Planta Med 2008; 74 - PG51
DOI: 10.1055/s-0028-1084804

Use development of functional materials in the leaves of Perilla frutescens (L.) Britton var. acuta Kudo (red perilla) with Japanese dietary pickled plum (Umeboshi)

A Sawabe 1, 2, T Satake 2, R Aizawa 1, C Ozeki 2, Y Hamada 3, S Komemushi 1, 2
  • 1Department of Applied Biological Chemistry, Graduate School of Agriculture, Kinki University, 3327–204, Nakamachi, Nara 631–8505, Japan
  • 2Department of Agricultural Chemistry, Faculty of Agriculture, Kinki University, 3327–204, Nakamachi, Nara 631–8505, Japan
  • 3Hamada Co., Ltd., 391, Kamihaya, Tanabe-shi, Wakayama 646–0101, Japan

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). Their structures were determined based on UV, MS, 1H-NMR and 13C-NMR spectroscopic data as β-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 inhibitory effect 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 similar structure and pharmacological effects such as superoxide scavenging activity used metabolite (vanillic acid, 4-hydroxy cinnamic acid, ferulic acid, 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, isoferulic acid (3,4-CA) and their methyl ester (3,4-CAM), and 4-hydroxy cinnamic acid (4-CA) were good activity of 43.6, 57.9 and 55.2%, respectively.