Melanogenesis Inhibitory and Fibroblast Proliferation Accelerating Effects of Noroleanane- and Oleanane-Type Triterpene Oligoglycosides from the Flower Buds of Camellia japonica

Abstract

A 28-noroleanane-type triterpene oligoglycoside, camellioside E (4), an oleanane-type triterpene oligoglycoside, camellioside F (5), and the known compounds camelliosides A (1) and D (3) were isolated from a 50% EtOH extract of Camellia japonica flower buds from Korea. The principal constituents (1 and 5) significantly inhibited melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. Camellioside B (2), a major constituent of C. japonica grown in Japan, showed potent inhibition of melanogenesis [95.0 ± 1.0% (p < 0.01) at 20 μM]. The inhibitory effects of 1, 2, and 5 were stronger than that of the reference compound, arbutin. We believe the melanogenesis inhibitory effects of 2 and 5 are partly related to the proliferation inhibitory effects in B16 melanoma 4A5 cells. Conversely, camelliosides tended to enhance proliferation in normal human neonatal skin fibroblasts. Interestingly, camellioside B (2) significantly accelerated fibroblast proliferation. This biological selectivity could make camellioside B useful for treating skin disorders. Herein, we report the first scientific investigation of a triterpene that displays an inhibitory effect on melanogenesis, but that also has an enhancing effect on fibroblast proliferation.

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>

“…7 : 3 mixture of two diastereoisomers. The proton and carbon signals of the dihydroisocoumarin part in the 1 Hand 13 C-NMR spectra of 4 were superimposable on those of 1, while the proton and carbon signals due to the 3-phenyl part were very similar to those of hydrangenol 8-O-β-dglucopyranoside (13). 16,18) On the basis of the DQF-COSY and HMBC experiments (Fig.…”

“…On the basis of all this evidence, the chemical structure of 3 was determined to be as shown. On the other hand, the 1 H-NMR (methanol-d 4 ) and 13 C-NMR (Table 1) spectra of 4 revealed the products to be a ca. 7 : 3 mixture of two diastereoisomers.…”

“…On the other hand, the 1 H-NMR (methanol-d 4 ) and 13 C-NMR (Table 1) spectra of 2, 39) showed signals assignable to thunberinol E with a β-d-glucopyranosyl moiety as well as 1. In addition, on the basis of the comparison of the NMR data for 2 with those of 1 and the DQF-COSY and HMBC experiments on 2 (Fig.…”

“…[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.…”

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

“…1) As a continuing study, five new acylated sucroses termed mumeoses F (1), G (2), H (3), I (4), and J (5) were isolated from the flower buds of Chinese Prunus mume together with 29 known compounds including acylated quinic acid analogs. This paper deals with the structure elucidation of new acylated sucroses (1)(2)(3)(4)(5) and the inhibitory effects of principle constituents on aldose reductase.…”