Laevifins A-G, clerodane diterpenoids from the Bark of Croton oblongus Burm.f

Aziz AN 1 , Ismail NH 2 , Halim SNA 3 , Looi CY 4 , Anouar EH 5 , Langat MK 6 Show all authors , Mulholland D 6 , Awang K 3

Affiliations 

  • 1 School of Fundamental Science, Universiti Malaysia Terengganu, 21030, Kuala Nerus, Terengganu, Malaysia; Atta-ur-Rahman Institute for Natural Products Discovery, Level 9, FF3, Universiti Teknologi MARA Puncak Alam Campus, 42300, Bandar Puncak Alam, Selangor, Malaysia
  • 2 Atta-ur-Rahman Institute for Natural Products Discovery, Level 9, FF3, Universiti Teknologi MARA Puncak Alam Campus, 42300, Bandar Puncak Alam, Selangor, Malaysia. Electronic address: norhadiani@salam.uitm.edu.my
  • 3 Department of Chemistry, Faculty of Science, Universiti Malaya, 50603, Kuala Lumpur, Malaysia
  • 4 Department of Pharmacology, Faculty of Medicine, Universiti Malaya, 50603, Kuala Lumpur, Malaysia; Faculty of Health and Medical Sciences, School of Biosciences, Taylor's University Lakeside Campus, 47500, Subang Jaya, Malaysia
  • 5 Chemistry Department, College of Sciences and Humanities, Prince Sattam Bin Abdulaziz University, P.O. Box 83, 11942, Al Kharj, Saudi Arabia
  • 6 Natural Products Research Group, Department of Chemistry, University of Surrey, Guildford, GU2 7XH, Surrey, United Kingdom; School of Chemistry and Physics, University of Natal, Durban, 4041, South Africa
Phytochemistry, 2018 Dec;156:193-200.
PMID: 30316148 DOI: 10.1016/j.phytochem.2018.10.002

Abstract

A phytochemical investigation of the stem barks of the Malaysian Croton oblongus Burm.f. (Syn. Croton laevifolius Blume) (Euphorbiaceae) yielded seven previously undescribed ent-neo-clerodane diterpenoids, laevifins A - G and the known crovatin (3). Structures were established by a combination of spectroscopic methods including HRESIMS, NMR spectroscopy and X-ray crystallography. The absolute configuration of crovatin and laevifins A-G was established by comparison of experimental ECD and theoretical TDDFT ECD calculated spectra. This is the first report on the occurrence of the sesquiterpenoid cryptomeridiol in a Croton species. In vitro cytotoxicity assays on laevifins A, B and G showed moderate activities against the MCF-7 cancer cell line (IC50 102, 115 and 106 μM, respectively) while β-amyrin and acetyl aleuritolic acid showed good anti-inflammatory activity on the LPS-induced NF-κB translocation inhibition in RAW 264.7 cells assay with IC50 values of 23.5 and 35.4 μg/mL, respectively.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

MeSH terms
Similar publications