Medicinal Flowers. XXXVIII. Structures of Acylated Sucroses and Inhibitory Effects of Constituents on Aldose Reducatase from the Flower Buds of Prunus mume

Abstract

The methanolic extract from the flower buds of Prunus mume, cultivated in Zhejiang province, China, showed an inhibitory effect on aldose reductase. From the methanolic extract, five new acylated sucroses, mumeoses F-J, were isolated together with 29 known compounds. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated compounds on aldose reductase were also investigated. Acylated quinic acid analogs, which are one of the major compounds of the flower buds of P. mume, were shown to substantially inhibit aldose reductase. In particular, mumeic acid-A was found to exhibit a potent inhibitory effect [IC 50 =0.4 µm].Key words Prunus mume; mumeose; acylated sucrose; medicinal flower; aldose reductase; acylated quinic acid analogIn the course of our studies on bioactive constituents from medicinal flower, 2-6) we previously reported the isolation and structure elucidation of acylated sucroses named prunoses I (11), II (12), and III (13) with inhibitory effects on platelet aggregation and aldose reductase and radical scavenging effect from the flower buds of Prunus (P.) mume Sieb. et Zucc.(Rosaceae) cultivated in Wakayama prefecture, Japan. 7,8) In addition, the methanolic (MeOH) extract from the flower buds of P. mume cultivated in Zhejiang province, China, showed inhibitory effects on melanogenesis. From the MeOH extract, five new acylated sucroses, mumeoses A (6), B (7), C (8), D (9), and E (10), and three new acylated quinic acid analogs, mumeic acid-A (15) and its methyl ester (16) and 5-O-(E)-pcoumaroylquinic acid ethyl ester (22), were isolated and their structures as well as the inhibitory effects on melanogenesis were characterized.

Genome-Wide Analysis of the NAC Transcription Factor Gene Family Reveals Differential Expression Patterns and Cold-Stress Responses in the Woody Plant Prunus mume

“…This species harbors ornamental value including a fragrance, wonderful flower types and rich colors [ 51 ]. Additionally, P. mume ’s flower buds contain multiple acylated sucrose [ 52 ]. It is well known that P. mume blooms earlier than most other plants in the early spring, and can tolerate −4 °C to −2 °C [ 53 ].…”

Medicinal Flowers. XXXX.¹⁾ Structures of Dihydroisocoumarin Glycosides and Inhibitory Effects on Aldose Reducatase from the Flowers of <i>Hydrangea macrophylla</i> var. <i>thunbergii</i>

“…[2][3][4][5][6] However, a full chemical analysis of the flowers from this plant has not yet been performed. In the course of our chemical and pharmacological studies on Hydrangea plants [2][3][4][5][6][7][8] and medicinal flowers, [9][10][11][12][13][14] we recently reported the isolation and structure elucidation of secoiridoid glycosides named hydrangeamines A and B with a pyridine ring from the flowers of H. macrophylla var. thunbergii cultivated in Nagano prefecture, Japan.…”

“…The aqueous layer was further extracted with 1-butanol (1-BuOH) to give a 1-BuOH (12.5%) and a H 2 O (11.0%) soluble fraction. The EtOAc-and 1-BuOH-soluble fractions were subjected to normal-phase and reversed-phase silica gel column chromatography and repeated HPLC to give florahydrosides I (1, 0.068%) and II (2, 0.014%), thunberginol (3R)-thunberginol I 4′-O-β-d-glucopyranoside (10, 0.056%), 18) (+)-3-(4-methoxyphenyl)-8-hydroxy-3,4-dihydroisocoumarin (11, hydrangenol monomethyl ether, 0.011%), 19) phyllodulcin (12, 0.19%), 20,21) hydrangenol 8-O-β-d-glucopyranoside (13, 2.87%), 16,18) thunberginol G 3′-O-β-d-glucopyranoside (14, 0.16%), 16,22) hydrangenol (15, 4.79%), 23,24) thunberginol G (16, 0.067%), 5,25) neochlorogenic acid (17, 0.075%), 26,27) 29) chlorogenic acid (20, 0.054%), 30) chlorogenic acid methyl ester (21, 0.049%), 9,31) taxiphyllin (22, 0.076%), 8,32,33) umbelliferone glucoside (23, 0.11%), 34,35) α-morroniside (24, 0.021%), 36) trans-p-coumaric acid (0.013%), 30,37) and shikimic acid (0.36%) 38) (Fig. 1 C-NMR spectra of 1 were superimposable on those of (3R)-thunberginol E [(3R)-3,4-dihydro-6,8-dihydroxy-3-(3-hydroxy-4-methoxyphenyl) isocoumarin], 22) except for the signals around the 8-position, while the proton and carbon signals due to the dihydroisocoumarin part including glycoside moiety were very similar to those of…”

Cataract Preventive Role of Isolated Phytoconstituents: Findings from a Decade of Research

“…In an attempt to obtain inhibitors of RLAR from Prunus mume (Japanese apricot), mumeic acid-A was found to be the most potent inhibitor from all isolated secondary metabolites. The IC 50 concentration of mumeic acid-A (IC 50 = 0.4 µM) was almost twice that of chlorogenic acid (IC 50 = 0.7 µM) as the positive control [ 119 , 120 ].…”