Chavicol β-d-glucoside, a phenylpropanoid heteroside, benzyl-β-d-glucoside and glycosidically bound volatiles from subspecies of Cedronella canariensis

Coen, Matthias; Engel, Ralf; Nahrstedt, Adolf

doi:10.1016/0031-9422(95)00241-x

Cited by 23 publications

(14 citation statements)

References 22 publications

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“…Additionally, 26 known compounds were assigned as acacetin-7- O -(2″- O -acetyl-6″- O -malonyl)-β- d -glucopyranoside ( 2 ), acacetin-7 -O -(6″- O -malonyl) - β- d -glucopyranoside ( 3 ), acacetin-7- O -(3″- O -acetyl)-β- d -glucopyranoside ( 4 ), isoagastachoside ( 5 ), diosmetin-7- O -β- d -glucopyranoside ( 6 ), acacetin-7- O -β- d -glucopyranoside ( 7 ), apigetrin ( 8 ), luteoloside ( 9 ), diosmetin ( 10 ), acacetin ( 11 ), apigenin ( 12 ), luteolin ( 13 ), phlorizin ( 16 ), 1-hydroxy-2- O -β- d -glucopyranosyl-4-allylbenzene ( 19 ), 1- O -β- d -glucopyranosyl-2-hydroxy-4-allylbenzene ( 20 ), chavicol-β- d -glucopyranoside ( 21 ), citrusin C ( 22 ), (2 S )-poncirenin ( 23 ), (6 R ,7 E ,9 R )-9-hydroxymegastigma-4,7-dien-3-one-9- O -β- d -glucopyranoside ( 24 ), rosmarinic acid ( 25 ), methyl rosmarinate ( 26 ), ethyl rosmarinate ( 27 ), nepetoidin B ( 28 ), methyl caffeate ( 29 ), ethyl caffeate ( 30 ), and anisic acid ( 31 ) . Compounds 3 , 4 , 10 , 23 , 27 , 28 , and 30 were isolated from A. rugosa for the first time.…”

Section: Resultsmentioning

confidence: 99%

Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

et al. 2019

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A new flavone glucoside, acacetin-7-O-(3″-O-acetyl-6″-O-malonyl)-β-d-glucopyranoside (1), two new phenolic glucosides, (3R,7R)-tuberonic acid-12-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (14) and salicylic acid-2-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (15), and two new phenylpropanoid glucosides, chavicol-1-O-(6′-O-methylmalonyl)-β-d-glucopyranoside (17) and chavicol-1-O-(6′-O-acetyl)-β-d-glucopyranoside(18), as well as 26 known compounds, 2–13, 16, and 19–31, were isolated from the aerial parts of Agastache rugose. The structures of the new compounds were established by spectroscopic/spectrometric methods such as HRESIMS, NMR, and ECD. The anti-inflammatory effect of the isolated compounds was evaluated by measuring their inhibitory activities on prostaglandin E2 (PGE2) in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. New compounds 1, 15, 17, and 18 inhibited LPS-induced PGE2 production with IC50 values of 16.8 ± 0.8, 33.9 ± 4.8, 14.3 ± 2.1, and 48.8 ± 4.4 μM, respectively. Compounds 5, 7, 9−11, 13, 19, 20, 22, and 27–30 showed potent inhibitory activities with IC50 values of 1.7–8.4 μM.

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Section: Resultsmentioning

confidence: 99%

Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

et al. 2019

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“…In addition to this, signals of an allylic side chain (terminal olefinic proton at δ 5.08 ppm; multiplet at δ 6.01 ppm and doublet at δ 3.35 ppm) were also detected and the structure of compound 21 was confirmed to be chavicol-β- d -glucopyranoside, a compound previously isolated from Cedronella canariensis (L.) Webb and Berth. (Lamiaceae) [18] and Alpinia officinarum Hance (Zingiberaceae) [19].…”

Section: Resultsmentioning

confidence: 99%

Phenylalkanoid Glycosides (Non-Salicinoids) from Wood Chips of Salix triandra × dasyclados Hybrid Willow

Dias

Bellisai

et al. 2019

Molecules

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Salix triandra (almond leaved willow) is an established crop, grown in coppicing regimes for basket-making materials. It is known as a source of non-salicinoid phenolic glycosides, such as triandrin and salidroside. A spontaneous natural hybrid of S. triandra and S. dasyclados was subjected to metabolite profiling by high resolution LC-MS, and 22 phenolic glycosides, including 18 that are new to the Salicaceae, were identified. Structures were determined by HPLC isolation and NMR methods. The hybridisation process has introduced novel chemistry into the Salix phenolic glycoside palette, in particular, the ability to generate disaccharide conjugates where the glycosyl group is further extended by a range of sugars, including apiose, rhamnose, xylose, and arabinose. Also of note is the appearance of chavicol derivatives, also not previously seen in Salix spp. The work demonstrates the plasticity of the phenolic glycoside biosynthetic pathway, and the potential to improve established crops such as S. triandra and S. dasyclados, via high-value metabolites, for both basketry and bioenergy markets.

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“…The following instruments were used to obtain physical data: specific rotations, Horiba SEPA-300 digital polarimeter (lϭ5 cm); UV spectra, Shimadzu UV-1600 spectrometer; IR spectra, Shimadzu FTIR-8100 spectrometer; EI-MS and high-resolution MS, JEOL JMS-GCMATE mass spectrometer; 1 H-NMR spectra, JNM-LA500 (500 MHz) spectrometer; 13 C-NMR spectra, JNM-LA500 (125 MHz) spectrometer with tetramethylsilane as an internal standard; and HPLC detector, Shimadzu RID-6A refractive index detector.…”

Section: Methodsmentioning

confidence: 99%

Inhibitors of Nitric Oxide Production from the Rhizomes of Alpinia galanga: Structures of New 8-9' Linked Neolignans and Sesquineolignan

et al. 2005

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The 80% aqueous acetone extract from the rhizomes of Alpinia galanga showed nitric oxide (NO) production inhibitory activities in mouse peritoneal macrophages. From the aqueous acetone extract, three new 8-9 linked neolignans, galanganal, galanganols A and B, and a sesquineolignan, galanganol C, were isolated together with nine known phenylpropanoids and p-hydroxybenzaldehyde. The structures of new neolignans were determined on the basis of physicochemical and chemical evidence. In addition, the inhibitory effects of the constituents from the rhizomes of A. galanga on NO production induced by lipopolysaccharide in mouse peritoneal macrophages were examined. Among them, galanganal (IC 50 ‫86؍‬ m mM), galanganols B (88 m mM) and C (33 m mM), 1S-1-acetoxychavicol acetate (2.3 m mM), 1S-1-acetoxyeugenol acetate (11 m mM), trans-p-hydroxycinnamaldehyde (ca. 20 m mM), trans-p-coumaryl alcohol (72 m mM), and trans-p-coumaryl diacetate (19 m mM) were found to show inhibitory activity.

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Chavicol β-d-glucoside, a phenylpropanoid heteroside, benzyl-β-d-glucoside and glycosidically bound volatiles from subspecies of Cedronella canariensis

Cited by 23 publications

References 22 publications

Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Phenylalkanoid Glycosides (Non-Salicinoids) from Wood Chips of Salix triandra × dasyclados Hybrid Willow

Inhibitors of Nitric Oxide Production from the Rhizomes of Alpinia galanga: Structures of New 8-9' Linked Neolignans and Sesquineolignan

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Chavicol β-d-glucoside, a phenylpropanoid heteroside, benzyl-β-d-glucoside and glycosidically bound volatiles from subspecies of Cedronella canariensis

Cited by 23 publications

References 22 publications

Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E2 Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E2 Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Phenylalkanoid Glycosides (Non-Salicinoids) from Wood Chips of Salix triandra × dasyclados Hybrid Willow

Inhibitors of Nitric Oxide Production from the Rhizomes of Alpinia galanga: Structures of New 8-9' Linked Neolignans and Sesquineolignan

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Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages