The Composition of a Mixture of Ingol Esters from<i>Euphorbia kamerunica</i>

Abo, None Kio Anthony; Evans, Fred J.

doi:10.1055/s-2007-971531

Cited by 16 publications

(15 citation statements)

References 2 publications

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“…The 1 H-and 13 C-NMR data of the isolates 1 ± 7 exhibited close similarity to the known esters of ingol and were identified as esters of ingol [1], [2], [3], [4], [5], [6], [7], [8], [9]. The spin system of ingol was identified by COSY-45 o experiments (Fig.…”

Section: Resultsmentioning

confidence: 66%

“…Ingol esters are lathyrane-derived, non-irritant, non-toxic, cytotoxic and potent anti-leukemic diterpenes [1], [2], [3], [4], [5], [6], [7], [8], [9], [10]. Therefore, a huge amount of work is ongoing for identifying those plants that are rich in such compounds [1], [2], [3], [4], [5], [6], [7], [8], [9], [10], [11], [12], [13], [14]. The Euphorbiaceae family is commonly found in Pakistan [11], [12].…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Macrocyclic Diterpenoid Esters from Euphorbia cornigera

Baloch¹,

Baloch²,

Saqib³

2006

Planta med

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Root extract of Euphorbia cornigera Boiss. (Euphorbiaceae) was separated into seven (compound 1-7) isolates through multiple Craig's distributions and preparative HPLC. The structures and relative configuration of theses compounds were established via spectral analyses as 7,8,12- O-triacetyl-3- O-(2-methylbutanoyl)-ingol (1), 3,8,12- O-triacetyl-7- O-(2-methylbutanoyl = -ingol (2), 3,7,12- O-triacetyl-8- O-(2-methylbutanoyl)-ingol (3), 3,7,8- O-triacetyl-12- O-(2-methylbutanoyl)-ingol (4), 7,12- O-diacetyl-3- O-(2-methylbutanoyl)-8- O-methylingol (5), 3,12- O-diacetyl-7- O-(2-methylbutanoyl)-8- O-methylingol (6) and 3,7- O-diacetyl-12- O-(2-methylbutanoyl)-8- O-methylingol (7). All these compounds, except for 2, are novel metabolites and have not been reported earlier. It has further been demonstrated that all the compounds (1 - 7) are cytotoxic.

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Section: Resultsmentioning

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Cytotoxic Macrocyclic Diterpenoid Esters from Euphorbia cornigera

Baloch¹,

Baloch²,

Saqib³

2006

Planta med

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“…Diterpenoid esters 1-9 were described earlier from only a few plant species. Ingol 3,12diacetate 7-tigliate (1) was previously isolated from E. hermentiana [28], 8-O-methyl-ingol 3,12-diacetate 7-tigliate (2) from E. acrurensis [29], E. hermentiana [28], and E. kamerunica [30], 8-O-methyl-ingol 3,12-diacetate 7-benzoate (3) from E. antiquorum [31], E. hermentiana [28], and E. kamerunica [30], ingol 3,7,12-triacetate 8-benzoate (4) from E. antiquorum [31], E. nivulia [16,32] E. hermentiana [28], and E. kamerunica [33], and ingol 3,7,12-triacetate 8-tigliate (5) from E. antiquorum [31], and E. kamerunica [33]. The ingenane-type compound 17acetoxyingenol 3-angelate 20-acetate (6) was previously reported from E. canariensis [34] and E. hermentiana [35], 17-acetoxyingenol 3 angelate 5,20-diacetate ( 7) from E. hermentiana [35], E. kamerunica [30], E. royleana [36], and E. trigona [20], 17-acetoxy-20-deoxyingenol 3-angelate ( 8) from E. acrurensis [29], E. hermentiana [35] and E. trigona [20], and 17-acetoxy-20-deoxyingenol 5-angelate ( 9) from E. hermentiana [35].…”

Section: Resultsmentioning

confidence: 99%

Ingol and Ingenol-Type Diterpenes from Euphorbia trigona Miller with Keratinocyte Inhibitory Activity

Hammadi

Kúsz

Dávid

et al. 2021

Plants

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Ingenol mebutate, isolated from Euphorbia peplus, is an ingenane-type diterpenoid, primarily used for the topical treatment of actinic keratosis, a premalignant skin condition. The aim of our work was to investigate other Euphorbia species to find structurally similar diterpenes that can be used as alternatives to ingenol mebutate. Pharmacological investigation of Euphorbia candelabrum, Euphorbia cotinifolia, Euphorbia ramipressa, and Euphorbia trigona revealed the potent keratinocyte (HPV-Ker cell line) inhibitory activity of these spurge species. From the methanolic extract of the aerial parts of Euphorbia trigona Miller, the most active species, five ingol (1–5) and four ingenane-type diterpenoids (6–9) were isolated by various chromatographic separation techniques, including open column chromatography, vacuum liquid chromatography, thin-layer chromatography, and high-performance liquid chromatography. The structures of the compounds were determined by NMR spectroscopic analysis and by comparison of the assignations with the literature data. The cytotoxic activity of the compounds against keratinocytes was tested in vitro by using ingenol mebutate as a positive control. Among the isolated compounds, two ingenane derivatives (6 and 7) exhibited remarkably stronger cytotoxic activity (IC50 values 0.39 μM and 0.32 μM, respectively) on keratinocytes than ingenol mebutate (IC50 value 0.84 μM). These compounds could serve as starting materials for further investigations to find alternatives to Picato® (with active substance ingenol mebutate), which was withdrawn from marketing authorization in the European Union.

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“…The three known diterpenoids were identified , in turn, as 3,12-O-diacetyl-7-O-benzoyl-8-methoxyingol (2) [15], ingol-12-acetate (3) [16], [17], ingol (4) [16], [18] from their spectral data.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Diterpenoids from Euphorbia pekinensis

Kong

et al. 2002

Planta med

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A new diterpenoid, named euphpekinensin, along with three known diterpenoids, was isolated from the roots of Euphorbia pekinensis for the first time and the structures were elucidated by spectral analysis. The 2D-NMR techniques such as 1H-1H COSY, HMQC, HMBC and NOESY spectra were mainly applied to determine the structure of the new diterpenoid. The four diterpenoids showed cytotoxic activity against human KB cells in vitro.

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The Composition of a Mixture of Ingol Esters fromEuphorbia kamerunica

Cited by 16 publications

References 2 publications

Cytotoxic Macrocyclic Diterpenoid Esters from Euphorbia cornigera

Cytotoxic Macrocyclic Diterpenoid Esters from Euphorbia cornigera

Ingol and Ingenol-Type Diterpenes from Euphorbia trigona Miller with Keratinocyte Inhibitory Activity

Cytotoxic Diterpenoids from Euphorbia pekinensis

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