Aryltetralin lignans

Podophyllotoxin is an aryltetralin lignan which has been isoiated from severai plants of the Podophyllum species, it is a potent cytotoxic agent against various cancer celi iines, stopping the cell cycle in metaphase through the inhibition of microtubules assembly by binding the colchicine site of the tubulin [112]. Because of numerous side effects, podophyllotoxin cannot be used as a drug. 

Oxidation of an allyiic ether. Oxidation of aryltetralin lignanes such as 1 results in two products, 2 and 3, which are believed to be formed as indicated in equation... 

Aryltetralin lignans. This ring system can be prepared in high yield by a Prins reaction of a 1,4-diaryl-1-butene with paraformaldehyde catalyzed by an alkylaluminum halide prepared from CHjAlCh and (CH,) A1C1 (1 1), which is more acidic than (CHO AICI alone. 

Broomhead, A.J. and Dewick, P.M. (1990) Aryltetralin lignans from Linum flavum and Linum capitatum. Phytochemistry, 29, 3839-44. 

Federolf, K., Alfermann, A.W. and Fuss, E. (2007) Aryltetralin-lignan formation in two different cell suspension cultures of Linum album Deoxypodophyllotoxin 6-hydroxylase, a key enzyme for the formation of 6-methoxypodophyllotoxin. Phytochemistry, 68,1397-A06. 

Jackson, D.E. and Dewick, P.M. (1984) Biosynthesis of Podophyllum lignans. II. Interconversions of aryltetralin lignans in Podophyllum hexandrum. Phytochemistry, 23, 1037-12. 

In certain cases, structure elucidation of aryltetralin lignans has only been established by total synthesis of the ( )-compounds. Noteworthy in this respect have been the constituents of Phyllanthus nlruri Linn. (Euphorbiaceae), extracts of which have been used medicinally (in treatment of asthma, jaundice and bronchial infections) (140). Considerable confusion resulted mainly from differing interpretations of spectroscopic data, and at least five different structures were proposed for the major constituent, hypophyllanthin. The structure of the aryltetralin constituents established by unequivocal synthesis (141) are shown in Scheme 30 they were given the names hypophyllanthin (1411. nirtetralin (1421. phyltetralin (1431 and lintetralin (1441. 

Chart 16 CD Curves of 4-Aryltetralin Lignan in EtOH ---- hernandin (15) ------compound (58) ---------compound (59)... 

Recently, the methodology has been extended to the synthesis of an aryltetraline lignan by completing a straightforward synthesis of (+)-lintetralin (140), Scheme (25) [85], Adduct 137 was easily accesible via the Enders methodology in virtually enantiopure form and excellent... 

The similarity between the mode of action of aryltetralin lignans as anticancer and antiviral agents is noteworthy. Because of their ability to bind tubulin, these lignans disrupt the cellular cytoskeleton and thus interfere with viral replication. The development of successful... 

Several aryltetralin lignans including isodeoxypodophyllotoxin and isopeltatin have been prepared by the acid-catalysed cyclisation route... 

SYNTHESIS OF THE ARYLTETRALIN LIGNAN SKELETON BY TANDEM ENE AND PRINS REACTIONS. 

Figure 8. Synthesis of the aryltetralin lignan skeleton via the Prins reaction.

Jackson D E, Dewick P M 1984 Aryltetralin lignans from Podophyllum hexandrum and Podophyllum peltatum. Phytochemistry 23 1147-1152... 

Jackson D E, Dewick P M 1985 Tumor-inhibitory aryltetralin lignans from Podophyllum pleian-thum. Phytochemistry 24 2407-2409... 

Schneiders G E, Stevenson R 1982 Structure and synthesis of the aryltetralin lignans hypophyllan-thin and nirtetralin. J Chem Soc Perkin Trans I 999-1003... 

Dayan, F.E. et al. (2003) Podophyllumpeltatum possesses a )3-glucosidase with high substrate specificity for the aryltetralin lignan podophyl-lotoxin. Biochem. Biophys. Act. 1646, 157-163... 

Puri, S.C., Nazir, A., Chawla, R., Arora, R. et al (2006) The endophytic fungus Trametes hirsuta as a novel alternative source of podophyllotoxin and related aryltetralin lignans. /. Biotechnol, 122, 494-510. 

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