Evaluation of cytotoxic activity of patriscabratine, tetracosane and various flavonoids isolated from the Bangladeshi medicinal plant Acrostichum aureum

Context: Acrostichum aureumL. (Pteridaceae), a mangrove fern, has been used as a Bangladeshi traditional medicine for a variety of diseases including peptic ulcer. Objective: Isolation and structural elucidation of cytotoxic secondary metabolites from the methanol extract of the aerial parts of A. aureum. Materials and methods: Compounds were isolated using HPLC. The compound structures were elucidated by 1D and 2D NMR, MS and other spectroscopic methods using published data. The compounds were tested for their cytotoxic activity against healthy and cancer cells using the MTT assay. Active compounds were further evaluated for apoptosis–and necrosis-inducing potential against gastric cancer cells (AGS) using the FITC Annexin V apoptosis assay. Results and discussion:Seven known compounds, patriscabratine, tetracosane and 5 flavonoids (quercetin-3-O-β-d-glucoside, quercetin-3-O-β-d-glucosyl-(6→1)-α-l-rhamnoside, quercetin-3-O-α-l-rhamnoside, quercetin-3-O-α-l-rhamnosyl-7-O-β-d-glucoside and kaempferol) were isolated. Patriscabratine was found moderately cytotoxic against AGS, MDA-MB-231 and MCF-7 cells with IC50 values ranging from 69.8 to 197.3 μM. Tetracosane showed some cytotoxic activity against AGS, MDA-MB-231, HT-29 and NIH 3T3 cells with IC50 values ranging from 128.7 to >250 μM. Patriscabratine and tetracosane displayed an apoptotic effect (10%) on AGS cells within 24 h which was increased (20%) after 48 h, and was comparable to, if not greater, than the positive control, cycloheximide. Conclusion:Except for quercetin-3-O-β-d-glucoside and kaempferol; compounds were isolated for the first time from this plant and evaluated for their cytotoxic activity. The results highlight the potential of this plant as a source of bioactive compounds and provide a rationale for its traditional use in peptic ulcer treatment.

[1]  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.

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

[3]  M. M. Abd El Aziz,et al.  Phytochemical investigation and medicinal evaluation of fixed oil of Balanites aegyptiaca fruits (Balantiaceae). , 2010, Journal of ethnopharmacology.

[4]  Tiemin Sun,et al.  Total synthesis and anticancer activity studies of the stereoisomers of asperphenamate and patriscabratine , 2010 .

[5]  R. Liu,et al.  Synergistic effect of apple extracts and quercetin 3-beta-d-glucoside combination on antiproliferative activity in MCF-7 human breast cancer cells in vitro. , 2009, Journal of agricultural and food chemistry.

[6]  N. Seeram,et al.  Identification and bioactivities of resveratrol oligomers and flavonoids from Carex folliculata seeds. , 2009, Journal of agricultural and food chemistry.

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

[8]  B. Schneider,et al.  Occurrence of rosmarinic acid, chlorogenic acid and rutin in Marantaceae species , 2008 .

[9]  F. Imperato A New Flavone Glucoside, Apigenin 7-O-glucoside 4′-acetate and a New Fern Constituent, Quercetin 3-O-rhamnoside-7-O-glucoside from Dryopteris villarii , 2008 .

[10]  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.

[11]  H. Aisa,et al.  Kaempferol and quercetin flavonoids from Rosa rugosa , 2006, Chemistry of Natural Compounds.

[12]  H. Matsuura,et al.  Isolation and Measurement of Quercetin Glucosides in Flower Buds of Japanese Butterbur (Petasites japonicus subsp. gigantea Kitam.) , 2002, Bioscience, biotechnology, and biochemistry.

[13]  M. Blanco-Molina,et al.  New glycosides from Capsicum annuum L. var. acuminatum. Isolation, structure determination, and biological activity. , 2001, Journal of agricultural and food chemistry.

[14]  T. Fossen,et al.  Flavonoids from blue flowers of Nymphaèa caerulea , 1999 .

[15]  M. Mochizuki,et al.  Chemical and Chemotaxonomical Studies of Ferns. XXXIX. Chemical Studies on the Constituents of Pteris bella TAGAWA and Pteridium aquilinum subsp. wightianum (WALL) SHICH , 1982 .

[16]  T. Satake,et al.  Chemical and chemotaxonomical studies on filices. LI. Chemical studies on the constituents of Costa Rican ferns. 3. , 1981 .

[17]  Ruiwen Zhang,et al.  Anti-Inflammatory Agents for Cancer Therapy. , 2009, Molecular and cellular pharmacology.

[18]  A. Kansoh,et al.  Chemical composition, antimicrobial and cytotoxic activities of essential oil and lipoidal matter of the flowers and pods of Tipuana tipu growing in Egypt. , 2009 .

[19]  E. Mezzina,et al.  AIST:RIO-DB Spectral Database for Organic Compounds,SDBS , 2009 .

[20]  Z. Begum,et al.  Encyclopedia of flora and fauna of Bangladesh , 2007 .

[21]  Ze-Hong YanBo,et al.  Screening of the tumor cytotoxic activity of sixteen species of mangrove plants in Hainan , 2005 .

[22]  Yong,et al.  A New Alkaloid from Patrinia scabra , 2002 .

[23]  Rc Cambie,et al.  Fijian medicinal plants , 1994 .