Flavone Tetraglycosides and Benzyl Alcohol Glycosides from the Mongolian Medicinal Plant Dracocephalum ruyschiana

Abstract

From an extract of the aerial parts of Dracocephalum ruyschiana, five new flavone tetraglycosides, five new benzyl alcohol glycosides, and 19 known compounds were isolated. The tetraglycosides contain a 7-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranosyl moiety. The benzyl alcohol glycosides had acyl groups on their glycosyl or aglycone moieties. The compounds were tested for antioxidant activity using DPPH. Although the new compounds were not active, phenylpropanoylquinic acid derivatives were revealed as radical scavengers in D. ruyschiana.

Transformed Shoots of Dracocephalum forrestii W.W. Smith from Different Bioreactor Systems as a Rich Source of Natural Phenolic Compounds

“…The acacetin glycosides, particularly their monoglycosides, have already been identified in aerial parts of other Dracocephalum species, for Dracocephalum ruyschiana or Dracocephalum foetidum [ 19 , 20 ] and also in transformed shoots of D. forrestii grown on agar-solidified media [ 22 ]. Several studies have reported that acacetin glycoside derivatives inhibited enzymes such as acetylcholinesterase and hyaluronidase [ 20 , 53 ]. In addition, these compounds are expected to have antioxidant, anti-inflammatory, and anti-cancer activity [ 20 , 54 , 55 ].…”

“…Several studies have reported that acacetin glycoside derivatives inhibited enzymes such as acetylcholinesterase and hyaluronidase [ 20 , 53 ]. In addition, these compounds are expected to have antioxidant, anti-inflammatory, and anti-cancer activity [ 20 , 54 , 55 ].…”

“…These properties are conditioned by the secondary metabolites present in the plant, with the flavonoids, lignans, terpenoids, and phenolic acids being most frequently mentioned in the literature [ 17 , 18 ]. It is known that Dracocephalum species plants are a particularly good source of phenolic compounds such as the following caffeic acid derivatives: rosmarinic acid; chlorogenic acid; and salvianolic acid B and flavonoid glycosides, e.g., acacetin and apigenin derivatives [ 17 , 18 , 19 , 20 , 21 ].…”

Cytotoxic Terpenoids from the Roots of Dracocephalum taliense

“…Previous phytochemical investigation has revealed that flavonoids and terpenoids were the major constituents of genus Dracocephalum [ 11 ]. Biological studies on these flavonoids have revealed their broad pharmacological activities, especially antioxidant, immunomodulatory, and cytotoxic activities, as well as cardiovascular protective effects [ 11 , 13 , 14 , 15 , 38 , 39 ]. Trypanocidal diterpenoids with icetexane and octahydroindene skeletons were discovered from the whole plants of D. komarovi [ 16 , 19 ].…”

“…Some plants in this genus, including D. moldavica and D. tanguticum , are broadly used in traditional medicine for gastropathy, tracheitis, and cardiovascular disease in Xinjiang and Tibet [ 11 , 12 ]. Typical metabolites in the plants of this genus were flavonoids and terpenoids [ 13 , 14 , 15 , 16 ]. Monoterpenes limonene and α-terpineol might be responsible for antinociceptive properties in the essential oil of D. kotschyi [ 17 ].…”