Table 3 in Comparison of glucosinolate diversity in the crucifer tribe Cardamineae and the remaining order Brassicales highlights repetitive evolutionary loss and gain of biosynthetic steps

Table 3 Glucosinolates from the tribe Cardamineae tentatively concluded (or suggested, bottom of table) to have evolved de novo in the tribe Cardamineae or generally in the family Brassicaceae.
Precursor aminoGlucosinolateKey structural characteristicDeduced biochemistryGeneral commentsacidVal1hmEt (57 R)Non-ancient β- hydroxylationPossibly GS-OH like?Widespread in familyIle1hmPr (30)Do.Do.Do.2HomoIle3mPe (58)PrecursorTwice chain elongation of IleAlso in tribe Brassiceae2HomoIle2h3mPe (149)Do.Do.Unique for C. pratensis.2HomoIle3hmPe (141)Precursor and atypical position ofTwice chain elongation of Ile, atypical GS-Unique for C. pratensis.hydroxylation (δ)OH?HomoPhe3hPE (148)PhenolicRing-oxidation (meta)Unique for BarbareaHomoPhe3hEBAR (142 R)Do.Do.Do.HomoPhe/4hPE (140)Do.Tyr as precursor or ring-oxidation (para)In Barbarea and also in tribe ArabideaehomoTyrHomoPhe/4hBAR (139 S)Do.Do.In Barbarea, 139 R also in Planodes and tribehomoTyr4hEBAR (139 R)ArabideaeHomoPhe/3/4hmoPE (x2)Di-substituted with further methylRing-oxidation twice or Tyr as precursor,Unique for Barbarea, position of methyl nothomoTyr3/4hmoEBAR (x1)methylationclarifiedTrp1,4moIM (138)Combined 1- and 4-substitutionCYP81F + IGMTAlso in tribe BrassiceaePhe6’iF PE (129)6′-Isoferuloyl groupAcylationUnique for Barbarea but 6′-acylation6’iF BAR (131 S)widespread6’iF EBAR (131 R)Phe/Tyr6’iF 4hEBARDo.DoDo.(132 R)Trp6’iF IM (130)Do.DoDo.Tentative de novo evolved:HomoIle2mBu (54)PrecursorChain elongation of IleAlso in other families and non-BrassicalesHomoIle2h2mBu (29 S)Do.Do.Do.7-8HomoMet65, 68, 77, 79,Highly elongatedMAM characteristicsWidespread in family[89]