Rotenoid

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Philip C. Stevenson - One of the best experts on this subject based on the ideXlab platform.

  • phytochemical analysis of tephrosia vogelii across east africa reveals three chemotypes that influence its use as a pesticidal plant
    Plants (Basel Switzerland), 2019
    Co-Authors: Angela G Mkindi, Yolice Tembo, Beth Medvecky, Amy Kendalsmith, Steven R Belmain, Iain W. Farrell, Ernest R. Mbega, Patrick A. Ndakidemi, Philip C. Stevenson
    Abstract:

    Tephrosia vogelii is a plant species chemically characterized by the presence of entomotoxic Rotenoids and used widely across Africa as a botanical pesticide. Phytochemical analysis was conducted to establish the presence and abundance of the bioactive principles in this species across three countries in East Africa: Tanzania, Kenya, and Malawi. Analysis of methanolic extracts of foliar parts of T. vogelii revealed the occurrence of two distinct chemotypes that were separated by the presence of Rotenoids in one, and flavanones and flavones that are not bioactive against insects on the other. Specifically, chemotype 1 contained deguelin as the major Rotenoid along with tephrosin, and rotenone as a minor component, while these compounds were absent from chemotype 2, which contained previously reported flavanones and flavones including obovatin-3-O-methylether. Chemotype 3 contained a combination of the chemical profiles of both chemotype 1 and 2 suggesting a chemical hybrid. Plant samples identified as chemotype 1 showed chemical consistency across seasons and altitudes, except in the wet season where a significant difference was observed for samples in Tanzania. Since farmers are unable to determine the chemical content of material available care must be taken in promoting this species for pest management without first establishing efficacy. While phytochemical analysis serves as an important tool for quality control of pesticidal plants, where analytical facilities are not available simple bioassays could be developed to enable extension staff and farmers to determine the efficacy of their plants and ensure only effective materials are adopted.

  • highly variable insect control efficacy of tephrosia vogelii chemotypes
    Journal of Agricultural and Food Chemistry, 2012
    Co-Authors: Steven R Belmain, Barbara A Amoah, Stephen P. Nyirenda, John F. Kamanula, Philip C. Stevenson
    Abstract:

    Tephrosia vogelii has been used for generations as a pest control material in Africa. Recently, two chemotypes have been reported based on the occurrence (chemotype 1) or absence (chemotype 2) of Rotenoids. This could have an impact on the efficacy and reliability of this material for pest control. We report that chemotype 2 has no pesticidal activity against Callosobruchus maculatus Fabricius (family Chrysomelidae) and that this is associated with the absence of Rotenoids. We present a first report of the comparative biological activity of deguelin, tephrosin, α-toxicarol, and sarcolobine and show that not all Rotenoids are equally effective. Tephrosin was less toxic than deguelin which was less active than rotenone, while obovatin 5-methyl ether, the major flavonoid in chemotype 2 was inactive. We also report that in chemotype 1 the occurrence of Rotenoids shows substantial seasonal variation.

  • distinct chemotypes of tephrosia vogelii and implications for their use in pest control and soil enrichment
    Phytochemistry, 2012
    Co-Authors: Gwilym P. Lewis, Fe Lix Forest, Stephen P. Nyirenda, Steven R Belmain, Philip C. Stevenson, Geoffrey C Kite, Nigel C Veitch
    Abstract:

    Tephrosia vogelii Hook. f. (Leguminosae) is being promoted as a pest control and soil enrichment agent for poorly-resourced small-scale farmers in southern and eastern Africa. This study examined plants being cultivated by farmers and found two chemotypes. Chemotype 1 (C1) contained Rotenoids, including deguelin, rotenone, sarcolobine, tephrosin and α-toxicarol, required for pest control efficacy. Rotenoids were absent from chemotype 2 (C2), which was characterised by prenylated flavanones, including the previously unrecorded examples (2S)-5,7-dimethoxy-8-(3-hydroxy-3-methylbut-1Z-enyl)flavanone, (2S)-5,7-dimethoxy-8-(3-methylbut-1,3-dienyl)flavanone, (2S)-4′-hydroxy-5-methoxy-6″,6″-dimethylpyrano[2″,3″:7,8]flavanone, (2S)-5-methoxy-6″,6″-dimethyl-4″,5″-dihydrocyclopropa[4″,5″]furano[2″,3″:7,8]flavanone, (2S)-7-hydroxy-5-methoxy-8-prenylflavanone, and (2R,3R)-3-hydroxy-5-methoxy-6″,6″-dimethylpyrano[2″,3″:7,8]flavanone. The known compounds (2S)-5-methoxy-6″,6″-dimethylpyrano[2″,3″:7,8]flavanone (obovatin 5-methyl ether) and 5,7-dimethoxy-8-(3-hydroxy-3-methylbut-1Z-enyl)flavone (Z-tephrostachin) were also found in C2. This chemotype, although designated Tephrosia candida DC. in collections originating from the World Agroforestry Centre (ICRAF), was confirmed to be T. vogelii on the basis of morphological comparison with verified herbarium specimens and DNA sequence analysis. Sampling from 13 locations in Malawi where farmers cultivate Tephrosia species for insecticidal use indicated that almost 1 in 4 plants were T. vogelii C2, and so were unsuitable for this application. Leaf material sourced from a herbarium specimen of T. candida contained most of the flavanones found in T. vogelii C2, but no Rotenoids. However, the profile of flavonol glycosides was different to that of T. vogelii C1 and C2, with 6-hydroxy-kaempferol 6-methyl ether as the predominant aglycone rather than kaempferol and quercetin. The structures of four unrecorded flavonol glycosides present in T. candida were determined using cryoprobe NMR spectroscopy and MS as the 3-O-α-rhamnopyranosyl(1 → 6)-β-galactopyranoside-7-O-α-rhamnopyranoside, 3-O-α-rhamnopyranosyl(1 → 2)[α-rhamnopyranosyl(1 → 6)]-β-galactopyranoside, 3-O-α-rhamnopyranosyl(1 → 2)[α-rhamnopyranosyl(1 → 6)]-β-galactopyranoside-7-O-α-rhamnopyranoside, and 3-O-α-rhamnopyranosyl(1 → 2)[(3-O-E-feruloyl)-α-rhamnopyranosyl(1 → 6)]-β-galactopyranosides of 6-hydroxykaempferol 6-methyl ether. Tentative structures for a further 37 flavonol glycosides of T. candida were assigned by LC–MS/MS. The correct chemotype of T. vogelii (i.e. C1) needs to be promoted for use by farmers in pest control applications.

John M Pezzuto - One of the best experts on this subject based on the ideXlab platform.

  • potential cancer chemopreventive constituents of the leaves of macaranga triloba
    Phytochemistry, 2004
    Co-Authors: Dae Sik Jang, John M Pezzuto, Harry H S Fong, Norman R. Farnsworth, Muriel Cuendet, Alison D Pawlus, Leonardus B S Kardono, Kazuko Kawanishi, Douglas A Kinghorn
    Abstract:

    Activity-guided fractionation of the leaves of Macaranga triloba, using an in vitro bioassay based on the inhibition of cyclooxygenase-2, resulted in the isolation of a Rotenoid, 4,5-dihydro-5'alpha-hydroxy-4'alpha-methoxy-6a,12a-dehydro-alpha-toxicarol (1), as well as 12 known compounds, (+)-clovan-2beta,9alpha-diol, ferulic acid, 3,7,3',4'-tetramethylquercetin, 3,7,3'-trimethylquercetin, 3,7-dimethylquercetin, abscisic acid, 1beta,6alpha-dihydroxy-4(15)-eudesmene, 3beta-hydroxy-24-ethylcholest-5-en-7-one, loliolide, scopoletin, taraxerol, and 3-epi-taraxerol. The structure of compound 1 was determined using spectroscopic methods. All isolates were evaluated for their potential to inhibit cyclooxygenases-1 and -2 by measuring PGE(2) production, and to induce quinone reductase in cultured Hepa 1c1c7 mouse hepatoma cells.

  • potential cancer chemopreventive flavonoids from the stems of tephrosia toxicaria
    Journal of Natural Products, 2003
    Co-Authors: Dae Sik Jang, Harry H S Fong, Rajendra G Mehta, Eunjung Park, Michael E. Hawthorne, Young Hwa Kang, Jose Schunke Vigo, James G Graham, Fernando Cabieses, John M Pezzuto
    Abstract:

    A new butenylflavanone, (2S)-5-hydroxy-7-methoxy-8-[(E)-3-oxo-1-butenyl]flavanone (1), and a new Rotenoid, 4‘,5‘-dihydro-11,5‘-dihydroxy-4‘-methoxytephrosin (2), as well as three active flavonoids of previously known structure, isoliquiritigenin (3), genistein (4), and chrysoeriol (5), along with nine known inactive compounds, α-toxicarol (6), sumatrol, 6a,12a-dehydro-α-toxicarol, 11-hydroxytephrosin, obovatin, marmesin, lupenone, benzyl benzoate, and benzyl trans-cinnamate, were isolated from an ethyl acetate-soluble extract of the stems of Tephrosia toxicaria, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells to monitor chromatographic fractionation. The structures of compounds 1 and 2 were elucidated by spectroscopic data interpretation. All isolates were evaluated for their potential cancer chemopreventive properties utilizing an in vitro assay to determine quinone reductase induction. Selected compounds were tested in a mouse mammary organ c...

  • Cytotoxic flavonoids from the stem bark of Lonchocarpus aff. fluvialis.
    Phytotherapy research : PTR, 2002
    Co-Authors: Cecília T. T. Blatt, John M Pezzuto, James G Graham, Fernando Cabieses, Geoffrey A Cordell, Hee-byung Chai, Daniel Chávez, Norman R. Farnsworth, A. Douglas Kinghorn
    Abstract:

    Activity-guided fractionation of a chloroform-soluble extract of Lonchocarpus aff. fluvialis stem bark using a human epidermoid (KB) tumour cell line as a monitor afforded five Rotenoids, one pterocarpan, one chalcone, three flavanones, one flavone and one triterpenoid. All of the compounds isolated proved to be of previously known structure. Among them, the Rotenoids (-)-sumatrol and (+/-)-villosinol, the dibenzoylmethane derivative (+)-3,4-methylenedioxy-2'-methoxy-[2",3":4',3']-furanodibenzoylmethane, and the flavanones (-)-isoglabrachromene and (-)-candidone have been shown to exhibit significant cytotoxic activity against human cancer cells for the first time. This is the first report of the chemical constituents of this species, and the profile of compounds obtained was in accordance with the established chemosystematic patterns of species in the tribe Tephrosieae (Leguminosae, Papilionoideae).

A. Douglas Kinghorn - One of the best experts on this subject based on the ideXlab platform.

  • Isolation of Bioactive Rotenoids and Isoflavonoids from the Fruits of Millettia caerulea.
    Planta medica, 2016
    Co-Authors: Yulin Ren, Hee-byung Chai, Tran Ngoc Ninh, Djaja D. Soejarto, P. Annécie Benatrehina, Ulyana Muñoz Acuña, Chunhua Yuan, Esperanza J. Carcache De Blanco, A. Douglas Kinghorn
    Abstract:

    Three new Rotenoids (1–3), two new isoflavonoids (4 and 5), and six known analogues (6–11) 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. 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.

  • Cytotoxic flavonoids from the stem bark of Lonchocarpus aff. fluvialis.
    Phytotherapy research : PTR, 2002
    Co-Authors: Cecília T. T. Blatt, John M Pezzuto, James G Graham, Fernando Cabieses, Geoffrey A Cordell, Hee-byung Chai, Daniel Chávez, Norman R. Farnsworth, A. Douglas Kinghorn
    Abstract:

    Activity-guided fractionation of a chloroform-soluble extract of Lonchocarpus aff. fluvialis stem bark using a human epidermoid (KB) tumour cell line as a monitor afforded five Rotenoids, one pterocarpan, one chalcone, three flavanones, one flavone and one triterpenoid. All of the compounds isolated proved to be of previously known structure. Among them, the Rotenoids (-)-sumatrol and (+/-)-villosinol, the dibenzoylmethane derivative (+)-3,4-methylenedioxy-2'-methoxy-[2",3":4',3']-furanodibenzoylmethane, and the flavanones (-)-isoglabrachromene and (-)-candidone have been shown to exhibit significant cytotoxic activity against human cancer cells for the first time. This is the first report of the chemical constituents of this species, and the profile of compounds obtained was in accordance with the established chemosystematic patterns of species in the tribe Tephrosieae (Leguminosae, Papilionoideae).

  • Rotenoids mediate potent cancer chemopreventive activity through transcriptional regulation of ornithine decarboxylase.
    Nature medicine, 1995
    Co-Authors: Clarissa Gerhäuser, Harry H S Fong, A. Douglas Kinghorn, Sang Kook Lee, Lumonadio Luyengi, Woongchon Mar, Nanjoo Suh, Ying-de Luo, Jerome W. Kosmeder, Robert M. Moriarty
    Abstract:

    For the discovery of new cancer chemopreventive agents, we have studied the potential of plant extracts to inhibit phorbol ester-induced ornithine decarboxylase (ODC) activity in cell culture. Four active Rotenoids were obtained from the African plant Mundulea sericea (Leguminosae). These isolates were highly potent when evaluated for inhibition of chemically induced preneoplastic lesions in mammary organ culture and inhibition of papillomas in the two-stage mouse skin model, and they appear to function by a unique mechanism at the level of ODC messenger RNA expression. Based on our findings, Rotenoids can be regarded as promising new chemopreventive or anticancer agents.

Douglas A Kinghorn - One of the best experts on this subject based on the ideXlab platform.

  • Caeruleanone A, a Rotenoid with a New Arrangement of the D‑Ring from the Fruits of Millettia caerulea
    2016
    Co-Authors: Lynette Bueno Peŕez, Li Pan, Hee-byung Chai, Tran Ngoc Ninh, Esperanza Carcache J. De Blanco, Djaja D. Soejarto, Judith C. Gallucci, Douglas A Kinghorn
    Abstract:

    ABSTRACT: Caeruleanone A (1), a novel Rotenoid with an unprecedented arrangement of the D-ring, was isolated with another two new analogues, caeruleanones B (2) and C (3), together with 11 known Rotenoids from the fruits of Millettia caerulea. The structures of the new compounds were determined by spectroscopic data analysis, with that of 1 being confirmed by single-crystal X-ray diffraction. Com-pounds 2 and 3 displayed potent mitochondrial trans-membrane potential inhibitory and quinone reductase induction activities. Millettia caerulea (Graham) Baker (Fabaceae-Papilionoideae) is a large shrub growing in dry, thorny, and stunted forests and is native to Myanmar, Thailand, and Vietnam.1 The stems and leaves of this plant are applied to wounds in Thai folkloric medicine to reduce infection.2 No previous phytochemical investigation has been performed on M. caerulea. Millettia spp.

  • Caeruleanone A, a Rotenoid with a New Arrangement of the D‑Ring from the Fruits of Millettia caerulea
    2015
    Co-Authors: Lynette Bueno Pérez, Li Pan, Ulyana Muñoz Acuña, Hee-byung Chai, Judith C. Gallucci, Tran Ngoc Ninh, Esperanza Carcache J. De Blanco, Djaja D. Soejarto, Douglas A Kinghorn
    Abstract:

    Caeruleanone A (1), a novel Rotenoid with an unprecedented arrangement of the D-ring, was isolated with another two new analogues, caeruleanones B (2) and C (3), together with 11 known Rotenoids from the fruits of Millettia caerulea. The structures of the new compounds were determined by spectroscopic data analysis, with that of 1 being confirmed by single-crystal X-ray diffraction. Compounds 2 and 3 displayed potent mitochondrial transmembrane potential inhibitory and quinone reductase induction activities

  • potential cancer chemopreventive constituents of the leaves of macaranga triloba
    Phytochemistry, 2004
    Co-Authors: Dae Sik Jang, John M Pezzuto, Harry H S Fong, Norman R. Farnsworth, Muriel Cuendet, Alison D Pawlus, Leonardus B S Kardono, Kazuko Kawanishi, Douglas A Kinghorn
    Abstract:

    Activity-guided fractionation of the leaves of Macaranga triloba, using an in vitro bioassay based on the inhibition of cyclooxygenase-2, resulted in the isolation of a Rotenoid, 4,5-dihydro-5'alpha-hydroxy-4'alpha-methoxy-6a,12a-dehydro-alpha-toxicarol (1), as well as 12 known compounds, (+)-clovan-2beta,9alpha-diol, ferulic acid, 3,7,3',4'-tetramethylquercetin, 3,7,3'-trimethylquercetin, 3,7-dimethylquercetin, abscisic acid, 1beta,6alpha-dihydroxy-4(15)-eudesmene, 3beta-hydroxy-24-ethylcholest-5-en-7-one, loliolide, scopoletin, taraxerol, and 3-epi-taraxerol. The structure of compound 1 was determined using spectroscopic methods. All isolates were evaluated for their potential to inhibit cyclooxygenases-1 and -2 by measuring PGE(2) production, and to induce quinone reductase in cultured Hepa 1c1c7 mouse hepatoma cells.

  • identification of degradation product of deguelin and its stability using liquid chromatography and electrospray mass spectrometry
    Journal of Liquid Chromatography & Related Technologies, 2004
    Co-Authors: Young G Shin, Robert M. Moriarty, Jerome W. Kosmeder, George Udeani, Guo Min Zhao, Sumeet Dagar, Hayat Onyuksel, Geoffrey A Cordell, Richard C Moon, Douglas A Kinghorn
    Abstract:

    Abstract The degradation product and its stability of deguelin, a naturally occurring Rotenoid and potential cancer chemopreventive agent, was evaluated in several vehicles using liquid chromatography‐electrospray mass spectrometry. Deguelin was prepared as a 2 mg/mL solution in acetonitrile, corn oil, yohimbine oil, Tween‐80, Cremophor‐EL, liposomes, and phospholipid micelles, and chemical stability was monitored for 28 days using HPLC‐UV and HPLC‐MS systems coupled to C18 reverse phase columns. Deguelin was stable in acetonitrile, corn oil, and yohimbine oil for 28 days when stored at 4°C. However, it rapidly decomposed in liposomes, Cremophor‐EL, Tween 80, and phospholipid micelles, with daily decay rates of 0.39%, 0.86%, 1.93%, and 2.82%, respectively. The degradation product was determined by physical and spectral data to be tephrosin after isolation by semi‐preparative HPLC. Tephrosin was produced by deguelin auto‐oxidation, and this was likely accelerated by endogenous peroxides found in Cremophor‐...

Ikyon Kim - One of the best experts on this subject based on the ideXlab platform.

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