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Bioactivities of Allicin and Related Organosulfur Compounds From 1 Egypt.J.Chem. Vol. 62, Special Issue (Part 1), pp. 1 - 11 (2019) Egyptian Journal of Chemistry http://ejchem.journals.ekb.eg/ Bioactivities of Allicin and Related Organosulfur Compounds from Garlic: Overview of the Literature Since 2010 Sudip Kumar Mandal1, Agnidipta Das1, Suddhasattya Dey1, Ujjwal Sahoo1, Sankhadip Bose2, Anindya Bose3, Neerupma Dhiman4, Swati Madan4, Mohamed A. Ramadan5* 1Dr. B. C. Roy College of Pharmacy & Allied Health Sciences, Bidhannagar, Durgapur-713206, India. 2NSHM Knowledge Campus, Kolkata – Group of Institutions, 124, B.L.Saha Road, Kolkata-700053, India. 3School of Pharmaceutical Sciences, Siksha O Anusandhan University, K8 Kalinga Nagar, Bhubaneswar, India. 4Amity Institute of Pharmacy, Amity University, Noida, Uttar Pradesh-201303, India. 5Textile Research Division, National Research Center, Egypt (Scopus affiliation ID 60014618). HE medical values of garlic, a traditionally used allium vegetable, were recognized as early as T3000 BC. Allicin, one of the major organosulfur compounds present in garlic, is associated with a wide variety of benificial activities like anticancer, anti-inflammatory, antiarthritic, antimicrobial, anti-diabetic, cholesterol-lowering, the potential to lower cardiovascular disorders, ameliorating neuron functions, etc. In this article, we have reviewed biological activities of allicin and related organosulfur compounds since the year 2010, using various scientific websites like Pub med, Google Scholar, Science Direct etc. Our literature review has highlighted many organo sulphur components of garlic and their possible mechanisms in curing different diseases. The information provided in this review will provide strategies for efficient organosulfur-based treatments of several diseases in future. Further research efforts are needed for a clear understanding of the interconnection between these functional components and various chronic diseases. Keywords: Allicin, Organosulfur compounds, Garlic, Pharmacology, Clinical trials. Introduction trisulfide (DATS), S-allyl-L-cysteine (SAC), vinyldithiin, S-allyl mercaptocysteine (SAMC), In recent days, due to high efficacy and low etc [2]. Allicin is the major and most biologically adverse effects, natural products have attracted active organosulphur compound in garlic, isolated the drug inventors as useful therapeutic agents and identified in 1944. Allicin is poorly miscible for the treatment of various diseases [1]. Allium in water, which has a characteristic odour like vegetables, such as garlic (Allium sativum) is freshly crushed garlic [3]. It is readily obtained used in many countries throughout the world as from alliin by the enzymatic activity of alliinase medicine since ancient days for the therapeutic (Fig. 1). Alliin, an oxygenated sulphur amino acid efficacies, as a result of organosulphur compounds, present in the garlic clove, is the stable precursor present in it. Garlic contains volatile oil and of allicin [4]. approximately 33 sulfur compounds like allicin, alliin, ajoene, diallyl disulfide (DADS), diallyl In spite of enough scientific evidence all *Corresponding author e-mail: [email protected] DOI: 10.21608/ejchem.2019.15787.1954 Received 8/8/2018; Accepted 20/8/2019 ©2019 National Information and Documentation Center (NIDOC) 2 SUDIP KUMAR MANDAL et al. through the past decade concerning the biological cell population in the G0/G1 phase and persuade effects of allicin and related organosulfur G2/M phase arrest [9]. compounds, there are lacks of updated reviews on them. In this article, we have reviewed biological Allicin has been reported to show the activities of allicin and related organosulfur hepatoprotective effect and antitumor activity. compounds from the year 2010, using various Researchers demonstrated through the in vivo scientific websites like Pubmed, Google Scholar experiment that combined therapy of allicin and and Science Direct etc. Our aim is to focus the 5-fluorouracil (5-FU) exhibited an outstanding recent scientific evidence in our review paper, inhibitory effect on the growth of hepatocellular trying to find the right mechanisms of these carcinoma (HCC) in mice. Allicin increased compounds for various diseases. Moreover, we 5-FU induced cytotoxicity in HCC cells. have discussed some chemistry and clinical trial Allicin sensitized HCC cells to 5-FU persuaded study findings of allicin to provide a complete apoptosis through ROS (Reactive oxygenated picture. species)-mediated mitochondrial pathway. Therefore, allicin may be a perfect booster to the Clinical Trials chemotherapy regimen of HCC [10]. A clinical trial was executed on allicin for Allicin ameliorated the apoptotic death of investigating its effectiveness and safety profile, colon cancer cells mediated by NF-E2-related in stage II oral submucous fibrosis (OSF). Some factor-2 (Nrf2). The in vitro studies suggested quality of life such as mouth opening, burning that allicin affected the multiplication of colon sensation, and oral health were improved in the cancer cell lines HCT-116, LS174T, HT-29, and patients with allicin showing its potentiality as an Caco-2. HCT-116 apoptotic cell death took place adjunctive therapeutic drug [5]. Another clinical after administering allicin through enhancing trial was carried out on allicin to evaluate the hypodiploid DNA level, decreasing counts efficacy and safety profile of topical application of B-cell non-Hodgkin lymphoma-2 (Bcl-2), of allicin oral adhesive tablets in minor recurrent increasing amounts of Bcl-2-associated X protein aphthous ulcerations (MiRAU). This clinical study (BAX) and the increasing ability to liberate showed that these tablets reduced ulcer size and Cytochrome-C from mitochondria [4]. removed ulcer pain of the without significant side effects [6]. In another clinical study allicin was Allicin was seen to be chemopreventive to orally administered for the treatment of Behcet’s gastric cancer. It decreased the growth of cancer disease (BD), occurs due to oxidative stress cells at G2/M phase via the caspase-dependent/- (OS) aggression, in patients with mucocutaneous independent pathway. The probable mechanism lesions. Allicin significantly improved OS-related may be enzymatic activity modulation [11]. parameters by inhibiting OS and regulating oxidant/antioxidant status balance. Moreover, A study was performed to investigate the allicin was found to be safe and was effective in effects of allicin in buccal pouch carcinogens is the treatment of BD [7]. In a previously reported induced by 7, 12-dimethylbenz(a) anthracene clinical trial, a high dose (180 mg/day) of allicin (DMBA). The experiment showed that allicin showed effectiveness to prevent the common cold remarkably reduced tumour volume and tumour [8]. load. Allicin treatment was observed to normalise DMBA altered glycoconjugates in plasma as well Biological Activities as buccal mucosa tumours. Researchers concluded that the allicin has appreciable power to safeguard Anticancer & antitumor activity and reinstate the cell surface glycoconjugates Though the exact pathway by which allicin during oral carcinogenesis [12]. affects the growth of cancer cell lines is still not clear, its anticancer activity has been reported A n t i - i n fl a m m a t o r y & a n t i - a r t h r i t i c a c t i v i t y : through various studies. Allicin acted as a novel Inflammation has long been a well-known anti-oesophageal cancer agent for oesophageal symptom of many diseases, including arthritis. squamous cell carcinoma (ESCC). Investigators Arthritis is a major problem in the people reported that cell viability and invasion ability throughout the world, which affects the joints and in ESCC cells were considerably alleviated after connective tissues like bones, muscles, cartilage, allicin therapy. Allicin was seen to reduce the and tendon [13]. In arthritis, cyclooxygenase-2 Egypt. J. Chem. 62, Special Issue (Part 1) (2019) BIOACTIVITIES OF ALLICIN AND RELATED ORGANOSULFUR COMPOUNDS ... 3 Fig. 1. Allicin from garlic Fig. 2. Different biological activities of allicin and related organosulfur compounds from garlic Egypt. J. Chem. 62, Special Issue (Part 1) (2019) 4 SUDIP KUMAR MANDAL et al. (COX-2) selective inhibitors are very much acts as an antioxidantat the physiological level in effective. Most of the currently available COX- lower doses. Allicin regulates the expression of 2 inhibitors are sulphur-containing molecules various anti-oxidative enzymes via Nrf2/Keap1 [14,15] allicin is one of them. Very recently a binding [23]. study has shown that allicin is a significant COX- 2 inhibitor, in a dose-dependent manner [16]. Allicin is considered as a cardioprotective agent Some other sulfur compounds of from garlic such and showed effects on vascular oxidative stress in as (Z, E)-ajoene and its three sulfonyl analogs cultured human umbilical vein endothelial cells were also tested for their anti-inflammatory (HUVECs) by activating Nrf2, which controls the properties. These compounds showed their defense against oxidative stress and inflammation anti-inflammatory potential by suppressing the [24]. LPS-induced production of nitric oxide (NO) and prostaglandin E2 (PGE2) in macrophages. The antihypertensive activity of allicin in Additionally, they hindered the expression of NO dexamethasone-induced hypertension has been synthase (iNOS) and cyclooxygenase-2 (COX- investigated. An experiment showed that systolic 2) genes in lipopolysaccharide (LPS)-activated blood pressure (SBP) increased significantly due macrophages [17]. to dexamethasone
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