Planta Med 2016; 82(11/12): 1096-1104
DOI: 10.1055/s-0042-108059
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Isolation of Bioactive Rotenoids and Isoflavonoids from the Fruits of Millettia caerulea [*]

Yulin Ren
1  Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, United States
,
P. Annécie Benatrehina
1  Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, United States
,
Ulyana Muñoz Acuña
2  Division of Pharmacy Practice and Science, College of Pharmacy, The Ohio State University, Columbus, Ohio, United States
,
Chunhua Yuan
3  Campus Chemical Instrument Center, The Ohio State University, Columbus, Ohio, United States
,
Hee-Byung Chai
1  Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, United States
,
Tran Ngoc Ninh
4  Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
,
Esperanza J. Carcache de Blanco
1  Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, United States
2  Division of Pharmacy Practice and Science, College of Pharmacy, The Ohio State University, Columbus, Ohio, United States
,
Djaja D. Soejarto
5  Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois, United States
6  Science and Education, Field Museum of Natural History, Chicago, Illinois, United States
,
A. Douglas Kinghorn
1  Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, United States
› Author Affiliations
Further Information

Publication History

received 05 February 2016
revised 20 April 2016

accepted 21 April 2016

Publication Date:
09 June 2016 (eFirst)

Abstract

Three new rotenoids (13), two new isoflavonoids (4 and 5), and six known analogues (611) were isolated from an n-hexane partition of a methanol extract of the fruits of Millettia caerulea, with the structures of the new compounds elucidated by analysis of their spectroscopic data. The relative configurations of the rotenoids were determined by interpretation of their NMR spectroscopic data, and their absolute configurations were established using electronic circular dichroism spectra and specific rotation values. All compounds isolated were evaluated for their cell growth inhibitory activity against the HT-29 human colon cancer cell line, and the known compounds, (−)-3-hydroxyrotenone (6) and (−)-rotenone (7), were found to be potently active. When tested in an NF-κB inhibition assay, compound 6 showed activity. This compound, along with the new compound, (−)-caeruleanone D (1), and the known compound, ichthynone (8), exhibited K-Ras inhibitory potency. Further bioactivity studies showed that the new compounds, (−)-3-deoxycaeruleanone D (2) and (−)-3-hydroxycaeruleanone A (3), and the known compounds 8 and 11 induced quinone reductase in murine Hepa 1c1c7 cells.

* Dedicated to Professor Dr. Dr. h. c. mult. Kurt Hostettmann in recognition of his outstanding contributions to natural product research.


Supporting Information