Synthesis and Characterization of a New Hydroquinone Derivative: Disodium p-Phenylene Diisostearyl Diphosphate.

A novel amphiphilic hydroquinone derivative having a C18 alkyl chain phosphate attached to the hydroquinone (HQ) moiety was chemically synthesized. The thermal stability, distribution between organic and aqueous phases, and in vitro skin permeability were evaluated. This HQ derivative was identified as disodium p-phenylene diisostearyl diphosphate (HQ-2P2IS) by UV, infrared, mass, and nuclear magnetic resonance spectroscopies.

Inhibitory effects of phytoncide solution on melanin biosynthesis.

To determine the component-activity relationships of phytoncide solutions on inhibitory activity in melanin biosynthesis, four types of phytoncide solution (A-type, AB-type, D-type, and G-type) were evaluated for inhibition of mushroom tyrosinase activity and melanin synthesis on murine B-16 melanoma cells and a human reconstituted skin model. The A-type, AB-type, D-type, and G-type of phytoncide solution treatment resulted in significant inhibition of tyrosinase activity. The amount of melanin was increased by treatment with phytoncide solutions in a concentration-dependent manner on murine B-16 melanoma cells without affecting cell growth.

Application of the reconstructed rabbit corneal epithelium model to assess the in-vitro eye irritant test of chemicals.

The rabbit corneal epithelium model (RCE model) was developed as a three-dimensional in vitro model to replace animal testing for the assessment of eye irritation. In the model, a stratified culture of rabbit corneal epithelial cells is grown at the air-liquid interface on collagen gel that acts as a parabasal membrane. Histological cross-sections show that the structure of the RCE model closely parallels that of the rabbit corneal epithelium.

In vitro eye irritancy test of lauryl derivatives and polyoxyethylene alkyl derivatives with the reconstructed rabbit corneal epithelium model.

The rabbit corneal epithelium model (RCE model) was developed as a three-dimensional in vitro model to replace animal testing for the assessment of eye tolerance. In the model, a stratified culture of rabbit corneal epithelial cells is grown at the air-liquid interface on a collagen gel acting as a parabasal membrane. Histological cross-sections show that the structure of RCE model closely parallels that of the rabbit corneal epithelium.

Protecting effect of phytoncide solution, on normal human dermal fibroblasts against reactive oxygen species.

Four types of phytoncide solutions (A-Type, AB-Type, D-Type and G-Type) was evaluated for reduction of cell damage induced by oxidative stress, ultraviolet A (UVA), ultraviolet B (UVB), hydroxyperoxide (H2O2) and t-butyl-hydroperoxide (t-BHP); stimulation of collagen synthesis against UVA irradiation; and inhibition of matrix metalloproteinase-1 (MMP-1) activity induced by UVA in human normal dermal fibroblasts and human reconstituted skin model. The A-Type, AB-Type, D-Type and G-Type of phytoncide solutions pretreatment resulted in significant protection against cell damage induced by UVB, UVA, H2O2 and t-BHP. The amount of type I collagen following UVA irradiation was increased by treatment with phytoncide solutions in a concentration-dependent manner.

In vitro eye irritancy test of lauryl derivatives using the reconstructed rabbit corneal epithelium model.

The rabbit corneal epithelium model (RCE model) was developed as a three-dimensional in vitro model to replace animal testing for the assessment of eye tolerance. In the model, a stratified culture of rabbit corneal epithelial cells is grown at the air-liquid interface on an amniotic membrane acting as a parabasal membrane. The alkaline exposure was restored each day in the presence of no irritants, although with the addition of SLS, which is a major irritant, the restoration of deficit was inhibited on the RCE model in a dose-dependent manner.

In vitro eye irritancy test of polyoxyethylene alkyl derivatives using a reconstructed rabbit corneal epithelium model.

We have developed the Rabbit Corneal Epithelial (RCE) Model to evaluate the in vitro eye irritation potential of chemicals including pharmaceuticals, cosmetics and their raw ingredients. In the model, a stratified culture of rabbit corneal epithelial cells is grown at the air-liquid interface on an amnion acting as a parabasal membrane. The alkaline exposure was restored each day in the presence of no irritants, although with the addition of sodium lauryl sulfate (SLS), which is a major irritant, the restoration of deficit was inhibited on the RCE model in a dose-dependent manner.

Suppression of mutagens-induced SOS response by phytoncide solution using Salmonella typhimurium TA1535/pSK1002 umu test.

Four types of phytoncide solution (A-Type, AB-Type, D-Type and G-Type) were evaluated as antimutagenic agents with suppressive effects on the SOS-inducing activity of the mutagen 2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide (furylfuramide) using Salmonella typhimurium TA1535/pSK1002 umu test. The A-Type, AB-Type, D-Type and G-Type of phytoncide solution suppressed the SOS-inducing activity on furylfuramide at a concentration of 100 microg/mL by 86.1%, 74.

Antimutagenic activity of a novel ascorbic derivative, disodium isostearyl 2-O-L-ascorbyl phosphate.

A novel amphiphilic vitamin C derivative, disodium isostearyl 2-O-L-ascorbyl phosphate (VCP-IS-2Na) possessing an alkyl chain of C(18) to a stable ascorbate derivative sodium L-ascorbic acid 2-phosphate (VCP-Na), was synthesized and evaluated as an anti-mutagen with suppressive effect on SOS-inducing activity on mutagen in the Salmonella typhimurium TA1535/pSK1002 umu test. VCP-IS-2Na was assayed with chemical mutagens, N-methyl-N'-nitro-N-nitrosoguanidine (MNNG), 2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide (furylfuramide) and 4-nitroquinolin 1-oxide (4NQO), which do not require liver metabolizing enzymes. VCP-IS-2Na at a concentration of 0.

Antioxidant effects and antimicrobial activites of phytoncide.

Physiological activities of four types of phytoncide solutions (A, AB, CY and D-types), prepared from various plants widely distributed in nature, were examined. We assayed these phytoncide solutions, testing for active oxygen inhibition, DPPH radical scavenging effects, nitrogen monoxide inhibition, and lipid peroxide inhibition. The AB- and D-types of phytoncide solutions especially showed comparably potent antioxidant effects.

Effect of a novel ascorbic derivative, disodium isostearyl 2-O-L-ascorbyl phosphate, on normal human dermal fibroblasts against reactive oxygen species.

The novel amphiphilic vitamin C derivative disodium isostearyl 2-O-L-ascorbyl phosphate (VCP-IS-2Na), which has a C(18) alkyl chain attached to the stable ascorbate derivative sodium L-ascorbic acid 2-phosphate (VCP-Na), was evaluated for reduction of cell damage induced by oxidative stress, ultraviolet A (UVA), ultraviolet B (UVB), and H(2)O(2); stimulation of collagen synthesis against UVA irradiation; and inhibition of matrix metalloproteinase-1 (MMP-1) activity induced by UVA in human normal dermal fibroblasts. VCP-IS-2Na pretreatment resulted in significant protection against cell damage induced by UVB, UVA, and H(2)O(2). The amount of type I collagen following UVA irradiation was increased by treatment with VCP-IS-2Na in a concentration-dependent manner.

Effect of a novel ascorbic derivative, disodium isostearyl 2-O-L-ascorbyl phosphate on human dermal fibroblasts: increased collagen synthesis and inhibition of MMP-1.

The effects of a novel amphiphilic vitamin C derivative, disodium isostearyl 2-O-L-ascorbyl phosphate (disodium 2-(1,3,3-trimethyl-n-butyl)-5,7,7-trimethyl-n-octyl-L-ascorbyl phosphate, VCP-IS-2Na), possessing a C18 alkyl chain attached to a stable sodium L-ascorbic acid 2-phosphate (VCP-Na), on the proliferation of fibroblasts and collagen synthesis, and inhibition of matrix metalloproteinase-1 (MMP-1) in normal human fibroblasts, NHDFs and NB1RGBs, were evaluated. Compared with proliferation of non-treated fibroblasts, VCP-IS-2Na at 50 microM increased proliferation to 123 and 135% of that in NHDFs and NB1RGBs. On the other hand, L-ascorbic acid (vitamin C) and VCP-Na had little effect on proliferation.

Inhibitory effects of a novel ascorbic derivative, disodium isostearyl 2-O-L-ascorbyl phosphate on melanogenesis.

We investigated the inhibitory effects of a novel amphiphilic ascorbic derivative, disodium isostearyl 2-O-L-ascorbyl phosphate (VCP-IS-2Na), synthesized from a hydrophilic ascorbic derivative, sodium-2-O-L-ascorbyl phosphate (VCP-Na), on melanogenesis in cultured human melanoma cells, normal human melanocytes, and three-dimensional cultured human skin models. Melanin synthesis in melanoma cells treated with VCP-IS-2Na at 300 muM and melanocytes treated with VCP-IS-2Na at 100 muM decreased to 23% and 52% of that in non-treated cells, respectively, and the cell viability was not affected. VCP-IS-2Na also significantly suppressed the cellular tyrosinase activity of melanoma cells and melanocytes.

Antimutagenic activity of flavonoids from Chrysanthemum morifolium.

A methanol extract from the flower heads of Chrysanthemum morifolium showed a suppressive effect on umu gene expression of the SOS response in Salmonella typhimurium TA1535/pSK1002 against the mutagen 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide). The methanol extract was re-extracted with hexane, chloroform, ethyl acetate, butanol, and water. The ethyl acetate fraction showed a suppressive effect.

Antimutagenic activity of phenylpropanoids from clove (Syzygium aromaticum).

Phenylpropanoids that possess antimutagenic activity were isolated from the buds of clove (Syzygium aromaticum). The isolated compounds suppressed the expression of the umu gene following the induction of SOS response in the Salmonella typhimurium TA1535/pSK1002 that have been treated with various mutagens. The suppressive compounds were mainly localized in the ethyl acetate extract fraction of the processed clove.