secoiridoid

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iridoid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/12/29 11:57:55」(JST)

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Chemical structure of iridomyrmecin

Iridoids are a class of secondary metabolites found in a wide variety of plants and in some animals. They are monoterpenes biosynthesized from isoprene and they are often intermediates in the biosynthesis of alkaloids. Chemically, the iridoids usually consist of a cyclopentane ring fused to a six-membered oxygen heterocycle. The chemical structure is exemplified by iridomyrmecin, a defensive chemical produced by the Iridomyrmex genus, for which iridoids are named. Cleavage of a bond in the cyclopentane ring gives rise to a subclass known as seco-iridoids, such as amarogentin. Iridoids are typically found in plants as glycosides, most often bound to glucose.

Iridoids are found in many medicinal plants and may be responsible for some of their pharmaceutical activities. Isolated and purified, iridoids exhibit a wide range of bioactivities including cardiovascular, antihepatotoxic, choleretic, hypoglycemic, analgesic, anti-inflammatory, antimutagenic, antispasmodic, antitumor, antiviral, immunomodulator, and purgative activities.

The iridoids are produced by plants primarily as a defense against herbivores or against infection by microorganisms. To humans and other mammals, iridoids are often characterized by a deterrent bitter taste.

Aucubin and catalpol are two of the most common iridoids in the plant kingdom. Iridoids are prevalent in the plant subclass Asteridae, such as Ericaceae, Loganiaceae, Gentianaceae, Rubiaceae, Verbenaceae, Lamiaceae, Oleaceae, Plantaginaceae, Scrophulariaceae, Valerianaceae, and Menyanthaceae.

References

English Journal

• Centauries as underestimated food additives: Antioxidant and antimicrobial potential.

• Siler B, Zivković S, Banjanac T, Cvetković J, Nestorović Živković J, Cirić A, Soković M, Mišić D.SourceInstitute for Biological Research "Siniša Stanković", University of Belgrade, Bulevar despota Stefana 142, 11060 Belgrade, Serbia.
• Food chemistry.Food Chem.2014 Mar 15;147:367-76. doi: 10.1016/j.foodchem.2013.10.007. Epub 2013 Oct 11.
• Methanol extracts of aerial parts and roots of five centaury species (Centaurium erythraea, C. tenuiflorum, C. littorale ssp. uliginosum, C. pulchellum, and Schenkia spicata) were analysed for their main secondary metabolites: secoiridoid glycosides, a group of monoterpenoid compounds, and phenolics
• PMID 24206732

• New secoiridoids from the fruits of Ligustrum lucidum Ait with triglyceride accumulation inhibitory effects.

• Zhang Y, Liu L, Gao J, Wu C, Han L, Liu E, Shi P, Gao X, Wang T.SourceTianjin State Key Laboratory of Modern Chinese Medicine, 312 Anshanxi Road, Nankai District, Tianjin, 300193, China.
• Fitoterapia.Fitoterapia.2013 Dec;91:107-12. doi: 10.1016/j.fitote.2013.08.022. Epub 2013 Aug 31.
• Five new secoiridoids, nuzhenal C (1), 6'-O-trans-cinnamoyl iso-8-epikingisidic acid (2), ligulucidumosides A (3), B (4), and C (5), were obtained from the fruits of Ligustrum lucidum Ait. Their structures were elucidated by chemical and spectroscopic methods (UV, IR, HRESI-TOF-MS, 1D and 2D NMR). A
• PMID 24001714

• Rigenolide A, a new secoiridoid glucoside with a cyclobutane skeleton, and three new acylated secoiridoid glucosides from Gentiana rigescens Franch.

• Suyama Y, Kurimoto S, Kawazoe K, Murakami K, Sun HD, Li SL, Takaishi Y, Kashiwada Y.SourceGraduate school of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi,Uncorrected proof. Tokushima 770-8505, Japan.
• Fitoterapia.Fitoterapia.2013 Dec;91:166-72. doi: 10.1016/j.fitote.2013.08.006. Epub 2013 Aug 27.
• Rigenolide A (1), a new secoiridoid glucoside with a cyclobutane skeleton and three new acylated secoiridoid glucosides, 2'-(2,3-dihydroxybenzoyl)-gentiopicroside (2), 2'-(2,3-dihydroxybenzoyl)-swertiamarin (3), 3'-(2,3-dihydroxybenzoyl)-sweroside (4), along with two noriridoids (7 and 8) and two kn
• PMID 23994629

Japanese Journal

• Secoiridoid glycosides from the root of Gentiana crassicaulis with inhibitory effects against LPS-induced NO and IL-6 production in RAW264 macrophages

• Journal of natural medicines 69(3), 366-374, 2015
• NAID 40020494383

• The anti-inflammatory secoiridoid glycosides from Gentianae Scabrae Radix : the root and rhizome of Gentiana scabra

• Journal of natural medicines 69(3), 303-312, 2015
• NAID 40020494283

• Dipasperoside A, a Novel Pyridine Alkaloid-Coupled Iridoid Glucoside from the Roots of Dipsacus asper

• Chemical and Pharmaceutical Bulletin 61(12), 1318-1322, 2013
• NAID 130003381796

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