EFSA Compendium of Botanicals

Draft - work in progress

Croton flavens L.

Family:: Euphorbiaceae
Approval state:: Approved
Number of articles retrieved:: 27
Number of processed references:: 6

Compositions

#1: Flavinantine #2: Flavinine #3: Sinoacutine #4: Norsinoacutine #5: Amuronine #6: Phenanthrenes (2,5-Dihydroxy-3,6-dimethoxyphenanthrene) #7: Coreximine #8: Salutaridine (synonym name of sinoacutine) #9: Scoulerine #10: Norsinoacutine #11: Flavinantine #12: Sebiferine #13: Saludimerine A (and enantiomer saludimerine B)

Endpoint Studies

#1: Phorbol derivatives Cocarcinogenic on oesophagus

Genotoxicity

Composition #1: Stuart, Kenneth L., Chambers, Clinton., Byfield, D. Morphinandienone alkaloids from Croton flavens. Journal of the Chemical Society [Section] C: Organic, 1969, p. 1681–1684. .

Language:

English (en)
Plant part:

Unspecified (A07XD)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

Acid, chloroform
Substance:

Flavinantine (RF-00010935-PAR)
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Analytical method - additional description:

IR, UV
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Flavinantine

Composition #2: Stuart, Kenneth L., Chambers, Clinton., Byfield, D. Morphinandienone alkaloids from Croton flavens. Journal of the Chemical Society [Section] C: Organic, 1969, p. 1681–1684. .

Language:

English (en)
Plant part:

Unspecified (A07XD)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

Acid, chloroform
Substance:

Flavinine (RF-00010934-PAR)
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Analytical method - additional description:

IR, UV
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Flavinine

Composition #3: Stuart, Kenneth L., Chambers, Clinton., Byfield, D. Morphinandienone alkaloids from Croton flavens. Journal of the Chemical Society [Section] C: Organic, 1969, p. 1681–1684. .

Language:

English (en)
Plant part:

Unspecified (A07XD)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

Acid, chloroform
Substance:

sinoacutine (RF-00004056-PAR)
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Analytical method - additional description:

IR, UV
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Sinoacutine

Composition #4: Stuart, Kenneth L., Chambers, Clinton., Byfield, D. Morphinandienone alkaloids from Croton flavens. Journal of the Chemical Society [Section] C: Organic, 1969, p. 1681–1684. .

Language:

English (en)
Plant part:

Unspecified (A07XD)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

Acid, chloroform
Substance:

Norsinoacutine (RF-00011152-PAR)
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Analytical method - additional description:

IR, UV
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Norsinoacutine

Composition #5: Charris, J., Dominguez, J., de la Rosa, C., Caro, C. (-)-amuronine from the leaves of Croton flavens L. (Euphorbiaceae). BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 2000, vol. 28, no. 8, p. 795–797. DOI: 10.1016/S0305-1978(99)00112-X. [DOI link]

Language:

English (en)
Plant part:

Leaves (as part-nature) (A0EKT)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

Ethanolic extract
Substance:

Amuronine (RF-00011172-PAR)
Additional substance description:

(-)-amuronine
Analytical method code:

Standard Chromatographic tests (paper- thin layer- and column chromatography) (F016A)
Analytical method - additional description:

IR, NMR
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Amuronine

Composition #6: Eisenreich, WJ., Bracher, F. Crotoflavol, a new phenanthrene from Croton flavens. NATURAL PRODUCT LETTERS, 2001, vol. 15, no. 2, p. 147–150. DOI: 10.1080/10575630108041272. [DOI link]

Language:

English (en)
Plant part:

Leaves (as part-nature) (A0EKT)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

methanol extraction
Substance:

Phenanthrenes (RF-00010826-PAR)
Additional substance description:

2,5-Dihydroxy-3,6-dimethoxyphenanthrene, 3,6-dimethoxyphenanthrene-2,5-diol, crotoflavol
Analytical method code:

HPLC-DAD (F587A)
Analytical method - additional description:

IR, NMR
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Phenanthrenes (2,5-Dihydroxy-3,6-dimethoxyphenanthrene)

Composition #7: Eisenreich, WJ., Hofner, G., Bracher, F. Alkaloids from Croton flavens L. and their affinities to GABA-receptors. NATURAL PRODUCT RESEARCH, 2003, vol. 17, no. 6, p. 437–440. DOI: 10.1080/1478641031000111516. [DOI link]

Language:

English (en)
Plant part:

Leaves (as part-nature) (A0EKT)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

Methanol
Substance:

Coreximine (RF-00011151-PAR)
Analytical method code:

Colorimetry, Spectroscopy (Spectrometry) and Photometry (F008A)
Analytical method - additional description:

NMR, IR, MS, optical rotation
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Coreximine

Composition #8: Eisenreich, WJ., Hofner, G., Bracher, F. Alkaloids from Croton flavens L. and their affinities to GABA-receptors. NATURAL PRODUCT RESEARCH, 2003, vol. 17, no. 6, p. 437–440. DOI: 10.1080/1478641031000111516. [DOI link]

Language:

English (en)
Plant part:

Leaves (as part-nature) (A0EKT)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

methanol
Substance:

sinoacutine (RF-00004056-PAR)
Additional substance description:

Salutaridine
Analytical method code:

Colorimetry, Spectroscopy (Spectrometry) and Photometry (F008A)
Analytical method - additional description:

NMR, IR, MS, optical rotation
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Salutaridine (synonym name of sinoacutine)

Composition #9: Eisenreich, WJ., Hofner, G., Bracher, F. Alkaloids from Croton flavens L. and their affinities to GABA-receptors. NATURAL PRODUCT RESEARCH, 2003, vol. 17, no. 6, p. 437–440. DOI: 10.1080/1478641031000111516. [DOI link]

Language:

English (en)
Plant part:

Leaves (as part-nature) (A0EKT)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

methanol
Substance:

scoulerine (RF-00004049-PAR)
Analytical method code:

Colorimetry, Spectroscopy (Spectrometry) and Photometry (F008A)
Analytical method - additional description:

NMR, IR, MS, optical rotation
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Scoulerine

Composition #10: Eisenreich, WJ., Hofner, G., Bracher, F. Alkaloids from Croton flavens L. and their affinities to GABA-receptors. NATURAL PRODUCT RESEARCH, 2003, vol. 17, no. 6, p. 437–440. DOI: 10.1080/1478641031000111516. [DOI link]

Language:

English (en)
Plant part:

Leaves (as part-nature) (A0EKT)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

methanol
Substance:

Norsinoacutine (RF-00011152-PAR)
Analytical method code:

Colorimetry, Spectroscopy (Spectrometry) and Photometry (F008A)
Analytical method - additional description:

NMR, IR, MS, optical rotation
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Norsinoacutine

Composition #11: Eisenreich, WJ., Hofner, G., Bracher, F. Alkaloids from Croton flavens L. and their affinities to GABA-receptors. NATURAL PRODUCT RESEARCH, 2003, vol. 17, no. 6, p. 437–440. DOI: 10.1080/1478641031000111516. [DOI link]

Language:

English (en)
Plant part:

Leaves (as part-nature) (A0EKT)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

methanol
Substance:

Flavinantine (RF-00010935-PAR)
Analytical method code:

Colorimetry, Spectroscopy (Spectrometry) and Photometry (F008A)
Analytical method - additional description:

NMR, IR, MS, optical rotation
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Flavinantine

Composition #12: Eisenreich, WJ., Hofner, G., Bracher, F. Alkaloids from Croton flavens L. and their affinities to GABA-receptors. NATURAL PRODUCT RESEARCH, 2003, vol. 17, no. 6, p. 437–440. DOI: 10.1080/1478641031000111516. [DOI link]

Language:

English (en)
Plant part:

Leaves (as part-nature) (A0EKT)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

methanol
Substance:

Sebiferine (RF-00011160-PAR)
Analytical method code:

Colorimetry, Spectroscopy (Spectrometry) and Photometry (F008A)
Analytical method - additional description:

NMR, IR, MS, optical rotation
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Sebiferine

Composition #13: Bracher, F., Eisenreich, WJ., Muhlbacher, J., Dreyer, M., Bringmann, G. Saludimerines A and B, novel-type dimeric alkaloids with stereogenic centers and configurationally semistable biaryl axes. JOURNAL OF ORGANIC CHEMISTRY, 2004, vol. 69, no. 25, p. 8602–8608. DOI: 10.1021/jo48631p. [DOI link]

Language:

English (en)
Plant part:

Leaves (as part-nature) (A0EKT)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

MeOH extract
Substance:

Saludimerine A (RF-00011378-PAR)
Additional substance description:

saludimerine A and enantiomer saludimerine B
Analytical method code:

Standard Chromatographic tests (paper- thin layer- and column chromatography) (F016A)
Analytical method - additional description:

NMR
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Saludimerine A (and enantiomer saludimerine B)

Endpoint study #1: Weber, J., Hecker, E. Cocarcinogens of the diterpene ester type from Croton flavens L. and esophageal cancer in Curacao. Experientia, 1978, p. 679–682. .

Study relevance:

Human health
Substance:

Phorbol esters (RF-00004310-PAR)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Type of toxicological test:

case report (CHD060TT)
Tested organism:

Human (as organism) (A056J)
Sex:

No data
Route of exposure:

ORAL: UNSPECIFIED (OECD2234PL)
Control groups used:

no
Endpoint measured:

Dose not reported (CHD066EP)
Critical effect:

Other toxicities (TOX19A)
Target tissue:

digestive: Esophagus (TT019A)
Effect description:

exceptionally high rate of esophageal cancer on Curacao may be causally related to cocarcinogenic phorbol derivatives ingested by the widespread and frequent use of Croton flavens
Effect or parameter linked to the endpoint:

Co-carcinogenic (CHD037BE)
Internal remarks:

Phorbol derivatives Cocarcinogenic on oesophagus