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Novel Inhibitors for Histidine Decarboxylase from Plant Components

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Novel Inhibitors for Histidine Decarboxylase from Plant Components International Biology Review, Vol. 1, Issue 2, August 2017 Novel inhibitors for histidine decarboxylase from plant components Novel inhibitors for histidine decarboxylase from plant components Author: Abstract Yoko Nitta1* Histamine is a bioactive amine that affects a wide range 2 of biological activities in the human body. In this Hiroe Kikuzaki review, we discuss the active components of spices and 3 Hiroshi Ueno herbs that can inhibit histidine decarboxylase (HDC), an enzyme that catalyzes synthesis of histamine. We Affiliation: screened 21 spices and 122 medicinal plants by 1 Department of Nutritional carrying out inhibition assays with recombinant human Science, Faculty of Health and HDC. Among spices, flavonoid glycosides of allspice, Welfare Science, Okayama quercetin 3-O--D-glucuronide 6"-methyl ester and Prefectural University, 111 Kuboki, quercetin 3-O-(2-O-galloyl) glucoside, at 1 mM Soja, Okayama, 719-1197 Japan inhibited HDC by 64 and 55%, respectively. Among E-mail: medicinal plants, ellagitannins of meadowsweet, [email protected] rugosin D, rugosin A, rugosin A methyl ester, and * Correspondence author tellimagrandin II inhibited HDC significantly with Ki values of approximately 0.35-1 M. These results 2 Department of Food Science indicate that plant components are promising sources and Nutrition, Nara Women's for novel inhibitors of HDC. University, Kitauoyanishi-machi, Nara, 630-8506 Japan E-mail: Keywords: histamine, inhibitors, flavonoid glycoside, [email protected] ellagitannin, medicinal plant 3 Laboratory of Applied Microbiology and Biochemistry, School of Agriculture, Ryukoku University, Shiga 520-2194, Japan E-mail: [email protected] Copyright 2017 KEI Journals. All Rights Reserved Page │1 International Biology Review, Vol. 1, Issue 2, August 2017 Novel inhibitors for histidine decarboxylase from plant components 1. Introduction inhibitory activity on HDC. While both ethanol and water extracts were examined, Histidine decarboxylase (HDC) catalyzes the synthesis of histamine, a bioactive amine significant inhibition was observed for allspice, that affects various biological activities cinnamon, clove, and Japanese pepper (10). including gastric acid secretion, capillary Essential oils can be extracted from these spices; thus, the inhibitory activities of essential dilatation, smooth muscle contraction, neurotransmission, inflammation, and allergic oil components, i.e. eugenol, α-pinene, β-pinene, reactions. HDC inhibition would lead to limonene, cineole, phellandrene, terpineol, and control of some of these activities, so it is anethole, were also examined (10). Eugenol desirable to develop suitable HDC inhibitors for inhibited most potently among these pharmacological purposes; however, no such compounds; however, the tested concentration inhibitors are available for clinical use. Highly was much higher than that estimated from the purified native HDC from mammalian sources spice extracts (10). The results suggest that is available (1-6); for example, HDC from livers there are other more potent inhibitors existing in of fetal rats and from mouse mastocytoma these spices. P-815 cells (7, 8). However, the amounts of 2.2 Flavonoid glycosides of allspice these highly purified native HDC is limited, inhibit HDC activity (11) making them unsuitable for pharmacological studies. Recently, expression of the active form We investigated the inhibitory activities of of human recombinant HDC was carried out and compounds obtained from Pimenta dioica, its crystal structure was determined (9). Hence, called allspice. Two quercetin glycosides from P. it is now possible to perform inhibition studies dioica, quercetin 3-O--D-glucuronide to seek active components from plant sources 6"-methyl ester and quercetin 3-O-(2-O-galloyl) with the use of recombinant human HDC. In glucoside, inhibited most potently, with 64 and this review, we summarize the recent findings. 55% inhibition at 1 mM, respectively. Other compounds tested were 14 P. dioica compounds including gallic acid, quercetin, quercetin 2. Spices 3-O--D-glucopyranoside, hyperoside 2.1. Some spices show HDC inhibitory (quercetin 3-O--D-galactopyranoside), activity (10). quercetin 3-O-arabinoside, quercetin 3-O- Twenty-one species of spices, including (2-O-galloyl) glucoside, quercetin 3-O--D- clove, allspice, cinnamon, Japanese pepper, glucuronide 6"-methyl ester, quercetin rosemary, bay leaf, sage, peppermint, mustard, 3-O--D-glucuronide, ampelopsin, pimentol, anise, tarragon, marjoram, fenugreek, cumin, eugenol 4-O--D-(6-O-galloyl) glucopyrano- paprika, garlic, saffron, ginger, black pepper, side, (4S)--terpineol 8-O--D-(6-O-galloyl) red pepper and nutmeg, were tested for their glucopyranoside, (4R)--terpineol 8-O--D- Copyright 2017 KEI Journals. All Rights Reserved Page │2 International Biology Review, Vol. 1, Issue 2, August 2017 Novel inhibitors for histidine decarboxylase from plant components (6-O-galloyl)glucopyranoside, and eugenol as Epigallocatechin gallate, a green tea polyphenol, summarized in Table 1. Gallic acid, quercetin, has been previously reported to inhibit HDC quercetin 3-O--D-glucuronide, (4S)-- activity (12, 13) with an inhibitory rate of 75% terpineol 8-O--D-(6-O-galloyl) glucopyrano- at 1 mM, higher than those of quercetin side, and eugenol did not show inhibitory 3-O--D-glucuronide 6"-methyl ester and activity in the examined conditions. quercetin 3-O-(2-O-galloyl) glucoside. Table 1. Compounds used for HDC inhibition Compound Structure Inhibitory rate % at 1 mM HO O Gallic acid < 1 HO OH OH Quercetin R = H < 1 Quercetin 3-O--D-glucopyranoside R = -D-Glc 15 ± 3 Hyperoside R = --D-Gal 28 ± 1 OH Quercetin 3-O-arabinoside OH R = -Ara 30 ± 2 Quercetin HO O R = 2 55 ± 6 3 3-O-(2-O-galloyl)--D-glucoside 4 -(2-O-galloyl)Glc OR Quercetin 3-O--D-glucuronide O R = -methyl OH 64 ± 7 6"-methyl ester glucuronide Quercetin 3-O--D-glucuronide R = -glucronide < 1 OH OH HO O Ampelopsin OH 20 ± 6 OH OH O OH OH OH HO OH HO O OH O OH Pimentol O HO 7 ± 1 OMe OH O O O HO HO OH Copyright 2017 KEI Journals. All Rights Reserved Page │3 International Biology Review, Vol. 1, Issue 2, August 2017 Novel inhibitors for histidine decarboxylase from plant components OH HO OH Eugenol O < 1 4-O--D-(6-O-galloyl)glucopyranoside O MeO O HO O HO OH (4S)--terpineol OH HO OH 19 ± 2 8-O--D-(6-O-galloyl)glucopyranoside (4R)--terpineol O O 21 ± 6 8-O--D-(6-O-galloyl)glucopyranoside O HO O HO OH OH OMe Eugenol < 1 OH OH HO O OH Epigallocatechin gallate 75 ± 3 O OH OH O OH OH 3. Medicinal plants HDC activity significantly, with a >30% inhibitory rate. In particular, Artocarpus 3.1. Plants of rose family can inhibit lakoocha, amla, and meadowsweet showed HDC activity (14) more than 90% inhibitory activity. Table 3 Exploration of possible candidates for summarizes the results of 21 extract samples as inhibition of HDC activity was carried out with listed by their taxonomic family category. 122 species of medicinal plants (Table 2). Over 30% of these samples belong to the rose Plant samples were prepared by 50% ethanol family (Fig. 1). extraction. Of these, 21 samples inhibited Copyright 2017 KEI Journals. All Rights Reserved Page │4 International Biology Review, Vol. 1, Issue 2, August 2017 Novel inhibitors for histidine decarboxylase from plant components Table 2. Medicinal plants tested for HDC inhibition. Taxonomic family Binomial name (common name) Acoraceae Acorus calamus Adoxaceae Sambucus nigra (Elder) Amaranthaceae Bassia scoparia Amaryllidaceae Allium fistulosum (Welsh onion seed) Allium tuberosum (Chinese chives seed) Apiaceae Angelica keiskei (Ashitaba) Angelica pubescens (Angelica pubescens rhizome) Centella asiatica Daucus carota (Carrot) Foeniculum vulgare (Fennel) Peucedanum praeruptorum (Peucedanum Root) Apocynaceae Gymnema sylvestre Aquifoliaceae Ilex kaushue (Kuding) Araceae Pinellia ternate Araliaceae Aralia elata (Aralia elata root bark) Eleutherococcus senticosus (Siberian ginseng) Panax notoginseng Asparagaceae Polygonatum falcatum (Polygonatum rhizome) Polygonatum odoratum Ruscus aculeatus (Butcher's broom) Asteraceae Arnica montana Artemisia capillaris (Capillary wormwood) Aster tataricus Atractylodes lancea Echinacea purpurea (Purple coneflower) Helianthus annuus (Sunflower) Solidago virgaurea (Goldenrod) Tanacetum vulgare (Tansy) Xanthium strumarium (Xanthium fruit) Berberidaceae Epimedium grandiflorum (Horny goat weed) Bignoniaceae Handroanthus impetiginosus (Lapacho) Brassicaceae Brassica juncea (Mustards) Brassicaceae Draba nemorosa (Woodland draba seed) Burseraceae Boswellia serrata Campanulaceae Codonopsis pilosula (Codonopsis Root) Caprifoliaceae Lonicera japonica (Lonicera leaf and stem) Caryophyllaceae Stellaria media (Chickweed) Combretaceae Terminalia chebula (Chebulic myrobalan) Convolvulaceae Cuscuta japonica (Japanese dodder seed) Cucurbitaceae Cucurbita moschata (Pumpkin seed) Gynostemma pentaphyllum (Jiaogulan, Amachazuru) Trichosanthes kirilowii (Trichosanthes seed) Copyright 2017 KEI Journals. All Rights Reserved Page │5 International Biology Review, Vol. 1, Issue 2, August 2017 Novel inhibitors for histidine decarboxylase from plant components Cupressaceae Juniperus communis (Common juniper) Dioscoreaceae Dioscorea mexicana (Mexican yam) Euphorbiaceae Euphorbia kansui Euphorbia lathyris (Caper spurge) Fabaceae Astragalus sinicus (Astragalus sinicus seed) Cassia mimosoides Dolichos lablab (Dolichos seed) Melilotus officinalis (Yellow sweet clover) Senna alexandrina (Alexandrian senna) Trifolium pretense (Red clover)
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