title: Subulatin, an antioxidic caffeic acid derivative isolated from the in vitro cultured liverworts, Jungermannia subulata, Lophocolea heterophylla, and Scapania parvitexta.
abstract: 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.
authors: Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine, Japan. tazaki@obihiro.ac.jp
authors: Hiroyuki
authors: H
authors: Tazaki
authors: Mayumi
authors: M
authors: Ito
authors: Masako
authors: M
authors: Miyoshi
authors: Jun
authors: J
authors: Kawabata
authors: Eri
authors: E
authors: Fukushi
authors: Takashi
authors: T
authors: Fujita
authors: Mutsumi
authors: M
authors: Motouri
authors: Tatsuo
authors: T
authors: Furuki
authors: Kensuke
authors: K
authors: Nabeta
mesh_terms: 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*
chemical_list: D000975:Antioxidants; D002109:Caffeic Acids; D005960:Glucosides; D008293:Malates; C521943:phaselic acid; C467712:subulatin