Subulatin, an antioxidic caffeic acid derivative isolated from the in vitro cultured liverworts, Jungermannia subulata, Lophocolea heterophylla, and Scapania parvitexta.
The new caffeic acid derivative, subulatin (1), was isolated from in vitro cultured liverworts, Jungermannia subulata, Lophocolea heterophylla, and Scapania parvitexta. The structure of 1 involved two caffeic acids, D-glucose, and 2-carboxy-6-(1,2-dihydroxy-ethyl)-4,5-dihydroxy-5,6-dihydro-4H-pyran. The connectivity of those and the absolute stereochemistry of 1 were elucidated on the basis of spectroscopic evidence. The antioxidative activity of 1 was comparable to that of alpha-tocopherol. (2'R)-Phaselic acid (2a) and (-)-9,2''-epiphylloyl-L-malic acid (4) were also isolated from J. subulata and L. heterophylla, respectively. A chiral HPLC analysis of the p-bromobenzoyl-malic acids derived from 2a showed that 2a from J. subulata was unusual (+)-trans-caffeoyl-D-malic acid.
Tazaki
Hiroyuki
H
Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine, Japan. tazaki@obihiro.ac.jp
Ito
Mayumi
M
Miyoshi
Masako
M
Kawabata
Jun
J
Fukushi
Eri
E
Fujita
Takashi
T
Motouri
Mutsumi
M
Furuki
Tatsuo
T
Nabeta
Kensuke
K
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification*; D002109:Caffeic Acids / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D008293:Malates / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D010944:Plants / Q000737:chemistry*
D000975:Antioxidants; D002109:Caffeic Acids; D005960:Glucosides; D008293:Malates; C521943:phaselic acid; C467712:subulatin