(10R,13R)-17-(6-Hy­droxy-5-methyl­heptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta­[a]phen­anthren-3-ol hemihydrate: a bioactive steroid isolated from the Indian herb Artemisia reticulata

The title tetra­cyclic steroidal compound, C27H46O2·0.5H2O, crystallized as a monohydrate with two independent mol­ecules (1 and 2) in the asymmetric unit. In both mol­ecules, the conformations of the three cyclo­hexane rings (A, B and C) are chair, half-chair and chair, respectively. The fourth ring, D, has a twisted conformation on the bond linking the D and C rings. The crystal structure is stabilized by hydrogen bonding with the two independent mol­ecules being linked through the solvent water mol­ecule via various O—H⋯O hydrogen bonds, forming layers parallel to (-101).

[1]  G. Sheldrick.  Crystal structure refinement with SHELXL , 2015, Acta crystallographica. Section C, Structural chemistry.

[2]  S. Parsons,et al.  Use of intensity quotients and differences in absolute structure refinement , 2013, Acta crystallographica Section B, Structural science, crystal engineering and materials.

[3]  H. Drury.  The Useful Plants of India: With Notices of Their Chief Value in Commerce, Medicine, and the Arts , 2010 .

[4]  Anthony L. Spek,et al.  Structure validation in chemical crystallography , 2009, Acta crystallographica. Section D, Biological crystallography.

[5]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[6]  T. Efferth,et al.  The anti-malarial artesunate is also active against cancer. , 2001, International journal of oncology.

[7]  M. Gyamfi,et al.  Antioxidant and hepatoprotective actions of the medicinal herb Artemisia campestris from the Okinawa Islands. , 2000, Biological & pharmaceutical bulletin.

[8]  A. Guantai,et al.  Cardiovascular Effect of Artemisia Afra and its Constituents , 1999 .

[9]  P. Newton,et al.  Malaria: new developments in treatment and prevention. , 1999, Annual review of medicine.

[10]  S. Yoganarasimhan.  Medicinal plants of India , 1996 .

[11]  P. Latha,et al.  Effects of Artemisia pallens Wall. on blood glucose levels in normal and alloxan-induced diabetic rats. , 1996, Journal of ethnopharmacology.

[12]  N. Singh,et al.  Selective cancer cell cytotoxicity from exposure to dihydroartemisinin and holotransferrin. , 1995, Cancer letters.

[13]  D. L. Klayman,et al.  Qinghaosu (artemisinin): an antimalarial drug from China , 1985 .

[14]  N. Acton,et al.  Isolation of artemisinin (qinghaosu) from Artemisia annua growing in the United States. , 1984, Journal of natural products.

[15]  G. Li,et al.  Clinical studies on treatment of cerebral malaria with qinghaosu and its derivatives. , 1982, Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan.

[16]  H. Drury.  The Useful Plants Of India , 1978 .

[17]  B. Craven,et al.  Crystal structure of cholesterol monohydrate , 1976, Nature.

[18]  N. G. Kovaleva,et al.  [Medicinal plants]. , 1954, Aptechnoe delo.