Secondary metabolites from Stachys tetragona Boiss. & Heldr. ex Boiss. and their chemotaxonomic significance

Genus Stachys: A Review of Traditional Uses, Phytochemistry and Bioactivity

“…Furthermore, derivatives of apigenin p -coumaroyl glucosides and chrysoeriol p -coumaroyl glucosides were reported in Stachys species, though some p -coumaroyl glucosides (not determined) were also identified [ 5 , 75 ]. To be mentioned that chrysoeriol 7- O- glucoside ( 43 ), chrysoeriol p -coumaroyl glucosides ( 46,47 ) and chrysoeriol 7-O-[6″′-O-acetyl-allosyl]-(1→2)-glucoside (stachyspinoside) ( 44 ) were mainly isolated from wild Greek taxa of the subgenus Stachys [ 3 , 77 , 98 , 99 , 102 ], apart from the Greek species S. ionica [ 20 ], S. tetragona [ 100 ] and the cultivated species S. iva [ 56 ]. Nazemiyeh et al (2006) investigated the phytochemical profile of the stems of S. schtschegleevii , reporting four flavonoids, among them were also two p -coumaroyl derivatives of apigenin and chrysoeriol [ 74 ].…”

“…( Table 4 and Table 18 ), mainly in species occurred in Greece. Afouxenidi and colleagues (2018) isolated kaempferol ( 91 ) from the n -butanol residue of the aerial parts of S. tetragona [ 100 ], which was also identified in the aerial parts of S. cretica subsp. smyrnaea [ 81 ].…”

“…Specifically, three lignans categorizing into two furanofuran-type derivatives (sesamin and paulownin) and one benzofuran-type lignan (urolignoside) were reported in two species of the subgenus Stachys ( Table 9 and Table 23 ). Laggoune et al (2016) isolated sesamin ( 112 ) and paulownin ( 113 ) from the aerial parts of S. mialhesii [ 103 ], while urolignoside ( 114 ) was isolated from the aerial parts of S. tetragona [ 100 ]. Given that up to now there is no study reported the presence of lignans in the subgenus Betonica , the identification of lignans might be considered as a chemotaxonomic difference between the two subgenera Stachys and Betonica .…”

“…Another study carried out by Karioti et al (2010) focused on the phenolic compounds from the aerial parts of S. recta , and reported many phenylethanoid glycosides from its aerial parts, including acteoside ( 118 ), isoacteoside ( 119 ), β-OH-acteoside ( 121 ), betunyoside E ( 127 ), campneoside I ( 136 ), forsythoside B ( 137 ), β-OH-forsythoside B methyl ether ( 138 ) [ 14 ]. Furthermore, lamiophloside A ( 141 ) was isolated with some other phenylethanoid glycosides from the aerial parts of S. tetragona [ 100 ]. Of great interest is that our survey revealed that this constituent is mentioned only in the specific species.…”

“…Triterpene derivatives and phytosterols are major secondary metabolites of Lamiaceae family. In genus Stachys , five phytosterol derivatives ( 220 – 224 ) were found in S. byzantina [ 17 , 35 ], S. annua [ 95 ], S. spinosa [ 99 ], S. tetragona [ 100 ], S. palustris [ 146 ] and S. alopecuros subsp. divulsa [ 119 ] ( Table 14 and Table 28 ).…”