Abstract
Perilla frutescens var. crispa (Lamiaceae) is an annual plant that is the botanical origin of the natural medicine “Soyo” listed in the Japanese Pharmacopoeia and is also used as a fragrant vegetable. Its characteristic components are essential oils and anthocyanins. Cyanogenic glycosides have also been isolated from perilla, but no reports have clarified which cyanogenic glycosides are abundant or differences in cyanogenic glycoside content according to the extent of perilla leaf growth or growth stage. Here, for the first time we determined the content and distributions of cyanogenic glycosides in perilla. The picric acid test, a common qualitative test for cyanogenic compounds, was used to quickly and semi-quantitatively detect cyanogenic compounds in perilla. Prunasin was the most abundant cyanogenic glycoside. The prunasin content per unit mass of perilla leaves varied by strain, regardless of leaf color or the main compound in the essential oils of each strain. Prunasin was higher in fresh leaves than in dried leaves and higher in young leaves than in mature leaves. When perilla was cultivated in an outdoor field, the prunasin content was initially high during the vegetative stage in summer before decreasing and then increasing until flower buds were beginning to form, and then gradually decreased again after flowering.
References
Gleadow RM, Møller BL (2014) Cyanogenic glycosides: synthesis, physiology, and phenotypic plasticity. Annu Rev Plant Biol 65:155–185
Yulvianti M, Zidorn C (2021) Chemical diversity of plant cyanogenic glycosides: an overview of reported natural products. Molecules 26:719
Nunome S (2011) Consideration on the usefulness of crude drugs (1) Required consistency and comprehensive judgment -Problems on peach kernel and apricot kernel-. Tokyo Crude Drugs Assoc Newsl 450:10–16
Ministry of Health, Labour and Welfare (2021) Japanese Pharmacopoeia, 18th edn. Ministry of Health, Labour and Welfare, Tokyo, p 1915
Akıl M, Kaya A, Aktar F (2013) Acute cyanide intoxication due to apricot seed ingestion. J Emerg Med 44:e285–e286
Ministry of Health, Labour and Welfare (2021) Japanese Pharmacopoeia, 18th edn. Ministry of Health Labour and Welfare, Tokyo, pp 1984–1985
Satake M, Kuroyanagi M, Shoyama Y, Wani K (2016) The encyclopedia of material plants for health/functional food -Botanical description and dietary/medical use. Tokyo, ChuohokiSyuppan Co., p 345
Aritomi M, Kumori T, Kawasaki T (1985) Cyanogenic glycosides in leaves of Perilla frutescens var. acuta. Phytochemistry 24:2438–2439
Aritomi M (1988) Cyanogenesity and practical use as food-colorant of Perilla frutescens var. acuta. J Home Econ Jpn 39:817–822
Fujita T, Terato K, Nakayama M (1996) Two jasmonoid glucosides and a phenylvaleric acid glucoside from Perilla frutesscens. Biosci Biotech Biochem 60:732–735
Mizushina Y, Takahashi N, Ogawa A, Tsurugaya K, Koshino H, Takemura M, Yoshida S, Matsukage A, Sugawara F, Sakaguchi K (1999) The cyanogenic glycoside, prunasin (d-mandelonitrile-beta-d-glucoside), is a novel inhibitor of DNA polymerase β. J Biochem 126:430–436
Ito M, Honda G (2007) Geraniol synthases from perilla and their taxonomical significance. Phytochemistry 68:446–453
Ministry of Health, Labour and Welfare (1959) Standards for foods and additives. https://www.mhlw.go.jp/web/t_doc?dataId=78334000&dataType=0&pageNo=61 (Accessed 29 September 2021)
Vo HQ, Nguyen PH, Zhao BT, Thi YN, Nguyen DH, Kim WI, Seo UM, Woo MH (2014) Bioactive constituents from the n-butanolic fraction of Aruncus dioicus var. kamtschaticus. Nat Prod Sci 20:274–280
Neilson EH, Goodger JQ, Motawia MS, Bjarnholt N, Frisch T, Olsen CE, Møller BL, Woodrow IE (2011) Phenylalanine derived cyanogenic diglucosides from Eucalyptus camphora and their abundances in relation to ontogeny and tissue type. Phytochemistry 72:2325–2334
Syah YM, Ghisalberti EL (1996) Biologically active cyanogenetic, iridoid and lignan glycosides from Eremophila maculata. Fitoterapia 67:447–451
Hosoi M, Ito M, Yagura T, Adams RP, Honda G (2004) cDNA Isolation and functional expression of myrcene synthase from Perilla frutescens. Biol Pharm Bull 27:1979–1985
Ito M, Toyoda M, Yuba A, Honda G (1999) Genetic analysis of nothoapiol in Perilla frutescens. Biol Pharm Bull 22:598–601
Sato-Masumoto N, Ito M (2014) Two types of alcohol dehydrogenase from Perilla can form citral and perillaldehyde. Phytochemistry 104:12–20
Nishizawa A, Honda G, Tabata M (1990) Genetic control of perillene accumulation in Perilla frutescens. Phytochemistry 29:2873–2875
Makino T, Ono T, Muso E, Honda G (1998) Inhibitory effect of Perilla frutescens and its phenolic constituents on cultured murine mesangial cell proliferation. Planta Med 64:541–545
Gleadow RM, Woodrow IE (2000) Temporal and spatial variation in cyanogenic glycosides in Eucalyptus cladocalyx. Tree Physiol 20:591–598
Godschalx LA, Stady L, Watzig B, Ballhorn JD (2016) Is protection against florivory consistent with the optimal defense hypothesis? BMC Plant Biol 16:32
Stamp N (2003) Out of the quagmire of plant defense hypotheses. Q Rev Biol 78:23–55
EFSA Panel on Contaminants in the Food Chain (2016) Acute health risks related to the presence of cyanogenic glycosides in raw apricot kernels and products derived from raw apricot kernels. EFSA J 14:4424
Takeya K, Kiuchi F, Komatsu K (2019) Partner pharmacognosy. Nankodo, Tokyo, pp 81–104
Morant AV, Bjarnholt N, Kragh ME, Kjærgaard CH, Jørgensen K, Paquette SM, Piotrowski M, Imberty A, Olsen CE, Møller BL, Bak S (2008) The β-glucosidases responsible for bioactivation of hydroxynitrile glucosides in Lotus japonicas. Plant Biol 147:1072–1091
Cueto JD, Ionescu IA, Pičmanová M, Gericke O, Motawia MS, Olsen CE, Campoy JA, Dicenta F, Møller BL, Sánchez-Pérez R (2017) Cyanogenic glucosides and derivatives in almond and sweet cherry flower buds from dormancy to flowering. Front Plant Sci 8:800
Lai D, Pičmanová M, Hachem MA, Motawia MS, Olsen CE, Møller BL, Rook F, Takos AM (2015) Lotus japonicus flowers are defended by a cyanogenic β-glucosidase with highly restricted expression to essential reproductive organs. Plant Mol Biol 89:21–34
Miller RE, Tuck KL (2013) The rare cyanogen proteacin, and dhurrin, from foliage of Polyscias australiana, a tropical Araliaceae. Phytochemistry 93:210–215
Acknowledgements
We thank Mae Chu Co. Ltd., Tochimoto Tenkaido Co. Ltd., Kotaro Pharmaceutical Co. Ltd., Mikuni & Co. Ltd., and Nippon Funmatsu Yakuhin Co. Ltd. for providing us with perilla herbs.
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Akatsuka, R., Ito, M. Content and distribution of prunasin in Perilla frutescens. J Nat Med 77, 207–218 (2023). https://doi.org/10.1007/s11418-022-01654-x
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DOI: https://doi.org/10.1007/s11418-022-01654-x