The flavonoids and phenolic acids of the genus Silphium and their chemosystematic value

Natural Product Communications

Volumn 4, Issue 3, 2009, Pages 435-446

  Williams, Jeffrey D ^a   Wojcińska, Małgorzata ^b   Calabria, Lalita M ^a   Linse, Klaus ^a   Clevinger, Jennifer A ^c   Mabry, Tom J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

^c WALSH UNIVERSITY   (United States)

Author keywords

Asteraceae; Chemosystematics; Flavonol O glycosides; Isorhamnetin and kaempferol; Phenolic acids; Quercetin; Silphium species

Indexed keywords

FLAVANOID; FLAVONOID GLYCOSIDE; ISORHAMNETIN 3O ALPHA LEVO RHAMNOSYL (1'''- 6'') O BETA DEXTRO GALACTOPYRANOSIDE 7 O BETA LEVO APIOFURANOSIDE; KAEMPFEROL 3 O BETA DEXTRO APIOFURANOSIDE 7 O ALPHA LEVO RHAMNOSYL (1''''- 6''') O BETA DEXTRO (2''' O CAFFEOYLGALACTOPYRANOSIDE); KAEMPFEROL 3 O BETA DEXTRO APIOFURANOSIDE 7 O ALPHA LEVO RHAMNOSYL (1''''-6''') O BETA DEXTRO GALACTOPYRANOSIDE; MYCOPHENOLIC ACID; QUERCETIN 3 O ALPHA LEVO RHAMNOSYL (1'''-6'') O BETA DEXTRO GALACTOPYRANOSIDE 7 O BETA LEVO APIOFURANOSIDE; QUERCETIN 3 O BETA LEVO GALACTOSYL (1'''-6'') O BETA DEXTRO RHAMNOPYRANOSIDE 7 O ALPHA LEVO APIOFURANOSIDE; UNCLASSIFIED DRUG; FLAVONOID; HYDROXYBENZOIC ACID DERIVATIVE; PHENOLIC ACID;

ASTERACEAE; CHEMOTAXONOMY; DNA BASE COMPOSITION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT MORPHOLOGY; REVIEW; SILPHIUM; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; PHYLOGENY; SPECIES DIFFERENCE;

ASTERACEAE; SILPHIUM;

ASTERACEAE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVONOIDS; HYDROXYBENZOIC ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PHYLOGENY; SPECIES SPECIFICITY;

EID: 66149120186     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0900400325     Document Type: Review

References (35)

1. Wink M. (2003) Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry, 64, 3-19. (Pubitemid 37101790)
2. Clevinger JA. (2006) Silphium. In Flora of North America, North of Mexico. Vol. 21 Asteraceae. Flora of North America Editorial Committee, Oxford University Press, New York and Oxford. pp 77-82.
3. Linnaeus C. (1826) Systema Vegetabilium. Vol. 3, Sumtibus Librariae Dieterichianae, Gottingae, 16-23.
4. Small JK. (1933) Silphium. In Manual of the Southeastern Flora. University of North Carolina Press, NC, 1408-1415.
5. Perry LM. (1937) Notes on Silphium. Rhodora, 39, 281-297.
6. Clevinger JA. (1999) Systematics of Silphium and its subtribe Engelemanniinae (Asteraceae: Heliantheae). Dissertation. The University of Texas at Austin.
7. Cronquist A. (1980) Silphium. In Vascular Flora of the Southeastern United States, Vol. 1, Asteraceae. University of North Carolina Press, Chapel Hill, NC, 67-72.
8. Medley ME. (1989) Silphium wasiotense (Asteraceae), a new species from the Appalachian Plateau in Eastern Kentucky. Sida 13, 285-291.
9. Clevinger JA, Panero JL. (2000) Phylogenetic analysis of Silphium and subtribe Engelmanniinae (Asteraceae:Heliantheae) based on ITS and ETS sequence data. American Journal of Botany, 87, 565-572.
10. El-Sayed NH, Wojcińska M, Drost-Karbowska K, Matlawska I, Williams J, Mabry TJ. (2002) Kaempferol triosides from Silphium perfoliatum. Phytochemistry, 60, 835-838.
11. Williams JD. (2006) The Flavonoids and Phenolic Acids of the Genus Silphium and Their Chemosystematic and Medicinal Value. Dissertation. The University of Texas at Austin.
12. Kowalski R, Wolski T. (2003) TLC and HPLC analysis of the phenolic acids in Silphium perfoliatum L. leaves, inflorescences and rhizomes. Journal of Planar Chromatography-Modern TLC, 16, 230-236.
13. Kowalski R, Wiercinski J, Mardarowicz M. (2005) Essential oil in leaves and inflorescences of Silphium integrifolium Michx. Journal of Essential Oil Research, 17, 220-222. (Pubitemid 41633814)
14. Bohlmann F, Jakupovic J. (1979) Naturally occurring terpene derivatives. 232. New labdane derivative and sesquiterpene in Silphium species. Phytochemistry, 18, 1987-1992.
15. Bohlmann F, Jakupovic J. (1980) Natural terpene derivatives. 238. New sesquiterpene hydrocarbons with anomalous carbon skeletons from Silphium species. Phytochemistry, 19, 259-265.
16. Pcolinski MJ, Doskotch RW, Lee AY, Clardy J. (1994) Chlorosilphanol A and silphanepoxol, labdane diterpenes from Silphium perfoliatum. Journal of Natural Products, 57, 776-783.
17. Davidyants ES. (2006) Growth-regulating activity of triterpene glycosides from Silphium perfoliatum (Asteraceae). Rastitel'nye Resursy, 42, 127-136.
18. Davidyants ES, Kartasheva IA, Neshin, IV. (1997) The effect of triterpene glycosides of Silphium perfoliatum L. on phytopathogenic fungi. Rastitel'nye Resursy, 33, 93-98.
19. Davidyants ES, Putieva ZhM, Bandyukova VA, Abubakirov NK. (1984) Triterpene glycosides of Silphium perfoliatum.Chemistry of Natural Compounds, 1, 120-121.
20. Davidyants ES, Putieva ZhM, Bandyukova VA, Abubakirov NK. (1984) Triterpene glycosides of Silphium perfoliatum. II. Chemistry of Natural Compounds, 20, 636.
21. Davidyants ES, Putieva ZhM, Bandyukova VA, Abubakirov NK. (1984) Triterpene glycosides of Silphium perfoliatum. III. Structure of Silphioside E. Chemistry of Natural Compounds, 20, 708-710.
22. Davidyants ES, Putieva ZhM, Shashkov AS, Bandyukova VA, Abubakirov NK. (1985) Triterpene glycosides of Silphium perfoliatum. IV. Structure of Silphioside C. Chemistry of Natural Compounds, 21, 486-489.
23. Davidyants ES, Putieva, ZhM, Bandyukova, VA, Abubakirov NK. (1986) Triterpene glycosides of Silphium perfoliatum. V. Structure of Silphioside A. Chemistry of Natural Compounds, 22, 58-60.
24. Calabria LM, Piacente S, Kapusta I, Dharmawardhane SF, Segarra FM, Pessiki PJ, Mabry TJ. (2008) Triterpene saponins from Silphium radula. Phytochemistry, 69, 961-972.
25. Wojcińska M, Williams JD, Mabry TJ, Ahmed A, Davis BD, Toth G, El-Sayed N, Matlawska I, Clevinger J. (2006) Flavonol Triglycosides from the Leaves of Silphium albiflorum. Natural Product Communications, 1, 941-948.
26. Wojcinska M, Drost-Karbowska K. (1998) Phenolic acids in Silphium perfoliatum L. flowers (Asteraceae: Compositae). Acta Poloniae Pharmaceutica Drug Research, 55, 413-416. (Pubitemid 28508519)
27. Valant-Vetschera KM., Wollenweber E. (2007) Exudate flavonoids in miscellaneous Asteraceae. Chemodiversity of exudate flavonoids in seven tribes of Cichorioideae and Asteroideae (Asteraceae). Journal of Bioscience, 62, 155-163.
28. Wollenweber E, Roitman JN. (2007) New reports on surface flavonoids from Chamaebatiaria (Rosaceae), Dodonaea (Sapindaceae), Elsholtzia (Lamiaceae), and Silphium (Asteraceae). Natural Product Communications, 2, 385-389.
29. Davis BD, Brodbelt JS. (2005) LC-MSn Methods for saccharide characterization of monoglycosyl flavonoids using postcolumn maganese complexation. Analytical Chemistry, 77, 1883-1890.
30. Mabry TJ, Markham KR, Thomas MB. (1970) The Systematic Identification of Flavonoids. Springer-Verlag, New York.
31. Barberá O, Sanz FJ, Sánchez-Parareda J, Marco JA. (1986) Further flavonol glycosides from Anthyllis onobrychiodes. Phytochemistry, 25, 2361-2365.
32. Yasukawa K, Takido M. (1987) A flavonol glycoside from Lysimachia mauritiana. Phytochemistry, 26, 1224-1226.
33. Bushi CA, Pomilio AB. (1982) Isorhamnetin 3-O-robinobioside from Gomphrena martiana. Journal of Natural Products, 45, 557-559.
34. Hilam AF, Saad H-EA, Hashish NE. (1995) Flavonol glycosides from Nitraria retusa. Phytochemistry, 40, 349-351.
35. Rastrelli L, Saturnino P, Schettino O, Dini A. (1995) Studies on the constituents of Chenopodium pallidicaule (Canihua) seeds. Isolation and characterization of two new flavonol glycosides. Journal of Agriculture and Food Chemistry, 43, 2020-2024.