Taxonomic significance of coumarins in species from the subfamily Mutisioideae, Asteraceae

Quantification of 5-methylcoumarin-4-glucoside and 11,12-dihydroxy-5-methylcoumestan in Six Peruvian Species of the Genus Mutisia (Asteraceae)

“…The chemical structure of compound 2 is related to wedelolactone and a remarkable antihepatotoxic effect has also been demonstrated for it Regarding 1, a high concentration of it has recently been reported in Vernonia glaberrima (Vernoniaeae, Cichoroideae, Asteraceae) [4] showing cytotoxic activity. The presence of 5-methylcoumarins in member of Mutisioideae subfamily has also been extensively reviewed by Vestena and coauthors 2022 [5], and members of Mutisia genus stands out as potential sources of 5-methylcoumarins with potential antihepatotoxic activity. Therefore, in the present work, both 5-methylcoumarin-4-glucoside (1) and 11,12-dihydroxy-5-methylcoumestane (2) were purified from a Peruvian assession of M. orbignyana.…”

(+)/(−)-Gerbeloid A, a pair of unprecedented coumarin-based polycyclic meroterpenoid enantiomers from Gerbera piloselloides: Structural elucidation, semi-synthesis, and lipid-lowering activity

“…This rare type of coumarin typically contains a hemiterpene (C5), monoterpene (C10), or sesquiterpene (C15) residue at C-3 to form unique 5-methylcoumarin meroterpenoids 8 . Such natural products are not frequently found in natural sources but have been isolated from species of Mutisioideae (the subfamily of Compositae) 9 . Specifically, the 5-methylcoumarin meroterpenoids consisting of prenyl- and geranyl-substituted coumarin are predominant in species of the Gerbera and Ainsliaea DC genera (Mutisieae, the tribe of Mutisioideae) 10 , 11 , 12 .…”

Isolation and structure elucidation of biological active compounds from Euphorbia deightonii and Centrapalus pauciflorus

“…They are mainly found from the members of tribes Vernonieae, Nassauvieae, Onoserideae and Mutisieae of the Asteraceae family, and occasionally from a few other taxa. 50,51 Unlike most coumarins that are synthesized through phenylpropanoid pathway, 5-methylcoumarins have been suggested to be derived through the acetate-malonate pathway via pentaketide intermediate. 52,53 The superfamily of type III polyketide synthases (PKSs) are key enzymes in generating the backbones of chalcones, stilbenes, chromones, pyrones and several other secondary metabolites in plants.…”

“…The terpene components could be hemiterpene (C5), monoterpene (C10) or sesquiterpene (C15). 51 The terpene components of Onoserideae and Nassauvieae are mainly sesquiterpene units while those from Mutisieae and Vernonieae are mainly monoterpenes. 51,[58][59][60][61][62] In the case of monoterpene component, its derivatives are modified to form one or two rings.…”

“…51 The terpene components of Onoserideae and Nassauvieae are mainly sesquiterpene units while those from Mutisieae and Vernonieae are mainly monoterpenes. 51,[58][59][60][61][62] In the case of monoterpene component, its derivatives are modified to form one or two rings. Based on literature search, 5-methylcoumarins of Vernonieae tribe and Nassauvieae tribe are unique because many of its derivatives have terminal vinyl and methyl (of terpene unit) attached to C-3′ and this C-3′ is attached to C-3 of the coumarin scaffold.…”