A Trachylobane Diterpenoid from <i>Xylopia aethiopica</i>

Ngouela, Silvère; Nyasse, Barthélémy; Tsamo, Etienne; Brochier, M. C.; Morin, Christophe

doi:10.1021/np970172i

Cited by 21 publications

(16 citation statements)

References 9 publications

(11 reference statements)

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“…The cytotoxic activity of its fruit ethanolic extracts has also been described on HCT 116 colon cancer cells and on KG1A, U937 leukemia cells [12]. Most studies were focused on the fruits of this spice and very few publications on the other organs [13]. The present study aimed at investigating the antioxidant properties and the protective effects of X. aethiopica extracts against ionmediated liver damages.…”

Section: Introductionmentioning

confidence: 95%

In vitro antioxidant and anti-lipoperoxidative activities of bark extracts of Xylopia aethiopica against ion-mediated toxicity on liver homogenates

Moukette

Pieme

Biapa

et al. 2015

Journal of Complementary and Integrative Medicine

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Reactive oxygen species (ROS), products of normal cell metabolism may cause damage to biological macromolecules leading to severe health threats when they are present in high concentrations. Aromatic plants contain phytochemicals rich of antioxidants that prevent oxidant formation or scavenge oxidants produced under oxidative stress conditions. In the present study, we investigated the free radical scavenging effects, the antioxidant and ion toxicity preventive effect of Xylopia aethiopica (X. aethiopica), a plant of the family of Annonaceae used as spice in Cameroon. The scavenging properties of extracts of X. aethiopica were tested on 2, 2-diphenyl-1-picrylhydrazyl (DPPH), nitric oxide (NO), hydroxyl (OH), 2,2'-azinobis(3-ethylbenzthiazoline)-6-sulfonic acid (ABTS) radicals. The total antioxidant capacity was assayed by ferric reducing ability of plasma (FRAP), phosphomolybdenum antioxidant power (PAP), reduction assays. The protective potential was carried on superoxide dismutase (SOD), catalase and peroxidases. The results showed that both the ethanolic (BEE) and the hydroethanolic (BEH) extracts from the barks of X. aethiopica scavenged all the tested radicals. The sample BEH showed the highest total antioxidant capacity both in the FRAP and the PAP. This result was positively correlated to its higher phenolic content (30.74±0.44 CAE/g dried extract). The higher protective capacity of BEH on SOD, catalase and peroxidase activities was comparable to that of the vitamin C used as standard. In conclusion, X. aethiopica has a higher antioxidant and protective potential against ion-mediated oxidative damage and may be considered as a potential drug against metal-mediated toxicity.

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Section: Introductionmentioning

confidence: 95%

In vitro antioxidant and anti-lipoperoxidative activities of bark extracts of Xylopia aethiopica against ion-mediated toxicity on liver homogenates

Moukette

Pieme

Biapa

et al. 2015

Journal of Complementary and Integrative Medicine

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“…The acute and sublethal behavioral effects of EO act by blocking octopamine receptors (Enan, 2005). The chemical constituents of X. aethiopica have been identified as diterpenes (Ngouela et al, 1998), diterpenes, phenolic amides and lignanamides (Lajide et al, 1995), monoterpenes, sesquiterpenes, oxygenated terpenes, and aromatic hydrocarbons (Boyom et al, 2003). Methanolic extract of the roots of D. tripetala isolated by chromatographic techniques resulted to the chromone alkaloid dennettine, three phenanthrene alkaloids identified as uvariopsine, stephenanthrine, and argentinine and a simple phenolic compound vanillin (López-Martin et al, 2002).…”

Section: Resultsmentioning

confidence: 99%

Insecticidal Effect of Fruit Extracts from Xylopia aethiopica and Dennettia tripetala (Annonaceae) against Sitophilus oryzae (Coleoptera: Curculionidae)

Ukeh

Oku

Udo

et al. 2012

Chilean J. Agric. Res.

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The insecticidal and repellent activities of fruit extracts of Xylopia aethiopica (Dunal) A. Rich. and Dennettia tripetala (Baker f.) G.E. Schatz belonging to the family Annonaceae was studied against Sitophilus oryzae (L.), an economic, primary post-harvest pest of rice, and other cereal products. Infested rice grains (100 g) treated with 1, 2, 3, 4, and 5% (w/w) powders of both plants were evaluated for toxicity against S. oryzae every 24 h for 3 d, and during F1 progeny emergence. The essential oils of both plants were also applied at 0.5, 1, 1.5 and 2 mg cm -2 filter paper in Petri dishes for toxicity bioassays at 24 h exposure. Repellence bioassay with 10 μL solution of essential oils on filter paper was performed in a Y-Tube airflow olfactometer. Results indicate that powders of both plants significantly (P < 0.001) caused adult weevil mortality and a reduction in F1 progeny emergence than the control. Essential oils were also significantly (P < 0.001) adulticidal to S. oryzae after 24 h with the highest dose (2 mg cm -2 ) producing 100% mortality respectively. Similarly, both male and female weevils significantly avoided the test arm compared to the control arm in the Y-Tube olfactometer repellence tests. These results suggest that X. aethiopica and D. tripetala natural extracts have potential for use as part of integrated pest management of stored product protection against S. oryzae.

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“…Xylopia aethiopica is an important evergreen medicinal plant indigenous to subtropical Africa. The stem bark is employed in traditional medicine for the treatment of dysentery, bronchitis, bile–borne diseases . The fruit, however, is the most commonly used part of the plant for medicinal and nutritional purposes .…”

Section: Introductionmentioning

confidence: 99%

“…The stem bark is employed in traditional medicine for the treatment of dysentery, bronchitis, bile-borne diseases. 1 The fruit, however, is the most commonly used part of the plant for medicinal and nutritional purposes. 2 The dried fruit, also known as African pepper, is widely used as a condiment by indigenes.…”

Section: Introductionmentioning

confidence: 99%

MALDI–HRMS imaging and HPLC–HRESI–MSⁿ characterisation of kaurane diterpenes in the fruits of Xylopia aethiopica (Dunal) A. Rich (Annonaceae)

Kyekyeku

Asare–Nkansah

Bekoe

et al. 2019

Phytochemical Analysis

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Introduction Kaurane diterpenes, notably xylopic acid, have demonstrated important biological activities including analgesia, anti‐oxidant, antimicrobial and cytotoxicity. The fruits of Xylopia aethiopica have been reported to be a rich source of kaurane diterpenes. Objective An analytical approach for detailed imaging and characterisation of selected kaurane diterpenes was developed using matrix‐assisted laser desorption/ionisation high‐resolution mass spectrometry (MALDI‐HRMS) imaging techniques and high‐performance liquid chromatography‐high resolution electrospray ionisation‐tandem mass spectrometry (HPLC‐HRESI‐MSn) studies, respectively. Methods The images of the compounds were constructed based on selected ions from their HRESI–MS spectra. The matrix employed comprised a solution of α–cyano–4–hydroxycinnamic acid (HCCA) in acetonitrile–water with trifluoroacetic acid (TFA). HPLC–HRESI–MSn measurements were conducted on an LTQ–Orbitrap spectrometer equipped with a heated electrospray ionisation (HESI)–II source. Results The analytical strategy adopted showed the spatial distribution of the compounds in the fruits of X. aethiopica based on the dominant ions at m/z 301.2163 [M + H – HOCOCH3]+ and m/z 399.1932 [M + K]+ for xylopic acid, m/z 317.2111 [M + H]+ and m/z 355.1670 [M + K]+ for 15–oxo–ent–kaur–16–en–19–oic acid and m/z 303.2319 [M + H]+ for ent–kaur–16–en–19–oic acid. The fragmentation patterns of the compounds were proposed based on the HRESI–MSn measurements. Conclusions The study revealed the spatial variability, differential behaviours and specificity of the selected kaurane diterpenes in the fruit, seed and pericarp. The compounds under study were predominantly restricted to the pericarp of the fruit with trace amounts in the seed.

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A Trachylobane Diterpenoid from Xylopia aethiopica

Abstract: A new trachylobane derivative identified as 7alpha-hydroxytrachyloban-19beta-oic acid (1) has been isolated from the bark of Xylopia aethiopica and its structure elucidated by various NMR techniques and molecular modeling.

Cited by 21 publications

References 9 publications

In vitro antioxidant and anti-lipoperoxidative activities of bark extracts of Xylopia aethiopica against ion-mediated toxicity on liver homogenates

In vitro antioxidant and anti-lipoperoxidative activities of bark extracts of Xylopia aethiopica against ion-mediated toxicity on liver homogenates

Insecticidal Effect of Fruit Extracts from Xylopia aethiopica and Dennettia tripetala (Annonaceae) against Sitophilus oryzae (Coleoptera: Curculionidae)

MALDI–HRMS imaging and HPLC–HRESI–MSⁿ characterisation of kaurane diterpenes in the fruits of Xylopia aethiopica (Dunal) A. Rich (Annonaceae)

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A Trachylobane Diterpenoid from Xylopia aethiopica

Abstract: A new trachylobane derivative identified as 7alpha-hydroxytrachyloban-19beta-oic acid (1) has been isolated from the bark of Xylopia aethiopica and its structure elucidated by various NMR techniques and molecular modeling.

Cited by 21 publications

References 9 publications

In vitro antioxidant and anti-lipoperoxidative activities of bark extracts of Xylopia aethiopica against ion-mediated toxicity on liver homogenates

In vitro antioxidant and anti-lipoperoxidative activities of bark extracts of Xylopia aethiopica against ion-mediated toxicity on liver homogenates

Insecticidal Effect of Fruit Extracts from Xylopia aethiopica and Dennettia tripetala (Annonaceae) against Sitophilus oryzae (Coleoptera: Curculionidae)

MALDI–HRMS imaging and HPLC–HRESI–MSn characterisation of kaurane diterpenes in the fruits of Xylopia aethiopica (Dunal) A. Rich (Annonaceae)

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MALDI–HRMS imaging and HPLC–HRESI–MSⁿ characterisation of kaurane diterpenes in the fruits of Xylopia aethiopica (Dunal) A. Rich (Annonaceae)