[Structural analyses of barbaloin-related compounds in aloe drinks].
Four kinds of barbaloin (BA)-related compounds (A, B, C, D) in aloe drinks were isolated by using preparative HPLC. LC/MS analyses of these compounds showed the identical quasimolecular ion peak at m/z 833 [M-H]-. The chemical structures were mainly determined by NMR, including 1H-1H two-dimensional correlation spectroscopy (COSY), nuclear Overhauser and exchange spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple-bond connectivity (HMBC) experiments. They were identified as BA-related compounds A (10R, 10"S), B (10S, 10"S), C (10S, 10"R), and D (10R, 10"R) coupled through a C-10 to C-7' linkage, and newly found in nature. These results suggested that BA is converted to dimers during storage of aloe drinks.
Shindo
Tetsuya
T
Tokyo Metropolitan Research Laboratory of Public Health: 3-24-1, Hyakunin-cho, Shinjuku-ku, Tokyo 169-0073, Japan.
Ushiyama
Hirofumi
H
Kan
Kimiko
K
Uehara
Shin-ichi
S
Yasuda
Kazuo
K
Takano
Ichiro
I
Saito
Kazuo
K
D000504:Aloe; D000873:Anthracenes / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005504:Food Analysis; D009682:Magnetic Resonance Spectroscopy
D000873:Anthracenes; C045601:barbaloin