Crystal Structure of Sandaracopimaric Acid, a Lipoxygenase Inhibitor from Juniperus phoenicea

Comte, Gilles; Allais, Daovy; Simon, A.; Es-Saady, D.; Chulia, Albert J.; Delage, Christiane; Saux, M.

doi:10.1021/np50116a012

Cited by 14 publications

(7 citation statements)

References 5 publications

(6 reference statements)

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“…For background to the biological activity of diterpenoids, see: Atta-ur-Rahman & Choudhary (1999); Azucena & Mobashery (2001); Panter et al (2002); Ulusu et al (2002). For their use in traditional medicine, see: Bellakhdar (1997) and for their medicinal properties, see: Barrero et al (2003); Comte et al (1995); Evidente et al (1997). For the synthesis see: Zeroual et al (2007).…”

Section: Related Literaturementioning

confidence: 99%

“…In our study, we were interested to the medicinal plant, Tetraclinis articulata which is used in Moroccan traditional medicine (Bellakhdar, 1997). Some of its oxygenated compounds are effective as an antifongic (Evidente et al, 1997), cytotoxic (Comte et al, 1995) and inhibit various human leukocyte functions (Barrero et al, 2003). In order to isolate similar compounds, we have studied the chloroform extract of Tetraclinis articulata wood.…”

Section: S1 Commentmentioning

confidence: 99%

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7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-4a,9,10,10a-tetrahydro-phenanthren-2(1H)-one

et al. 2011

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The title compound, C20H26O2, was isolated from a chloroform extract of Tetraclinis articulata wood. The molecule contains three fused rings which exhibit different conformations. The non-aromatic oxo-substituted ring has a screw-boat conformation, while the central ring has a half-chair conformation. In the crystal, molecules are linked to each other by intermolecular O—H⋯O hydrogen bonds involving the carbonyl and hydroxy groups.

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Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-4a,9,10,10a-tetrahydro-phenanthren-2(1H)-one

et al. 2011

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“…For related literature, see: Atta-Ur- Rahman & Choudary (1999); Barrero et al (2003); Bellakhdar (1997); Comte et al (1995); Cremer & Pople (1975); Evidente et al (1997); Lawsen et al (1988); Macias et al (2000); Panter et al (2002); Vlietinck (1987); Zeroual et al (2007).…”

Section: Related Literaturementioning

confidence: 99%

“…In our study, we are interested to the aromatic and medicinal plant: Tetraclinis articulata which was subsequently used in traditional medicine (Bellakhdar, 1997). Some of its oxygenated compounds are effective as an antibiotic (Vlietinck, 1987), antifongic (Evidente et al, 1997), cytotoxic (Comte et al, 1995) and inhibit various human leukocyte functions (Barrero et al, 2003). In order to isolate similar compounds, we have studied the hexanic extract of Tetraclinis articulata wood.…”

Section: S1 Commentmentioning

confidence: 99%

(4aS,10aR)-7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-one

Zeroual¹,

Mazoir²,

Berraho³

et al. 2007

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 298 K; mean (C-C) = 0.003 Å; R factor = 0.045; wR factor = 0.125; data-to-parameter ratio = 12.3.The title compound, C 20 H 28 O 2 , is a new totarolone which was isolated from Tetraclinis articulata wood. The molecule forms an extended sheet of three fused rings which exhibit different conformations. The non-aromatic oxo-substituted ring has a screw boat conformation, while the central ring has a halfchair conformation. Molecules are linked to each other by intermolecular O-HÁ Á ÁO hydrogen bonds involving carbonyl and hydroxyl groups.

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“…Thus, I was identified as a new natural compound 9-O-j3-n-glucopyranoside-3 ,4,5-trimethoxycinnamyl alcohol, named juniperoside. Identification of rosarin (2) and skimmin (3) isolated from the same acetone extract of J. plicenicea was achieved by NMR comparison (10,11). However, the structural data given for rosarin in the literature (10) were only based on a 'H-NMR experiment.…”

mentioning

confidence: 99%

Phenylpropane Glycosides fromJuniperus phœnicea

Comte

Chulia²,

Vercauteren³

et al. 1996

Planta Med

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Juniperoside, a new 9-O[beta- D-glucopyranoside]-3,4,5-trimethoxycinnamyl alcohol has been isolated along with the 9- O-[alpha-L-arabinofuranosyl-(1-->6)-beta- D-glucopyranoside]cinnamyl alcohol (rosarin) and coumarin 7- O-beta- D-glucopyranoside (skimmin) from the acetone extract of the aerial parts of Juniperus phoenicea L. The structure elucidation of these natural products was achieved mainly by mass and NMR spectroscopy.

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Crystal Structure of Sandaracopimaric Acid, a Lipoxygenase Inhibitor from Juniperus phoenicea

Cited by 14 publications

References 5 publications

7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-4a,9,10,10a-tetrahydro-phenanthren-2(1H)-one

7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-4a,9,10,10a-tetrahydro-phenanthren-2(1H)-one

(4aS,10aR)-7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-one

Phenylpropane Glycosides fromJuniperus phœnicea

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Crystal Structure of Sandaracopimaric Acid, a Lipoxygenase Inhibitor from Juniperus phoenicea

Cited by 14 publications

References 5 publications

7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-4a,9,10,10a-tetrahydro-phenanthren-2(1H)-one

7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-4a,9,10,10a-tetrahydro-phenanthren-2(1H)-one

(4aS*,10aR*)-7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-one

Phenylpropane Glycosides fromJuniperus phœnicea

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(4aS,10aR)-7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-one