The mass spectrometry of taxol

Abstract

The antitumor agent taxol has been examined by electron ionization, chemical ionization, and fast atom bombardment mass spectrometry. Three ion series are observed: (1) the M-series, characteristic of the intact molecule; (2) the T-series, with fragments derived from the taxane ring; and (3) the S-series representing the C-13 side chain. Neutral losses dominate each series of ions and serve to verify the presence and number of functionalities in each portion of the molecule. Fragmentation pathways and mechanisms of ion formation are proposed on the basis of product ion analysis and accurate mass measurements.

A Novel Endophytic Taxol-Producing Fungus Chaetomella raphigera Isolated From a Medicinal Plant, Terminalia arjuna

“…Characteristically, authentic Taxol yielded [M+H] + at m/z 854. Major fragment ions observed in the mass spectrum of Taxol can be placed into three categories representative of the major portions of the molecule [18]. The peaks corresponding to Taxol, exhibited mass-to-charge (m/z) ratios corresponding to the molecular ions [M+H] + of authentic Taxol (854) confirming the presence of Taxol.…”

Taxol, an anticancer drug produced by an endophytic fungus Bartalinia robillardoides Tassi, isolated from a medicinal plant, Aegle marmelos Correa ex Roxb.

“…By comparison, fungal taxol also yielded a peak MH + at m/z 854 with characteristic fragment peaks at 569, 551, 509, 464, 286 and 268. Major fragment ions observed in the mass spectrum of taxol can be placed into three categories which represents major portions of the molecule (McClure and Schram 1992). The peaks corresponding to taxol, exhibited mass-to-charge (m/z) ratios corresponding to the molecular ions (M+H) + of standard taxol (854) confirming the presence of taxol in the fungal extracts.…”

Isolation and identification of an anticancer drug, taxol from Phyllosticta tabernaemontanae, a leaf spot fungus of an angiosperm, Wrightia tinctoria

“…On comparison, fungal taxol also produced peaks (M+ H) + at m/z 854 and (M+Na) + at m/z 876 with characteristic fragment peaks at 344, 367, and 395. Major fragment ions observed in the mass spectrum of taxol are placed into three categories, which represent the major portion of the taxol molecule (McClure and Schram, 1992). The peaks analogous to taxol exhibited mass-to-charge (m/z) ratios corresponding to the molecular ions (M+H) + of the standard taxol (854), confirming the presence of taxol in the fungal extracts.…”