Pyrrolizidine alkaloids of Cynoglossum officinale and Cynoglossum amabile (family boraginaceae)

Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

“…PAs with 1,2-unsaturated necines but without a hydroxyl group at C-7 (as in supinidine type) with an esterification at C-9 results in a base peak m/z 122, while the saturated necine of the same type (trachelanthamidine, isoretroncanol, lindelofidine) shows a base peak at m/z 124. 1,2-unsaturated diester PAs esterified with angelic, tiglic or senecioic at C-7 shows a base peak at m/z 220 [40,42,59,67,70,90,91,96,163,193,200,201]. The fragmentation pathway of this type of PAs starts with the cleavage of the weak allylic ester bond at C-9.…”

“…and Trichodesma incanum [46]. For analytical purposes high-resolution capillary GLC alone or in combination with mass spectrometry is the method of choice for free PA bases [40,59,67,70,90,91,96,163,[191][192][193][194][195]. HPLC and HPLC-MS are also helpful but less sensitive than GLC and GLC-MS [60,93,[196][197][198][199].…”

“…9-angeloylretronecine, 9-angeloyl-7-viridiflorylretronecine, [60,67,68] C. australe Cynausine, cynaustraline.…”

“…High resolution Gas-liquid chromatography coupled with mass spectrometry (GLC-MS) has become a valuable and highly sensitive means for separation, convenient identification and quantification of complex PA mixtures, even in minute quantities or in diasteroisomeric forms [40,59,67,70,90,91,96,163,[191][192][193][194][195]. The combination of molecular weight, group mass fragmentation pattern and Kovats retention indices, enables an unequivocal identification of most of PA tertiary bases even in trace amounts or of closely related isomers.…”

“…Plants belongs to this genus contain alkaloids mainly derived from heliotridine type, in addition to (+)-and (−)-supinidine and trachelanthamidine bases [60,[67][68][69][70][71][72][73][74][75][76][77][78][80][81][82][83][84][85][86]239]. …”