دوره 25، شماره 4 - ( دو ماهنامه طب جنوب 1401 )                   جلد 25 شماره 4 صفحات 325-297 | برگشت به فهرست نسخه ها


XML English Abstract Print


Download citation:
BibTeX | RIS | EndNote | Medlars | ProCite | Reference Manager | RefWorks
Send citation to:

Dehghani H, Rashedinia M, Mohebbi G H, Vazirizadeh A, Maryamabadi A, Barmak A R. The in vitro and in silico Anticholinesterase Ac-tivities of Brittle Star (Ophiocoma erinaceus) crude venoms from the Persian Gulf-Bushehr. Iran South Med J 2022; 25 (4) :297-325
URL: http://ismj.bpums.ac.ir/article-1-1639-fa.html
دهقانی حمیده، راشدی‌نیا مرضیه، محبی غلامحسین، وزیری‌زاده امیر، مریم‌آبادی عمار، برمک علیرضا. مطالعه فعالیت‌های آنتی‌کولین استرازی در شرایط in vitro و in silico زهر خام ستاره شکننده اوفیوکوما اریناسئوس خلیج‌فارس- بوشهر. مجله طب جنوب. 1401; 25 (4) :297-325

URL: http://ismj.bpums.ac.ir/article-1-1639-fa.html


1- گروه سم‌شناسی و فارماکولوژی، دانشکده داروسازی، دانشگاه علوم پزشکی شیراز، شیراز- ایران
2- مرکز تحقیقات زیست فناوری دریایی‌ خلیج‌فارس، پژوهشکده علوم زیست پزشکی خلیج‌‌فارس، دانشگاه علوم پزشکی بوشهر، بوشهر، ایران ، Mohebbihsn@yahoo.com
3- گروه زیست‌شناسی دریا، مرکز مطالعات و پژوهش‌های خلیج‌فارس، دانشگاه خلیج‌فارس، بوشهر، ایران
4- مرکز تحقیقات زیست فناوری دریایی‌ خلیج‌فارس، پژوهشکده علوم زیست پزشکی خلیج‌‌فارس، دانشگاه علوم پزشکی بوشهر، بوشهر، ایران
چکیده:   (1150 مشاهده)
زمینه: ستاره‌های شکننده، علاوه بر دفاع فیزیکی، قادر به تولید توکسین‌های شناخته شده‌ای می‌باشند که مسئول فعالیت­های بیولوژیکی مختلف آن‌ها است. با توجه به فراوانی این زیست‌مندان دریایی در آب‌های ساحلی خلیج‌فارس و با علم به اثرات بیولوژیک متعدد آن‌ها، این مطالعه با هدف شناسایی متابولیت‌های ثانویه و ارزیابی فعالیت­های in vitro و in silico آنتی‌کولین استرازی زهر خام اکینودرم اوفیوکوما اریناسئوس خلیج‌فارس انجام گردید.
مواد و روش‌ها: در این مطالعه، پس از لیوفیلیزاسیون نمونه ستاره شکننده، آزمون­های LD50، فعالیت­های مهارکنندگی کولین­استرازی، شناسایی متابولیت­های ثانویه و ارزیابی درون­رایانه‌ای آن‌ها به‌ترتیب با روش‌های اسپیرمن-کاربر، اسپکتروسکوپی المن، کروماتوگرافی گازی- طیف‌سنجی جرمی (GC-MS) و روش محاسباتی داکینگ انجام گردیدند.
یافته‌ها: بر اساس نتایج، میزان LD50 نمونه 0.13±6.04 میلی‌گرم بر کیلوگرم بود. مقادیر IC50 مربوط به آنزیم استیل کولین‌استراز و بوتیریل کولین‌استراز آن‌ها به‌ترتیب 0.055±37/925 و نیز 0/02±5/388 میکروگرم بر میلی‌لیتر در مقایسه با استاندارد گالانتامین به دست آمدند. آنالیز GC-MS نمونه تعداد 25 ترکیب شیمیایی زیست­فعال با ساختارهای مختلف نظیر آلکالوئیدها، ترپن‌ها و استروئیدها را نشان داد. نتایج محاسباتی ترکیبات نیز، نتایج تجربی را تأئید نمودند. از این میان، ترکیب آلکالوئیدی BS4 دارای بیشترین تمایل برای هر دو آنزیم بود.
نتیجه‌گیری: از نظر قدرت سمیت، نمونه زهر خام ستاره شکننده در گروه "خیلی سمی" قرار گرفت. آنالیز کروماتوگرافی گازی زهر خام، متابولیت‌های زیست­فعال ثانویه متعددی با ساختارهای شیمیایی متفاوتی را نشان داد. نتایج تجربی و محاسباتی، روی فعالیت آنزیم­های کولین‌استرازی نمونه نشان داد که زهر، به‌عنوان مهارکننده قابل ملاحظه آنزیم­ها عمل می­نماید. مطالعات بیشتری برای تعیین اینکه آیا ترکیب BS4 می‌تواند کاندیدای درمان بیماری آلزایمر باشد، مورد نیاز است.
متن کامل [PDF 1156 kb]   (502 دریافت)    
نوع مطالعه: پژوهشي | موضوع مقاله: بیوشیمی
دریافت: 1401/2/25 | پذیرش: 1401/6/28 | انتشار: 1401/9/26

فهرست منابع
1. Mohebbi GH, Nabipour I, Vazirizadeh A. The Sea, the Future Pharmacy. Iran South Med J 2014; 17(4): 748-788. (Persian) [Article]
2. Lhullier C, Moritz MIG, Tabalipa EO, et al. Biological activities of marine invertebrates extracts from the northeast Brazilian coast. Braz J Biol 2020; 80(2): 393-404. [DOI]
3. Kong DX, Jiang YY, Zhang HY. Marine natural products as sources of novel scaffolds: achievement and concern. Drug Discov Today 2010; 15(21-22): 884-6. [DOI]
4. Ebrahimi H, Mohebbi GH, Vazirizadeh A, et al. Sea cucumbers, the ocean of bioactive compounds. Iran South Med J 2015; 18(3): 664-679. (Persian) [Article]
5. Brittle star. Encyclopedia Britannica 2018 (Accessed September 7, 2021, at https://www.britannica.com/animal/brittlestar). [Article]
6. Miller JE, Pawson DL. echinoderm. Encyclopedia Britannica 2020. (Accessed November 2, 2022, at https://www.britannica.com/animal/echinoderm). [Article]
7. Kalinin VI. Echinoderms Metabolites: Structure, Functions, and Biomedical Perspectives. Mar Drugs 2021; 19(3): 125. [DOI]
8. Mohebbi GH, Vazirizadeh A, Nabipour I. Sea urchin: toxinology, bioactive compounds and its treatment management. Iran South Med J 2016; 19(4): 704-735. (Persian) [Article]
9. Kamyab E, Kellermann MY, Kunzmann A, et al. Chemical biodiversity and bioactivities of saponins in Echinodermata with an emphasis on sea cucumbers (Holothuroidea), In: Jungblut S, Liebich V, Bode-Dalby M, editors. YOUMARES 9 - The Oceans: Our Research, Our Future 2020, 121-157. [DOI]
10. Stöhr S, O'Hara TD, Thuy B. Global diversity of brittle stars (Echinodermata: Ophiuroidea). PLoS One 2012; 7(3): e31940. [DOI]
11. Menzies RJ, George RY, Rowe GT. Abyssal environment and ecology of the world oceans. New York: Wiley, 1973, 488. [Article]
12. Blumenbach JF. Specimen archaeologiae telluris terrarvmqve inprimis Hannoveranarvm. Goettingae: Apvd Henricvm Dieterich, 1803, 28. [Article]
13. Wood JG. Animate Creation. In: Holder JB, editor. New York: Selmar Hess, 1898, 319. [Article]
14. Pomory CM. Key to the common shallow-water brittle stars (Echinodermata: Ophiuroidea) of the Gulf of Mexico and Caribbean Sea. Caribb J Sci 2007; 10: 1-43. [Article]
15. Fish JD, Fish S. A student’s guide to the seashore. 3rd ed. New York: Cambridge University Press, 2011, 572. [Article]
16. Zueva O, Khoury M, Heinzeller T, et al. The complex simplicity of the brittle star nervous system. Front Zool 2018; 15: 1. [DOI]
17. LeClair EE, LaBarbera MC. An in vivo Comparative Study of Intersegmental Flexibility in the Ophiuroid Arm. Biol Bull 1997; 193(1): 77-89. [DOI]
18. Tomholt L, Friesen LJ, Berdichevsky D, et al. The structural origins of brittle star arm kinematics: An integrated tomographic, additive manufacturing, and parametric modeling-based approach. J Struct Biol 2020; 211(1): 107481. [DOI]
19. Yücekutlu AN, Bildaci I. Determination of plant saponins and some of Gypsophila species: a review of the literature. Hacettepe J Biol Chem 2008; 36(2): 129-135. [Article]
20. Baharara J, Mahdavi–Shahri N, Shaddel N. The local effect of Persian Gulf brittle star (Ophiocoma erinaceus) alcoholic extract on cutaneous wound healing in Balb/C mouse. J Birjand Univ Med Sci 2014; 21(3): 312-323. [Article]
21. Man S, Gao W, Zhang Y, et al. Chemical study and medical application of saponins as anti-cancer agents. Fitoterapia 2010; 81(7): 703-714. [DOI]
22. Gunnarsson JS, Sköld M. Accumulation of polychlorinated biphenyls by the infaunal brittle stars Amphiura filiformis and A. chiajei: effects of eutrophication and selective feeding. Mar Ecol Prog Ser 1999; 186: 173-85. [Article]
23. Nuzzo G, Gomes BA, Amodeo P, et al. Isolation of Chamigrene Sesquiterpenes and Absolute Configuration of Isoobtusadiene from the Brittle Star Ophionereis reticulata. J Nat Prod 2017; 80(11): 3049-3053. [DOI]
24. Levin EV, Kalinovsky AI, Dmitrenok PS. Steroid compounds from the Far East starfish Pteraster obscurus and the ophiura Asteronyx loveni. Russ J Bioorganic Chem 2007; 33(3): 341–346. [Article]
25. Andersson L, Bohlin L, Iorizzi M, et al. Biological activity of saponins and saponin-like compounds from starfish and brittle-stars. Toxicon 1989; 27(2): 179-88. [DOI]
26. Prabhu K, Bragadeeswaran S. Biological properties of brittle star Ophiocnemis marmorata collected from Parangipettai, Southeast coast of India. J Microbiol Antimicrob 2013; 5(10): 110-118. [DOI]
27. Amini AA, Curwen RW, Klein AK, et al. Physics based snakes, Kalman snakes, and snake grids for feature localization and tracking in medical images 1995; 363-364. [Article]
28. Mohebbi GH, Nabipour I, Vazirizadeh A, et al. Acetylcholinesterase inhibitory activity of a neurosteroidal alkaloid from the upside-down jellyfish Cassiopea andromeda venom. Rev Bras Farmacogn 2018; 28(5): 568–574. [DOI]
29. Barmak A, Niknam K, Mohebbi GH, et al. Antibacterial studies of hydroxyspiro [indoline-3,9-xanthene] trione against spiro [indoline3,9-xanthene] trione and their use as acetyl and butyrylcholinesterase inhibitors. Microb Pathog 2019; 130: 95-99. [DOI]
30. Langjae R, Bussarawit S, Yuenyongsawad S, et al. Acetylcholinesterase-inhibiting steroidal alkaloid from the sponge Corticium sp. Steroids 2007; 72(9-10): 682-5. [DOI]
31. Darabi AH, Nabipour I, Mohebbi GH, et al. Studies on the cholinesterases inhibiting compounds from the Cassiopea andromeda venom. Bioinformation 2020; 16(9): 702-709. [DOI]
32. Spearman-karber R. Alternative methods of Analysis for Quantal Responses. In: Statistical Method in Biological Assay. Finney and Griffin, London 1978; 645. [Article]
33. Worek F, Mast U, Kiderlen D, et al. Improved determination of acetylcholinesterase activity in human whole blood. Clin Chim Acta 1999; 288(1-2): 73-90. [DOI]
34. Mohebbi GH, Jahangiri A, Hajeb P. Inhibition of acetyl cholinesterase activity farmers exposed to organophosphate pesticides in Bushehr, Iran. AEJTS 2011; 3(3): 127-29. [Article]
35. Moodie LWK, Sepčić K, Turk T, et al. Natural cholinesterase inhibitors from marine organisms. Nat Prod Rep 2019; 36(8): 1053-1092. [DOI]
36. Ramírez D, Caballero J. "Is it reliable to take the molecular docking top scoring position as the best solution without considering available structural data?” Molecules 2018; 23(5): 1038. [DOI]
37. Erhirhie EO, Ihekwereme CP, Ilodigwe EE. Advances in acute toxicity testing: strengths, weaknesses and regulatory acceptance. Interdiscip Toxicol 2018; 11(1): 5-12. [DOI]
38. Amini E, Nabiuni M, Baharara J, et al. Hemolytic and cytotoxic effects of saponin like compounds isolated from Persian Gulf brittle star (Ophiocoma erinaceus). J Coast Life Med 2014; 2(10): 762-68. [DOI]
39. Afzali M, Baharara J, Shahrokhabadi K, et al. Effect of the Persian Gulf Brittle Star (Ophiocoma erinaceus) Dichloromethane Extract on Induction of Apoptosis on EL4 Cell Line. J Rafsanjan Uni Med Sci 2015; 14(6): 467-480. (Persian) [Article]
40. Cragg GM, Newman DJ. Natural products: a continuing source of novel drug leads. Biochim Biophys Acta 2013; 1830(6): 3670-95. [DOI]
41. Murray AP, Faraoni MB, Castro MJ, et al. Natural AChE Inhibitors from Plants and their contribution to Alzheimer's Disease therapy. Curr Neuropharmacol 2013; 11(4): 388-413. [DOI]
42. Fenical W. Marine Pharmaceuticals: Past, Present, and Future. Oceanogr 2006; 19(2): 110-119. [Article]
43. Mohebbi GH, Nabipour I, Vazirizadeh A. Neurotoxic syndromes in marine poisonings a review. Iran South Med J 2014; 17(3): 451-475. (Persian) [Article]
44. Blunt JW, Carroll AR, Copp BR, et al. Marine natural products. Nat Prod Rep 2018; 35(1): 8-53. [DOI]
45. El Feky SE, Abd El Hafez MSM, Abd El Moneim NA, et al. Cytotoxic and antimicrobial activities of two new sesquiterpenoids from red sea brittle star Ophiocoma dentata. Sci Rep 2022; 12: 8209. [DOI]
46. Gokel MR, McKeever M, Meisel JW, et al. Crown ethers having side arms: a diverse and versatile supramolecular chemistry. J Coord Chem 2021; 74(1-3): 14-39. [DOI]
47. Taylor P, Radic Z. The Cholinesterases: From Genes to Proteins. Annu Rev Pharmacol Toxicol 1994; 34: 281–320. [DOI]
48. Li S, Li AJ, Travers J, et al. Identification of compounds for Butyrylcholinesterase inhibition. SLAS Discov 2021; 26(10): 1355-1364. [DOI]
49. Chen VP, Gao Y, Geng L, et al. Plasma butyrylcholinesterase regulates ghrelin to control aggression. Proc Natl Acad Sci U S A 2015; 112(7): 2251-6. [DOI]
50. Darvesh S, Walsh R, Kumar R, et al. Inhibition of human cholinesterases by drugs used to treat Alzheimer disease. Alzheimer Dis Assoc Disord 2003; 17(2): 117-26. [DOI]
51. Greig NH, Utsuki T, Ingram DK, et al. Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent. Proc Natl Acad Sci U S A 2005; 102(47): 17213-8. [DOI]
52. Kovarik Z, Radić Z, Grgas B, et al. Amino acid residues involved in the interaction of acetylcholinesterase and butyrylcholinesterase with the carbamates Ro 02-0683 and bambuterol, and with terbutaline. Biochim Biophys Acta 1999; 1433(1-2): 261-71. [DOI]
53. Giacobini E. Cholinesterase inhibitors stabilize Alzheimer's disease. Ann N Y Acad Sci 2000; 920: 321-7. [DOI]
54. Verpoorte R, Van der Heijden R, Schripsema J, et al. Plant cell biotechnology for the production of alkaloids: present status and prospects. J Nat Prod 1993; 56(2): 186-207. [DOI]
55. Dey P, Kundu A, Kumar A, et al. Analysis of alkaloids (indole alkaloids, isoquinoline alkaloids, tropane alkaloids). Recent Advances in Natural Products Analysis 2020: 505–567. [DOI]
56. Liew SY, Khaw KY, Murugaiyah V, et al. Natural indole butyrylcholinesterase inhibitors from Nauclea officinalis. Phytomedicine 2015; 22(1): 45-8. [DOI]
57. Bharate SB, Manda S, Joshi P, et al. Total synthesis and anti-cholinesterase activity of marine-derived bis-indole alkaloid fascaplysin. Med Chem Comm 2012; 3: 1098–1103. [DOI]
58. Vieira IJ, Medeiros WL, Monnerat CS, et al. Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc 2008; 80(3): 419-26. [DOI]
59. Belyagoubi-Benhammou N, Belyagoubi L, Gismondi A, et al. GC/MS analysis, and antioxidant and antimicrobial activities of alkaloids extracted by polar and apolar solvents from the stems of Anabasis articulata. Med Chem Res 2019; 28: 754–767. [DOI]
60. Mbundi L, Gallar-Ayala H, Rizwan Khan M, et al. Advances in the analysis of challenging food contaminants: nanoparticles, bisphenols, mycotoxins, and brominated flame retardants. Adv Mol Toxicol 2014; 8: 35-105. [DOI]
61. Riedel E, Kyriakopoulos I, Nündel M. 9, 10-Dihydroergotalkaloids as inhibitors of acetylcholinesterase. Arzneimittelforschung 1981; 31(9): 1387-8. [PubMed]
62. PubChem Compound Summary for CID 220401, Demecolcine. National Center for Biotechnology Information. (Accessed November 28, 2021, at https://pubchem.ncbi.nlm.nih.gov/compound/Demecolcine) [Article]
63. Li JC, Zhang J, Rodrigues MC, et al. Synthesis and evaluation of novel 1,2,3-triazole-based acetylcholinesterase inhibitors with neuroprotective activity. Bioorg Med Chem Lett 2016; 26(16): 3881-3885. [DOI]
64. Dos Santos TC, Gomes TM, Pinto BAS, et al. Naturally occurring acetylcholinesterase inhibitors and their potential use for Alzheimer's Disease Therapy. Front Pharmacol 2018; 9: 1192. [DOI]
65. Konrath EL, Passos Cdos S, Klein LC Jr, et al. Alkaloids as a source of potential anticholinesterase inhibitors for the treatment of Alzheimer's disease. J Pharm Pharmacol 2013; 65(12): 1701-25. [DOI]
66. Cole TJ, Short KL, Hooper SB. The science of steroids. Semin Fetal Neonatal Med 2019; 24(3): 170-175. [DOI]
67. St-Onge MP, Lamarche B, Mauger JF, et al. Consumption of a functional oil rich in phytosterols and medium-chain triglyceride oil improves plasma lipid profiles in men. J Nutr 2003; 133(6): 1815-1820. [DOI]
68. Reddy DS. Neurosteroids: endogenous role in the human brain and therapeutic potentials. Prog Brain Res 2010; 186: 113-37. [DOI]
69. Sultan A, Raza AR. Steroids: a diverse class of secondary metabolites. Med chem 2015; 5: 7. [DOI]
70. Zhao HY, Shao CL, Li ZY, et al. Bioactive pregnane steroids from a South China Sea gorgonian Carijoa sp. Molecules 2013; 18(3): 3458-3466. [DOI]
71. Khalid A, Zaheer-ul-Haq, Anjum S, et al. Kinetics and structure-activity relationship studies on pregnane-type steroidal alkaloids that inhibit cholinesterases. Bioorg Med Chem 2004; 12(9): 1995-2003. [DOI]
72. Zaheer-Ul-Haq ZU, Wellenzohn B, Liedl KR, et al. Molecular docking studies of natural cholinesterase-inhibiting steroidal alkaloids from Sarcococca saligna. J Med Chem 2003; 46(23): 5087-90. [DOI]
73. Riccio R, D’Auria MV, Minale L. Two new steroidal glycoside sulfates, Longicaudoside-A and -B, from the mediterranean Ophiuroid Ophioderma longicaudum. J Org Chem 1986; 51(4): 533–536. [DOI]
74. Comin MJ, Maier MS, Roccatagliata AJ, et al. Evaluation of the antiviral activity of natural sulfated polyhydroxysteroids and their synthetic derivatives and analogs. Steroids 1999; 64(5): 335-340. [DOI]
75. Roccatagliata AJ, Maier MS, Seldes AM, et al. Antiviral sulfated steroids from the ophiuroid Ophioplocus januarii. J Nat Prod 1996; 59(9): 887–889. [DOI]
76. Aminin DL, Agafonova IG, Fedorov SN. Biological activity of disulfated polyhydroxysteroids from the Pacific brittle star Ophiopholis aculeata. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol 1995; 112(2): 201-4. [DOI]
77. Güçlü-Ustündağ O, Mazza G. Saponins: properties, applications and processing. Crit Rev Food Sci Nutr 2007; 47(3): 231-58. [DOI]
78. Kubanek J, Pawlik JR, Eve TM, et al. Triterpene glycosides defend the Caribbean reef sponge Erylus formosus from predatory fishes. Mar Ecol Prog Ser 2000; 207: 69-77. [DOI]
79. Yamanouchi T. On the poisonous substance contained in Holothurians. Publ Mar Biol Lab 1955; 4(2-3): 183-203. [DOI]
80. Kitagawa I, Kobayashi M. On the structure of the major saponin from the starfish acanthaster planci. Tetrahedron Lett 1977; 18(10): 859-862. [DOI]
81. Minale L, Riccio R, Zollo F. "Structural studies on chemical constituents of echinoderms". Stud Nat Prod Chem 1995; 15: 43-110. [DOI]
82. Bahrami Y, Franco CM. Acetylated Triterpene Glycosides and Their Biological Activity from Holothuroidea Reported in the Past Six Decades. Mar Drugs 2016; 14(8): 147. [DOI]
83. Jesus M, Martins AP, Gallardo E, et al. Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology. J Anal Methods Chem 2016; 2016: 4156293. [DOI]
84. Mosquera MEG, Jiménez G, Tabernero V, et al. Terpenes and Terpenoids: Building Blocks to Produce Biopolymers. Sustain Chem 2021; 2(3): 467-492. [DOI]
85. Masyita A, Sari RM, Astuti AD, et al. Terpenes and terpenoids as main bioactive compounds of essential oils, their roles in human health and potential application as natural food preservatives. Food Chem X 2022; 13: 100217. [DOI]
86. Machado LP, Carvalho LR, Young MCM, et al. Evaluation of acetylcholinesterase inhibitory activity of Brazilian red macroalgae organic extracts. Rev Bras Farmacogn 2015; 25(6): 657-662. [DOI]
87. Ninkuu V, Zhang L, Yan J, et al. Biochemistry of terpenes and recent advances in plant protection. Int J Mol Sci 2021; 22(11): 5710. [DOI]
88. Abed SA, Sirat HM, Taher M. Tyrosinase inhibition, anti-acetylcholinesterase, and antimicrobial activities of the phytochemicals from Gynotroches axillaris Blume. Pak J Pharm Sci 2016; 29(6): 2071-78. [PubMed]
89. Sheeja MD, Beema SR, Karutha PS, et al. Cholinesterase inhibitory, anti-amyloidogenic and neuroprotective effect of the medicinal plant Grewia tiliaefolia - An in vitro and in silico study. Pharm Biol 2017; 55(1): 381–393. [DOI]
90. Lin J, Huang L, Yu J, et al. Fucoxanthin, a marine carotenoid, reverses scopolamineinduced cognitive impairments in mice and inhibits acetylcholinesterase in Vitro. Mar Drugs 2016; 14(4): 67. [DOI]
91. Galasso C, Orefice I, Pellone P, et al. On the neuroprotective role of Astaxanthin: new perspectives? Mar Drugs 2018; 16(8): 247. [DOI]
92. Alias A, Zabidi Z, Zakaria N, et al. Biological activity relationship of cyclic and noncyclic alkanes using quantum molecular descriptors. Open J Appl Sci 2021; 11: 966-984. [DOI]
93. Ahmed M, Latif N, Khan RA, et al. Inhibitory effect of arachidonic acid on venom acetylcholinesterase. Toxicol Environ Chem 2011; 93(8): 1659-1665. [DOI]

ارسال پیام به نویسنده مسئول


بازنشر اطلاعات
Creative Commons License این مقاله تحت شرایط Creative Commons Attribution-NonCommercial 4.0 International License قابل بازنشر است.

کلیه حقوق این وب سایت متعلق به مجله طب جنوب می‌باشد.

طراحی و برنامه نویسی: یکتاوب افزار شرق

© 2024 CC BY-NC 4.0 | Iranian South Medical Journal

Designed & Developed by: Yektaweb