title: Characterisation of galloylated cyanogenic glucosides and hydrolysable tannins from leaves of Phyllagathis rotundifolia by LC-ESI-MS/MS.
abstract: BACKGROUND
  Phyllagathis rotundifolia (Jack) Bl. (Melastomataceae) is a creeping herb found in Peninsular Malaysia and Sumatra. Traditionally, a decoction of the leaves is used in the treatment of malaria, fever and stomach ache.
  
  
  OBJECTIVE
  To provide ESI-MS(n) data which are applicable for chemical fingerprinting of P. rotundifolia to obviate laborious isolation and purification steps.
  
  
  METHODS
  The mass spectral data for the compounds isolated from the leaves of P. rotundifolia were obtained by liquid chromatography-electrospray ionisation tandem mass spectrometry.
  
  
  RESULTS
  The MS fragmentation patterns were obtained for galloylated cyanogenic glucosides based on prunasin (prunasin 6′‐O‐gallate 1, prunasin 2′,6′‐di‐O‐gallate 2, prunasin 3′,6′‐di‐O‐gallate 3, prunasin 4′,6′‐di‐O‐gallate 4, prunasin 2′,3′,6′‐tri‐Ogallate 5, prunasin 3′,4′,6′‐tri‐O‐gallate 6 and prunasin 2′,3′,4′,6′‐tetra‐O‐gallate 7), gallotannins (6‐O‐galloyl‐D‐glucose 8, 3,6‐di‐O‐galloyl‐D‐glucose 9, 1,2,3‐tri‐O‐galloyl‐β‐D‐glucose 10, 1,4,6‐tri‐O‐galloyl‐β‐D‐glucose 11, 3,4,6‐tri‐O‐galloyl‐D‐glucose 12, 1,2,3,6‐tetra‐O‐galloyl‐β‐D‐glucose 13 and 1,2,3,4,6‐penta‐O‐galloyl‐β‐D‐glucose 14), ellagitannins [6‐O‐galloyl‐2,3‐O‐(S)‐hexahydroxy‐diphenoyl‐D‐glucose 15, praecoxin B 16 and pterocarinin C 17], ellagic acid derivatives (3′‐O‐methyl‐3,4‐methylenedioxyellagic acid 4′‐O‐β‐D‐glucopyranoside 18 and 3,3′,4‐tri‐O‐methylellagic acid 4′‐O‐β‐D‐glucopyranoside 19) and gallic acid 20 that were isolated from the leaves of P. rotundifolia.
  
  
  CONCLUSIONS
  The ESI-MS(n) technique facilitates identification of galloylated cyanogenic glucosides, hydrolysable tannins and ellagic acid derivatives that were isolated from the leaves of P. rotundifolia. It yields MS(n) spectra that are useful for identification of these compounds in complex samples and permit more complete fingerprinting of plant materials.
authors.affiliation: Department of Chemistry, University of Malaya, 50603, Kuala Lumpur, Malaysia; Medicinal Plants Division, Forest Research Institute Malaysia, 52109 Kepong, Selangor, Malaysia. tanhp@frim.gov.my
authors.forename: Tan
authors.initials: T
authors.lastname: Hooi Poay
authors.forename: Ling
authors.initials: L
authors.lastname: Sui Kiong
authors.forename: Chuah
authors.initials: C
authors.lastname: Cheng Hock
mesh_terms: D005591:Chemical Fractionation / Q000379:methods; D002853:Chromatography, Liquid; D004610:Ellagic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D047348:Hydrolyzable Tannins / Q000737:chemistry* / Q000302:isolation & purification; D007214:Indonesia; D008296:Malaysia; D035322:Melastomataceae / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry* / Q000302:isolation & purification; D010936:Plant Extracts / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry*; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D053719:Tandem Mass Spectrometry / Q000379:methods
chemical_list: C473441:3'-O-methyl-3,4-methylenedioxyellagic acid 4'-O-beta-d-glucopyranoside; D005960:Glucosides; D047348:Hydrolyzable Tannins; D009570:Nitriles; D010936:Plant Extracts; C087111:6-O-galloylglucose; C019063:prunasin; D004610:Ellagic Acid