Caeruleanone A, a Rotenoid with a New Arrangement of the D-Ring from the Fruits of <i>Millettia caerulea</i>

Pérez, Lynette Bueno; Li, Pan; Acuña, Ulyana Muñoz; Li, Jie; Chai, Hee Byung; Gallucci, Judith C.; Ninh, Tran Ngoc; Blanco, Esperanza J. Carcache de; Soejarto, Djaja D.; Kinghorn, A. Douglas

doi:10.1021/ol500266z

Cited by 15 publications

(9 citation statements)

References 22 publications

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“…Comparison of the 1 H NMR chemical shift values for H-5, H-6, H-3', and H-6' or other protons of 3 and (−)-2,3-dehydrorotenone showed that no obvious changes were observed for any protons other than H-6', and a similar observation was evidenced in other rotenoids (Fig. S12, Supporting Information) [15, 18, 19, 33, 36, 44, 45]. This indicates that an anisotropic effect from the C-4 carbonyl group is not a major contributor to the downfield signal for the 1 H NMR resonance for H-6' of trans -rotenoids.…”

Section: Resultssupporting

confidence: 55%

“…S12 (Supporting Information), the downfield signal observed for the 1 H NMR resonance for H-6' of trans -rotenoids is not influenced by the choice of solvents used, as supported by the data measured in the same or different deuterated solvents for several rotenoids and their epimers [15, 18, 19, 33, 36, 44, 45]. Comparison of the 1 H NMR chemical shift values for H-5, H-6, H-3', and H-6' or other protons of 3 and (−)-2,3-dehydrorotenone showed that no obvious changes were observed for any protons other than H-6', and a similar observation was evidenced in other rotenoids (Fig.…”

Section: Resultsmentioning

confidence: 82%

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An Intramolecular CAr–H•••O=C Hydrogen Bond and the Configuration of Rotenoids

2017

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Over the past half a century, the structure and configuration of the rotenoids, a group of natural products showing multiple promising bioactivities, have been established by interpretation of their NMR and electronic circular dichroism spectra and confirmed by analysis of single-crystal X-ray diffraction data. The chemical shift of the H-6' 1H NMR resonance has been found to be an indicator of either a cis or trans C/D ring system. In the present study, four structures representing the central rings of a cis-, a trans-, a dehydro-, and an oxadehydro-rotenoid have been plotted using the Mercury program based on X-ray crystal structures reported previously, with the conformations of the C/D ring system, the local bond lengths or interatomic distances, hydrogen bond angles, and the H-6' chemical shift of these compounds presented. It is shown for the first time that a trans-fused C/D ring system of rotenoids is preferred for the formation of a potential intramolecular C6'–H6'•••O=C4 H-bond, and that such H-bonding results in the 1H NMR resonance for H-6' being shifted downfield.

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Section: Resultssupporting

confidence: 55%

Section: Resultsmentioning

confidence: 82%

An Intramolecular CAr–H•••O=C Hydrogen Bond and the Configuration of Rotenoids

2017

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“…For example, Millettia pachycarpa was used as an anthelminthic to evacuate the parasitic intestinal worms [7]. M. thonningii is known to treat dysentery, constipation, and diarrhea while M. carulea has anti-inflammatory effects [8,9]. M. macrophylla is also used to relieve menopausal symptoms [10].…”

Section: Introductionmentioning

confidence: 99%

Isoflavones Isolated from the Seeds of Millettia ferruginea Induced Apoptotic Cell Death in Human Ovarian Cancer Cells

et al. 2020

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The seeds of Millettia ferruginea are used in fishing, pesticides, and folk medicine in Ethiopia. Here, the anti-cancer effects of isoflavones isolated from M. ferruginea were evaluated in human ovarian cancer cells. We found that isoflavone ferrugone and 6,7-dimethoxy-3’,4’-methylenedioxy-8-(3,3-dimethylallyl)isoflavone (DMI) had potent cytotoxic effects on human ovarian cancer cell A2780 and SKOV3. Ferrugone and DMI treatment increased the sub-G1 cell population in a dose-dependent manner in A2780 cells. The cytotoxic activity of ferrugone and DMI was associated with the induction of apoptosis, as shown by an increase in annexin V-positive cells. Z-VAD-fmk, a broad-spectrum caspase inhibitor, and z-DEVD-fmk, a caspase-3 inhibitor, significantly reversed both the ferrugone and DMI-induced apoptosis, suggesting that cell death stimulated by the isoflavones is mediated by caspase-3-dependent apoptosis. Additionally, ferrugone-induced apoptosis was found to be caspase-8-dependent, while DMI-induced apoptosis was caspase-9-dependent. Notably, DMI, but not ferrugone, increased the intracellular levels of reactive oxygen species (ROS), and antioxidant N-acetyl-L-cysteine (NAC) attenuated the pro-apoptotic activity of DMI. These data suggest that DMI induced apoptotic cell death through the intrinsic pathway via ROS production, while ferrugone stimulated the extrinsic pathway in human ovarian cancer cells.

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“…In an initial investigation of the fruits of this species, three new rotenoids including caeruleanone C ( 5 ), were isolated, along with 11 rotenoids of known structure. 42 Of these, caeruleanone C proved to be a potent inhibitor of mitochondrial transmembrane potential (MTP) (IC 50 0.07 μM). 42 The loss of MTP is regarded as an indication of apoptosis, and hence has been correlated with the anticancer potential of a given test compound.…”

Section: Selected Lead Bioactive Compounds Obtainedmentioning

confidence: 99%