Abstract
Two quinazolone alkaloids, (+)-febrifugine (1) and isofebrifugine (2), along with three coumarin derivatives, 6-hydroxy coumarin (3), skimmin (5), and umbelliferone-7-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranoside (6), were isolated from the roots ofHydrangea chinensis. Compound6 is a new compound. In addition, umbelliferone (4), linoleic acid (7), two steroidal glycosides (8, 9), three furfural derivatives (10–12), and butyl-β-D-fructofuranoside (13) were isolated from the leaves of the same plant. The structures of all isolates were elucidated by spectral methods.
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References
Ablondi, F., Gordon, S., Morton, J. II, and Williams, J. H., An antimalarial alkaloid fromHydrangea.J. Org. Chem., 17, 14–18 (1952).
Chiang-Su New Medical College,The Dictionary of Chinese Medicine (I). Shanghai Scientific Technology, Shanghai, p.45, (1978).
Claudia, C., Mincione, E., Saladino, R. and Nicoletti, R., Oxidation of substituted 2-thiouracils and pyrimidine-2-thione with ozone and 3,3-dimethyl-1,2-dioxirane.Tetrahedron, 50, 3259–3272 (1994).
Fauhl, C., Reniero, F., and Guillou, C.,1H NMR as a tool for the analysis of mixtures of virgin olive oil with oils of different botanical origin.Magn. Reson. Chem., 38, 436–443 (2000).
Guidugli, F. H., Pestchanker, M. J., De Salmeron, M. S. A. and Giordano, O. S., 1-Hydroxyplatyphyllide, a norsesquiterpene lactone fromSenecio gilliesiano.Phytochemistry, 25, 1923–1926 (1986).
Hearn, T.W., Carbon-13 chemical shifts in some substituted furans and thiophenes.Aust. J. Chem., 29, 107–113 (1996).
Ichikawa, K.; Kinoshita, T. and Sankawa, U., The screening of Chinese crude drugs for Ca+2 antagonist activity: identification of active principles from the aerial part ofPogostemon cablin and the fruits ofPrunus mume.Chem. Pharm. Bull., 37, 345–348 (1989).
Jang, C. S., Fu, F. Y., Wang, C. Y., Huang, K. C., Lu, G., and Chou, T. C., Chang Shan, a Chinese antimalarial herb.Science, 103, 59 (1946).
Kobayashi, S., Ueno, M., Suzuki, R., Ishitani, H., Kim, H. S., and Wataya, Y., Catalytic asymmetric synthesis of antimalarial alkaloids febrifugine and isofebrifugine and their biological activity.J. Org. Chem., 64, 6833–6841 (1999).
Koepfli, J. B., Mead, J. F. and Brockman, J. A. Jr., An alkaloid with high anti-malarial activity fromDichroa febrifuga.J. Am. Chem. Soc., 69, 1837–38 (1947).
Kojima, H., Sato, N., Hatano, A., and Ogura, H., Sterol glucosides fromPrunella vulgaris.Phytochemistry, 29, 2351–2355 (1990).
Murata, K., Takano, E., Fushiya, S., and Oshima, Y., Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug,Dichroa febrifuga.J. Nat. Prod., 61, 729–733 (1998).
Nishibe, S., Hisada, S. and Inagaki, I., Isolation of 5-hydroxymethylfurfural fromTrachelospermum asciaticum var. intermedium.Chem. Pharm. Bull., 21, 1155–1157 (1973).
Numata, A., Takahashi, C., Fujiki, R., Kitano, E., Kitajima, A., and Takemura, T., Plant constituents biologically active to insects. VI. Antifeedants for larvae of the yellow butterflyEurema hecabe mandarina, inOsmunda japonica.Chem. Pharm. Bull., 38, 2862–2865 (1990).
Patnam, R., Chang, F.R., Chen, C.Y., Kuo, R.Y., Lee, Y.H., and Wu, Y.C., Hydrachine A., a novel alkaloid from the roots ofHydrangea chinensis.J. Nat. Prod., 64, 948–949 (2001).
Reisch, J. and Achenbach, S.H., Furanocoumarin glucoside from stembark ofSkimmia japonica.Phytochemistry, 31, 4376–4377 (1992).
Shimizu, M., Zenko, Y., Tanaka, R., Matsuzawa, T., and Morita, N., Studies on aldose reductase inhibitors from natural products. V. Active components of Hachimi-jio-gan (Kampo Medicine).Chem. Pharm. Bull., 41, 1469–1471 (1993).
Spasov, S. L., Atanasova, I. and Haimova, M., Carbon-13 and proton NMR spectra of 1(2H)-phthalazinone, 4(3H)- quinazolinone, and their substituted derivatives.Magn. Reson. Chem., 23, 795–799 (1985).
Strack, D., Heilemann, J., Wray, V., and Dirks, H., Structures and accumulation patterns of soluble and insoluble phenolics from Norway spruce needles.Phytochemistry, 28, 2071–2078 (1989).
Ulubelen, A., Oksuz, S. and Mericli, A.H., Palmitic acid ester of sitosteryl-3β-glucoside fromCentaurea regia.Phytochemistry, 27, 3964–3965 (1988).
Zhang, C. Z., Xu, X. Z. and Li, C., Fructosides fromCynomorium songaricum.Phytochemistry, 41, 975–976 (1996).
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Khalil, A.T., Chang, FR., Lee, YH. et al. Chemical constituents from theHydrangea chinensis . Arch Pharm Res 26, 15–20 (2003). https://doi.org/10.1007/BF03179924
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DOI: https://doi.org/10.1007/BF03179924