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Structure type: oligomer
C₃₁H₅₀O₁₁
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_153543,IEDB_983931,SB_192

• Article ID: 11382
  Sanogo R, Germano MP, De Tommasi N, Pizza C, Aquino R "Vernoniosides and an androstane glycoside from Vernonia kotschyana" - Phytochemistry 47(1) (1998) 73-78
  

  Five new stigmastane-type steroidal glycosides, vernoniosides D-1, D-2, D-3, F-1, and F-2 and a new androst-8-en glycoside have been isolated from the root of Vernonia kotschyana. The aglycones of the first five compounds possess a common 3 beta-hydroxy-Delta(8,14) steroidal nucleus and different side-chains; the glycosidic moieties are made up of one or two monosaccharides (glucose, xylose). Their structures have been elucidated using a combination of 1D and 2D NMR techniques as 3 beta,24 beta-trihydroxy-21,23:22,28:26,28-triepoxy-5 alpha-stigmasta-8(9),14(15)-dien-3-O-beta-D-glucopyranoside; 3 beta,24 beta-trihydroxy-21,23:22,28:26,28-triepoxy-5 alpha-stigmasta-8(9),14(15)-dien-3-O-beta-xylopyranosyl-(1 --> 3)-beta-D-glucopyranoside; 3 beta,24 beta-trihydroxy-21,23:22,28:26,28-triepoxy-5 alpha-stigmasta-8(9),14(15)-dien-3-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside; 3 beta,24 beta,26,28 alpha-tetrahydroxy-22,28-epoxy-5 alpha-stigmasta-8(9),14(15)-dien-21,23-lactone-3-O-beta-D-glucopyranoside; 3 beta,24 beta,26,28 alpha-tetrahydroxy-22,28-epoxy-5 alpha-stigmasta-8(9),14(15)-dien-21,23-lactone-3-O-beta-D-xylopyranosyl-(1 --> 3)-beta-D-glucopyranoside.

  steroidal glycosides, Asteraceae, Vernonia kostchyana, 3 beta, 24 beta-trihydroxy-21, 23 : 22, 28 : 26, 28-triepoxy-5 alpha-stigmasta-8(9), 14(15)-dien-3-O-beta-D-glucopyranoside, 14(15)-dien-3-O-beta-D-xylopyranosyl-(1 -> 3)-beta-D-glucopyranoside, 14(15)-dien-3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranoside, 24 beta, 26, 28 alpha-tetrahydroxy-22, 28-epoxy-5 alpha-stigmasta-8(9), 14(15)-dien-21, 23-lactone-3-O-beta-D-glucopyranoside, 23-lactone-3-O-beta-D-xylopyranosyl-(1 -> 3)-beta-D-glucopyranoside, androst-8-en-glycoside

  Publication DOI: 10.1016/S0031-9422(97)00477-9
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Dipartimento Farmaco-Biologico, Facoltà di Farmacia, Università di Messina, Messina, Italy, Centro Interdipartimentale di Chimica, Biologia e Tecnologia Farmaceutiche, Università degli Studi di Salerno, Penta di Fisciano, Salerno, Italy, Dipartimento di Chimica delle Sostanze Naturali, Università Federico II di Napoli via D. Montesano, Naples, Italy
  Methods: 13C NMR, 1H NMR, FAB-MS, GLC, methanolysis, HPLC, extraction, optical rotation measurement, CC, HMBC, COSY, HETCOR
  
   
  
  Vernonia kotschyana
  CSDB ID 61515 (all data & tools)