Guaianolides and other constituents from Artemisia douglasiana

Dimeric Guaianolides and a Fulvenoguaianolide from Artemisia myriantha

“…Our NMR data for compound 3 gave a better agreement with 1 H NMR data reported for arborescin and its derivatives as identified by both Ando and by Gutierrez (i.e., a 1β,10β-epoxide) than for their 1α,10α-epimers, and the stereochemistry of the epoxide group in 8α-hydroxyarborescin from A. myriantha has been assigned as 1β,10β- accordingly (i.e., compound 3 is 8α-hydroxy-1β,10β-epoxyguaia-3-en-12,6α-olide). 1β,10β-Epoxydehydroleucodin ( 4 ), dehydroleucodin ( 5 ) (mesatlantine E, which is reported as having the same structure as 5 , has a quite different 1 H NMR spectrum 4 ), , and desacetylmatricarin ( 6 ) − have all also been isolated previously from related species. Endoperoxide 7 was originally reported from Tanacetum parthenium as “tanparthin-β-peroxide”, although its structure has now been revised to tanparthin-α-peroxide on the basis of an X-ray crystallographic analysis .…”

“…Purification of the dichloromethane extract of A. myriantha by gradient column chromatography and HPLC has afforded seven known guaianolide derivatives (1)(2)(3)(4)(5)(6)(7), one new fulvenoguaianolide (8), and four novel dimeric guaianolides (10)(11)(12)(13). Structure elucidation of all compounds was performed by 2D NMR (HSQC, HMBC, 1 H-1 H COSY, and NOESY), resulting in unambiguous full NMR assignments for the known compounds.…”

“…1 β ,10 β -Epoxydehydroleucodin (4): see ref for physical properties; 13 C chemical shifts for C-1 and C-4 were incorrectly reported and C-5 was wrongly assigned as C-7 (and vice versa) in this reference; see Table for revised description of 13 C NMR of this compound.…”

Mugwort (<i>Artemisia vulgaris</i>, <i>Artemisia douglasiana</i>, <i>Artemisia argyi</i>) in the Treatment of Menopause, Premenstrual Syndrome, Dysmenorrhea and Attention Deficit Hyperactivity Disorder

“…American A. douglasiana contains a variety of pharmacologically active compounds including many sesquiterpene lactones such as vulgarin and psilostachyin [39][40][41][42][43][44][45][46][47][48][49][50], and probably monoterpenoids such as thujone and alpha-pinene [51]. Of course, the very lipophilic monoterpenoids, such as thujone, will not extract into an aqueous tea.…”