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Chemical Constituents from the Roots of Hydrangea chinensis Yue-Han Lee 1 ( 李岳翰 ), Fang-Rong Chang 1 ( 張芳榮 ), Ramesh Patnam 1, Yuh-Chwen Chang 1,2 ( 張裕純.

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Presentation on theme: "Chemical Constituents from the Roots of Hydrangea chinensis Yue-Han Lee 1 ( 李岳翰 ), Fang-Rong Chang 1 ( 張芳榮 ), Ramesh Patnam 1, Yuh-Chwen Chang 1,2 ( 張裕純."— Presentation transcript:

1 Chemical Constituents from the Roots of Hydrangea chinensis Yue-Han Lee 1 ( 李岳翰 ), Fang-Rong Chang 1 ( 張芳榮 ), Ramesh Patnam 1, Yuh-Chwen Chang 1,2 ( 張裕純 ), Yang- Chang Wu 1,* ( 吳永昌 ) 1 Graduate Institute of Natural Products, Kaohsiung Medical University 2 Department of Chemical Engineering, Kao Yuan Institute of Technology

2 Abstract Hydrangea chinensis (Saxifragaceae) is distributed in southern China, Ryukyu and Taiwan at low altitude islandwide. Its roots were used as a traditional chinese medicine for diuretic, anti-malaria and anti-headache agents. In previous study, bergenin 、 phyllodulcin 、 hydrangenol and febrifugine were isolated from the roots of Hydrangea genus. As our investigation of the phytochemical and bioactive components from the roots of Hydrangea chinensis, the roots of this species were extracted with MeOH at room temperature. The crude MeOH extract was subsequently partitioned by n-Hexane/H 2 O, EtOAc/H 2 O, and n-BuOH/H 2 O, respectively. One novel alkaloid, hydrachine A (1), along with five known compounds, 3H-quinazolin- 4-one (2), triacetyl glyceride (3), β-sitosterol-D-glucoside ester (4), β-sitosterol-D- glucoside (5), and glucose (6) were isolated from the n-BuOH layer. Fourteen known compoumds, boarborinal (7), rubiarbonol B (8), β-sitosterol (9), 6-hydroxy-coumarin (10), 7-hydroxy-coumarin (11), 7-methoxy-coumarin (12), 7-hydroxy-8-methoxy-coumarin (13), syringaldehyde (14), hydrangenol (15), hydrangenoside A (16), 4-hydroxy-trans- cinnamic acid methyl ester (17), p-coumarsaeuremethylester (18), triester glyceride (19), and p-anisaldehyde (20) were isolated from the EtOAc layer, The structural elucidation of these compounds was determined by spectroscopic analyses and their cytotoxicity are under investigation.

3 Hydrachine A (1) 3H-Quinazolin-4-one (2)Triacetyl glyceride (3)  -Sitosterol-D-glucoside ester (4)  -Sitosterol-D-glucoside (5) Glucose (6) Boarborinal (7) Rubiarbonol B (8) n=16

4  - sitosterol (9) 6-Hydroxy-coumarin (10)7-Hydroxy-coumarin (11) 7-Methoxy-coumarin (12)7-Hydroxy-8-methoxy-coumarin (13) Syringaldehyde (14) Hydrangenol (15)Hydrangenoside A (16)

5 4-Hydroxy-trans-cinnamic acid methyl ester (17) p-Coumarsaeuremethylester (18) Triester glyceride (19) p-Anisaldehyde (20)

6 Roots of Hydrangea chinensis (2 kg) Extracted with Methanol Crude Methanol Extracts (150 g) Partition Procedure Ethyl acetate n-Hexane n-Butanol 19.5 g20.0 g 70.5 g (83 % inhibition at the concentration of 50µg/ml) Hydrachine A (1) 3H-Quinazolin-4-one (2) Triacetyl glyceride (3)  -Sitosterol-D-glucoside ester (4)  -Sitosterol-D-glucoside (5) Glucose (6) Boarborinal (7) Rubiarbonol B (8)  - sitosterol (9) 6-Hydroxy-coumarin (10) 7-Hydroxy-coumarin (11) 7-Methoxy-coumarin (12) 7-Hydroxy-8-methoxy-coumarin (13) Syringaldehyde (14) Hydrangenol (15) Hydrangenoside A (16) 4-Hydroxy-trans-cinnamic acid methyl ester (17) p-Coumarsaeuremethylester (18) Triester glyceride (19) p-Anisaldehyde (20)

7 Hydrachine A (1) (3-[9  -hydroxy-2-oxo-4  -quinolizidyl]-4-quinazolinone) Semi solid [  ] 25 D  (c 0.2, CHCl 3 ) UV (MeOH) max (log  ) 224 (1.47), 230 (1.35), 233 (1.30), 265 (0.59), and 302 (0.28) nm IR (KBr) max 3600, , 1730, and 1670 cm -1 EIMS m/z 314 [M+1] + (7), 199 (3), 171 (31), 168 (31), 167 (96), 166 (84), 149 (42), 139 (25), 122 (25), 111 (24), 110 (100), and 103 (26) FABMS m/z 314 [M+1] + (39), 312 (17), 304 (27), 284 (35), 282 (58), 256 (13), 168 (47), 167 (28), 147 (28), and 133 (49) HREIMS m/z (calcd for C 17 H 19 N 3 O 3, ). 1

8 NO.δH a) (J Hz)δC b) (1H, s) a (1H, dd, J = 8.0, 1.6 Hz) (1H, ddd, J = 8.0, 7.2, 1.6 Hz) (1H, ddd, J = 8.4, 7.2, 1.6 Hz) (1H, dd, J = 8.4, 1.6 Hz) a ' pseudoeq 3.18 (1H, dd, J = 15.2, 3.2 Hz)43.8 1' pseudoaxi 2.50 (1H, dd, J = 15.2, 11.2 Hz)43.8 2' ' pseudoeq 3.34 (1H, dd, J = 10.4, 6.4 Hz)59.0 3' pseudoaxi 2.84 (1H, dd, J = 11.2, 10.4 Hz)59.0 4'5.70 (1H, dd, J = 11.2, 6.40 Hz)59.4 6' eq 2.18 (1H, br. dt, J = 13.0, 4.0 Hz)54.1 6' axi 2.93 (1H, br. dd, J = 13.0, 4.0 Hz)54.1 7' eq 1.74 (1H, m)23.0 7' axi 1.80 (1H, m)23.0 8' eq 2.07 (1H, m)32.8 8' axi 1.29 (1H, m)32.8 9'3.46 (1H, ddd, J = 11.0, 9.0, 5.0 Hz) '2.28 (1H, ddd, J = 11.2, 9.0, 3.2 Hz)67.1 OH1.93 (1H, brs) a) 1 H-NMR (400 MHz, CDCl 3 ) b) 13 C-NMR (100 MHz, CDCl 3 ) Table 1. 1 H-NMR and 13 C-NMR data of Hydrachine A

9 HONE-1 † NUGC ‡ 0% 8%1% 12%0% 21% compounds cell lines Hydrachine A (1) * 3H-Quinazolin-4-one (2) Triacetyl glyceride (3)  -Sitosterol-D-glucoside ester (4) n=16 * New compound † HONE-1:human nasopharyngeal carcinoma ‡ NUGC: human gastric cancer Positive compounds: % of control >50% Table 2. Structures and bioassay data of compounds (Inhibition percentage at the concentration, 50µg/ml)

10 HONE-1 † NUGC ‡ 16%0% 11%7% 13%4% 0%2% compounds cell lines Boarborinal (7) Rubiarbonol B (8)  - Sitosterol (9) 6-Hydroxy-coumarin (10)

11 HONE-1 † NUGC ‡ 10%29% 18%19% 4%3% 7%6% compounds cell lines 7-Hydroxy-coumarin (11) 7-Methoxy-coumarin (12) 7-Hydroxy-8-methoxy-coumarin (13) Syringaldehyde (14)

12 References and Notes 1.Chiang-Su New Medical College. The Dictionary of Chinese Medicine (I); Shun-Hai Scientific Technology: 1978; p Ablondi, F.; Gordon, S.; Morton II, J.; Williams, J. H. J. Org. Chem. 1952, 17, Takaya, Y.; Tasaka, H.; Chiba, T.; Uwai, K.; Tanitsu, M. A.; Kim, H. S.; Wataya, Y.; Miura, M.; Takeshita, M.; Oshima, Y. J. Med. Chem. 1999, 42, Bani, T.; Debabrata, C.; Swapna, D.; Subhas, M. J. Indian Chem. Soc. 1975, 52, Yoshikawa, M.; Harada, E.; Naitoh, Y.; Inoue, K.; Matsuda, H.; Shimoda, H.; Yamahara, J.; Murakami, N. Chem. Pharm. Bull. 1994, 42, Inouye, H.; Takeda, Y.; Uesato, S.; Uobe, K.; Hashimoto, T.; Shingu, T. Tetrahedron Lett. 1980, 21, Yoshikawa, M.; Murakami, T.; Ueda, T.; Shimoda, H.; Yamahara, Y.; Matsuda, H. Heterocycles 1999, 50, Pan, W. B.; Chang, F. R.; Wu, Y. C. Chem. Pharm. Bull. 2000, 48, Battacharyya, J.; Pakrashi, S. C. Heterocycles 1979, 12, Asres, K.; Gibbons, W. A.; Phillipson, J. D.; Mascagni, P. J. Nat. Prod. 1986, 49, Maximo, P.; Lourenco, A. J. Nat. Prod. 2000, 63, Banthorpe, D. V.; Bilyard, H. J.; Watson, D. G. Phytochemistry 1985, 24, Guidugli, F. H.; Pestchanker, M. J.; De Salmeron, M. S. A.; Giordano, O. S. Phytochemistry 1986, 25, Campbell, W. E.; Provan, G. J.; Waterman, P. G. Phytochemistry 1982, 21, Anjaneyulu, A. S. R.; Rao, D. S. Indian J. Chem. 1997, 36, Wu, Y. C.; Chang, G. Y.; Ko, F. N.; Teng, C. M. Planta Med. 1995, 61, Chen, C. Y.; Chang, F. R.; Teng, C. M.; Wu, Y. C. J. Chin. Chem. Soc. 1999, 46, Sanz, J. F.; Rustaiyan, A.; Marco, J. A. Phytochemistry 1990, 29, Murata, K.; Takano, F.; Fushiya, S.; Oshima, Y. J. Nat. Prod. 1998, 61,


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