STRUCTURES OF ANAGALLOSAPONINS IV AND THEIR COMPANION SUBSTANCES FROMANAGALLIS-ARVENSIS L

From the herb of Anagallis arvensis L., we have isolated five novel ol eanane glycosides, anagallosaponins I-V and the artifact, methyl anaga llosaponin I, besides anagallosides A, B, C, and desglucoanagallosides A and B. The structures of isolates were identified by the use of 2D- NMR techniques (H-1-H-1 correlation spectroscopy (COSY), H-1-detected heteronuclear multiple quantum coherence (HMQC), heteronuclear multipl e quantum coherence (HMBC), rotating frame Overhauser enhancement spec troscopy (ROESY), total correlation spectroscopy (TOCSY). The structur es of anagallosaponins I and II were characterized as anagallogenin A 3-O-{beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)-]beta -D-glucopyranosyl (1-->4)-[beta-D-glucopyranosyl (1-->2)]-alpha-L-arab inopyranoside} and anagallogenin A 22-acetate 3-O-{beta-D-xylopyranosy l (1-->2)-O-beta-D-glucopyranosyl (1-->4)-[beta-D-glucopyranosyl (1--> 2)]-alpha-L-arabinopyranoside}, respectively. The structures of anagal losaponins III, IV and V were characterized as priverogenin B 22-aceta te 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alph a-L-arabinopyranoside, 3-O-{beta-D-xylopyranosyl (1-->2)-beta-D-glucop yranosyl (1-->4)-[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyrano side}, 3-O-{beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2 )]-beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside}, respectiv ely. Methyl anagallosaponin I, the methylacetal of anagallosaponin I m ight be derived from anagallosaponin I during the isolation procedure.