Cycloeuphordenol, a new triterpene from Euphorbia tirucalli

Khan, Adnan; Rasheed, Tahir; Kazmi, Syed Najam-ul-Hussain; Ahmed, Zaheer; Malik, Abdul

doi:10.1016/0031-9422(88)80142-0

Cited by 21 publications

(4 citation statements)

References 7 publications

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“…27 Additionally, the H-3 methine signal was deduced to be axial (α)-oriented due to its coupling constants. 28,29 The absolute configuration of compound 1 was further determined by X-ray crystallography (CCDC 2083548) (Figure 2), which confirmed the β-orientation of the 10-hydroxy group. This allowed the structure of lepidozin A (1) to be defined as 3β,10β,16α-trihydroxy-9,10-seco-9,19-cyclolanost-9(11) 23, dd (11.4, 3.2) 3.24, dd (11.8, 3.7) 3.23, dd (11.4, 3.2) 3.24, dd (11.8, 3.8) 3.24, dd (11.8, 3.8 1 and 3) resembled those of 1, except for the presence of an oxygenated tertiary carbon (δ C 70.9) at C-25, which was supported by the HMBC correlations from H 3 -26 (δ H 1.31, s) to C-24 (δ C 139.9) and C-25 and from H-24 (δ H 5.66, m) to C-22 (δ C 38.9), C-23 (δ C 126.0), C-25, and C-27 (δ C 30.1) (Figure S2, Supporting Information).…”

Section: ■ Results and Discussionmentioning

confidence: 79%

“…Comparison of these correlations with literature values indicated that H-5 and H-19a [δ H 2.54 (br d, J = 15.6 Hz)] are α-oriented, while H-19b [δ H 2.21 (d, J = 15.6 Hz)] is β-oriented . Additionally, the H-3 methine signal was deduced to be axial (α)-oriented due to its coupling constants. , The absolute configuration of compound 1 was further determined by X-ray crystallography (CCDC 2083548) (Figure ), which confirmed the β-orientation of the 10-hydroxy group. This allowed the structure of lepidozin A ( 1 ) to be defined as 3β,10β,16α-trihydroxy-9,10- seco -9,19-cyclolanost-9(11),24(25)-diene.…”

Section: Resultsmentioning

confidence: 89%

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Cytotoxic Activities of 9,10-seco-Cycloartane-Type Triterpenoids from the Chinese Liverwort Lepidozia reptans

et al. 2021

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Ten new triterpenoids, including nine 9,10-secocycloartanes (1−9) and one 9,19-cyclolanostane (10), as well as one sesquiterpenoid (11) and four known compounds (12−15), were extracted and purified from the whole plant of the Chinese liverwort Lepidozia reptans. Multiple techniques (NMR, HRESIMS, IR, and Xray crystallographic analysis) were applied to determine the structures of the isolated compounds. Bioassay determinations showed that compound 7, which contains an α,β-unsaturated carbonyl moiety in its structure, inhibited the growth of a panel of cancer cell lines with IC 50 values ranging from 4.2 ± 0.2 to 5.7 ± 0.5 μM. Further investigation revealed that compound 7 induces PC-3 cell death via mitochondrial-related apoptosis.

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Section: ■ Results and Discussionmentioning

confidence: 79%

Section: Resultsmentioning

confidence: 89%

Cytotoxic Activities of 9,10-seco-Cycloartane-Type Triterpenoids from the Chinese Liverwort Lepidozia reptans

et al. 2021

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“…The presence of an axial (α)-oriented H-3 methine signal at δ H 3.00 (td, J = 10.7, 4.6 Hz) was deduced from its coupling constants, which suggested a diaxial vicinal interaction between H-3 and H-4. ,, This implied the presence of an α-oriented H 3 -28. NOESY correlations (Figure ) between H-3 and H 3 -28 confirmed this assumption.…”

Section: Resultsmentioning

confidence: 96%

Structural Characterization and Anti-infective Activity of 9,10-Seco-29-norcycloartane Glycosides Isolated from the Flowers of the Peruvian Medicinal Plant Cordia lutea

et al. 2019

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Six new secocycloartane glycosides (1−6) were isolated from the ethanol extract of the flowers of Cordia lutea Lam. on the basis of bioassay-guided fractionation. Their structures were determined by the application of NMR and MS data analyses together with X-ray crystallographic analyses for compounds 1 and 2. Compounds 1−6 represent the first examples of 9,10-seco-29-norcycloartane glycosides. These compounds showed significant in vitro anti-Helicobacter pylori activity, and no activity against either Escherichia coli or Pseudomonas aeruginosa. Significant activity was observed for 5 and 6 against Staphylococcus aureus. All compounds displayed weak cytotoxicity against RAW 264.7 cells. The in vitro antileishmanial and antiplasmodial activities of 1−6 were also evaluated.

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“…For instance, compounds such as 24-methyl-9,19-cyclolanost-24-en-3-ol and 19-norlanosta-5,24-dien-3-ol,9-methyl-,(3β, 9β,10α) were discovered in E. caducifolia latex extract [5]. In addition, cyclotirucanenol and cycloeuphordenol were isolated from E. tirucalli [6,7] latex, while 9,19-cyclolanost-22(22′),24-diene-3-ol (nerifoliene) and euphol were obtained from fresh latex of latex E. nerifolia [8]. Tese compounds play a crucial role in the identifcation and classifcation of Euphorbia species.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial and Antioxidant Activities of Triterpenoids Isolated from Endemic Euphorbia arbuscula Stem Latex

Al-Ansi,

Masaoud,

Hussein

et al. 2024

Advances in Pharmacological and Pharmaceutical Sciences

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This research study aimed to investigate the chemical constituents and evaluate the antibacterial and antioxidant activities of stem latex extracts from the endemic medicinal plant Euphorbia arbuscula found on Socotra Island, Yemen. The study aimed to assess the potential medicinal and veterinary uses of this plant, representing the first evaluation of its properties. The stem latex was extracted using ethanol, and the resulting oil underwent analysis using GC-MS to identify eight compounds. In addition, chromatographic techniques were employed to isolate two triterpenoids, lanosterol and lupeol, from the stem latex. The structures of these compounds were confirmed using IR, MS, and NMR techniques. The antibacterial activity of the extracts and isolated compounds was evaluated against three bacterial strains using the disc diffusion method, revealing only weak antibacterial effects. The study also investigated the antioxidant activity using the DPPH assay, where the ethyl acetate extract exhibited the highest activity with an IC50 value of ±13.55 µg/mL, followed by the chloroform extract with an IC50 of ±21.87 µg/mL. These findings emphasize the potential of Euphorbia arbuscula in the development of new medicines, particularly due to its notable antioxidant activity. The research methodology employed a scientifically rigorous approach, utilizing a comprehensive range of analytical techniques. However, further investigation is required to fully assess the plant’s potential as a therapeutic agent.

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Cycloeuphordenol, a new triterpene from Euphorbia tirucalli

Cited by 21 publications

References 7 publications

Cytotoxic Activities of 9,10-seco-Cycloartane-Type Triterpenoids from the Chinese Liverwort Lepidozia reptans

Cytotoxic Activities of 9,10-seco-Cycloartane-Type Triterpenoids from the Chinese Liverwort Lepidozia reptans

Structural Characterization and Anti-infective Activity of 9,10-Seco-29-norcycloartane Glycosides Isolated from the Flowers of the Peruvian Medicinal Plant Cordia lutea

Antibacterial and Antioxidant Activities of Triterpenoids Isolated from Endemic Euphorbia arbuscula Stem Latex

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