Isolation and structures of three new sesquiterpenes

Iguchi, Masanobu; Nishiyama, Atsuko; Koyama, H.; Yamamura, Shosuke; Hiratå, Yoshimasa

doi:10.1016/s0040-4039(00)75372-x

Cited by 31 publications

(12 citation statements)

References 18 publications

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“…They were previously identified in the rhizome oil of Acorus calamus from Japan. 21,22 Their mass spectra, as well as that of shyobunone 50, are shown in Figure 2.…”

Section: Commercial Oilmentioning

confidence: 99%

Identiﬁcation of the components of the essential oil from wild Corsican Daucus carota L. using ¹³C‐NMR spectroscopy

Gonny

Bradesi

Casanova

2004

Flavour & Fragrance J

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“…They were previously identified in the rhizome oil of Acorus calamus from Japan. 21,22 Their mass spectra, as well as that of shyobunone 50, are shown in Figure 2.…”

Section: Commercial Oilmentioning

confidence: 99%

Identiﬁcation of the components of the essential oil from wild Corsican Daucus carota L. using ¹³C‐NMR spectroscopy

Gonny

Bradesi

Casanova

2004

Flavour & Fragrance J

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“…[30][31][32][33][34][35][36][37] Compounds 1 and 3-6 have been previously isolated from A. calamus. [38][39][40][41] Their spectroscopic data are given as Supporting…”

Section: Resultsmentioning

confidence: 99%

Positive GABA_A Receptor Modulators from Acorus calamus and Structural Analysis of (+)-Dioxosarcoguaiacol by 1D and 2D NMR and Molecular Modeling

et al. 2011

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In a two-microelectrode voltage clamp with Xenopus laevis oocytes, a petroleum ether extract of Acorus calamus rhizomes enhanced the GABA-induced chloride current through GABA A receptors of the α 1 β 2 γ 2S subtype by 277% ± 9.7% (100 μg/mL). β-Asarone (1), (+)-dioxosarcoguaiacol (2), (+)-shyobunone (3), and (+)-preisocalamenediol (4) were subsequently identified as main active principles through HPLC-based activity profiling and targeted isolation. The compounds induced maximum potentiation of the chloride current ranging from 588% ± 126% (EC 50 : 65.3 ± 21.6 μM) (2) to 1200% ± 163% (EC 50 : 171.5 ± 34.6 μM) (1), whereas (−)-isoshyobunone (5) and (−)-acorenone (6) exhibited weak GABA A modulating properties (5: 164% ± 42.9%; EC 50 : 109.4 ± 46.6 μM and 6: 241% ± 23.1%; EC 50 : 34.0 ± 6.7 μM). The relative configuration of 2 was established as 4R*8S*10R* by NOESY experiments and conformational analysis.Acorus calamus L. (Acoraceae), commonly known as "sweet flag", is a polyploidic marsh plant indigenous to Asia and is now distributed along trade routes all over the northern hemisphere. 1 The aromatic rhizome has been widely used as an herbal remedy. It contains 1.7-9.3% of a volatile oil composed of monoterpenes, sesquiterpenes, and phenylpropanoids. The most characteristic constituent of the oil is β-asarone, even though Europe PMC Funders GroupAuthor Manuscript J Nat Prod. Author manuscript; available in PMC 2011 October 24. Europe PMC Funders Author ManuscriptsEurope PMC Funders Author Manuscripts its concentration may vary considerably (96% in the tetraploidic form found in eastern and tropical southern Asia, 5% in the triploidic form found in Europe, Himalayan, and temperate Indian regions, and 0% in the diploidic variety growing from North America to Siberia). [1][2][3][4] In European folk medicine, A. calamus rhizomes have been mainly used as "Amarum aromaticum" to alleviate gastrointestinal ailments such as acute and chronic dyspepsia, gastritis and gastric ulcer, intestinal colic, and anorexia. 5,6 Ayurvedic medicine and traditional Chinese medicine (TCM) use the drug preferably to treat central nervous system (CNS) related diseases such as epilepsy, insanity, mental weakness, or insomnia. 7-9 Several in vivo studies support a sedative and tranquillizing action of the essential oil and of ethanolic and aqueous extracts of A. calamus. [10][11][12] Up to now, the underlying mechanism of action has remained elusive despite various investigations, even though the pharmacological effect could be mainly attributed to α-asarone and β-asarone. 11,[13][14][15] GABA A receptors are pentameric ligand-gated chloride ion channels that are activated by GABA, the major inhibitory neurotransmitter in the CNS. Most likely more than 11 different receptor subtypes, assembled from five varying subunits, exist in the human brain. These are involved in distinct neuronal circuits and are targeted by numerous classes of drugs such as benzodiazepines, barbiturates, and some general anesthetics. The most abundant GABA...

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“…This essential oil shows large variations in its chemical composition in relation with its geographical origin and the polyploidy of the plant, particularly impacting its content of ␤-asarone and other toxic methoxylated phenylpropanoids [24][25][26][27]. The essential oil of A. calamus (shyobu in japanese) was originally described by Iguchi et al to contain a series of sesquiterpenic ketones sharing the same basic elemane skeleton, named shyobunones [28,29]. So far, five (stereo)isomers could be characterized.…”

Section: Dynamic Interconversion Of Shyobunones In Calamus Oilmentioning

confidence: 99%

“…In these early studies, shyobunones were reported as undergoing a thermally-induced isomerization during GC analysis [28]. The two main epimers-named at that time shyobunone 1 and 2-epishyobunone 2-were described to interconvert by epimerization in position-2 when exposed to heat.…”

Section: Dynamic Interconversion Of Shyobunones In Calamus Oilmentioning

confidence: 99%

Peak-bridges due to in-column analyte transformations as a new tool for establishing molecular connectivities by comprehensive two-dimensional gas chromatography–mass spectrometry

Filippi

Cocolo²,

Meierhenrich

2015

Journal of Chromatography A

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Isolation and structures of three new sesquiterpenes

Cited by 31 publications

References 18 publications

Identiﬁcation of the components of the essential oil from wild Corsican Daucus carota L. using ¹³C‐NMR spectroscopy

Identiﬁcation of the components of the essential oil from wild Corsican Daucus carota L. using ¹³C‐NMR spectroscopy

Positive GABA_A Receptor Modulators from Acorus calamus and Structural Analysis of (+)-Dioxosarcoguaiacol by 1D and 2D NMR and Molecular Modeling

Peak-bridges due to in-column analyte transformations as a new tool for establishing molecular connectivities by comprehensive two-dimensional gas chromatography–mass spectrometry

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Isolation and structures of three new sesquiterpenes

Cited by 31 publications

References 18 publications

Identiﬁcation of the components of the essential oil from wild Corsican Daucus carota L. using 13C‐NMR spectroscopy

Identiﬁcation of the components of the essential oil from wild Corsican Daucus carota L. using 13C‐NMR spectroscopy

Positive GABAA Receptor Modulators from Acorus calamus and Structural Analysis of (+)-Dioxosarcoguaiacol by 1D and 2D NMR and Molecular Modeling

Peak-bridges due to in-column analyte transformations as a new tool for establishing molecular connectivities by comprehensive two-dimensional gas chromatography–mass spectrometry

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Product

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Identiﬁcation of the components of the essential oil from wild Corsican Daucus carota L. using ¹³C‐NMR spectroscopy

Identiﬁcation of the components of the essential oil from wild Corsican Daucus carota L. using ¹³C‐NMR spectroscopy

Positive GABA_A Receptor Modulators from Acorus calamus and Structural Analysis of (+)-Dioxosarcoguaiacol by 1D and 2D NMR and Molecular Modeling