Flavonol glycosides and triterpenes from the leaves of Uncaria ...

Flavonol glycosides and triterpenes from the leaves of Uncaria rhynchophylla (Miq.) Jacks. / Asian Journal of TraditionalMedicines, 2009, 4 (3)Amorphous colorless powder. Liebermann-Burchard reaction: positive. ESI-MS (m/z): 495[M+Na] + , 471 [M-H] - . Molecular formula: C 30H 48O 4.1H NMR (300 MHz, C 5D 5N): δ H0.95 (3H, d, J = 6.3Hz, H-29), 1.00 (3H, d, J = 6.0 Hz, H-30), 1.25 (3H,s, H-23), 1.43 (3H, s, H-26), 1.61 (3H, s, H-24), 1.62(3H, s, H-25), 1.72 (3H, s, H-27), 3.11 (1H, m, 4.2 Hz,H-3), 4.86 (1H, brs, H-6), 5.44 (1H, brs, H-12). 13 CNMR (75 MHz, C 5D 5N) see Table 2. All data wereidentical to those of 6β-hydroxyursolic acid [9] .Compound 7Amorphous colorless powder. Liebermann-Burchard reaction: positive. ESI-MS (m/z): 511[M+Na] + , 487 [M-H] - . Molecular formula: C 30H 48O 5.1H NMR (300 MHz, C 5D 5N): δ H1.12 (3H, d, J = 6.3Hz, H-30), 1.42 (3H, s, H-23), 1.48 (3H, s, H-26), 1.63(3H, s, H-29), 1.69 (3H, s, H-24), 1.73 (3H, s, H-25),1.77 (3H, s, H-27), 2.51 (1H, m, H-16α), 3.46 (1H, dd,J = 11.4, 4.1 Hz, H-3), 5.44 (1H, brs, H-12). 13 C NMR(75 MHz, C 5D 5N) see Table 2. All data were identicalto those of 3β, 6β, 19α-trihydroxyurs-12-en-28-oicacid [10] .Compound 8Amorphous colorless powder. Liebermann-Burchard reaction: positive. ESI-MS (m/z): 511[M+Na] + , 487 [M-H] - . Molecular formula: C 30H 48O 5.1H NMR (300 MHz, C 5D 5N): δ H0.92 (3H, d, J = 4.2Hz, H-30), 1.01 (3H, d, J = 7.5 Hz, H-29), 1.20 (3H,s, H-26), 1.64 (3H, s, H-24), 1.67 (3H, s, H-27), 1.72(3H, s, H-25), 4.27 (1H, dd, J = 11.4, 4.1 Hz, H-3),4.42, 4.00 (2H, each 1H, d, J = 10.3 Hz, H-23), 5.45(1H, brs, H-12). 13 C NMR (75 MHz, C 5D 5N) seeTable 2. All data were identical to those of 3β, 6β,23-trihydroxyurs-12-en-28-oic acid [10, 11] .Compound 9Amorphous colorless powder. Liebermann-Burchard reaction: positive. Molecular formula:C 29H 50O. 1 H NMR (300 MHz, CDCl 3): δ H0.68 (3H,s, H-18), 0.80-0.93 (15H, each 3H, m), 3.53 (1H, m,H-3), 5.35 (1H, m, H-6). 13 C NMR (75 MHz, CDCl 3)see Table 2. All data were identical to those ofβ-sitosterol [12] .Compound 10Amorphous colorless powder. Liebermann-Burchard reaction and Molish reaction: positive.Molecular formula: C 35H 60O 6. 1 H NMR (300 MHz,C 5D 5N): δ H0.65 (3H, s, H-18), 0.84-1.01 (15H, each3H, m), 5.06 (1H, d, J = 7.8 Hz, glc-1′), 5.35 (1H, brs,H-6). 13 C NMR (75 MHz, C 5D 5N) see Table 2. Alldata were identical to those of daucosterol [9] .AcknowledgementThis study was supported by research fundsfrom the 2005 Scientific Technology Plan Project ofLiaoning Province Government, China.References[1] The State Pharmacopoeia Committee of China.Pharmacopoeia of the People’s Republic of China, 2005Edition, Vol. 1. Beijing: Chemical Industry Press, 2005,180.[2] Japanese Pharmacopoeia Editorial Committee. TheJapanese Pharmacopoeia, 15th Ed. Tokyo: HirohawaPress, 2006, 462-5.[3] Zhao Q, Watanabe Y, Sakakibara I, Zhang SH, MurakamiT, Higashida M, Matsumoto S. Antihypertensive activityand protection against cerebral ischemia of phenolcontainingfraction of Uncaria hooks and its components.Medical and Pharmaceutical Society for WAKAN-YAKU,2002, 8, Suppl 152.[4] Liang QL, Ding LS. Chemical study on the Leaves ofRaisin Tree (Hovenia acerba) (I). Zhongcaoyao, 1996,27(10): 581-3.[5] Jiang SJ, Zhu B, Zhang NP, Lin RC. Chemical study on theGaleobdolon chinense. Journal of China PharmaceuticalUniversity, 2002, 33(9): 487-8.[6] Zhang W, Zhao DB, Li MJ, Liu XH, Wang HQ. Studies onflavonoid constituents from herbs of Artemisia ordosicaII. China Journal of Chinese Materia Medica, 2006,31(23): 1959-61.[7] Brasseur T, Angenot L. Flavonol glycosides from leaves ofStrychnos variabilis. Phytochemistry, 1986, 25(2): 563-4.[8] Huang KY, Zhang DS, Gao HY, Wu LJ. Chemicalconstituents of Dioscorea bulbifera L. Journal of90