Crystal structure of a photobiologically active furanocoumarin from Artemisia reticulata
نویسندگان
چکیده
The title furan-ocoumarin, C14H12O4 [systematic name: 9-hy-droxy-2-(prop-1-en-2-yl)-2,3-di-hydro-7H-furo[3,2-g]chromen-7-one], crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The two mol-ecules differ essentially in the orientation of the propenyl group with respect to the mean plane of the furan-ocoumarin moiety; the O-C(H)-C=C torsion angle is 122.2 (7)° in mol-ecule A and -10.8 (11)° in mol-ecule B. In the crystal, the A and B mol-ecules are linked via O-H⋯O hydrogen bonds, forming zigzag -A-B-A-B- chains propagating along [001]. The chains are reinforced by bifurcated C-H⋯(O,O) hydrogen bonds, forming ribbons which are linked via C-H⋯π and π-π inter-actions [inter-centroid distance = 3.602 (2) Å], forming a three-dimensional structure.
منابع مشابه
Crystal structure of bergapten: a photomutagenic and photobiologically active furanocoumarin
The title compound, C12H8O4, is a furan-ocoumarin [systematic name: 4-meth-oxy-7H-furo[3,2-g]chromen-7-one], which was isolated from the Indian herb T. stictocarpum. The mol-ecule is almost planar with an r.m.s. deviation of 0.024 Å for the hetero atoms of the fused-ring system. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a three-dimensional framework. There are offse...
متن کاملCrystal structure of a bioactive sesquiterpene isolated from Artemisia reticulata
The title compound, C15H24O2 {systematic name: 1-[6-hy-droxy-7-(propan-2-yl)-4-methyl-idene-2,3,3a,4,5,6,7,7a-octa-hydro-1H-inden-1-yl]ethanone} was iso-la-ted from A. reticulata by column chromatography over silica gel by gradient solvent elution. The mol-ecule comprises a bi-cyclo-[4.3.0]nonane ring bearing acet-oxy, hy-droxy and isopropyl substituents, and an exocyclic double bond on the cyc...
متن کاملEvaluation of antioxidant activity and phenolic contents and identification of main compounds of various extracts from Artemisia aucheri aerial parts
Background and objectives: Artemisia aucheri Boiss. is regarded as one of 34 Artemisia species growing in Iran. The aim of this study was to undertake an investigation of the antioxidant activity as well as identification of main compound of different extracts and fractions of A. aucheri. Methods: Antioxidant activity and tot...
متن کاملCrystal structure of dibromomethoxyseselin (DBMS), a photobiologically active pyranocoumarin
The title compound, C15H14Br2O4 [systematic name: rac-(9S,10R)-3,9-dibromo-10-methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2(8H)-one], is a pyran-ocoumarin derivative formed by the bromination of seselin, which is a naturally occurring angular pyran-ocoumarin isolated from the Indian herb Trachyspermum stictocarpum. In the mol-ecule, the benzo-pyran ring system is essentially planar, w...
متن کاملCrystal structure of a photobiologically active brominated angular pyranocoumarin: bromo-hydroxy-seselin
The title compound, C14H13BrO3 [systematic name: rac-(9S,10R)-9-bromo-10-hy-droxy-8,8-dimethyl-9,10-di-hydro-2H,8H-pyrano[2,3-f]chromen-2-one], is a substituted pyran-ocoumarin, obtained by bromination of seselin [8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one], which was isolated from the Indian herb Trachyspermum stictocarpum (Aajmod). The pyrano ring has a distorted half-chair conformation an...
متن کامل