Modulatory Effect of Aliphatic Acid Amides from Zanthoxylum piperitum on Isolated Gastrointestinal Tract

Hashimoto, Kazunori; Satoh, Kaneo; Kase, Yoshio; Ishige, Atsushi; Kubo, Masayoshi; Sasaki, Hiroshi; Nishikawa, Shigeto; Kurosawa, Susumu; Yakabi, Koji; Nakamura, Takashi

doi:10.1055/s-2001-11513

Cited by 46 publications

(32 citation statements)

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“…Therefore, prolonged ingestion or topical application of capsaicinoids can be successful in managing painful conditions such as rheumatoid arthritis, osteoarthritis, diabetic neuropathy, postherpetic, neuralgia, postmastectomy pain syndrome, cluster headache, reflex sympathetic dystrophy and gastro-intestinal related problems like reflux and functional dyspepsia (Holzer, 2011;Philip and Thakur, 2011). On contrast, depending on the type of NAA, acute ingestion of NAAs induce gastric mobility via binding to the TRPV1 receptor (capsaicinoids), indirectly by releasing acethylcholine and other neurotransmitters or by acting directly on the smooth muscles (sanshools) (Hashimoto et al, 2001;Holzer, 2011).…”

Section: Othersmentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

137

109

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a b s t r a c tEthnopharmacological relevance: N-Alkylamides (NAAs) are a promising group of bioactive compounds, which are anticipated to act as important lead compounds for plant protection and biocidal products, functional food, cosmeceuticals and drugs in the next decennia. These molecules, currently found in more than 25 plant families and with a wide structural diversity, exert a variety of biologicalpharmacological effects and are of high ethnopharmacological importance. However, information is scattered in literature, with different, often unstandardized, pharmacological methodologies being used. Therefore, a comprehensive NAA database (acronym: Alkamid) was constructed to collect the available structural and functional NAA data, linked to their occurrence in plants (family, tribe, species, genus). Materials and methods: For loading information in the database, literature data was gathered over the period 1950-2010, by using several search engines. In order to represent the collected information about NAAs, the plants in which they occur and the functionalities for which they have been examined, a relational database is constructed and implemented on a MySQL back-end. Results: The database is supported by describing the NAA plant-, functional-and chemical-space. The chemical space includes a NAA classification, according to their fatty acid and amine structures. Conclusions: The Alkamid database (publicly available on the website http://alkamid.ugent.be/) is not only a central information point, but can also function as a useful tool to prioritize the NAA Q8 choice in the evaluation of their functionality, to perform data mining leading to quantitative structure-property relationships (QSPRs), functionality comparisons, clustering, plant biochemistry and taxonomic evaluations.

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Section: Othersmentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

137

109

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“…Hydroxy b -sanshool was isolated from the extract of Zanthoxylum fruit (Rutaceae, Zanthoxylum piperitum DE CANDOLLE, pericarpium) by the method described previously (10). Dai-kenchu-to extract powder {extracts in water from a 5:3:2 mixture of dried ginger root (Zingiberaceae, Zingiber officinale ROSCOE, rhizoma), ginseng (Araliaceae, Panax ginseng C.A.…”

Section: Drugsmentioning

confidence: 99%

“…It was reported that the contractile effect is due to the release of acetylcholine and other neurotransmitters (10). Natural pungent substances, capsaicin (red pepper), piperine (black pepper) and shogaol (ginger) have contractile effects on guinea pig ileum, and these effects were induced via release of substance P from sensory nerve endings (11 -15).…”

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Mechanism of Atropine-Resistant Contraction Induced by Dai-kenchu-to in Guinea Pig Ileum

Satoh

Hashimoto

Hayakawa

et al. 2001

Japanese Journal of Pharmacology

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ABSTRACT-To clarify the contractile mechanism of Dai-kenchu-to, the effects of hydroxy b -sanshool (an ingredient of Zanthoxylum fruit), Zanthoxylum fruit (a constituent herb of Dai-kenchu-to) and Daikenchu-to were studied in mucosa-free longitudinal muscle of guinea pig ileum. Hydroxy b -sanshool at 10 -7 -10 -5 g/ ml induced dose-related contractions accompanied by autonomous contraction and produced an initial contraction at a concentration of 10 -4 g/ml or more. The contraction induced by hydroxy b -sanshool (10 -5 g/ ml) was significantly inhibited by tetrodotoxin or the capsaicin-receptor antagonist capsazepine. Although atropine or the substance P antagonist spantide tended to inhibit the contraction, a combination of atropine and spantide almost abolished the contraction by hydroxy b-sanshool. The P2-purinoceptor antagonist pyridoxal-phosphate-6-azophenyl-2',4'-disulphonic acid did not affect hydroxy b-sanshool-induced contraction in the presence or absence of spantide. The tonic contractions by Zanthoxylum fruit (2´10 -4 g/ml) and Dai-kenchu-to (10 -3 g/ml) were significantly inhibited or tended to be inhibited by atropine, spantide, tetrodotoxin or capsazepine and were remarkably suppressed by the combination of atropine and spantide. These results suggested that acetylcholine release from intrinsic cholinergic nerves and tachykinins from sensory neurons are involved in the contractions induced by hydroxy b-sanshool and that tachykinins may be involved in the atropine-resistant contraction by Dai-kenchu-to.Keywords: Dai-kenchu-to, Zanthoxylum fruit, Hydroxy b-sanshool, Intestinal motility, Tachykinin Dai-kenchu-to (Da-Jian-Zhong-Tang in Chinese) is a traditional Chinese herbal medicine, called Kampo medicine in Japan, and is a mixture of Zanthoxylum fruit, ginseng, dried ginger root and malt sugar. This formula is known for clinical effects on intestinal obstruction subsequent to laparotomy (1, 2). In vivo studies have demonstrated that Dai-kenchu-to enhanced gastrointestinal motility in dogs and rabbits (2, 3), and prevented intestinal adhesion in rats (4). In experiments using isolated intestines, Daikenchu-to induced contractions in rabbit jejunum, guinea pig ileum and colon, and relaxed guinea pig gastric body (5 -8). These reports indicated that Zanthoxylum fruit induces contraction; however, the other constituent herbs had no significant contractile effect on the isolated intestine. In guinea pig ileum and colon, contractions due to Dai-kenchu-to and Zanthoxylum fruit are mediated by acetylcholine release from the ends of cholinergic nerves, and 5-HT4 receptors are involved (7,8). In addition, since we also noted that a mucosa-free preparation resists the contractile response to atropine (8), it was suggested that other neurotransmitters are involved in the contractile effect of Dai-kenchu-to.Hydroxy b-sanshool is considered to be one of the active compounds involved in inducing contraction by Zanthoxylum fruit (9, 10). It was reported that the contractile effect is due to the release of acetylch...

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“…Große chemische Ähnlichkeit besteht mit den Amiden des Szechuanpfeffers (Zanthoxylum spec., Rutaceae) [4,60,63,98,186,201,206 Auch Alkamide der Zanthoxylum-Species aus der Familie der Rutaceae weisen teilweise ähnliche bis identische Strukturen mit Acmella und anderen Vertretern der Ecliptinae (Asteraceae) auf [4,60,63,98,186,201,206]. Isobutyl-Rests stattfindet [4,122,186,187].…”

Section: Vergleich Der Pollenunclassified

Acmella Ciliata (H.B.K.) Cassini

Keipert¹,

Melzig²

2009

Z Phytother

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Modulatory Effect of Aliphatic Acid Amides from Zanthoxylum piperitum on Isolated Gastrointestinal Tract

Cited by 46 publications

References 0 publications

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Mechanism of Atropine-Resistant Contraction Induced by Dai-kenchu-to in Guinea Pig Ileum

Acmella Ciliata (H.B.K.) Cassini

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