Highly hydroxylated guaianolides of Achillea asiatica and Middle European Achillea species.
From flower heads of Achillea asiatica (L.) Serg., three new guaianolides were isolated by repeated column chromatography and HPLC. The constitution and the stereochemistry of these new, labile compounds were determined by MS, one ((1)H, (13)C, selective (1)H-TOCSY and (1)H-NOESY) and two-dimensional NMR experiments ((1)H, (1)H-COSY, (1)H, (13)C-HSQC, (1)H, (13)C-HMBC). The substances were identified as 8 alpha-angeloxy-2 alpha, 4 alpha,10 beta-trihydroxy-6 beta H,7 alpha H, 11 beta H-1(5)-guaien-12,6 alpha-olide (1), 8 alpha-angeloxy-1 beta,2 beta:4 beta,5 beta-diepoxy-10 beta-hydroxy-6 beta H, 7 alpha H, 11 beta H-12,6 alpha-guaianolide (2) and 8 alpha-angeloxy-4 alpha,10 beta-dihydroxy-2-oxo-6 beta H,7 alpha H, 11 beta H-1(5)-guaien-12,6 alpha-olide (3). They were also detected in Middle European species (Achillea collina, Achillea ceretanica (2x and 4x), Achillea roseoalba, Achillea asplenifolia) by HPLC, TLC and off line MS and have not been described before. The possibility that these compounds might be products of an oxidation process is discussed.
Glasl
S
S
Institute of Pharmacognosy, University of Vienna, Althanstrasse 14, A-1090 Wien, Austria. sabine.glasl@univie.ac.at
Presser
A
A
Gunbilig
D
D
Werner
I
I
Narantuya
S
S
Haslinger
E
E
Jurenitsch
J
J
Kubelka
W
W
D019659:Asteraceae / Q000737:chemistry*; D005060:Europe; D006900:Hydroxylation; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D045789:Sesquiterpenes, Guaiane
C447005:8-angeloxy-2,4,10-trihydroxy-6-H,7- H, 11-,H-1(5)-guaien-12,6-olide; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane