Literature DB >> 33525713

New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray.

Kim-Thao Le1, Jan J Bandolik2, Matthias U Kassack2, Kenneth R Wood3, Claudia Paetzold4,5, Marc S Appelhans4, Claus M Passreiter1.   

Abstract

The dichloromethane extract from leaves of Melicope barbigera (Rutaceae), endemic to the Hawaiian island of Kaua'i, yielded four new and three previously known acetophenones and 2H-chromenes, all found for the first time in M. barbigera. The structures of the new compounds obtained from the dichloromethane extract after purification by chromatographic methods were unambiguously elucidated by spectroscopic analyses including 1D/2D NMR spectroscopy and HRESIMS. The absolute configuration was determined by modified Mosher's method. Compounds 2, 4 and the mixture of 6 and 7 exhibited moderate cytotoxic activities against the human ovarian cancer cell line A2780 with IC50 values of 30.0 and 75.7 µM for 2 and 4, respectively, in a nuclear shrinkage cytotoxicity assay.

Entities:  

Keywords:  Melicope barbigera; Rutaceae; acetophenones; chromenes; cytotoxicity; melibarbichromen A and B; melibarbinon A and B; ovarian cancer cell line A2780

Mesh:

Substances:

Year:  2021        PMID: 33525713      PMCID: PMC7865373          DOI: 10.3390/molecules26030688

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  46 in total

1.  Antipyretic, analgesic, anti-inflammatory and antioxidant activities of two major chromenes from Melicope lunu-ankenda.

Authors:  Anil J Johnson; Arun Kumar R; Sherin A Rasheed; Sreeja P Chandrika; Arun Chandrasekhar; Sabulal Baby; Appian Subramoniam
Journal:  J Ethnopharmacol       Date:  2010-05-08       Impact factor: 4.360

2.  Prenylated Acetophloroglucinol Dimers from Acronychia trifoliolata: Structure Elucidation and Total Synthesis.

Authors:  Katsunori Miyake; Chihiro Morita; Airi Suzuki; Natsuko Matsushita; Yohei Saito; Masuo Goto; David J Newman; Barry R O'Keefe; Kuo-Hsiung Lee; Kyoko Nakagawa-Goto
Journal:  J Nat Prod       Date:  2019-09-24       Impact factor: 4.050

3.  Acrofolione A and B, acetophenone dimers from Acronychia pendunculata, induce an apoptotic effect on human NALM-6 pre-B cell leukaemia cells.

Authors:  Takuya Matsui; Chihiro Ito; Ayumi Kato; Tian-Shung Wu; Masataka Itoigawa
Journal:  J Pharm Pharmacol       Date:  2018-10-25       Impact factor: 3.765

4.  Cytotoxic prenylated acetophenone dimers from Acronychia pedunculata.

Authors:  Eirini Kouloura; Maria Halabalaki; Marie-Christine Lallemand; Sangkil Nam; Richard Jove; Marc Litaudon; Khalijah Awang; Hamid A Hadi; Alexios-Leandros Skaltsounis
Journal:  J Nat Prod       Date:  2012-06-18       Impact factor: 4.050

5.  Chemical constituents of Lycoris albiflora and their cytotoxic activities.

Authors:  Maki Jitsuno; Akihito Yokosuka; Ken Hashimoto; Osamu Amano; Hiroshi Sakagami; Yoshihiro Mimaki
Journal:  Nat Prod Commun       Date:  2011-02       Impact factor: 0.986

6.  Bi-, tri-, and polycyclic acylphloroglucinols from Hypericum empetrifolium.

Authors:  Sebastian Schmidt; Guido Jürgenliemk; Thomas J Schmidt; Helen Skaltsa; Jörg Heilmann
Journal:  J Nat Prod       Date:  2012-10-02       Impact factor: 4.050

7.  Apoptosis and antimigration induction in human skin cancer cells by rhodomyrtone.

Authors:  Malatee Tayeh; Sirinun Nilwarangkoon; Chantra Tanunyutthawongse; Wilawan Mahabusarakum; Ramida Watanapokasin
Journal:  Exp Ther Med       Date:  2018-04-10       Impact factor: 2.447

8.  New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes.

Authors:  Bao-Ning Su; Eun Jung Park; Zakaria H Mbwambo; Bernard D Santarsiero; Andrew D Mesecar; Harry H S Fong; John M Pezzuto; A Douglas Kinghorn
Journal:  J Nat Prod       Date:  2002-09       Impact factor: 4.050

9.  Melicope oppenheimeri, section Pelea (Rutaceae), a new species from West Maui, Hawaiian Islands: with notes on its ecology, conservation, and phylogenetic placement.

Authors:  Kennetah R Wood; Marc S Appelhans; Warren L Wagner
Journal:  PhytoKeys       Date:  2016-08-25       Impact factor: 1.635

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