Isolation and Synthesis of Cosmetic Substances from African Dietary Leaves, Celosia argentea L. for Skin Depigmentation.

Sawabe, Akiyoshi; Nomura, Masato; Fujihara, Yoshihito; Tada, Takahiro; Hattori, Fumihiro; Shiohara, Satoko; Shimomura, Kenji; Matsubara, Yoshiharu; Komemushi, Sadao; Okamoto, Tadashi; Kawamura, Saburou

doi:10.5650/jos.51.203

Cited by 5 publications

(4 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Humulene (HL) and caryophylene (CA) were distilled and purified from essential oil of Eugenia caryophylla. Eugenol (Eug) from citrus fruit peels (16,17), sesamol (Ses) from sesames, vanillyl alcohol (VanAlc) from vanilla bean, and trans-ferulic acid (FerA) from Celosia argentea L. (18) were isolated and purified from 70% ethanol-water extract. Anacardic acid monoene (AM) and triene (AT) were isolated and purified from methanol extract of cashew nuts (19).…”

Section: Methodsmentioning

confidence: 99%

Inhibitory Actions of Several Natural Products on Proliferation of Rat Vascular Smooth Muscle Cells Induced by Hsp60 from Chlamydia pneumoniae J138

Fukuoka

Sawabe

Sugimoto

et al. 2004

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

Atherosclerosis is a vascular disorder involving inflammation, a narrowed vascular lumen in the entire tunica intima, and reduced elasticity of the arterial wall. It has been found that Hsp60 from Chlamydia pneumoniae, an obligate bacterial pathogen associated with atheroma lesions, mimics human Hsp60, thereby causing attacks by immune cells on stressed endothelial cells expressing endogenous Hsp60 on their surface. Furthermore, Hsp60 from C. pneumoniae has been shown to promote the growth of vascular smooth muscle cells (VSMCs). To explore probes that can be used for studying signal transduction elicited by the chlamydial Hsp60, we have tested several natural products for their inhibitory actions on the Hsp60-induced proliferation of rat arterial smooth muscle cells. Sesamol, vanillyl alcohol, and trans-ferulic acid exhibited moderate inhibitory actions on the Hsp60-induced cell proliferation; zerumbone, humulene, and caryophylene effectively inhibited it at low concentrations with IC(50) values of 529, 122, and 110 nM, respectively. The results indicated that the 11-membered alicyclic ring is favorable for interactions with receptors involved in the Hsp60-induced VSMC proliferation.

show abstract

Section: Methodsmentioning

confidence: 99%

Inhibitory Actions of Several Natural Products on Proliferation of Rat Vascular Smooth Muscle Cells Induced by Hsp60 from Chlamydia pneumoniae J138

Fukuoka

Sawabe

Sugimoto

et al. 2004

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…We conducted an in vitro assessment test using various enzymes to assess the compounds for their effectiveness as a whitening cosmetic in preventing stains and freckles. We were able to identify compounds that had a higher rate of tyrosinase than that of arbutin, which is already used in commercial product, and we reported its effective ability as a whitening agent (5,6). In this report, in order to increase the effectiveness of the whitening effect, we synthesized 10 kinds of glycosides by a condensation reaction between compounds (1)~(4), and acetobromo-a-D-glucose (2, 3, 4, 6-tetraacetyl-a-D-glucopyranosyl bromide) and acetobromo-a-D-galactose (2, 3, 4, 6-tetraacetyl-a-Dgalactopyranosyl bromide), achieved by a simple method with the structure of the glycosides in mind and the idea that these naturally derived products are likely to be safe for the human body.…”

Section: Introductionmentioning

confidence: 94%

“…This higher rate of tyrosinase inhibition is due to the increased water solubility of the synthesized glycosides (1a), (2a) and (2b), which is an important factor for compound ingredients of cosmetics. The compounds that we previously synthesized and reported (4)(5)(6) to have whitening effects are almost oil-soluble. These compounds inhibit the activation of hyaluronidase, an enzyme that decomposes these compounds hyaluronic Table 1 Cosmetic Whitening Effect of (1) ~ (4b).…”

Section: Extraction and Isolationmentioning

confidence: 99%

Synthesis and Cosmetic Whitening Effect of Glycosides Derived from Anacardic Acids.

et al. 2003

Self Cite

View full text Add to dashboard Cite

Anacardic acids, (6-[(8Z)-8-pentadecenyl] salicylic acid (1) and 6-[(8Z,11Z)-8,11,14-pentadecatrienyl] salicylic acid (2)) were isolated from the shell oil of Indonesian cashew nut and used to synthesize glycosides via glycosidation of the carboxyl group on the benzene ring. We examined these compounds for their inhibition of the enzyme tyrosinase, their superoxide scavenging activity and their inhibition of enzyme hyaluronidase. The glucosides derived from (1) and (2) were found to inhibit tyrosinase (using L-DOPA as a substrate) activity by more than 80%. The inhibitory rates exceeded that of arbutin, a compound that is used in commercial cosmetics. As the comparison, cardanols, (3-[(8Z)-8-pentadecenyl] phenol (3) and 3-[(8Z, 11Z)-8, 11, 14-pentadecatrienyl] phenol (4)) were isolated from the cashew nut shell oil and used to synthesize glycosides that we also examined for their inhibitory activity.

show abstract

“…We previously reported that citrusin C (eugenyl O-b-D-glucopyranoside) (16) was a very effective skinwhitening agent among the components isolated from leaves of Celosia argentea L. (17) and Hibiscus sabdariffa (14) native to Africa. In section 1, we indicated that rosmarinic acid contained in perilla leaves had high SOD-like activity.…”

Section: Toward Use Of the Leaves Of Red Perilla 3 2 Synthesis Of Metmentioning

confidence: 99%

Toward Use of the Leaves of Perilla frutescens (L.) Britton var. Acuta Kudo (red perilla) with Japanese Dietary Pickled Plum (Umeboshi)

et al. 2006

Self Cite

View full text Add to dashboard Cite

Six phenolic compounds and one steroid were isolated from the leaves of Perilla frutescens Britton var. acuta (red perilla) with Japanese dietary pickled plum (Ume). These compounds were identified based on UV, MS, 1 H-NMR and 13 C-NMR spectroscopic data as b-sitosterol [1], shisonin [2], kaempferol 3-O-rutinoside [3], rosmarinic acid [4], rosmarinic acid methyl ester [5], 4-glucopyranosylcinnamic acid [6], and caffeic acid methyl ester [7]. In the bioassay, remarkable superoxide scavenging activity was found in the 1-butanol extract, and 20% methanol-water eluate, 50% methanol-water eluate and methanol eluate of an Amberlite XAD-2. In addition, remarkable superoxide scavenging activity was found in rosmarinic acid and rosmarinic acid methyl ester which are those isolation compounds. Moreover, we synthesized caffeic acid derivatives which were metabolic product of citrusin C and rosmarinic acid, and pharmacological effects such as superoxide scavenging activity used metabolite (vanillic acid, 4-hydroxy cinnamic acid, ferulic acid and isoferulic acid) of the chlorogenic acid as a starting material, and synthesized glycoside. And we examined their superoxide scavenging activity and tyrosinase inhibitory activity (Step1 as L-Tyrosine substrate; Step 2 as L-DOPA substrate), and their synthesized compounds investigated for cosmetic use. As a result, for tyrosinase inhibitory activity, isoferulic acid (3,4-CA) and their methyl ester (3,4-CAM), good inhibition of 67.5 and 93.9% of Step 1 and 65.1 and 53.8% of Step 2 were noted. These compounds inhibited tyrosinase activity more than arbutin (63.0% of Step 1 and 7.7% of Step 2). For superoxide scavenging activity, ferulic acid (4,3-CA) and their methyl ester (4,3-CAM), and 4-hydroxy cinnamic acid (4-CA) were good activity of 43.6, 57.9 and 55.2%, respectively. Melanin inhibition and cytotoxicity were examined by using cultured B16 melanoma cells. More than 40% suppression was observed in 3-b-glucopyranosyl isoferulic acid methyl ester (3,4-CAGlc) and 4-hydroxy cinnamic acid methyl ester (4-CAM).

show abstract

Isolation and Synthesis of Cosmetic Substances from African Dietary Leaves, Celosia argentea L. for Skin Depigmentation.

Cited by 5 publications

References 7 publications

Inhibitory Actions of Several Natural Products on Proliferation of Rat Vascular Smooth Muscle Cells Induced by Hsp60 from Chlamydia pneumoniae J138

Inhibitory Actions of Several Natural Products on Proliferation of Rat Vascular Smooth Muscle Cells Induced by Hsp60 from Chlamydia pneumoniae J138

Synthesis and Cosmetic Whitening Effect of Glycosides Derived from Anacardic Acids.

Toward Use of the Leaves of Perilla frutescens (L.) Britton var. Acuta Kudo (red perilla) with Japanese Dietary Pickled Plum (Umeboshi)

Contact Info

Product

Resources

About