Isoflavones and Rotenoids from the Leaves of Millettia oblata ssp. teitensis

Tsegaye Deyou; Makungu Marco; Matthias Heydenreich; Fangfang Pan; Amra Gruhonjic; Paul A Fitzpatrick; Andreas Koch; Solomon Derese; Jerry Pelletier; Kari Rissanen; Abiy Yenesew; Máté Erdélyi

doi:10.1021/acs.jnatprod.7b00255

Isoflavones and Rotenoids from the Leaves of Millettia oblata ssp. teitensis

J Nat Prod. 2017 Jul 28;80(7):2060-2066. doi: 10.1021/acs.jnatprod.7b00255. Epub 2017 Jun 30.

Authors

Tsegaye Deyou^{1

2}, Makungu Marco¹, Matthias Heydenreich³, Fangfang Pan^{4

5}, Amra Gruhonjic^{2

6}, Paul A Fitzpatrick⁶, Andreas Koch³, Solomon Derese¹, Jerry Pelletier⁷, Kari Rissanen⁴, Abiy Yenesew¹, Máté Erdélyi^{2

8}

Affiliations

¹ Department of Chemistry, University of Nairobi , P.O. Box 30197-00100, Nairobi, Kenya.
² Department of Chemistry and Molecular Biology, University of Gothenburg , SE-412 96 Gothenburg, Sweden.
³ Institut für Chemie, Universität Potsdam , Karl-Liebknecht-Straße 24-25, D-14476, Potsdam, Germany.
⁴ Department of Chemistry, Nanoscience Center, University of Jyvaskyla , P.O. Box 35, FI-40014, Jyvaskyla, Finland.
⁵ College of Chemistry, Central China Normal University , Wuhan, 430079, People's Republic of China.
⁶ Sahlgrenska Cancer Centre, University of Gothenburg , SE-405 30 Gothenburg, Sweden.
⁷ Department of Biochemistry, McGill University , Montreal, QC H3G 1Y6, Canada.
⁸ Swedish NMR Center, University of Gothenburg , P.O. Box 465, SE-405 30, Gothenburg, Sweden.

PMID: 28665590
DOI: 10.1021/acs.jnatprod.7b00255

Abstract

A new isoflavone, 8-prenylmilldrone (1), and four new rotenoids, oblarotenoids A-D (2-5), along with nine known compounds (6-14), were isolated from the CH₂Cl₂/CH₃OH (1:1) extract of the leaves of Millettia oblata ssp. teitensis by chromatographic separation. The purified compounds were identified by NMR spectroscopic and mass spectrometric analyses, whereas the absolute configurations of the rotenoids were established on the basis of chiroptical data and in some cases by single-crystal X-ray crystallography. Maximaisoflavone J (11) and oblarotenoid C (4) showed weak activity against the human breast cancer cell line MDA-MB-231 with IC₅₀ values of 33.3 and 93.8 μM, respectively.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Drug Screening Assays, Antitumor
Humans
Inhibitory Concentration 50
Isoflavones / chemistry
Isoflavones / isolation & purification*
Isoflavones / pharmacology
Kenya
Millettia / chemistry*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Leaves / chemistry*
Rotenone / chemistry
Rotenone / isolation & purification*
Rotenone / pharmacology

Substances

Isoflavones
Rotenone