid, benzophenone glycoside, and triterpenoids were the main compounds from leaves of A. sinensis (Feng et al. 2011; Nie et al. 2009; Qi et al. 2009; Wang et al. 2008). In order to find structurally unique and bioactive natural products, an investigation of the ethanol extract of the leaves of A. sinensis was carried out, which led to the isolation of two new tirucallane triterpenoids, aquilacallanes A–B (1–2), together with 15 known compounds (3–17). In the present study, we describe the isolation, structural elucidation, and cytotoxicity of these compounds.

Materials and methods General Optical rotations were measured with a JASCO P-1020 polarimeter. UV spectra were recorded with a Shimadzu UV-2401A spectrophotometer. IR spectra were recorded on Tensor 27 spectrometer with a KBr disk. 1H and 13C NMR spectra were recorded on a Bruker AM-400 spectrometer and 2D NMR spectra were recorded on a Bruker Advance III 600 spectrometer. Chemical shifts were reported using TMS as the internal sta