title: Proanthocyanidins from Spenceria ramalana and their effects on AGE formation in vitro and hyaloid-retinal vessel dilation in larval zebrafish in vivo.
abstract: Three new A-type proanthocyanidins (1-3), ent-epiafzelechin-(2α→O→7,4α→8)-ent-afzelechin 3'-O-β-D-glycopyranoside (1), ent-epiafzelechin-(2α→O→7,4α→8)-ent-epiafzelechin-(2α→O→7,4α→8)-ent-afzelechin (2), and ent-epiafzelechin-(2α→O→7,4α→8)-ent-epicatechin-(2α→O→7,4α→8)-ent-afzelechin (3), and three known compounds (4-6) were isolated from the whole plant of Spenceria ramalana. The structures of the new proanthocyanidins were established by spectroscopic and chemical studies. The inhibitory effects of compounds 1-6 on the formation of advanced glycation end products were examined in vitro. Compounds 3 and 6 showed the strongest inhibition, with IC50 values of 17.4 ± 0.5 and 14.1 ± 1.6 μM, respectively. The effects of these isolates on the dilation of hyaloid-retinal vessels induced by high glucose (HG) in larval zebrafish were also investigated. Compound 3 reduced the dilation of HG-induced hyaloid-retinal vessels most effectively. This compound reduced the diameters of HG-induced hyaloid-retinal vessels by about 157.7% and 164.1% at 10 and 20 μM, respectively, versus the HG-treated control group.
authors.affiliation: KM-Based Herbal Drug Research Group, Herbal Medicine Research Division, Korea Institute of Oriental Medicine , Daejeon 305-811, Republic of Korea.
authors.forename: Ik-Soo
authors.initials: IS
authors.lastname: Lee
authors.forename: Song Yi
authors.initials: SY
authors.lastname: Yu
authors.forename: Seung-Hyun
authors.initials: SH
authors.lastname: Jung
authors.forename: Yu-Ri
authors.initials: YR
authors.lastname: Lee
authors.forename: Yun Mi
authors.initials: YM
authors.lastname: Lee
authors.forename: Joo-Hwan
authors.initials: JH
authors.lastname: Kim
authors.forename: Hang
authors.initials: H
authors.lastname: Sun
authors.forename: Jin Sook
authors.initials: JS
authors.lastname: Kim
mesh_terms: D000818:Animals; D002392:Catechin / Q000737:chemistry; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005419:Flavonoids / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D044945:Proanthocyanidins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D012171:Retinal Vessels / Q000187:drug effects; D027824:Rosaceae / Q000737:chemistry*; D013237:Stereoisomerism; D015027:Zebrafish / Q000502:physiology
chemical_list: D004365:Drugs, Chinese Herbal; D005419:Flavonoids; D006027:Glycosides; D010636:Phenols; D044945:Proanthocyanidins; C585307:ent-epiafzelechin-(2alpha-O-7,4alpha-8)-ent-epiafzelechin-(2alpha-O-7,4alpha-8)-ent-afzelechin; C585306:ent-epiafzelechin-(2alpha-O-7,4alpha-8)-ent-epicatechin-(2alpha-O-7,4alpha-8)-ent-afzelechin; C585305:ent-epiafzelechin-(2alpha-O-7,4alpha-B)-ent-afzelechin-3'-O-beta-D-glycopyranoside; D002392:Catechin; C510796:afzelechin