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Chemical Constituents from the Leaves of Aglaia Odorata

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Chemical Constituents from the Leaves of Aglaia Odorata Chemical Constituents from the Leaves of Aglaia odorata Dong-Xiao Wanga and Shu-Min Yangb,* a Department of Pharmaceutical Care, General Hospital of Chinese PLA, Beijing, 100853, P. R. China b School of Chemical Biology and Pharmaceutical Sciences, Capital Medical University, Beijing, 100069, P. R. China. Fax: +86 01 83911533. E-mail: [email protected] * Author for correspondence and reprint requests Z. Naturforsch. 68 c, 82 − 86 (2013); received March 26/October 19, 2012 A new dammarane triterpene, 3-acetoxy aglinin C (1), and a new aglain, 10-oxo-aglaxif- lorin D (2), along with fi ve known compounds, 3 – 7, were isolated from the leaves of Aglaia odorata using chromatographic methods. The structures of 1 and 2 were determined on the basis of spectroscopic analyses. Bioactivities of 1 – 7 against AGZY 83-a (human lung cancer cell line) and SMMC-7721 (human liver cancer cell line) cells were determined. Key words: Aglaia odorata, 3-Acetoxy Aglinin C, 10-Oxo-aglaxifl orin D Introduction by HR-ESI-MS (m/z 541.3859 [M+Na]+). The 13C NMR (DEPT) spectrum of 1 displayed signals The genus Aglaia (Meliaceae) comprises nearly for 32 carbon atoms, eight tertiary methyl groups 120 species and is distributed mainly in the tropi- (δC 24.9, 24.5, 27.9, 21.4, 16.0, 24.2/24.0, 16.6/16.5, cal forest of Southeast Asia (Pannell, 1992). Previ- 15.5 ppm), ten methylene groups (δC 34.3, 22.9, ous phytochemical investigation has revealed the 18.1, 35.2, 21.4/21.2, 25.9/25.2, 31.6, 27.3/26.9, presence of unique secondary metabolities such 36.8/34.6, 31.5/31.1 ppm), fi ve methane groups (δC as bisamides, lignans, and triterpenes (Fuzzati et 78.4, 50.6, 50.9, 43.3/42.8, 50.6/50.4 ppm), seven al., 1996; Xie et al., 2007; Kim et al., 2006). Some of quaternary carbon atoms (δC 37.2, 40.6, 36.8, 50.1, these compounds exhibited insecticidal, antifun- 88.7/88.0, 108.6, 74.7/74.1 ppm), and an acetyl gal, anti-infl ammatory, and antiproliferative activ- group at δC 170.8 (s, CH3COO) and 21.7 ppm (q, 1 13 ities against cancer cell lines (Bacher et al., 1999; CH3COO). The H and C NMR spectral data Saifah et al., 1999; Puripattanavong et al., 2000; were quite similar to those of aglinin C with the Proksch et al., 2005). We have previously also exception of additional signals for an acetyl group reported on dammaranes and pregnanes from (Mohamad et al., 1999). The downshift (1.23 ppm) the genus Aglaia (Yang et al., 2008a, b). Here we of H-3 in 1 compared to aglinin C and the sig- present a new dammarane triterpene, 3-acetoxy nals of the additional acetyl group at δC 170.8 (s), aglinin C (1), and a new aglain, 10-oxo-aglaxifl or- 21.7 ppm (q) and δH 2.10 ppm (s, 3H) revealed an in D (2), together with fi ve known compounds, acetyl group instead of a hydroxy group attached aglain C (3), aglaxifl orin D (4), 10-O-acetylaglain to C-3. This was proven by the HMBC correla- C (5), rocaglaol (6), and odorinol (7), obtained tions between δH 4.83 ppm (1H, brs, H-3) and δC from the leaves of Aglaia odorata. The bioac- 78.4 (d, C-3), 37.2 ppm (s, C-4) (see Fig. 1). So tivities of 1 − 7 against AGZY 83-a (human lung 1 was named 3-acetoxy aglinin C. The observed cancer cell line) and SMMC-7721 (human liver ‘peak doubling’ in the 13C NMR spectrum sug- cancer cell line) cells were assessed. Among them, gested that 1 was a mixture of C-24 epimers which compound 6 exhibited remarkable cytotoxicity were probably interconvertible just as aglinins A, towards the two cell lines with IC50 values of 0.03 B, and C (Mohamad et al., 1999). Attempts to and 3.62 μM, respectively. separate these isomers were not successful. Compound 2 was obtained as a colourless Results and Discussion gum. The molecular formula was determined as C36H40N2O9 by HR-ESI-MS (m/z 667.2623 Compound 1, a white powder, was found to pos- [M + Na]+). The 1H NMR spectrum disclosed sess a molecular formula of C32H54O5 as evidenced three methoxy groups at δH 3.84 (3H, s, MeO-8), © 2013 Verlag der Zeitschrift für Naturforschung, Tübingen · http://znaturforsch.com D.-X. Wang and S.-M. Yang · Chemical Constituents from Aglaia odorata 83 27 O OH 18 13 26 16 25 OCH3 N OH N 21 6 H 22 5 11 OH 24 OH 4 22 20 5a 21 O O 8 10 O 17 H3CO 11 9a 1'' 19 18 O 1 2 1' 4'' 10 3 30 7 5 AcO 4' 28 29 OCH3 1 2 Fig. 1. Key HMBC correlations of 3-acetoxy aglinin (1) and 10-oxo-aglaxifl orin D (2). 3.79 (3H, s, MeO-6), 3.74 ppm (3H, s, MeO-4’). All above-mentioned observations in the Three aromatic rings related to those observed NMR spectra suggested that compound 2 is a for rocaglaol (6) were deduced to be one mono- cyclopenta[bc]benzopyran derivative (Xu et al., substituted phenyl group: δH 7.04 (2H, dd, J = 7.7, 2000; Inada et al., 2000; Joycharat et al., 2008; 1.8 Hz, H-2’’, 6’’), 7.11 – 7.15 ppm (3H, m, H-3’’, Salim et al., 2007). 4’’, 5’’), one p-substituted phenyl group: δH 6.97 In the HMBC spectrum, the correlations be- (2H, d, J = 8.8 Hz, H-2’, 6’), 6.73 ppm (2H, d, J = tween δH 0.97 ppm (3H, t, J = 7.5 Hz, Me-21) 8.8 Hz, H-3’, 5’), and two m-coupled aromatic with δC 76.3 (s, C-19) and 33.4 ppm (t, C-20), δH protons: δH 6.35 (1H, d, J = 1.5 Hz, H-9), 6.11 ppm 1.58 ppm (3H, s, Me-22) with δC 175.5 (s, C-18) (1H, d, J = 1.5 Hz, H-7). In addition, resonances and 76.3 ppm (s, C-19) indicated the presence of a for a methane pair appeared at δH 4.59 (1H, d, J = 2-hydroxy-2-methylbutyryl group located at C-18. 12.9 Hz, H-4), 4.38 ppm (1H, d, J = 12.9 Hz, H-3), The molecular formula of 2 comprised two hy- and were mutually coupled in the 1H-1H COSY drogen atoms less than that of aglaxifl orin D (4) spectrum. Based on the observed HMQC, these (Xu et al., 2000), and the 1H and 13C NMR spec- two signals were found to correspond to the 13C tral data of 2 were in good agreement with those NMR signals at δC 53.1 (C-3) and 55.5 ppm (C- of 4, except that the methylene carbon atom at δC 4), respectively. Characteristic signals of a pyr- 79.7 ppm (d, C-10) was replaced by a ketonyl car- rolidine-type bisamide unit in 2 were apparent, bon atom at δC 207.5 ppm (C-10). In the HMBC with two carbonyl groups at δC 166.4 (C-11) and spectrum, the correlation of H-4 (δH 4.59 ppm, 175.5 ppm (C-18) (Kim et al., 2005). 1H, d, J = 12.9 Hz) to C-10 (δC 207.5 ppm, s) was The HMBC spectrum showed the following observed (see Fig. 1). So 2 was determined as long-range correlations: δH 3.74 ppm (3H, s, MeO- 10-oxo-aglaxifl orin D. 4’) to δC 158.9 ppm (s, C-4’); δH 3.84 ppm (3H, s, To date, tetracyclic triterpenes of the damma- MeO-8) to δC 164.8 ppm (s, C-8); δH 3.79 ppm (3H, rane, tirucallane, or cycloartane series have been s, MeO-6) to δC 158.6 ppm (s, C-6); δH 4.38 ppm found in all Aglaia species studied. Cyclopentatet- (1H, d, J = 12.9 Hz, H-3) to δC 99.9 (s, C-2), 55.5 rahydrobenzofurans of the rocaglaol type are also (d, C-4), 166.4 (s, C-11), 125.4 (s, C-1’), 135.8 (s, frequently encountered (Mohamad et al., 1999; C-1’’), 128.4 ppm (d, C-2’’, 6’’); δH 4.59 ppm (1H, Wang et al., 2004). Bioactivity investigations re- d, J = 12.9 Hz, H-4) to δC 53.1 (d, C-3), 166.4 (s, vealed that the cyclopentatetrahydrobenzofurans C-11), 135.8 ppm (s, C-1’’). Therefore, it was de- were apparently the active components respon- duced that a p-substituted phenyl group was lo- sible for the cytotoxicity, while they had lower cated at C-2, and a unsubstituted phenyl group cytotoxic activity and even no cytotoxic activity at C-3. at all (Bohnenstengel et al., 1999a, b; Proksch et 84 D.-X. Wang and S.-M. Yang · Chemical Constituents from Aglaia odorata al., 2001). In our study, Compounds 1 – 7 were as- Extraction and isolation sayed for their cytotoxic activity towards AGZY The air-dried leaves of A. odorata (15 kg) were 83-a (human lung cancer cell line) and SMMC- crushed and extracted with 95% EtOH at refl ux 7721 (human liver cancer cell line) cells; the result temperature to yield an EtOH extract. After re- are given in Table I. We found that compound 6, moval of EtOH in vacuo, the remaining viscous rocaglaol, exhibited distinctive antiproliferative concentrate was successively partitioned between activities against the two cell lines with IC val- 50 H O and petroleum ether, CHCl , and n-BuOH, ues of 0.03 μM and 3.62 μM, respectively.
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