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Volumn 79, Issue C, 2009, Pages 583-598

Dioicine: A novel prenylated purine alkaloid from Gymnocladus dioicus

Author keywords

Caffeine; Coffeetree; Guanine; NMR Spectrometry; Xanthine

Indexed keywords


EID: 67749111660     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(D)19     Document Type: Article
Times cited : (4)

References (51)
  • 8
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    • Poisonous Plants of Maryland In Relation to Livestock
    • The University of Maryland Agricultural Experiment Station, College Park, MD
    • Reynard G., and Norton J.B.S. Poisonous Plants of Maryland In Relation to Livestock. Bulletin A 10 (1942), The University of Maryland Agricultural Experiment Station, College Park, MD 266-268
    • (1942) Bulletin A 10 , pp. 266-268
    • Reynard, G.1    Norton, J.B.S.2
  • 9
    • 67749139043 scopus 로고
    • 100 Poisonous Plants of Maryland
    • The University of Maryland Cooperative Extension Service, College Park, MD
    • Hill S.R. 100 Poisonous Plants of Maryland. Bulletin 314 (1985), The University of Maryland Cooperative Extension Service, College Park, MD 20-21
    • (1985) Bulletin 314 , pp. 20-21
    • Hill, S.R.1
  • 13
    • 67749145002 scopus 로고
    • Principal Poisonous Plants of the United States
    • United States Department of Agriculture
    • Chestnut V.K. Principal Poisonous Plants of the United States. Bulletin 20 (1898), United States Department of Agriculture 28
    • (1898) Bulletin 20 , pp. 28
    • Chestnut, V.K.1
  • 14
    • 0003406351 scopus 로고
    • Yorston and Co., Philadelphia, PA plate 53 (3 pp). This work has been reproduded several times, most recently in 1974 by Dover Publications, New York
    • Millspaugh C.F. Medicinal Plants Vol. 1 (1892), Yorston and Co., Philadelphia, PA plate 53 (3 pp). This work has been reproduded several times, most recently in 1974 by Dover Publications, New York
    • (1892) Medicinal Plants , vol.1
    • Millspaugh, C.F.1
  • 15
    • 0011392361 scopus 로고
    • Blanchard and Lea, Philadelphia This is the earliest reference we identified which describes the tree (Gymnocladus canadensis, syn.) as containing cytisine in the leaves, while subsequent references list the seeds, fruit pulp and/or leaves
    • Dunglinson R.D. Medical Lexicon: A Dictionary of Medical Science (1860), Blanchard and Lea, Philadelphia 438 This is the earliest reference we identified which describes the tree (Gymnocladus canadensis, syn.) as containing cytisine in the leaves, while subsequent references list the seeds, fruit pulp and/or leaves
    • (1860) Medical Lexicon: A Dictionary of Medical Science , pp. 438
    • Dunglinson, R.D.1
  • 16
    • 67749098953 scopus 로고
    • A number of other compounds have been described including lipids, amino acids, and carbohydrates. A quite thorough compilation is found. Bisby F.A., Buckingham J., and Harborne J.B. (Eds), Chapman & Hall, London, UK and references cited therein
    • A number of other compounds have been described including lipids, amino acids, and carbohydrates. A quite thorough compilation is found. In: Bisby F.A., Buckingham J., and Harborne J.B. (Eds). Phytochemical Dictionary of the Leguminosae Vol. 1 (1994), Chapman & Hall, London, UK 348 and references cited therein
    • (1994) Phytochemical Dictionary of the Leguminosae , vol.1 , pp. 348
  • 28
    • 67749132965 scopus 로고    scopus 로고
    • note
    • It should be noted that the less than fully substituted xanthines and guanines/isoguanines have very poor solubility in most solvents other than DMSO or water (less at neutral pH). They are especially difficult to analyze by GC and HPLC giving broad GC peaks in many cases and sometimes precipitating on HPLC columns.
  • 31
    • 0033930514 scopus 로고    scopus 로고
    • Seasonal variation in alkaloid content has been observed with other alkaloid bearing plants. For example, see
    • Seasonal variation in alkaloid content has been observed with other alkaloid bearing plants. For example, see. Ralphs M.H., Gardner R., and Pfister A. J. Chem. Ecol 26 (2000) 1595
    • (2000) J. Chem. Ecol , vol.26 , pp. 1595
    • Ralphs, M.H.1    Gardner, R.2    Pfister, A.3
  • 32
    • 0000697557 scopus 로고
    • The pods collected at site 1 in winter 2004 were small and almost exclusively sterile. Legumes and many other plants are known to abort seed production in response to water or nutrient stress as well as genetic factors. See
    • The pods collected at site 1 in winter 2004 were small and almost exclusively sterile. Legumes and many other plants are known to abort seed production in response to water or nutrient stress as well as genetic factors. See. Stephenson A.G. Ann. Rev. Ecol. Syst. 12 (1981) 253
    • (1981) Ann. Rev. Ecol. Syst. , vol.12 , pp. 253
    • Stephenson, A.G.1
  • 33
    • 0022165934 scopus 로고
    • Variation with age and elevation has been observed in other trees. For example, see
    • Variation with age and elevation has been observed in other trees. For example, see. Newbery D.McC., and de Foresta H. Biotropica 17 (1985) 238
    • (1985) Biotropica , vol.17 , pp. 238
    • Newbery, D.McC.1    de Foresta, H.2
  • 34
    • 67749087653 scopus 로고    scopus 로고
    • note
    • While the Z-isomer was not isolated in pure form, it has an identical EI mass spectrum to dioicine. The isolated dioicine is determined to be the E-isomer based on the large (J = 14 Hz) coupling constant between the H1' and H2'.
  • 35
    • 67749098954 scopus 로고    scopus 로고
    • note
    • Unfortunately, this tree was later damaged in a storm and removed from the site. The immature pods collected from this tree were collected several days after the tree was felled, precluding comparison with the leaves, which had already deteriorated. The degradation of the leaves allowed more sun exposure to the pods, which we believe contributed to the unexpectedly high Z/E ratio.
  • 37
    • 67749100728 scopus 로고
    • 7 and as Jefferson's horticultural interest is well-documented, the request for seeds may have had little to do with the beverage.
    • 7 and as Jefferson's horticultural interest is well-documented, the request for seeds may have had little to do with the beverage.
    • (1900) The Jeffersonian Cyclopedia , pp. 45
    • Jefferson, T.1
  • 41
    • 26444527513 scopus 로고
    • 9d describes coffeetree poisoning, yet performed no apparent study on the alkaloids from this tree. However, he does perform analyses of Cassina (Ilex vomicus, Aquafoliaceae), the source of caffeine in a tea-like beverage called the black drink. See
    • 9d describes coffeetree poisoning, yet performed no apparent study on the alkaloids from this tree. However, he does perform analyses of Cassina (Ilex vomicus, Aquafoliaceae), the source of caffeine in a tea-like beverage called the black drink. See. Power F.B., and Chestnut K. J. Am. Chem. Soc. 41 (1919) 1307
    • (1919) J. Am. Chem. Soc. , vol.41 , pp. 1307
    • Power, F.B.1    Chestnut, K.2
  • 42
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    • See also. Hudson C.M. (Ed), University of Georgia Press, Athens, GA
    • See also. In: Hudson C.M. (Ed). Black Drink: A Native American Tea (1979), University of Georgia Press, Athens, GA
    • (1979) Black Drink: A Native American Tea
  • 43
    • 67749145001 scopus 로고    scopus 로고
    • note
    • A number of other as yet incompletely characterized methylpurines are present in the extracts. Further compounds will be described as their structures are determined and a complete profile assembled.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.