Isopicropodophyllone

Identification of lignans and related compounds in Anthriscus sylvestris by LC-ESI-MS/MS and LC-SPE-NMR.[Pubmed:21889175]

Phytochemistry. 2011 Dec;72(17):2172-9.

The aryltetralin lignan deoxypodophyllotoxin is much more widespread in the plant kingdom than podophyllotoxin. The latter serves as a starting compound for the production of cytostatic drugs like etoposide. A better insight into the occurrence of deoxypodophyllotoxin combined with detailed knowledge of its biosynthestic pathway(s) may help to develop alternative sources for podophyllotoxin. Using HPLC combined with electrospray tandem mass spectrometry and NMR spectroscopy techniques, we found nine lignans and five related structures in roots of Anthriscus sylvestris (L.) Hoffm. (Apiaceae), a common wild plant in temperate regions of the world. Podophyllotoxone, deoxypodophyllotoxin, yatein, anhydropodorhizol, 1-(3'-methoxy-4',5'-methylenedioxyphenyl)1-xi-methoxy-2-propene, and 2-butenoic acid, 2-methyl-4-[[(2Z)-2-methyl-1-oxo-2-buten-1-yl]oxy]-, (2E)-3-(7-methoxy-1,3-benzodioxol-5-yl)-2-propen-1-yl ester, (2Z)- were the major compounds. alpha-Peltatin, podophyllotoxin, beta-peltatin, Isopicropodophyllone, beta-peltatin-a-methylether, (Z)-2-angeloyloxymethyl-2-butenoic acid, anthriscinol methylether, and anthriscrusin were present in lower concentrations. alpha-Peltatin, beta-peltatin, Isopicropodophyllone, podophyllotoxone, and beta-peltatin-a-methylether have not been previously reported to be present in A. sylvestris. Based on our findings we propose a hypothetical biosynthetic pathway of aryltetralin lignans in A. sylvestris.

[Study on lignans from Diphylleia sinensis].[Pubmed:8010016]

Yao Xue Xue Bao. 1993;28(9):690-4.

A new lignan along with eight known lignans and a flavonoid were isolated from the rhizomes of Diphylleia sinensis Li.. Their structures were elucidated on the basis of chemical and spectral analysis. The new lignan, compound IX, was named as picropodophyllin-1-ethyl ether (IX). The eight known lignans were identified as podophyllotoxin (I), Isopicropodophyllone (II), dehydropodophyllotoxin (III), diphyllin (IV), picropodophyllin (V), podophyllotoxone (VI), 4'-demethylpodophyllotoxin (VII) and picropodophyllin glucoside (VIII). Compounds II, VI, VII and VIII were found for the first time from the rhizome of this plant. The flavonoid was identified as kaempferol.

[Studies on the TLC scanning determination of lignans in Diphylleia sinensis Li].[Pubmed:1299145]

Yao Xue Xue Bao. 1992;27(12):934-8.

A simple, sensitive and accurate method for the separation and determination of the lignans: podophylltoxone (I), Isopicropodophyllone (II), picropodophyllone (III), dehydropodophyllotoxin (IV), picropodophyllin (V), podophyllotoxin (VI), 4'-demethylpodophyllotoxin (VII) and diphyllin (VIII) is described. The sample solution was applied at a point 1 cm from the bottom edge of the HPTLC silica gel plate (10 cm x 10 cm), dichloromethane-diethyl ether (4:1) was used as the developing solvent. The plate was saturated for 30 min and then developed twice for 9.5 cm using ascending technique. The plate was sprayed with 2.5% ammonium ceric sulphate--20% nitric acid and toasted for 15 min at 120 degrees C, then fumigated with ammonia solution for 20 min at room temperature to intensify the spot color. The spots were scanned with a Shimadzu CS-930 TLC scanner. The contents of eight lignans in Diphylleia sinensis was calculated by comparison with standards spotted on the same plate. The standard curves were linear in the range of 0.48-2.52 micrograms for the eight lignans. The method has been applied to the analysis of various samples and can be used for the quality control of Diphylleia sinensis, podophyllum and dysosma preparations used in clinic.

[Chemical constituents of Dysosma aurantiocaulis (H.-M.) Hu and Dysosma pleianthum Woods].[Pubmed:2558670]

Zhongguo Zhong Yao Za Zhi. 1989 Jul;14(7):420-1, 447.

Roots of D. aurantiocaulis and D. pleianthum contain ten lignans: picropodophyllin, podophyllotoxin, 4'-demethylpodophyllotoxin, diphyllin, dehydropodophyllotoxin, podophyllotoxone, picropodophyllone, Isopicropodophyllone, 4'-demethylpodophyllotoxone and dysosmajol; two anthraquinones: physcion and dysoanthraquinone. A HPLC method for the identification of aryltetralin lignans is described.

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