Crystal structure of methyl 8-hydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylate, C21H34O3

Brito, Iván; Bórquez, Jorge; Simirgiotis, Mario J.; Cárdenas, Alejandro; Molina-Salinas, Gloria María; Jerz, Gerold; Peña‐Rodríguez, Luis M.; Winterhalter, Peter

doi:10.1515/ncrs-2015-0197

Cited by 2 publications

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“…The A/B and B/C rings are trans and cis fused respectively. The main differences between the title compound and the similar compounds 17,24 are in the conformation of the C ring, (chair in both compounds). In other closely related compounds, the conformation of the rings A, B and C are retained respect to of the title compound 22,23 .…”

Section: Resultsmentioning

confidence: 98%

CRYSTAL AND MOLECULAR STRUCTURE OF 14α-ACETOXY-13α-HYDROXYMULIN-11-EN-20-OIC ACID MONOHYDRATE

Brito

Bórquez

Muñoz

et al. 2018

J. Chil. Chem. Soc.

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The structure of this 14α-acetoxy-13α-hydroxymulin-11-en-20-oic acid monohydrate consists of a mulinane skeleton and the corresponding isopropyl, methyl, carboxyl and methyl groups at C3, C8, C5, C13, respectively, which are β-oriented, whereas the hydroxyl and acetoxy groups at C13 and C-14 are α-oriented. The cyclopentane (A), cyclohexane (B) and cycloheptene (C) rings are trans (A/B) and (B/C) cis fused, and in an envelope, chair, and twist conformation respectively. In the crystal the organic molecules are linked by the water molecules by two intermolecular OH⋅⋅⋅O hydrogen bond forming 1D-dimensional chains with graph-set notation (9).

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Section: Resultsmentioning

confidence: 98%

CRYSTAL AND MOLECULAR STRUCTURE OF 14α-ACETOXY-13α-HYDROXYMULIN-11-EN-20-OIC ACID MONOHYDRATE

Brito

Bórquez

Muñoz

et al. 2018

J. Chil. Chem. Soc.

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Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C₁₉H₁₈O₈

Brito

Bórquez

Simirgiotis

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 19 H 18 O 8 , monoclinic, P2 1 /c (no. 14), a = 12.689(2) Å, b = 20.321(4) Å, c = 7.0820(13) Å, β = 105.368(13)°, V = 1760.8(6) Å 3 , Z = 4, R gt = 0.0662, wR ref (F 2 ) = 0.1788, T = 295 K. CCDC no.: 1581467The title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement con- ditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound is a highly biologically active polymethoxylated flavonoid, which is anti-inflammatory and antiproliferative [1, 2], can inhibit leukocyte chemotaxis and oxygen free radical formation [3,4] and prevents cyclophosphamide and ifosfamide-induced hemorrhagic cystitis in rats [5]. The title compound was isolated using medium pressure column chromatography (MPCC) from Parastrephia quadrangularis, a medicinal plant used by the Aymara Amerindians [6,7], a known producer of several flavonoids and benzoic acid derivatives with antioxidant activity [8][9][10][11]. Following our program to isolate interesting metabolites from the Atacama Desert Flora, Northern Chile [12][13][14][15][16][17][18], dried aerial parts of P. quadrangularis (1622 g) collected in april 2015 in "El Tatio", Andean mountain range of the of Atacama Desert, II Region, Northern Chile, were defatted with hexane (3 liters, 3 times in the dark, 24 hours each time) and 54.82 g were obtained after evaporation of the solvent. Then the plant material was extracted with ethyl acetate (3 liters, 3 times in the dark, 24 hours each time. After evaporation of the solvent under vacuo at 40 o C, 485 g of a dark gummy extract was obtained. A portion of the extract (10.0 g) was filtered and submitted to a medium pressure column chromatography system composed of an 2.5 cm × 48 cm medium pressure column packed with silicagel using an isocratic solvent system of

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Crystal structure of methyl 8-hydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylate, C₂₁H₃₄O₃

Cited by 2 publications

References 17 publications

CRYSTAL AND MOLECULAR STRUCTURE OF 14α-ACETOXY-13α-HYDROXYMULIN-11-EN-20-OIC ACID MONOHYDRATE

CRYSTAL AND MOLECULAR STRUCTURE OF 14α-ACETOXY-13α-HYDROXYMULIN-11-EN-20-OIC ACID MONOHYDRATE

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C₁₉H₁₈O₈

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Crystal structure of methyl 8-hydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylate, C21H34O3

Cited by 2 publications

References 17 publications

CRYSTAL AND MOLECULAR STRUCTURE OF 14&#945;-ACETOXY-13&#945;-HYDROXYMULIN-11-EN-20-OIC ACID MONOHYDRATE

CRYSTAL AND MOLECULAR STRUCTURE OF 14&#945;-ACETOXY-13&#945;-HYDROXYMULIN-11-EN-20-OIC ACID MONOHYDRATE

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C19H18O8

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Crystal structure of methyl 8-hydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylate, C₂₁H₃₄O₃

CRYSTAL AND MOLECULAR STRUCTURE OF 14α-ACETOXY-13α-HYDROXYMULIN-11-EN-20-OIC ACID MONOHYDRATE

CRYSTAL AND MOLECULAR STRUCTURE OF 14α-ACETOXY-13α-HYDROXYMULIN-11-EN-20-OIC ACID MONOHYDRATE

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C₁₉H₁₈O₈