ChemInform Abstract: Caeruleanone A, a Rotenoid with a New Arrangement of the D‐Ring from the Fruits of Millettia caerulea.

Abstract

Caeruleanone A, a Rotenoid with a New Arrangement of the D-Ring from the Fruits of Millettia caerulea. -(BUENO PEREZ, L.; PAN, L.; MUNOZ ACUNA, U.; LI, J.; CHAI, H.-B.; GALLUCCI, J. C.; NINH, T. N.; CARCACHE DE BLANCO, E. J.; SOEJARTO, D. D.; KINGHORN*, A. D.; Org. Lett. 16 (2014) 5, 1462-1465, http://dx.doi.org/10.1021/ol500266z ; Div. Med. Chem. Pharmacogn., Coll. Pharm., Ohio State Univ., Columbus, OH 43210, USA; Eng.) -U. Scheffler 34-214

Isolation of Bioactive Rotenoids and Isoflavonoids from the Fruits of Millettia caerulea

“…447.1050) observed in the HRESIMS, in conjunction with the 13 C NMR spectroscopic data. The UV spectrum showed absorption maxima at λ max 248 and 303 nm, consistent with a rotenoid skeleton [2,15]. This was supported by the absorptions at ν max 3454, 1669, 1640, 1599, and 1503 cm −1 in the IR spectrum, corresponding to the presence of hydroxy and conjugated carbonyl groups, a double bond, and an aromatic ring, respectively [19,20].…”

“…Supporting information available online at http://www.thieme-connect.de/products tography guided by this activity, several rotenoids were purified, of which (−)-3-hydroxyrotenone (6) and (−)-rotenone (7) were characterized as cytotoxic components of M. caerulea, with caeruleanones B and C found to potently induce QR in vitro [2]. In a continuation of this initial work, as presented herein, an n-hexane-soluble extract of M. caerulea fruits has been investigated, and several new and known rotenoids and isoflavonoids were identified and evaluated for their cytotoxicity toward HT-29 cells and NF-κB and K-Ras inhibitory and QR induction activities.…”

“…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, (−)-3deoxycaeruleanone D (2) and (−)-3-hydroxycaeruleanone A (3), and the known compounds 8 and 11 induced quinone reductase in murine Hepa 1c1c7 cells.…”

“…The genus Millettia, comprising around 260 species distributed mainly in Africa, Asia, America, and Australia, is a large member of the plant family Fabaceae (subfamily Papilionoideae) [1]. Species of this genus produce rotenoids [2], isoflavonoids [3], and chalcones [4,5] as characteristic secondary metabolite constituents, which have shown anti-inflammatory [3], anti-insecticidal [1], and antimalarial [5] activities as well as cytotoxicity for cancer cell lines [2,4,5]. Millepachine has been identified as a new prenylchalcone from Millettia pachycarpa Benth.…”

“…Using column chroma-Abstract ! Three new rotenoids (1)(2)(3), two new isoflavonoids (4 and 5), and six known analogues (6)(7)(8)(9)(10)(11) 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.…”