Denticulatains A and B: unique stilbene-diterpene heterodimers from Macaranga denticulata†

Two novel heterodimers, denticulatains A (1) and B (2), were isolated from the fronds of Macaranga denticulata. They possess an unprecedented stilbene–diterpene-type skeleton, which represents a unique class of prenylated stilbene. Their structures were elucidated by comprehensive analyses of extensive NMR and MS spectroscopic data. Compounds 1 and 2 exhibited inhibitory activity against acetylcholinesterase with the inhibition ratios of 22.1% and 27.5%, respectively, at a concentration of 50 μM.

[1]  Ke-Chun Liu,et al.  Cytotoxic prenylated bibenzyls and flavonoids from Macaranga kurzii. , 2014, Fitoterapia.

[2]  J. J. Magadula.  Phytochemistry and pharmacology of the genus Macaranga: A review , 2014 .

[3]  Zi-Lei Li,et al.  Jatropholane-type diterpenes from Euphorbia sikkimensis. , 2013, Journal of natural products.

[4]  M. Litaudon,et al.  Acetylcholinesterase inhibitors from the leaves of Macaranga kurzii. , 2012, Journal of natural products.

[5]  Xianwen Yang,et al.  Pseudolaridimers A and B, hetero-cycloartane-labdane Diels-Alder adducts from the cone of Pseudolarix amabilis. , 2012, Organic letters.

[6]  J. Beutler,et al.  Schweinfurthins I and J from Macaranga schweinfurthii. , 2010, Journal of natural products.

[7]  E. Ghisalberti,et al.  Phenolic Derivatives with an Irregular Sesquiterpenyl Side Chain from Macaranga pruinosa , 2010 .

[8]  J. Topczewski,et al.  Total synthesis of (+)-schweinfurthins B and E. , 2009, The Journal of organic chemistry.

[9]  H. Lou,et al.  Natural stilbenes: an overview. , 2009, Natural product reports.

[10]  Liangxiong Xu,et al.  Prenylflavonols from the leaves of Macaranga sampsonii. , 2009, Chemical & pharmaceutical bulletin.

[11]  Hiromasa Kiyota,et al.  Chemical and pharmacological research of the plants in genus Euphorbia. , 2008, Chemical reviews.

[12]  K C Nicolaou,et al.  Cascade reactions involving formal [2+2] thermal cycloadditions: total synthesis of artochamins F, H, I, and J. , 2007, Angewandte Chemie.

[13]  J. Miller,et al.  Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest. , 2007, Journal of natural products.

[14]  A. Wendel,et al.  Prenylated Stilbenes and Their Novel Biogenetic Derivatives from Artocarpus chama , 2006 .

[15]  X. She,et al.  Total synthesis of (+)-machaeriol D with a key regio- and stereoselective S(N)2' reaction. , 2006, Angewandte Chemie.

[16]  Reiko Tanaka,et al.  Isolation, DNA Topoisomerase‐II Inhibition, and Cytotoxicity of Three New Terpenoids from the Bark of Macaranga tanarius , 2006, Chemistry & biodiversity.

[17]  I. Khan,et al.  Antifungal clerodane diterpenes from Macaranga monandra (L) Muell. et Arg. (Euphorbiaceae). , 2003, Journal of agricultural and food chemistry.

[18]  A. Suksamrarn,et al.  Diterpenylated and prenylated flavonoids from Macaranga denticulata , 2002 .

[19]  M. Boyd,et al.  Cytotoxic geranyl stilbenes from Macaranga schweinfurthii. , 1998, Journal of natural products.

[20]  T. Row,et al.  Clerodane diterpenoids from Polyalthia longifolia , 1988 .

[21]  E. Wenkert,et al.  13C‐NMR. Spectroscopy of Naturally Occurring Substances. XXXV. Labdanic diterpenes , 1975 .

[22]  K. Nakanishi,et al.  Isolation and structure of macarangonol, a diterpene ketol from Macaranga tanarius , 1971 .

[23]  K. Courtney,et al.  A new and rapid colorimetric determination of acetylcholinesterase activity. , 1961, Biochemical pharmacology.

[24]  Albert,et al.  Food , 1917, Nature.