Diterpenoids with diverse carbon skeletons from the roots of Pieris formosa and their analgesic and antifeedant activities

Bioorg Chem. 2020 Jan:95:103502. doi: 10.1016/j.bioorg.2019.103502. Epub 2019 Dec 23.

Abstract

Seven new diterpenoids, including four ent-kaurane-type pierisentkaurans B-E (1-4), one 4,5-seco- ent-kaurane-type pierisentkauran F (5), two leucothane-type 3β,7α,14β-trihydroxy-leucoth-10(20),15-dien-5-one (6) and 10α,16α-dihydroxy-leucoth-5-one (7), along with three known diterpenoids ent-kaurane-type 16α-dihydroxy-6-oxo-ent-kauran-18-oic-acid (8), kalmane-type rhodomollein XXIII (9), and grayanane-type pierisformosoid J (10), were isolated from the roots of Pieris formosa. Their structures with absolute configurations were determined by a series of spectroscopic methods and electronic circular dichroism (ECD) calculations. Compounds 2 and 7 displayed weak analgesic activity at a dose of 5.0 mg/kg (i.p.) compared to the vehicle tests (p < 0.05) in an acetic acid-induced writhing test. At a dose of 0.5 mg/mL, compounds 3 and 7 showed antifeedant activity against Plutella xylostella larvae with inhibition ratios of 27.1% and 52.5%, respectively.

Keywords: Anagesic; Antifeedant; Diterpenoids; Ent-kaurane; Grayanane; Kalmane; Leucothane; Pieris formosa.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid
  • Analgesics / chemistry
  • Analgesics / isolation & purification
  • Analgesics / pharmacology*
  • Animals
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Dose-Response Relationship, Drug
  • Ericaceae / chemistry*
  • Feeding Behavior / drug effects*
  • Larva / drug effects
  • Larva / growth & development
  • Molecular Structure
  • Moths
  • Pain / chemically induced
  • Pain / drug therapy*
  • Plant Roots / chemistry*
  • Structure-Activity Relationship

Substances

  • Analgesics
  • Diterpenes
  • Acetic Acid