Estrogenic Activity of Phenylpropanoids from Sarcomelicope megistophylla and Structure Determination of a New Norneolignan

Abstract

Bioassay-guided fractionation of the neutral extract of the bark of Sarcomelicope megistophylla resulted in the isolation of the new nor-neolignan sarcomeginal (1), together with the known ailanthoidol (2) and (±)-seco-isolariciresinol (3). The structure of 1 was determined by spectroscopic means. Estrogenic activity of the isolated compounds was tested using estrogen receptor-positive MCF7 and estrogen receptor-negative MDA-MB-231 human mammary adenocarcinoma cell lines. Compound 3 displayed significant estrogenic activity.

References

• 1 Davis S R, Dalais F S, Simpson E R, Murkies A L. Phytoestrogens in health and disease.  Recent Progress in Hormone Research. 1999;  54 185-210
• 2 Adlercreutz H. Phyto-oestrogens and cancer.  Lancet Oncology. 2002;  3 364-73
• 3 Halabalaki M, Aligiannis N, Papoutsi Z, Mitakou S, Moutsatsou P, Sekeris S ,. et al . Three new arylbenzofurans from Onobrychis ebenoides and evaluation of their binding affinity for the estrogen receptor.  Journal of Natural Products. 2000;  63 672-4
• 4 Hartley T G. A revision of the genus Sarcomelicope (Rutaceae).  Australian Journal of Botany. 1982;  30 359-72
• 5 Hartley T G. Three new species of Sarcomelicope (Rutaceae) from New Caledonia (with a new key to the species of the genus).  Adansonia. 1986;  8 83-9
• 6 Tillequin F. Alkaloids in the genus Sarcomelicope .  Recent Research Developments in Phytochemistry. 1997;  1 675-87
• 7 Fokialakis N, Magiatis P, Terzis A, Tillequin F, Skaltsounis A -L. Cyclomegistine, the first alkaloid with the new cyclobuta[b]quinoline ring system from Sarcomelicope megistophylla .  Tetrahedron Letters. 2001;  42 5323-5
• 8 Tillequin F, Michel S, Skaltsounis A -L. Acronycine-type alkaloids: chemistry and biology. In: Pelletier SW, editor Alkaloids: chemical and biological perspectives. Vol. 12 Elsevier, Amsterdam; 1998: pp. 1-102
• 9 Guilbaud N, Léonce S, Tillequin F, Koch M, Hickman J A, Pierré A. Acronycine derivatives as promising antitumor agents.  Anti-Cancer Drugs. 2002;  13 445-9
• 10 Sheen W -S, Tsai I -L, Teng C -M, Chen I -S. Nor-neolignan and phenyl propanoid from Zanthoxylum ailanthoides .  Phytochemistry. 1994;  36 213-5
• 11 Arnone A, Di Modungo V, Nasini G, Venturini I. Isolation and structure determination of new active neolignans and norneolignans from Rathania.  Gazzetta Chimica Italiana. 1988;  118 675-82
• 12 Karikome H, Mimaki Y, Sachida Y. A butanolide and phenolics from Machilus thunbergii .  Phytochemistry. 1991;  30 315-9
• 13 Ward R S, Hughes D D. Oxidative cyclisation of 3,4-dibenzyltetrahydrofurans using ruthenium tetra(trifluoroacetate).  Tetrahedron. 2001;  57 2057-64
• 14 Matsuda H, Shimoda H, Morikawa T, Yoshikawa M. Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): Structure-requirement of hydroxyanthraquinones for estrogenic activity.  Bioorganic & Medicinal Chemistry Letters. 2001;  11 1839-42
• 15 Setchell K D, Lawson A M, Borriello S P, Harkness R, Gordon H, Morgan D M, Kirk D N, Adlercreatz H, Anderson L C, Axelson M. Lignan formation in man - microbial involvement and possible roles in relation to cancer.  Lancet. 1981;  2 4-7
• 16 Kalpoutzakis E, Aligiannis N, Mitakou S, Skaltsounis A L. Verbaspinoside, a new iridoid glycoside from Verbascum spinosum .  Journal of Natural Products. 1999;  62 42-4
• 17 Kasiotis K M, Magiatis P, Pratsinis H, Skaltsounis A -L, Abadji V, Charalambous A, Moutsatsou P, Haroutounian S A. Synthesis and biological evaluation of novel daunorubicin-estrogen conjugates.  Steroids. 2001;  66 785-91
• 18 Berthois Y, Katzenellenbogen J A, Katzenellenbogen B S. Phenol red in tissue culture media is a weak estrogen: implications concerning the study of estrogen-responsive cells in culture.  Proceedings of the National Academy of Sciences of USA. 1986;  83 2496-500
• 19 Leclercq G, Devleeschouwer N, Heuson J C. Guide-lines in the design of new antiestrogens and cytotoxic-linked estrogens for the treatment of breast cancer.  Journal of Steroid Biochemistry. 1983;  19 73-85
• 20 Kostakis I K, Magiatis P, Pouli N, Marakos P, Skaltsounis A -L, Pratsinis H, Léonce S, Pierré A. Design, synthesis, and antiproliferative activity of some new pyrazole-fused amino derivatives of the pyranoxanthenone, pyranothioxanthenone, and pyranoacridone ring systems: A new class of cytotoxic agents.  Journal of Medicinal Chemistry. 2002;  45 2599-609