DOCSLIB.ORG

Anacardic Acid Article

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Anacardic Acid Article Basic & Clinical Pharmacology & Toxicology, 110, 122–132 Doi: 10.1111/j.1742-7843.2011.00833.x MiniReview Emerging Roles of Anacardic Acid and Its Derivatives: A Pharmacological Overview Mahadevappa Hemshekhar, Martin Sebastin Santhosh, Kempaiah Kemparaju and Kesturu S. Girish Department of Biochemistry, University of Mysore, Manasagangothri, Mysore, India (Received 1 July 2011; Accepted 9 November 2011) Abstract: Anacardic acid (AA) is a bioactive phytochemical found in nutshell of Anacardium occidentale. Chemically, it is a mixture of several closely related organic compounds, each consisting of salicylic acid substituted with an alkyl chain. The traditional Ayurveda depicts nutshell oil as a medicinal remedy for alexeritic, amebicidal, gingivitis, malaria and syphilitic ulcers. However, the enduring research and emerging evidence suggests that AA could be a potent target molecule with bactericide, fungicide, insecticide, anti-termite and molluscicide properties and as a therapeutic agent in the treatment of the most serious pathophysiological disorders like cancer, oxidative damage, inflammation and obesity. Furthermore, AA was found to be a common inhibitor of several clinically targeted enzymes such as NFjB kinase, his- tone acetyltransferase (HATs), lipoxygenase (LOX-1), xanthine oxidase, tyrosinase and ureases. In view of this, we have made an effort to summarize the ongoing research on the therapeutical role of AA and its derivatives. The current MiniReview sheds light on the pharmacological applications, toxicity and allergic responses associated with AA and its derivatives. Although the available records are promising, much more detailed investigations into the therapeutical prop- erties, particularly the anti-cancer and anti-inflammatory activities, are urgently needed. We hope the present MiniRe- view will attract and encourage further research on elucidating and appreciating the possible curative properties of AA and its derivatives in the management of multifactorial diseases. Plant medicines play a vital role in human health and consisting of a salicylic acid substituted with saturated or diseases. According to the WHO, in recent times, more than unsaturated alkyl chain that has 15–17 carbon. 80% of the world’s population in developing countries Outstandingly, AA claims a lion’s share in the medicinal depends primarily on herbal medicines for basic healthcare value of the nutshell as it offers a better protection against needs. The ancient ayurvedic preparations and usage have several pathophysiological disorders ranging from oxidative proven the healing abilities of plants, undoubtedly. Hence, a damage to cancer (Table 1). On the other hand, cardanol and large proportion of drugs used in modern medicine are either cardol are the phenolic components that are less effective in all directly isolated from plants or synthetically modified from a sorts of biological activity exhibited by AA. However, these are lead compound of natural origin. Medicinal plant extracts largely employed in the chemical industry in the preparation of and their isolated compounds are often used as an alterna- resins, coatings, frictional materials, surfactants and pigment tive for the drugs with associated complications in the treat- dispersants for water-based inks. Friction particles are made by ment of many disorders [1,2]. polymerizing the unsaturated side chain of cardanol, followed In the course, anacardic acid (AA) (fig. 1A) and its related by cross-polymerization with phenol to yield a cardanol- compounds from Anacardium occidentale (an angiosperm formaldehyde resin by a process analogous to the formation of belonging to the Anacardiaceae family) seed (Cashew nut- phenol-formaldehyde resin such as Bakelite. shell) have received great attention by the chemicobiology researchers and pharmaceutical companies. AA alone consti- Ethnopharmacology tutes about 90% of the cashew nutshell liquid (CNSL), and the remaining part is constituted by AA-related compounds Many parts of the Anacardium occidentale have been such as cardanol, cardol and 2-methyl cardol (fig. 1B–D) [3]. exploited for its medicinal value. The fruit juice and the nut- It is a yellow liquid partially miscible in alcohol and ether shell oil are both said to be folk remedies for cancerous but nearly immiscible in water [4,5]. Chemically, AA is a ulcers, elephantiasis and warts. The oily substance from peri- mixture of several closely related organic compounds each carp is used for cracks on the feet. Old leaves are applied to skin afflictions and burns. In the Gold Coast, the bark and leaves are used for sore gums and toothache. Decoction of the astringent bark is suggested for severe diarrhoea and Author for correspondence: K. S. Girish, Department of Studies in Biochemistry, University of Mysore, Manasagangothri, Mysore-570 thrush. In India, bark is used in herbal tea for asthma, cold 006, India (fax 0821-2419622, e-mail [email protected]). and congestion and as an antidote for snake envenomations. Ó 2011 The Authors Basic & Clinical Pharmacology & Toxicology Ó 2011 Nordic Pharmacological Society MiniReview PHARMACOLOGICAL ROLES OF AA AND ITS DERIVATIVES 123 ABCDOH OH OH OH COOH H3C HO HO Anacardic acid Cardol Cardanol 2-methyl cardol E OHFG OH OH HOH COOH COOH COOH COOH C15:3 C15:2 C15:1 C12:0 IJKOH OH COOH COOH CF3 H H N O N O Cl N N OO H NO2 N H N N Hydrazone derivative Hydrazone derivative CTPB CF L 3 MNCOOH OH Cl O O HO COOH N H CH3CH2(CH2)15CH2CH(CH2)4CH3 CTB C12:1 C24:1 O PQ R EtOO N OH i-OO N EtOO C COOH NNO N 2 H CH2CH2(CH2)17CH3 Synthones Synthones Synthones C20:0 STUVO O CH3 CH3 MeO HN N EtO HN N N N O N N OH CH CH CH CH CH CH CH 2 2 3 3 2 2 3 CH CH (CH ) CH N CH2CH2(CH2)12CH3 2 2 2 12 3 EtO HN COOH S S O O OO N N N N N N CH2CH2CH3 CH CH (CH ) CH CH CH 2 2 2 14 3 3 3 CH2CH2(CH2)12CH3 C17:0 Benzamide derivative Benzamide derivative Benzamide derivative Fig. 1. Structures of anacardic acid and its derivatives. The seed oil is believed to be alexeritic and amebicidal and is Pharmacology and Medicine used to treat gingivitis, malaria and syphilitic ulcers. Tradi- tional Ayurveda recommends the fruit for cancer, oxidative Antioxidant activity. stress, anti-helminthic, aphrodisiac, ascites, haemoptysis, Cellular injury from ROS (reactive oxygen species) has been dysentery, fever, inappetence, leucoderma, piles and obsti- implicated in the development and progression of several dis- nate ulcers and hyperglycaemia. Sap from young leaves eases [6]. AA (fig. 1A) effectively prevents cell damage and budding fruits is considered fungicidal and insect induced by H2O2 because this can be converted to ROS, repellent [3,5]. hydroxyl radicals, in the presence of metal ions. AA acts as Ó 2011 The Authors Basic & Clinical Pharmacology & Toxicology Ó 2011 Nordic Pharmacological Society. Basic & Clinical Pharmacology & Toxicology, 110, 122–132 124 M. HEMSHEKHAR ET AL. MiniReview Table 1. Pharmacological roles of AA and its derivatives. Compounds Pharmacological role Model used to test Dose Anacardic acid (C15:0) ROS generation inhibition 0.053 € 0.005 mM Xanthine oxidase inhibition 0.0043 € 0.0005 mM Anti-bacterial Propionibacterium acnes 0.0015 mg ⁄ mL Corynebacterium xerosis 0.0062 mg ⁄ mL S. aureus 0.025 mg ⁄ mL MSSA ATCC12598 0.0031–0.0062 mg ⁄ mL MRSA B. subtilis Zoosporicidal activity Aphanomyces cochlioides Anti-parasitic activity Colorado potato beetle larvae HATs inhibition 0.0085 mM p300 PCAF 0.005 mM Cytotoxicity 0.008 mM PfGCN5 HATs inhibition NFjB inhibition Anti-cancer activity Pituitary adenoma cells, melanoma cells Aurora kinase A activation Anti-obase activity Wistar rats Tyrosinase inhibition Mashroom tyrosinase 0.18 mg ⁄ mL Urease inhibition 0.12 mg ⁄ mL Selective metal ion chelation Anacardic acid (C15:1) LOX-15 inhibition Soybean lipoxygenase 0.05 mM Cytotoxicity HeLa cells 0.01 mM Anacardic acid (C15:2) Anti-bacterial Helicobacter pylori 0.2 mg ⁄ mL Anacardic acid (C15:3) Anti-bacterial, Molluscidal H. pylori, Snails 0.2 mg ⁄ mL activity Anacardic acid (C24:1) Anti-proliferation of ERa MCF-10A, MCF-7, MDA-MB-231 breast cancer cells Cardol (C12:0) Anti-bacterial H. pylori 0.2 mg ⁄ mL LOX-15 inhibition Soybean lipoxygenase 0.06 mM Cytotoxicity HeLa cells 0.01 mM N-isonicotinoyl-N’-8-[(2-carbohydroxy- Anti-bacterial Mycobacterium 4mg⁄ mL 3-hydroxy) phenyl] octanal hydrazone. smegmatis N-isonicotinoyl- N’-8-[(2-carbohydroxy- 5mg⁄ mL 3-hydroxy-6-nitro) phenyl] octanal hydrazone N-(4-chloro-3-trifluoromethyl-phenyl)- p300 activation 2-ethoxy-6-pentadecyl-benzamide N-(4-chloro-3-trifluoromethyl-phenyl) – 2-ethoxy-benzamide 2-isopropoxy-6-pentadecyl-N-pyridin-4- Cytotoxicity HeLa cells 11.02 mM ylbenzamide. 2-ethoxy-N-(3-nitrophenyl)-6- 13.55 mM pentadecylbenzamide. 2-ethoxy-6-pentadecyl-N-pyridin- 15.29 mM 4-ylbenzamide 6-n-pentadecyl salicylic acid Amidolytic activity sTF ⁄ VIIa 0.3–0.4 mmol ⁄ L GAPDH inhibition 0.028 mM 6-n-dodecylsalicylic acid 0.055 mM 6-n-heptadecylsalicylic acid Amidolytic activity sTF ⁄ VIIa 0.3–0.4 mmol ⁄ L 5-[2-Ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)- PDE5 inhibition 0.145 mM 6-pentadecylphenyl]-1,6-dihydro-7H- pyrazolo[4,3-d]pyrimidin-7-one 5-[2-Methoxy-5-(4-methylpiperazin-1-ylsulfonyl)- 0.125 mM 6-pentadecylphenyl]-1,6-dihydro-7H- pyrazolo[4,3-d]pyrimidin-7- one AA, anacardic acid; HATs, histone acetyltransferase. Ó 2011 The Authors Basic & Clinical Pharmacology & Toxicology Ó 2011 Nordic Pharmacological Society. Basic & Clinical Pharmacology & Toxicology, 110, 122–132 MiniReview PHARMACOLOGICAL ROLES OF AA AND ITS DERIVATIVES 125 an antioxidant in multiple ways including inhibition of vari- AA also showed anti-bacterial activity against the strains of ous pro-oxidant enzymes involved in the production of ROS MSSA ATCC 12598 and MRSA with minimal inhibitory and by chelating the divalent metal ions. The high selectivity concentrations ranging from 0.0031 to 0.0062 mg ⁄ mL [14].
Load more

Recommended publications
  • Monocyclic Phenolic Acids; Hydroxy- and Polyhydroxybenzoic Acids: Occurrence and Recent Bioactivity Studies
    Molecules 2010, 15, 7985-8005; doi:10.3390/molecules15117985 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Review Monocyclic Phenolic Acids; Hydroxy- and Polyhydroxybenzoic Acids: Occurrence and Recent Bioactivity Studies Shahriar Khadem * and Robin J. Marles Natural Health Products Directorate, Health Products and Food Branch, Health Canada, 2936 Baseline Road, Ottawa, Ontario K1A 0K9, Canada * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +1-613-954-7526; Fax: +1-613-954-1617. Received: 19 October 2010; in revised form: 3 November 2010 / Accepted: 4 November 2010 / Published: 8 November 2010 Abstract: Among the wide diversity of naturally occurring phenolic acids, at least 30 hydroxy- and polyhydroxybenzoic acids have been reported in the last 10 years to have biological activities. The chemical structures, natural occurrence throughout the plant, algal, bacterial, fungal and animal kingdoms, and recently described bioactivities of these phenolic and polyphenolic acids are reviewed to illustrate their wide distribution, biological and ecological importance, and potential as new leads for the development of pharmaceutical and agricultural products to improve human health and nutrition. Keywords: polyphenols; phenolic acids; hydroxybenzoic acids; natural occurrence; bioactivities 1. Introduction Phenolic compounds exist in most plant tissues as secondary metabolites, i.e. they are not essential for growth, development or reproduction but may play roles as antioxidants and in interactions between the plant and its biological environment. Phenolics are also important components of the human diet due to their potential antioxidant activity [1], their capacity to diminish oxidative stress- induced tissue damage resulted from chronic diseases [2], and their potentially important properties such as anticancer activities [3-5].
    [Show full text]
  • Bioactivity and Potential Therapeutic Benefits of Some Medicinal Plants from the Caatinga (Semi-Arid) Vegetation of Northeast Brazil: a Review of the Maria I
    Revista Brasileira de Farmacognosia Brazilian Journal of Pharmacognosy Bioactivity and potential therapeutic benefi ts 22(1): 193-207, Jan./Feb. 2012 of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature Maria I. G. Silva, Carla T. V. de Melo, Leonardo F. Vasconcelos, Alyne M. R. de Carvalho, Francisca C. F. Sousa* Review Departamento de Fisiologia e Farmacologia, Faculdade de Medicina, Universidade Federal do Ceará, Brazil. Received 14 Mar 2011 Accepted 22 Jun 2011 Available online 16 Sep 2011 Abstract: Medicinal plants have been used in traditional medicine for several thousand years all over the world. In this sense, information from Brazilian ethnic groups on folk medicine have contributed to the discovery of pharmacological activities from various plant-derived agents potentially leading to the innovative drugs. The Caatinga (semi-arid) vegetation is a highly threatened biome, covering Keywords: a vast area in northeastern Brazil and has suffered from strong human influence for caatinga many decades. Many plants species found in the Caatinga have been widely used medicinal plants in folk medicine and for commercial manufacturing of phytotherapeutic products. potential therapeutic Thus, the present review aims to disseminate to the scientific community some pharmacological assays known species of medicinal plants found in the Caatinga that have been studied and analyzed in pharmacological scientific assays. Among the species that stood out for their local importance and multiplicity of uses were: Amburana cearensis (umburana-de-cheiro), Anadenanthera colubrina (Vell.) Brenan (angico-branco), Anacardium occidentalis L. (cajueiro), Bauhinia forficata Link (mororó), Cissus sicyoides L. (insulina-vegetal), Myracrodruon urundeuva Allemão (aroeira-do- sertão) and Zingiber officinalis L.
    [Show full text]
  • Antioxidant and Antimicrobial Properties of Selected Plant Leaves
    European Journal of Medicinal Plants 3(3): 465-473, 2013 SCIENCEDOMAIN international www.sciencedomain.org Antioxidant and Antimicrobial Properties of Selected Plant Leaves B. O. T. Ifesan1*, J. F. Fashakin2, F. Ebosele1 and A. S. Oyerinde3 1Department of Food Science and Technology, Federal University of Technology, Akure. Nigeria. 2Department of Hospitality Management Technology, Lagos State Polytechnic, Nigeria. 3Department of Agriculture Engineering, Federal University of Technology Akure, Nigeria. Authors’ contributions This work was carried out in collaboration between all authors. Author BOTI designed the study, managed the literature searches and wrote the first draft of the manuscript. Authors JFF and FE carried out the research in the laboratory. Author ASO performed the statistical analysis. All authors read and approved the final manuscript. Received 22nd February 2013 st Research Article Accepted 1 May 2013 Published 22nd June 2013 ABSTRACT Aims: To determine the antimicrobial and antioxidant potentials of some readily available plant leaves in order to source for alternate antioxidants and antibiotics. Study Design: Randomized complete block design. Place and Duration of Study: Department of Food Science and Technology, Federal University of Technology Akure Nigeria between Feb 2010 and Jan 2011. Methodology: Ethanol, hexane and water extracts from leaves of Anacardium occidentale (cashew), Cocos nucifera (coconut), Citrus sinesis (sweet orange), Citrus limon (lemon) and Carica papaya (pawpaw) were prepared and screened
    [Show full text]
  • Antibacterial and Anti-Inflammatory Effects of Syzygium Jambos L
    Sharma et al. BMC Complementary and Alternative Medicine 2013, 13:292 http://www.biomedcentral.com/1472-6882/13/292 RESEARCH ARTICLE Open Access Antibacterial and anti-inflammatory effects of Syzygium jambos L. (Alston) and isolated compounds on acne vulgaris Richa Sharma1†, Navneet Kishore1†, Ahmed Hussein1,2† and Namrita Lall1*† Abstract Background: Acne vulgaris is a chronic skin disorder leading to inflammation as a result of the production of reactive oxygen species due to the active involvement of Propionibacterium acnes (P. acnes) in the infection site of the skin. The current study was designed to assess the potential of the leaf extract of Syzygium jambos L. (Alston) and its compounds for antibacterial and anti-inflammatory activity against the pathogenic P. acnes. Methods: The broth dilution method was used to assess the antibacterial activity. The cytotoxicity investigation on mouse melanocyte (B16-F10) and human leukemic monocyte lymphoma (U937) cells was done using sodium 3’-[1-(phenyl amino-carbonyl)-3,4-tetrazolium]-bis-[4-methoxy-6-nitrobenzene sulfonic acid hydrate (XTT) reagent. The non-toxic concentrations of the samples was investigated for the suppression of cytokines interleukin 8 (IL 8) and tumour necrosis factor (TNF α) by testing the supernatants in the co-culture of the human U937 cells and heat killed P. acnes using enzyme immunoassay kits (ELISA). The statistical analysis was done using the Graph Pad Prism 4 program. Results: Bioassay guided isolation of ethanol extract of the leaves of S. jambos led to the isolation of three known compounds namely; squalene, an anacardic acid analogue and ursolic acid which are reported for the first time from this plant.
    [Show full text]
  • World Journal of Advance Healthcare Research
    SJIF Impact Factor: 5.464 WORLD JOURNAL OF ADVANCE ISSN: 2457-0400 Nandi et al. World Journal of Advance HealthcareVolume: Research 5. HEALTHCARE RESEARCH Issue: 1. Page N. 320-323 Year: 2021 Review Article www.wjahr.com INDIGENOUS POLYPHENOLS OF CASHEW: THE ALMA MATER IN NATURAL NUTRITION 1*Kushal Nandi, 1Dr. Dhrubo Jyoti Sen, 2Dr. Dhananjoy Saha and 3Dr. Sudip Kumar Mandal 1Department of Pharmaceutical Chemistry, School of Pharmacy, Techno India University, Salt Lake City, Sector-V, EM-4, Kolkata-700091, West Bengal, India. 2Deputy Director, Directorate of Technical Education, Bikash Bhavan, Salt Lake City, Kolkata‒700091, West Bengal, India. 3Dr. B. C. Roy College of Pharmacy and A.H.S, Dr. Meghnad Saha Sarani, Bidhan Nagar, Durgapur-713206, West Bengal, India. Received date: 04 December 2020 Revised date: 25 December 2020 Accepted date: 15 January 2021 *Corresponding author: Kushal Nandi Department of Pharmaceutical Chemistry, School of Pharmacy, Techno India University, Salt Lake City, Sector-V, EM-4, Kolkata-700091, West Bengal, India. ABSTRACT The cashew tree (Anacardium occidentale) is a tropical evergreen tree that produces the cashew seed and the cashew apple. The tree can grow as high as 14 m (46 ft), but the dwarf cashew, growing up to 6 m (20 ft), has proven more profitable, with earlier maturity and greater yields. The cashew seed is often considered a nut in the culinary sense; this cashew nut is eaten on its own, used in recipes, or processed into cashew cheese or cashew butter. Like the tree, the nut is often simply called cashew. The species is native to Central America, the Caribbean, and northern South America, including north-eastern Brazil.
    [Show full text]
  • Administration of Cashew Extracts in the Treatment of Some Infections and Diseases
    Advancement in Medicinal Plant Research Vol. 3(3), pp. 75-86, July 2015 ISSN: 2354-2152 Review Administration of cashew extracts in the treatment of some infections and diseases Aderiye B. I.*, David O. M. and Atere V. A. Microbiology Department, Ekiti State University, Ado-Ekiti, Nigeria. Accepted 24 June, 2014 ABSTRACT The cashew, Anacardium occidentale (L), has been reported for its usage in many life applications. Some of the medicinal uses of cashew include the antimicrobial effect of extracts of the leaves, apple, stem and the nut shell oil against many microorganisms including Escherichia coli, Candida albicans, Ascaridia galli and Leishmania sp. The anti-microbial activities of cashew extract involve the anti-bacterial, antifungal, anti- helminthics, anti-protozoan and anti-viral. The phytochemicals present in cashew extracts such as anacardic acid, flavonoid and tannins are responsible for the anti-microbial activities of the extract by inactivation of microbial adhesions enzymes and cell envelop transport cells, flavonoids, which are responsible for the inhibition of DNA gyrase thereby inhibiting DNA synthesis; phenolic compounds like anacardic acids, cardols, triterpenoids, methylcardols, xantoprotein and cardanols that are responsible for bacteria cell wall inhibition, by inhibiting the cell wall synthesis in addition to a growing cell and blocking the DNA, RNA and protein pathways. The extracts of cashew have also been used in treating gastro-intestinal tract syndromes such as diarrhea, dysentery, dyspepsia and nausea. Allergies and inflammation syndromes are also managed by administration of extracts from cashew; tannins inhibit the migration of leucocytes to an inflammatory site thereby reducing inflammatory response; on the other hand flavonoids present in extracts of cashew inhibit the cyclo-oxygenase, which is important in the genesis of edema and pain.
    [Show full text]
  • In Vitro Gas Production Kinetics and Digestibility in Ruminant Diets with Different Levels of Cashew Nut Shell Liquid Semina: Ciências Agrárias, Vol
    Semina: Ciências Agrárias ISSN: 1676-546X ISSN: 1679-0359 Universidade Estadual de Londrina Díaz, Tatiana García; Branco, Antonio Ferriani; Ítavo, Luís Carlos Vinhas; Santos, Geraldo Tadeu dos; Carvalho, Silvana Teixeira; Teodoro, Ana Lúcia; Oliveira, Ronaldo Lopes In vitro gas production kinetics and digestibility in ruminant diets with different levels of cashew nut shell liquid Semina: Ciências Agrárias, vol. 39, no. 4, 2018, July-August, pp. 1669-1682 Universidade Estadual de Londrina DOI: https://doi.org/10.5433/1679-0359.2018v39n4p1669 Available in: https://www.redalyc.org/articulo.oa?id=445759824025 How to cite Complete issue Scientific Information System Redalyc More information about this article Network of Scientific Journals from Latin America and the Caribbean, Spain and Journal's webpage in redalyc.org Portugal Project academic non-profit, developed under the open access initiative DOI: 10.5433/1679-0359.2018v39n4p1669 In vitro gas production kinetics and digestibility in ruminant diets with different levels of cashew nut shell liquid Cinética da produção de gases e digestibilidade in vitro em dietas para ruminantes com diferentes níveis de líquido de casca de castanha de caju Tatiana García Díaz1; Antonio Ferriani Branco2*; Luís Carlos Vinhas Ítavo3; Geraldo Tadeu dos Santos2; Silvana Teixeira Carvalho4; Ana Lúcia Teodoro5; Ronaldo Lopes Oliveira6 Abstract The aim of this study was to evaluate the effect of increasing levels of cashew nut shell liquid (CNSL) in ruminant diets on in vitro dry matter digestibility (IVDMD), gas production kinetics, ruminal fermentation parameters, ammoniacal nitrogen concentration (NH3-N), and pH of the artificial rumen contents. The experimental design was completely randomized in a factorial 5 x 4 + 1 design, with five concentrate levels (200, 400, 600, 800, and 1,000 g kg-1 DM) and four CNSL levels (0, 0.3, 0.6, and 1.2 g kg-1 DM), as well as a control diet comprising only whole-plant corn silage, totaling 21 treatments.
    [Show full text]
  • Structure-Astringency Relationship of Anacardic Acids from Cashew Apple
    1 1 Structure-astringency relationship of anacardic acids from 2 cashew apple (Anacardium occidentale L.) 3 Liana Maria Ramos Mendesa,b, Deborah dos Santos Garrutib, Guilherme Julião Zocolob, 4 Marcelo de Freitas Limac, Edy Sousa de Britob,* 5 6 a Departamento de Engenharia Química, Universidade Federal do Ceará, Fortaleza, 7 Brazil. 8 b Embrapa Agroindústria Tropical, Rua Dra Sara Mesquita, 2270, Pici, Fortaleza, CE, 9 60511-110, Brazil 10 c Universidade Estadual Paulista (Unesp), Instituto de Biociências Letras e Ciências 11 Exatas, Departamento de Química e Ciências Ambientais, São José do Rio Preto, SP, 12 15054-000, Brazil 13 14 15 16 17 *Corresponding author: Edy Sousa de Brito 18 E-mail addresses: [email protected] (L.M.R. Mendes), 19 [email protected] (D.S. Garruti), [email protected] (G.J. 20 Zocolo), [email protected] (M.F. Lima), [email protected] (E.S. de Brito) 21 2 22 ABSTRACT 23 Cashew apple presents a characteristic astringency. However, the compounds responsible 24 for this characteristic were not described yet. A cashew apple extract was added to a BSA 25 solution and the compounds before and after precipitation were analyzed by UPLC- 26 QTOF/MSE. The extract astringency was measured on a 5-point scale (0: non astringent 27 and 4: extremely astringent). Among the phenolics detected anacardic acids were 28 identified and evaluated for their astringent effect. In the sensorial tests the cashew apple 29 extract was considered very astringent (average of 2.5). A mixture of anacardic acids, had 30 an average of 1.76 (astringent).
    [Show full text]
  • Cytotoxic 6-Alkylsalicylic Acids from the Endophytic Streptomyces Laceyi
    J. Antibiot. 59(12): 797–800, 2006 THE JOURNAL OF NOTE ANTIBIOTICS Cytotoxic 6-Alkylsalicylic Acids from the Endophytic Streptomyces laceyi Nahyun Kim, Jin Chul Shin, Woncheol Kim, Bang Yeon Hwang, Beom Seok Kim, Young-Soo Hong, Dongho Lee Received: October 18, 2006 / Accepted: November 10, 2006 © Japan Antibiotics Research Association Abstract Two new 6-alkylsalicylic acids, salaceyins A activities of the isolates against a human breast cancer and B were isolated by bioassay-guided fractionation from cell line. the culture of the endophytic Streptomyces laceyi MS53 and their structures were determined on the basis of spectroscopic data. Salaceyins A and B exhibited modest Results and Discussion cytotoxicity against a human breast cancer cell line (SKBR3) with IC50 values of 3.0 and 5.5 mg/ml, An endophytic Streptomyces strain (MS53) was isolated respectively. from a surface-sterilized stem of Ricinus communis L. Chemotaxonomic tests showed that the cell wall of the Keywords alkysalicylic acid, Streptomyces, cytotoxic strain contained LL-diaminopimelic acid, indicating that it has cell-wall type I; no diagnostic sugars were detected in the hydrolysates of whole cells. Using partial 16S Introduction ribosomal DNA sequence analysis, the strain was identified to be closely related to Streptomyces laceyi. The 16S In our search for biologically active agents of natural ribosomal DNA sequence identity was 99.38% (1460/ origin, the culture broth of an endophytic actinomycete 1469 bp) [10ϳ12]. strain exhibited cytotoxic activity against a human breast Compound 1 was obtained as a colorless amorphous cancer (SKBR3) cell line. Bioassay-guided fractionation of powder and was shown to possess a molecular formula of an EtOAc extract of a culture broth of Streptomyces laceyi MS53 resulted in the isolation of two new 6-alkylsalicylic acids (1 and 2, Fig.
    [Show full text]
  • 19 the Prevalence of Natural 3-Alk(En)Yl-Substituted
    THE PREVALENCE OF NATURAL 3-ALK(EN)YL-SUBSTITUTED PHENOLS AND THEIR POTENTIAL SEMISYNTHESES FROM CASHEW NUT SHELL LIQUID Stephen JM Mdachi Chemistry Department, University of Dar es Salaam, P.O. Box 35061, Dar es Salaam, Tanzania. E-mail: [email protected] ABSTRACT The focus of this mini-review is to assemble an instructive sample of natural products possessing structural features present in phenolic constituents of Cashew Nut Shell Liquid (CNSL) and, thus, inspire researchers to undertake semisyntheses of these natural products using the relatively abundant phenolic components of CNSL as raw materials. In this review, the author attempts to identify (or point out to) a 3-alk(en)yl-substituted phenolic sub-structure embedded in a particular natural product and reveal the CNSL phenolic component that has the corresponding structural motif. In addition, the author prompts the reader into a thinking process that should eventually lead him/her to developing a comprehensive retrosynthesis of a particular natural product culminating to that CNSL phenolic component as the starting material. Thus, in some way this paper is a tutorial review to the newcomers in the field of natural product synthesis utilizing natural resources. The seasoned synthetic chemists will also benefit from this collection as they guide and inspire their research trainees to take up natural product synthesis. In this article, a brief introduction to the composition and applications of CNSL is presented. This is followed by a compilation from the literature of reported natural products possessing the 3-alk(en)yl-substituted phenolic moiety. Alongside this compilation, a diagnostic discussion is presented aiming at pinpointing CNSL phenols as prospective precursors for the semisyntheses of some selected natural products as illustrative examples.
    [Show full text]
  • The Poisoned Weed: Plants Toxic to Skin
    The Poisoned Weed: Plants Toxic to Skin DONALD G. CROSBY OXFORD UNIVERSITY PRESS THE POISONED WEED DONALD G. CROSBY The poisoned weed PLANTS TOXIC TO SKIN 1 2004 1 Oxford New York Auckland Bangkok Buenos Aires Cape Town Chennai Dar es Salaam Delhi Hong Kong Istanbul Karachi Kolkata Kuala Lumpur Madrid Melbourne Mexico City Mumbai Nairobi Sa˜o Paulo Shanghai Taipei Tokyo Toronto Copyright # 2004 by Oxford University Press Published by Oxford University Press, Inc., 198 Madison Avenue, New York, New York 10016 www.oup.com Oxford is a registered trademark of Oxford University Press All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without the prior permission of Oxford University Press. Library of Congress Cataloging-in-Publication Data Crosby, Donald G. The Poisoned Weed: Plants toxic to skin / Donald G. Crosby. p. cm. Includes bibliographical references and index. ISBN 0-19-515548-3 1. Dermatotoxicology. 2. Poisonous plants. 3. Plant toxins. I. Title. RL803.C76 2003 616.5007—dc21 2003046272 987654321 Printed in the United States of America on acid-free paper To Nancy, whose struggles with T. diversilobum, T. radicans, M. indica, S. terebinthefolius, E. maculata, U. dioica, and sundry other plants inspired this book. This page intentionally left blank PREFACE Human dermatitis from plants is almost universal. In the United States alone, more than two-thirds of the population reacts to poison oak, poison ivy, and their relatives—more than 160 million people, including me.
    [Show full text]
  • Nuts As Dietary Source of Fatty Acids and Micro Nutrients in Human Health Chiranjiv Pradhan, Nikhila Peter and Namitha Dileep
    Chapter Nuts as Dietary Source of Fatty Acids and Micro Nutrients in Human Health Chiranjiv Pradhan, Nikhila Peter and Namitha Dileep Abstract In recent times, the Mediterranean diet plans are very popular because it has a lot of advantage in protecting from chronic health problems. Nuts are the integral part of the Mediterranean diet and advised to be incorporated in diet for health benefits. Both tree nuts and pea nut are good source of unsaturated fatty acids, soluble and insoluble fibers, good quantity of vitamins, minerals and phytochemi- cals with recognized benefits to human health. Due to life style disorders many chronic diseases are increasing in human beings. There are many epidemiological studies and research conducted on the relationship between consumption of nuts and chronic disease risks. This book chapter elaborately discusses about the nutri- tional composition of the nuts and their effect on cardiovascular disease, obesity, diabetes and cancer. Keywords: nuts, chemical composition, cardiovascular disease, obesity, diabetes, cancer 1. Introduction Nuts are excellent source of nutrients and bio active compounds. It is consumed by majority of the populations of the world in some form or other depending upon the availability in the geographical area. Nuts can be divided in to two types such as tree nuts and legumes. The important tree nuts are viz., almonds, walnuts, pista- chios, cashew nuts, Brazil nuts, hazelnuts, macadamia, and pine nut. Peanut is a legume commonly consumed as roasted or as pea nut butter. Pea nut is more economical than other nuts and popularly called as ‘poor man’s almond’. These nuts due to their unique nutritional properties are very much appreciated in vegan diets, gluten free diets and paleo diets [1].
    [Show full text]