Abstract
High-quality perilla leaves are defined as those having purple upper and lower surfaces and a pleasant smell. The Japanese Pharmacopoeia specifies the content of essential oils in perilla leaves but not the content of rosmarinic acid. Rosmarinic acid is a common component of Labiatae plants such as shiso (Perilla frutescens Britton var. crispa W. Deane). Rosmarinic acid has been reported to exhibit anti-inflammatory and anti-oxidant activity but the factors affecting the content of rosmarinic acid in plants remain unknown. This study describes a simple and reproducible method for quantifying rosmarinic acid. We elucidated the main causes for the different rosmarinic acid contents of plants by examining various samples of perilla using the proposed method. Significant differences in rosmarinic acid content between varieties and cultivators were observed. The rosmarinic acid content was higher in green perilla compared with red perilla, in wild species compared with cultivated species, and in plants cultivated in outdoor nurseries compared with in indoor nurseries. The proposed quantitative method was used to examine the rosmarinic acid content in a Kampo formula, Hangekobokuto, and was found to be higher in decoctions prepared using the Kouge method compared with the typical preparation method. We examined the chlorophyll and caffeic acid contents of several samples and their relationship with the rosmarinic acid content.
Similar content being viewed by others
References
The Ministry of Health, Labour and Welfare (2016) The Japanese Pharmacopoeia, 17th editon. The Ministry of Health, Labour and Welfare, Tokyo, pp 1843–1844
Yamamoto H, Sakakibara J, Nagatsu A, Sekiya K (1998) Inhibitors of arachidonate lipoxygenase from deffated perilla seed. J Agric Food Chem 46:862–865
Nakamura Y, Ohto Y, Murakami A, Ohigashi H (1998) Superoxide scavenging activity of rosmarinic acid from Perilla frutescens Britton var. acuta f. viridis. J Agric Food Chem 46:545–4550
Sanbongi C, Takano H, Osakabe N, Sasa N, Natsume M, Yanagisawa R, Inoue K-I, Sadakane K, Ichinose T, Yoshikawa T (2004) Rosmarinic acid in perilla extract inhibits allergic inflammation induced by mite allergen, in a mouse model. Clin Exp Allergy 34:971–977
Inoue K, Kosakabe N, Sanbongi C, Yasuda A, Yanagisawa T, Ichiishi E, Takano M, Yoshikawa T (2002) An case of Japanese cedar pollonosis patients who were successfully treated with oral intake of rosmarinic acid derived from red perilla. Allergy 51(9–10):1004
Yoshikawa T, Takano M, Kosakabe N, Sanbongi C, Yasuda A, Yanagisawa T, Inoue K, Ichiishi E (2002) The effect of oral intake of rosmarinic acid derived from red perilla in patients with cedar pollinosis. Allergy 51(9–10):1004
Ishigaki Y, Tanaka H, Akama H, Ogara T, Uwai K, Tokuraku K (2013) A microliter-scale high-throughput screening system with quantum-dot nanoprobes for amyloid-β aggregation inhibitors. PLOS One 8(8)
Makino T, Ono T, Muso E, Yoshida H, Honda G, Sasayama S (2000) Inhibitory effects of rosmarinic acid on the proliferation of cultured murine mesangial cells. Nephrol Dial Transplant 15:1140–1145
Makino T, Ono T, Liu N, Nakamura T, Muso E, Honda G (2002) Suppresive effects of rosmarinic acid on mesangioproliferative glomerulonephritis in rats. Nephron 92:898–904
Eicher T, Ott M, Speicher A (1996) Bryophyte constituents; 7: new synthesis of (+)-rosmarinic acid and related compounds. Synthesis 6:755–762
Petersen M, Abdullah Y, Benner J, Eberle D, Gehlen K, Hucherig S, Janiak V, Kim KH, Sander M, Weitzel C, Wolters S (2009) Evolution of rosmarinic acid biosynthesis. Phytochemistry 70:1663–1679
Weitzel C, Peterson M (2011) Cloning and characterization of rosmarinic acid synthase from Melissa officinalis L. Phytochemistry 72:572–578
Ito M, Honda G (1996) A taxonomic study of Japanese Wild Perilla (Labiatae). J Phytogeogr Taxon 44:43–52
Ito M, Kato H, Oka Y, Honda G (1998) Phylogenetic analysis of Japanese perilla species by using DNA polymorphisms. Nat Med 52(3):248–252
Watanabe T, Kobayashi M (1988) Chlorophylls as functional molecules in photosynthesis—molecular comparison in vivo and physical chemistry in vitro. Chem Soc Jpn 4:383–395
Watanabe T, Kobayashi M (1989) Methods for analysis of chlorophylls. Yukagaku 38(10):876–885
Lu N, Bernardo EL, Tippayadarapanich T, Takagaki M, Kagawa N, Yamori W (2017) Growth and accumulation of secondary metabolites in perilla as affected by phytosynthetic photon flux density and electrical conductivity of the nutrient solution. Front Plant Sci 8:708
Gong Z, Yamazaki M, Sugiyama M, Tanaka Y, Saito K (1997) Cloning and molecular analysis of structural genes involved in anthocyanin biosynthesis and expressed in a forma-specific manner in Perilla frutescens. Plant Mol Biol 35(6):915–927
Honda G, Yuba A, Kojima T, Tabata M (1994) Chemotaxonomic and cytogenetic studies on Perilla frutescens var. citriodora (“Lemon Egoma”). Nat Med 48(3):185–190
Yukizaki C, Komura M, Kosaka T, Dozono M (2004) Antioxidant activity of herbs and effect of drying and extracting condition. Research report of Miyazaki Prefecture Industrial Technology Center and Miyazaki Prefecture Foods Development Center No.49
Acknowledgments
We are very grateful to Mae Chu Co., Ltd., Nippon Funmatsu Yakuhin Co., Ltd., Tochimoto Tenkaido Co., Ltd., Mikuni & Co., Ltd., and Kotaro Pharmaceutical Co., Ltd. for providing perilla herb marketed items. In addition, part of this research was conducted as a joint research project with Science Create Co., Ltd.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Deguchi, Y., Ito, M. Rosmarinic acid in Perilla frutescens and perilla herb analyzed by HPLC. J Nat Med 74, 341–352 (2020). https://doi.org/10.1007/s11418-019-01367-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-019-01367-8