Dataset Information

Ent-(15S)-Pimar-8(14)-ene-15,16-diol.

ABSTRACT: The title compound {systematic name: (S)-1-[(2S,4aR,8aR)-2,4b,8,8-tetra-methyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodeca-hydro-phenanthren-2-yl]ethane-1,2-diol}, C(20)H(34)O(2), is an ent-pimarane diterpenoid which was isolated from the stem bark of Ceriops tagal. In the asymmetric unit, there are two crystallographically independent mol-ecules, which are conformationally almost identical. In each mol-ecule, the two cyclo-hexane rings of the fused three-ring system adopt chair conformations, while the cyclo-hexene ring is in an envelope conformation, with the methylene C atom next to the side chain as the flap atom. In the crystal, mol-ecules are stacked in columns along the b axis through O-H?O hydrogen bonds.

SUBMITTER: Fun HK

PROVIDER: S-EPMC3275262 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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ent-(15S)-Pimar-8(14)-ene-15,16-diol.

Fun Hoong-Kun HK Chantrapromma Suchada S Pakhathirathien Charoen C Karalai Chatchanok C Chantrapromma Kan K

Acta crystallographica. Section E, Structure reports online 20120125 Pt 2

The title compound {systematic name: (S)-1-[(2S,4aR,8aR)-2,4b,8,8-tetra-methyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodeca-hydro-phenanthren-2-yl]ethane-1,2-diol}, C(20)H(34)O(2), is an ent-pimarane diterpenoid which was isolated from the stem bark of Ceriops tagal. In the asymmetric unit, there are two crystallographically independent mol-ecules, which are conformationally almost identical. In each mol-ecule, the two cyclo-hexane rings of the fused three-ring system adopt chair conformations, while the ...[more]

PMID: 22347118

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Project description:Background and purposeNew antileishmanials from natural products are urgently needed due to the emergence of drug resistance complicated by severe cytotoxic effects. 16alpha-Hydroxycleroda-3,13 (14)Z-dien-15,16-olide (Compound 1) from Polyalthia longifolia was found to be a potential antileishmanial and non-cytotoxic, as evidenced by long-term survival (>6 months) of treated animals. This prompted us to determine its target and, using molecular modelling, identify the interactions responsible for its specific antileishmanial activity.Experimental approachIn vitro activity of compound was assessed using intracellular transgenic green fluorescent protein-stably expressed Leishmania donovani parasites. In vivo activity and survival of animals post-treatment were evaluated in L. donovani-infected hamsters. Known property of clerodane diterpenes as potent human DNA topoisomerase inhibitors led us to evaluate the inhibition of recombinant L. donovani topoisomerase I using relaxation assay. Mode of cell death induced by Compound 1 was assessed by phosphotidylserine exposure post-treatment. Molecular modelling studies were conducted with DNA topoisomerase I to identify the binding interactions responsible for its activity.Key resultsBioassay-guided fractionation led to isolation of Compound 1 as a non-cytotoxic, orally active antileishmanial. Compound 1 inhibited recombinant DNA topoisomerase I which, ultimately, induced apoptosis. Molecular docking studies indicated that five strong hydrogen-bonding interactions and hydrophobic interactions of Compound 1 with L. donovani DNA-topoisomerase are responsible for its antileishmanial activity.Conclusions and implicationsThe data reveal Compound 1 is a potent and safe antileishmanial. The study further exploited the structural determinants responsible for its non-cytotoxic and potent activity, to raise the feasibility of specifically targeting the target enzyme responsible for its activity through rational drug design.

Dataset Information

Ent-(15S)-Pimar-8(14)-ene-15,16-diol.

Publications

ent-(15S)-Pimar-8(14)-ene-15,16-diol.

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