EFSA Compendium of Botanicals

Draft - work in progress

Vincetoxicum hirundinaria Medik. // Asclepias vincetoxicum L. // Cynanchum vincetoxicum (L.) Pers.

Family:: Apocynaceae
Approval state:: Approved
Number of articles retrieved:: 246
Number of processed references:: 6

Compositions

#1: Hirundoside A #2: anhydrohirundigenin #3: antofine and related compounds in root/stem bark #4: antofine N-oxide derivatives in root/stem bark #5: Cynatratoside C in roots #6: 2-hydroxyacetophenone in essential oil of roots #7: Hirundicoside D in roots #8: Cynatratoside E in roots #9: 4-hydroxyacetophenone in roots #10: Hirundicoside B in roots #11: Hirundicoside C in roots #12: 2-hydroxyacetophenone in roots #13: Apiole in essential oil of roots #14: Antofine and related compounds in leaves #15: Antofine-N-oxide in plant #16: Vincentine and an unspecified alkaloid in aerial parts #17: Tylophorine in aerial parts

Endpoint Studies

Genotoxicity

Composition #1: Stoeckel, K., Reichstein, Tadeus. Glycosides of Vincetoxicum hirundinaria. scientia pharmaceutica, 1969, vol. 37, no. 1, p. 47–9. .

Language:

English (en)
Plant part:

Unspecified (A07XD)
Substance:

hirundoside A (RF-00011260-PAR)
Analytical method code:

Unspecified (F598A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Hirundoside A

Composition #2: Stoeckel, K., Reichstein, Tadeus. Glycosides of Vincetoxicum hirundinaria. scientia pharmaceutica, 1969, vol. 37, no. 1, p. 47–9. .

Language:

English (en)
Plant part:

Unspecified (A07XD)
Substance:

anhydrohirundigenin (RF-00011187-PAR)
Analytical method code:

Unspecified (F598A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

anhydrohirundigenin

Composition #3: Lavault, M., Richomme, P., Bruneton, J. New phenatroindolizidine N-oxides alkaloids isolated from Vincetoxicum hirudinaria medic.. pharmaceutica acta helvetiae, 1994, vol. 68, no. 4, p. 225–227. DOI: 10.1016/0031-6865(94)90052-3. [DOI link]

Language:

English (en)
Plant part:

Bark (as part-nature) (A066X)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

Hexane and chloroform
Substance:

indole alkaloids (RF-00004503-PAR)
Additional substance description:

antofine, (-)-6-O-demethylantofine, (-)-14-hydroxyantofine
Analytical method code:

Standard Chromatographic tests (paper- thin layer- and column chromatography) (F016A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

antofine and related compounds in root/stem bark

Composition #4: Lavault, M., Richomme, P., Bruneton, J. New phenatroindolizidine N-oxides alkaloids isolated from Vincetoxicum hirudinaria medic.. pharmaceutica acta helvetiae, 1994, vol. 68, no. 4, p. 225–227. DOI: 10.1016/0031-6865(94)90052-3. [DOI link]

Language:

English (en)
Plant part:

Bark (as part-nature) (A066X)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

Hexane and chloroform extraction. Root and stem barks extracted separately, ranges reported include results for both extracts of both types of bark.
Substance:

antofine N-oxide derivatives (RF-00004345-PAR)
Additional substance description:

10-beta-(-)-antofine N-oxide, 10-alpha-(-)-antofine N-oxide
Analytical method code:

Standard Chromatographic tests (paper- thin layer- and column chromatography) (F016A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

antofine N-oxide derivatives in root/stem bark

Composition #5: Lavault, M., Richomme, P., Bruneton, J. Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria . fitoterapia, 1999, vol. 70, no. 2, p. 216–220. DOI: 10.1016/S0367-326X(99)00023-4. [DOI link]

Language:

English (en)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Additional extraction description:

no extraction or preparation described
Substance:

pregnane derivatives (RF-00004313-PAR)
Additional substance description:

Cynatratoside C, a pregnane glycoside
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Result unit:

Percent (G138A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

0.0004
Internal remarks:

Cynatratoside C in roots

Composition #6: Lavault, M., Richomme, P., Bruneton, J. Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria . fitoterapia, 1999, vol. 70, no. 2, p. 216–220. DOI: 10.1016/S0367-326X(99)00023-4. [DOI link]

Language:

English (en)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Extraction/Preparation method:

Essential oil (as part-nature) (A166Q)
Additional extraction description:

no details
Substance:

2-Hydroxyacetophenone (RF-00002015-PAR)
Analytical method code:

GC-MS (F046A)
Result unit:

Percent (G138A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

84
Internal remarks:

2-hydroxyacetophenone in essential oil of roots

Composition #7: Lavault, M., Richomme, P., Bruneton, J. Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria . fitoterapia, 1999, vol. 70, no. 2, p. 216–220. DOI: 10.1016/S0367-326X(99)00023-4. [DOI link]

Language:

English (en)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Additional extraction description:

no extraction or preparation described
Substance:

hirundicoside D (RF-00003866-PAR)
Additional substance description:

also spelled "hirundigoside" in article
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Result unit:

Percent (G138A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

0.0002
Internal remarks:

Hirundicoside D in roots

Composition #8: Lavault, M., Richomme, P., Bruneton, J. Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria . fitoterapia, 1999, vol. 70, no. 2, p. 216–220. DOI: 10.1016/S0367-326X(99)00023-4. [DOI link]

Language:

English (en)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Additional extraction description:

no extraction or preparation described
Substance:

pregnane derivatives (RF-00004313-PAR)
Additional substance description:

Cynatratoside E, a pregnane glycoside
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Result unit:

Percent (G138A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

0.0025
Internal remarks:

Cynatratoside E in roots

Composition #9: Lavault, M., Richomme, P., Bruneton, J. Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria . fitoterapia, 1999, vol. 70, no. 2, p. 216–220. DOI: 10.1016/S0367-326X(99)00023-4. [DOI link]

Language:

English (en)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Additional extraction description:

no extraction or preparation described
Substance:

4-Hydroxyacetophenone (RF-00002341-PAR)
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Result unit:

Percent (G138A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

0.012
Internal remarks:

4-hydroxyacetophenone in roots

Composition #10: Lavault, M., Richomme, P., Bruneton, J. Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria . fitoterapia, 1999, vol. 70, no. 2, p. 216–220. DOI: 10.1016/S0367-326X(99)00023-4. [DOI link]

Language:

English (en)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Additional extraction description:

no extraction or preparation described
Substance:

hirundicoside B (RF-00003864-PAR)
Additional substance description:

also spelled "hirundigoside" in article
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Result unit:

Percent (G138A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

0.0003
Internal remarks:

Hirundicoside B in roots

Composition #11: Lavault, M., Richomme, P., Bruneton, J. Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria . fitoterapia, 1999, vol. 70, no. 2, p. 216–220. DOI: 10.1016/S0367-326X(99)00023-4. [DOI link]

Language:

English (en)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Additional extraction description:

no extraction or preparation described
Substance:

hirundicoside C (RF-00003865-PAR)
Additional substance description:

also spelled "hirundigoside" in article
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Result unit:

Percent (G138A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

0.0002
Internal remarks:

Hirundicoside C in roots

Composition #12: Lavault, M., Richomme, P., Bruneton, J. Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria . fitoterapia, 1999, vol. 70, no. 2, p. 216–220. DOI: 10.1016/S0367-326X(99)00023-4. [DOI link]

Language:

English (en)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Additional extraction description:

no extraction or preparation described
Substance:

2-Hydroxyacetophenone (RF-00002015-PAR)
Analytical method code:

Nuclear Magnetic Resonance (NMR) (F061A)
Result unit:

Percent (G138A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

0.06
Internal remarks:

2-hydroxyacetophenone in roots

Composition #13: Lavault, M., Richomme, P., Bruneton, J. Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria . fitoterapia, 1999, vol. 70, no. 2, p. 216–220. DOI: 10.1016/S0367-326X(99)00023-4. [DOI link]

Language:

English (en)
Plant part:

Roots and other underground parts (as part-nature) (A067M)
Extraction/Preparation method:

Essential oil (as part-nature) (A166Q)
Additional extraction description:

no details
Substance:

apiole (RF-00003690-PAR)
Analytical method code:

GC-MS (F046A)
Result unit:

Percent (G138A)
Result type:

Numerical Value (VAL)
Value (concentration, content):

1
Internal remarks:

Apiole in essential oil of roots

Composition #14: Staerk, D., Lykkeberg, AK., Christensen, J., Budnik, BA., Abe, F., Jaroszewski, JW. In vitro cytotoxic activity of phenanthroindolizidine alkaloids from Cynanchum vincetoxicum and Tylophora tanakae against drug-sensitive and multidrug-resistant cancer cells . journal of natural products, 2002, vol. 65, no. 9, p. 1299–1302. DOI: 10.1021/np0106384. [DOI link]

Language:

English (en)
Plant part:

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

Solvent extraction (A0BZR)
Additional extraction description:

CH2Cl2 then MeOH-CH2Cl2 (1:1)
Substance:

indole alkaloids (RF-00004503-PAR)
Additional substance description:

antofine and derivatives: 6-O-desmethylantofine, 6-O-desmethylsecoantofine and secoantofine
Analytical method code:

High Performance Liquid Chromatography (HPLC)/Liquid Chromatography (LC) (F018A)
Analytical method - additional description:

Also: NMR
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Antofine and related compounds in leaves

Composition #15: Bour, Tania., Yang, Xianwen., Li, Weihong., Bernardin, Franois., Kaoma, Tony., Muller, Arnaud., Vallar, Laurent., Steinmetz, Andre. Differential Effects of Antofine N-Oxide on Solid Tumor and Leukemia Cells . anti-cancer agents in medicinal chemistry, 2014, vol. 14, no. 10, p. 1315–1323. .

Language:

English (en)
Plant part:

Live plants (as part-nature) (A0BA0)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

maceration in 99% EtOH at room temperature for 5 times
Substance:

antofine N-oxide derivatives (RF-00004345-PAR)
Additional substance description:

(-)-10ß,13a alpha-antofine N-oxide.
Analytical method code:

Standard Chromatographic tests (paper- thin layer- and column chromatography) (F016A)
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Antofine-N-oxide in plant

Composition #16: TANNER, U., WIEGREBE, W. ALKALOIDS OF CYNANCHUM-VINCETOXICUM - EFFICACY AGAINST MDA-MB-231 MAMMARY-CARCINOMA CELLS . archiv der pharmazie, 1993, vol. 326, no. 2, p. 67–72. DOI: 10.1002/ardp.19933260203. [DOI link]

Language:

English (en)
Plant part:

Aerial part of plants (as part-nature) (A166F)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

methanol
Substance:

Alkaloids (RF-00004360-PAR)
Additional substance description:

"Vincetine" and an unspecified alkaloid
Analytical method code:

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

also UV spec
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Vincentine and an unspecified alkaloid in aerial parts

Composition #17: TANNER, U., WIEGREBE, W. ALKALOIDS OF CYNANCHUM-VINCETOXICUM - EFFICACY AGAINST MDA-MB-231 MAMMARY-CARCINOMA CELLS . archiv der pharmazie, 1993, vol. 326, no. 2, p. 67–72. DOI: 10.1002/ardp.19933260203. [DOI link]

Language:

English (en)
Plant part:

Aerial part of plants (as part-nature) (A166F)
Extraction/Preparation method:

Solvent extraction (A0BZR)
Additional extraction description:

methanol
Substance:

tylophorine (RF-00004095-PAR)
Analytical method code:

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

also UV spec
Yes/No Qualitative:

Positive/Present (POS)
Result type:

Qualitative Value (Binary) (BIN)
Internal remarks:

Tylophorine in aerial parts