Three new ingenane derivatives from the latex of Euphorbia canariensis L

Lin, Lihao; Kinghorn, A. D.

doi:10.1021/jf00116a053

Cited by 28 publications

(11 citation statements)

References 11 publications

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“…The physical and UV, IR, mass, and NMR data of compounds 6 and 7 are identical to those reported for 3-O-angeloyl-17-(benzoyloxy)ingenol and 20-O-acetyl-3-O-angeloyl-17(benzoyloxy)ingenol, respectively [16].…”

supporting

confidence: 76%

Tumor‐Promoting Diterpene Esters from Latex of Euphorbia cauducifolia L.

Baloch

Saqib

2005

Helvetica Chimica Acta

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Tumor-promoting characteristics of seven esters, 1 -7, obtained from the latex of Euphorbia cauducifolia L. was appraised by carrying out NMRI mice back skin. The structures of 1 -7 were elucidated by spectroscopic techniques like 1 H-and (7). Compounds 1 -4 were isolated for the first time, whereas 5 -7 are known metabolites but detected for the first time in this plant. Biological investigations revealed that these compounds are tumor promoters.

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supporting

confidence: 76%

Tumor‐Promoting Diterpene Esters from Latex of Euphorbia cauducifolia L.

Baloch

Saqib

2005

Helvetica Chimica Acta

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“…In the present contribution we wish to report the identification and characterization of five ingenane derivatives present in an acetone extract of the latex of E. hermentiana, which comprise the 16-hydroxyingenol esters, 1-3, the ingenol ester, 4, and the 20deoxy-16-hydroxyingenol ester, 5. Successful resolution of the E. hermentiana latex constituents 1-5 from several esters of the macrocyclic diterpene, ingol, whose characterization will be reported separately, was achieved by means of a combination of droplet counter-current chromatography3 and preparative tic.…”

mentioning

confidence: 99%

The Dermatitis-Producing Constituents of Euphorbia hermentiana Latex

Li¹,

Marshall²,

Kinghorn³

1983

J. Nat. Prod.

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Five ingenane derivatives, 3-O-n-(deca-2,4,6-trienoyl)-16-O-[(Z)-2-methyl-2-butenoyl]-16-hydroxyingenol (1), 3-O-[(Z)-2-methyl-2-butenoyl]-5,16,20-O-triacetyl-16-hydroxyingenol (2), 3-O-[(Z)-2-methyl-2-butenoyl]-16,20-O-diacetyl-16-hydroxyingenol (3), 3-O-[(Z)-2-methyl-2-butenoyl]-20-O-acetylingenol (4), and 3-O-[(Z)-2-methyl-2-butenoyl]-16-O-acetyl-20-deoxy-16-hydroxyingenol (5) were isolated with a new procedure that uses droplet counter-current chromatography, from a dermatitis-producing fraction of the latex of Euphorbia hermentiana Lem. The structures of the new compounds 2,3, and 5 were established by the interpretation of their spectroscopic data and those of their hydrolytic and acetylated derivatives.

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“…Eight known diterpenoids were characterized as hydroxyjatropha-6(17),11 E -diene-9,14-dione ( 5 ) [ 17 ], 3,5,7,15-tetraacetoxy-9-nicotinoyloxy-14-oxojatropha-6(17),11-diene ( 6 ) [ 19 ], pepluanin D ( 7 ) [ 20 ], ingenol-20-angelate ( 8 ) [ 21 ], ingenol-3-angelate ( 9 ) [ 22 ], 5- O -benzoyl-20-deoxyingenol ( 10 ) [ 23 ], 5,8,9,15-tetraacetoxy-3-benzoyloxy-11,16-dihydroxypepluane ( 11 ) [ 24 ], and 5,8,9,11,15-pentaacetoxy-3-benzoyloxy-16-hydroxypepluane ( 12 ) [ 25 ] by comparing their spectroscopic data with those in the literatures.…”

Section: Resultsmentioning

confidence: 99%

Jatrophane Diterpenoids from the Seeds of Euphorbia peplus with Potential Bioactivities in Lysosomal-Autophagy Pathway

Ding

et al. 2021

Nat. Prod. Bioprospect.

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Euphopepluanones F − K (1 − 4), four new jatrophane type diterpenoids were isolated from the seeds of Euphorbia peplus, along with eight known diterpenoids (5 − 12). Their structures were established on the basis of extensive spectroscopic analysis and X-ray crystallographic experiments. The new compounds 1 − 4 were assessed for their activities to induce lysosomal biogenesis through LysoTracker Red staining. Compound 2 significantly induced lysosomal biogenesis. In addition, compound 2 could increase the number of LC3 dots, indicating that it could activate the lysosomal-autophagy pathway. Graphic Abstract

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Three new ingenane derivatives from the latex of Euphorbia canariensis L

Cited by 28 publications

References 11 publications

Tumor‐Promoting Diterpene Esters from Latex of Euphorbia cauducifolia L.

Tumor‐Promoting Diterpene Esters from Latex of Euphorbia cauducifolia L.

The Dermatitis-Producing Constituents of Euphorbia hermentiana Latex

Jatrophane Diterpenoids from the Seeds of Euphorbia peplus with Potential Bioactivities in Lysosomal-Autophagy Pathway

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