Tirucallane triterpenes from the roots of Ozoroa insignis

Liu, Yonghong; Abreu, Pedro

doi:10.1016/j.phytochem.2006.05.004

Cited by 28 publications

(20 citation statements)

References 43 publications

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“…These configurations were consistent with either a euphane or a tirucallane triterpene that only differ by the configuration of C-20 [60]. NMR spectral data of tetracyclic triterpenes indicate that carbon resonances are too similar between euphane (20R) and tirucallane (20S) triterpenoids to afford a clear-cut discrimination between these structural classes on this sole basis, which led to several erroneous structural reports [61]. A reliable spectroscopic approach to differentiate between these structural classes is the nuclear Overhauser effect of H-21 with H-16α,β in euphanes and with H-12α in tirucallanes [62][63][64]47,48,65].…”

Section: Figurementioning

confidence: 94%

Further terpenoids from Euphorbia tirucalli

et al. 2019

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The phytochemical investigation of Euphorbia tirucalli L. (Euphorbiaceae) yielded four new compounds, including a rare cadalene-type sesquiterpene (tirucadalenone), two tirucallane triterpenoids, euphorol L and euphorol M, with the latter being described as an epimeric mixture, and a euphane triterpene, namely, euphorol N, together with 7 known compounds. Their structures and absolute configurations were elucidated from analysis of 1D (1H, J-modulated 13 C) and 2D NMR (HSQC, HMBC and NOESY), high-resolution mass spectrometry (HRESIMS), optical rotation, and GIAO NMR shift calculation followed by CP3 analysis, along with comparison with literature reports. All these compounds were tested for cytotoxicity against K562, MCF-7 and/or and HepG2 tumor cell lines. Only tirucadalenone displayed a mild cytotoxic activity. Graphical abstractFour previously undescribed terpenoids: a cadalene (1), two tirucallanes (2 and 3a/3b), and a euphane (4) were isolated from Euphorbia tirucalli L. ACCEPTED MANUSCRIPT

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Section: Figurementioning

confidence: 94%

Further terpenoids from Euphorbia tirucalli

et al. 2019

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“…Previous chemical investigations of the genus Ozoroa have focused on the root, root bark and stem bark, and resulted in the isolation of mainly cardanols, alkaylanarcadic acids, and triterpenoids [14–18] . Amentoflavone was previously reported in only one species of Ozoroa , O. sphaerocarpa , [39] but robustaflavone is reported from the Ozoroa genus here for the first time.…”

Section: Resultsmentioning

confidence: 86%

“…These biological activities could be ascribed to the presence of bioactive compounds present in Ozoroa species. Phytochemical investigation of the Ozoroa genus has led to the isolation of a wide array of metabolites, including, triterpenoids, [14,15] flavonoids, [15] alkylanacardic acids, alkylphenols, [16–18] and ceramides [19] . The rich phytochemical profile and associated interesting biological activities of the Ozoroa genus makes it attractive for natural product drug discovery.…”

Section: Introductionmentioning

confidence: 99%

Antiplasmodial and Cytotoxic Activities of Extract and Compounds from Ozoroa obovata (Oliv.) R. & A. Fern. var. obovata

Tajuddeen

Swart

Hoppe

et al. 2021

Chemistry & Biodiversity

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Ozoroa obovata (Oliv.) R. & A. Fern. var. obovata found in KwaZulu‐Natal in South Africa was investigated for phytochemical constituents, and for antiplasmodial and cytotoxic effects. The plant leaves were collected from the University of KwaZulu‐Natal (UKZN) arboretum on the Pietermaritzburg Campus, in March 2019. The inhibitory activity against 3D7 Plasmodium falciparum was determined using the parasite lactate dehydrogenase (pLDH) assay and cytotoxicity against HeLa cells was evaluated using the resazurin assay. The bioactive compounds were isolated by chromatographic purification and their structures were established with spectroscopic and spectrometric techniques. The plant leaf extract displayed significant antiplasmodial activity at 50 μg/mL and was also cytotoxic against HeLa cells. Chromatographic purification of the extract led to the isolation of two biflavonoids, four flavonoid glycosides, a steroid glycoside, and a megastigmene derivative. The compounds displayed antiplasmodial and antiproliferative activities at 50 μg/mL but the activity was substantially reduced at 10 μg/mL. The activities and compounds are being reported in O. obovata for the first time.

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“…NOESY cross-peaks of H-17/H-30/CH 3 -21 indicated β-configuration of CH 3 -18 and α-configuration of CH 3 -30. This configuration was very important to distinguish tirucallane-type (C-18α, C-30β) with lanostane-type (C-18β, C-30α) triterpenoids [17]. Consequently, compound 1 was determined as a new lanostane-type triterpenoid and named 3β-hydroxy-25-ethyl-lanost-9(11),24(24′)-diene.…”

Section: Resultsmentioning

confidence: 99%

Cytototoxic constituents from the bark of Chisocheton cumingianus (Meliaceae)

Katja

Farabi

Nurlelasari

et al. 2016

Journal of Asian Natural Products Research

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A new lanostane-type triterpenoid, 3β-hydroxy-25-ethyl-lanost-9(11),24(24')-diene (1), along with 3β-hydroxy-lanost-7-ene (2) and β-sitosterol-3-O-acetate (3) was isolated from the stem bark of C. cumingianus. The chemical structure of the new compound was elucidated on the basis of spectroscopic data. All of the compounds were evaluated for their cytotoxic effects against P-388 murine leukemia cells. Compounds 1-3 showed cytotoxicity against P-388 murine leukemia cells with IC values of 28.8 ± 0.10, 4.29 ± 0.03, and 100.18 ± 0.16 μg/ml, respectively.

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Tirucallane triterpenes from the roots of Ozoroa insignis

Cited by 28 publications

References 43 publications

Further terpenoids from Euphorbia tirucalli

Further terpenoids from Euphorbia tirucalli

Antiplasmodial and Cytotoxic Activities of Extract and Compounds from Ozoroa obovata (Oliv.) R. & A. Fern. var. obovata

Cytototoxic constituents from the bark of Chisocheton cumingianus (Meliaceae)

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