(2S,3S)-sulfated pterosin C, a cytotoxic sesquiterpene from the Bangladeshi mangrove fern Acrostichum aureum.

Two new sesquiterpenes, (2R,3S)-sulfated pterosin C (1) and (2S,3S)-sulfated pterosin C (2), along with two known derivatives, (2S,3S)-pterosin C and (2R)-pterosin P, were isolated from a methanolic extract of the aerial parts of Acrostichum aureum. The structures of 1 and 2 were determined by the interpretation of their spectroscopic data. The isolated pterosins were evaluated for their cytotoxic activity against the AGS, HT-29, MDA-MB-231, and MCF-7 human cancer cell lines and the NIH3T3 normal mouse fibroblast cell line, using the MTT assay. Compound 2 showed IC50 values in the range 23.9-68.8 μM. The lowest IC50 value (23.9 μM) was recorded against AGS gastric adenocarcinoma cells. Compound 2 was found to exert an apoptotic effect on AGS cells within 24 h of treatment, which increased with time and was greater than the positive control, cycloheximide. The cytotoxicity of 2 seems to be due in part to the sulfate group on C-14 and the configuration at C-2.

[1]  T. Mcmorris,et al.  An efficient synthesis of pterosin C and other pterosins , 1984 .

[2]  S. Matsunaga,et al.  Dictyodendrins A-E, the first telomerase-inhibitory marine natural products from the sponge Dictyodendrilla verongiformis. , 2003, The Journal of organic chemistry.

[3]  H. Maehashi,et al.  Chemical and chemotaxonomical studies of ferns. LIV. Pterosin derivatives of the genus Microlepia (Pteridaceae). , 1985 .

[4]  B. Bay,et al.  Chondroitin Sulfate in Palatal Wound Healing , 2004, Journal of dental research.

[5]  J. Mcmahon,et al.  HIV-inhibitory natural products. 11. Comparative studies of sulfated sterols from marine invertebrates. , 1994, Journal of medicinal chemistry.

[6]  P. Komesaroff,et al.  A Chinese Herbal Preparation Containing Radix Salviae Miltiorrhizae, Radix Notoginseng and Borneolum Syntheticum Reduces Circulating Adhesion Molecules , 2011, Evidence-based complementary and alternative medicine : eCAM.

[7]  M. Fukuoka,et al.  Chemical and Toxicological Studies on Bracken Fern, Pteridium aquilinum var. latiusculum. III. Further Characterization of Pterosins and Pterosides, Sesquiterpenes and the Glucosides having 1-Indanone Skeleton, from the Rhizomes , 1979 .

[8]  B. Casu,et al.  Infrared absorption and raman scattering of sulfate groups of heparin and related glycosaminoglycans in aqueous solution , 1978 .

[9]  T. Veenstra,et al.  Identification of Sokotrasterol Sulfate As a Novel Proangiogenic Steroid , 2006, Circulation research.

[10]  Hai-Yan Xu,et al.  Pterosins from Pteris multifida. , 2010, Planta medica.

[11]  J. Koropatnick,et al.  ODN 491, a novel antisense oligodeoxynucleotide that targets thymidylate synthase, exerts cell-specific effects in human tumor cell lines. , 2008, DNA and cell biology.

[12]  E. Tiralongo,et al.  Cytotoxic Effects of Bangladeshi Medicinal Plant Extracts , 2011, Evidence-based complementary and alternative medicine : eCAM.

[13]  M. Fukuoka,et al.  Circular Dichroism and Conformations of Pterosins, 1-Indanone Derivatives from Bracken , 1979 .

[14]  M. Fukuoka,et al.  Carbon-13 Nuclear Magnetic Resonance Spectra of Pterosin-Sesquiterpenes and Related Indan-1-one Derivatives , 1983 .

[15]  Y. Lim,et al.  Antioxidative, Tyrosinase Inhibiting and Antibacterial Activities of Leaf Extracts from Medicinal Ferns , 2009, Bioscience, biotechnology, and biochemistry.

[16]  C. Ottow.  Natural Resources Conservation Service Web Site , 2000 .