(±)-Acortatarinowins A-F, Norlignan, Neolignan, and Lignan Enantiomers from Acorus tatarinowii

J Nat Prod. 2015 Sep 25;78(9):2205-14. doi: 10.1021/acs.jnatprod.5b00328. Epub 2015 Aug 25.

Abstract

Three pairs of new 8-O-4'-type dinorneolignan enantiomers, (±)-acortatarinowins A-C (1a/1b-3a/3b), a pair of new 8-O-4'-type (4a/4b) and a pair of rare C7-C8'-type (5a/5b) neolignan enantiomers, (±)-acortatarinowins D and E, and a pair of new furofuran-type lignan enantiomers, (±)-acortatarinowin F (6a/6b), along with two pairs of known lignan enantiomers (7a/7b and 8a/8b), were obtained from the rhizomes of Acorus tatarinowii. The separation of 1-8 by chiral HPLC using a Daicel IC column led to the isolation of eight pairs of enantiomers, 1a/1b-8a/8b, which had variable enantiomeric excess (ee) values of approximately 66, 71, 63, 60, 0, 38, 48, and 75%, respectively. The structures were elucidated by extensive spectroscopic and chemical methods, and their absolute configurations were determined by a combined analysis of single-crystal X-ray diffraction and a modified Mosher's method, assisted by experimental and calculated electronic circular dichroism data. Among them, compounds 1a, 3a, 6b, 8a, and 8b showed weak inhibitory activities against NO production in activated macrophages with IC50 values ranging from 23.3 to 38.0 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acorus / chemistry*
  • Animals
  • Chromatography, High Pressure Liquid
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Inhibitory Concentration 50
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Rhizome / chemistry
  • Stereoisomerism

Substances

  • Drugs, Chinese Herbal
  • Lignans
  • Nitric Oxide