Abstract

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 cyclo-hexane ring. In the bicyclic skeleton, the cyclo-hexane ring adopts a chair conformation ring and the cyclo-pentane ring is in an envelope conformation. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains along [010]. These chains are cross-linked by C-H⋯O hydrogen bonds.

Highlights

  • The cyclohexane ring adopts a chair conformation ring and the cyclopentane ring is in an envelope conformation

  • The title compound is a natural product, which has been isolated from the Indian herb A. reticulata by column chromatography over silica gel

  • The Artemisia species are a rich source of bioactive sesquiterpenenoids (Klayman et al, 1984) such as artemisinin, artemisin etc

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Summary

Chemical context

The title compound is a natural product, which has been isolated from the Indian herb A. reticulata by column chromatography over silica gel. A. reticulata (family: Asteraceae) is a traditional herb which has many applications in folklore medicine for conventional therapy against several diseases such as malaria (Klayman et al, 1984; Malagon et al., 1997; Newton & White, 1999), cancer (Efferth et al, 2001; Lai et al, 1995), cardiovascular (Guantai et al, 1999), vasodilatory (Walker, 1996), hepatitis (Aniya et al, 2000) and diabetes (Iriadam et al, 2006) It is found as a constituent in many ayurvedic or herbal drug preparations such as forkolin and Afsanteen in Indian traditional medicinal systems (Nadkarni, 1954; Satyavati et al, 1987; Subramoniam et al., 1996; Drury, 1978). Our group are currently searching for artemisin, artemisinin or their analogues from other varieties of Artemisia species and as part of these studies, the structure of the title compound is reported

Structural commentary
Synthesis and crystallization
Database survey
Refinement
Full Text
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