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Chemical Constituents of Polygonaceous Plants. I: Studies on the Components of Ko-jô-kon. (Polygonum cuspidatum SIEB. et ZUCC.)
Open accessAbstract
A glycoside, isolated from the fresh root of Polygonum cuspidatum SIEB. et ZUCC. and named polydatin, was newly examined. Its molecular formula corresponded to C20H22O8⋅3H2O and its constants were m. p. 225-226°, [α]D27 -74.9° (c=1.709, EtOH). Its hydrolysis afforded a phenol, C14H12O3, and glucose. The aglycone formed an acetate (C20H18O6), methylate (methoxide) (C17H18O3), benzoate (C35H24O6), and a dihydro derivative (C14H14O3). The ultraviolet spectra of these derivatives resembled those of stilbene derivatives. Oxidative decomposition of the methylated glycoside afforded anisic acid and the same treatment of the methylated aglycone gave anisic acid and 3, 5-dimethoxybenzoic acid. These experimental evidences indicate that the aglycone is resveratrol and the glycoside was identified as 3, 4′, 5-trihydroxystilbene-3-β-mono-D-glucoside (piceid). An anthraquinone and resveratrol were isolated from the ether-soluble portion and the latter was identified through paper partition chromatography and mixed melting point determination.
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Citations
Cited by
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Resveratrol: A molecule whose time has come? And gone?
Soleas, G. J., Diamandis, E. P., & Goldberg, D. M. (1997) · Clinical Biochemistry · doi:10.1016/s0009-9120(96)00155-5 · Cited by 849
Resveratrol as an anticancer nutrient: molecular basis, open questions and promises
Signorelli, P., & Ghidoni, R. (2005) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2005.01.017 · Cited by 489
Resveratrol: Isomeric Molar Absorptivities and Stability
Trela, B. C., & Waterhouse, A. L. (1996) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf9504576 · Cited by 440
Chemistry and Biology of Resveratrol-Derived Natural Products
Keylor, M. H., Matsuura, B. S., & Stephenson, C. R. J. (2015) · Chemical Reviews · doi:10.1021/cr500689b · Cited by 366
Metadata
- Authors
- Nonomura, S., Kanagawa, H., & Makimoto, A.
- Venue
- YAKUGAKU ZASSHI
- Publisher
- Pharmaceutical Society of Japan
- Published
- 1963
- Volume
- 83
- Issue
- 10
- Pages
- 988-990
- ISSN
- 0031-6903 (ISSN-L)
- 1347-5231
- OpenAlex
- W2223295563
- Cited by
- 230
- References
- 0
- FWCI
- 0.00
- Type
- journal article
- Language
- en
- Open access
- bronze
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- Nonomura, S., Kanagawa, H., & Makimoto, A. (1963). Chemical Constituents of Polygonaceous Plants. I: Studies on the Components of Ko-jô-kon. (Polygonum cuspidatum SIEB. et ZUCC.). YAKUGAKU ZASSHI. https://doi.org/10.1248/yakushi1947.83.10_988
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