Stephen F. Austin State University SFA ScholarWorks Faculty Publications Agriculture 2011 Chemical composition and product quality control of turmeric (Curcuma longa L.) Shiyou Li Stephen F Austin State University, Arthur Temple College of Forestry and Agriculture, [email protected] Wei Yuan Stephen F Austin State University, Arthur Temple College of Forestry and Agriculture, [email protected] Guangrui Deng Ping Wang Stephen F Austin State University, Arthur Temple College of Forestry and Agriculture, [email protected] Peiying Yang See next page for additional authors Follow this and additional works at: http://scholarworks.sfasu.edu/agriculture_facultypubs Part of the Natural Products Chemistry and Pharmacognosy Commons, and the Pharmaceutical Preparations Commons Tell us how this article helped you. Recommended Citation Li, Shiyou; Yuan, Wei; Deng, Guangrui; Wang, Ping; Yang, Peiying; and Aggarwal, Bharat, "Chemical composition and product quality control of turmeric (Curcuma longa L.)" (2011). Faculty Publications. Paper 1. http://scholarworks.sfasu.edu/agriculture_facultypubs/1 This Article is brought to you for free and open access by the Agriculture at SFA ScholarWorks. It has been accepted for inclusion in Faculty Publications by an authorized administrator of SFA ScholarWorks. For more information, please contact [email protected]. Authors Shiyou Li, Wei Yuan, Guangrui Deng, Ping Wang, Peiying Yang, and Bharat Aggarwal This article is available at SFA ScholarWorks: http://scholarworks.sfasu.edu/agriculture_facultypubs/1 28 Pharmaceutical Crops, 2011, 2, 28-54 Open Access Chemical Composition and Product Quality Control of Turmeric (Curcuma longa L.) ,1 1 1 1 2 3 Shiyou Li* , Wei Yuan , Guangrui Deng , Ping Wang , Peiying Yang and Bharat B. Aggarwal 1National Center for Pharmaceutical Crops, Arthur Temple College of Forestry and Agriculture, Stephen F. Austin State University, Nacogdoches, TX 75972, USA 2Department of General Oncology, Integrative Medicine Program, M.D. Anderson Cancer Center, University of Texas, Houston, TX 77030, USA 3Cytokine Research Laboratory, Department of Experimental Therapeutics, M.D. Anderson Cancer Center, University of Texas, Houston, TX 77030, USA Abstract: Chemical constituents of various tissues of turmeric (Curcuma longa L.) have been extensively investigated. To date, at least 235 compounds, primarily phenolic compounds and terpenoids have been identified from the species, in- cluding 22 diarylheptanoids and diarylpentanoids, eight phenylpropene and other phenolic compounds, 68 monoterpenes, 109 sesquiterpenes, five diterpenes, three triterpenoids, four sterols, two alkaloids, and 14 other compounds. Curcumi- noids (diarylheptanoids) and essential oils are major bioactive ingredients showing various bioactivities in in vitro and in vivo bioassays. Curcuminoids in turmeric are primarily accumulated in rhizomes. The essential oils from leaves and flowers are usually dominated by monoterpenes while those from roots and rhizomes primarily contained sesquiterpenes. The contents of curcuminoids in turmeric rhizomes vary often with varieties, locations, sources, and cultivation condi- tions, while there are significant variations in composition of essential oils of turmeric rhizomes with varieties and geo- graphical locations. Further, both curcuminoids and essential oils vary in contents with different extraction methods and are unstable with extraction and storage processes. As a result, the quality of commercial turmeric products can be mark- edly varied. While curcumin (1), demethoxycurcumin (2), and bisdemethoxycurcumin (5) have been used as marker com- pounds for the quality control of rhizomes, powders, and extract (“curcumin”) products, Ar-turmerone (99), -turmerone (100), and -turmerone (101) may be used to control the product quality of turmeric oil and oleoresin products. Authentication of turmeric products can be achieved by chromatographic and NMR techniques, DNA markers, with morphological and anatomic data as well as GAP and other information available. Keywords: Turmeric, Curcuma longa L., rhizomes, ground turmeric, turmeric oils, turmeric oleoresin, curcuminoids, curcu- min, sesquiterpenes, marker compounds, adulteration, standardization. INTRODUCTION Longae but recently it has been separated as Rhizoma Wenyujin Concisum in the 2005 version of the Pharmaco- Turmeric (Curcuma longa L.) is a rhizomatous poeia of People’s Republic of China [5]. In Thailand and herbaceous perennial plant of the ginger family, some other countries, C. domestica Val. is also used as the Zingiberaceae. It is native to tropical South Asia but is now scientific name of turmeric [6-8] although it is recognized as widely cultivated in the tropical and subtropical regions of a synonym of C. longa [9]. the world. The deep orange-yellow powder known as turmeric is prepared from boiled and dried rhizomes of the There are extensive in vitro and in vivo investigations on plant. It has been commonly used as spice and medicine turmeric extracts (ethanol, methanol, water, and ethyl acetate (Rhizome Curcumae Longae), particularly in Asia. In extracts) or “pure” active “curcumin” (actually it was a mix- Ayurveda medicine, turmeric is primarily used as a treatment ture of three major curcumnnioids in many cases) powder for inflammatory conditions and in traditional Chinese over the last half century. The role of curcumin (1), one of medicine, it is used as stimulant, aspirant, carminative, cor- the most studied chemopreventive agents, on anti- deal, emenagogue, astringent, detergent, diuretic and martir- inflammatory and cancer activity has been well appreciated net [1-3]. In India and China, wild turmeric (C. aromatica [3, 10-19]. Data from cell culture, animal research, and clini- Salisb., commonly called as Kasthuri manjal or yujin) is cal trials indicate that curcumin may have potential as a sometimes used as turmeric production [4]. This species is therapeutic agent in diseases such as inflammatory bowel known as C. wenyujin Y.H. Chen et C. Ling in China. It was disease, pancreatitis, arthritis, and chronic anterior uveitis [3, also occasionally used to substitute Rhizome Curcumae 20]. The anti-cancer effect has been reported in a few clinical trials, mainly as a chemoprevention agent in colon and *Address correspondence to this author at the National Center for Pharma- pancreatic cancer, cervical neoplasia and Barrets metaplasia ceutical Crops, Arthur Temple College of Forestry and Agriculture, Stephen [16]. The compound modulates several molecular targets and F. Austin State University, Nacogdoches, TX 75972, USA; inhibits transcription factors (NF-kB, AP-1), enzymes Tel: 936-468-2071, 936-468-5600; Fax: 936-468-7058; (COX-1, COX-2, LOX), cytokines (TNF, IL-1, IL-6) and E-mail: [email protected] 2210-2906/11 2011 Bentham Open Chemical Composition and Product Quality Control of Turmeric (Curcuma longa L.) Pharmaceutical Crops, 2011, Volume 2 29 antiapoptotic genes (BCL2, BCL2L1) [21-24]. As a result, curcumin (1) is able to induce apoptosis and has antiangio- genic activity [25, 26]. Turmeric extracts or the active curcuminoids have also shown hepato- and cardioprotective [27, 28], hypoglycemic [29, 30], anti-amyloidogenic [31], antifungal [32], parasiti- cidal [33, 34], antioxidant [35, 36], and chemo-resistance and radio-resistance activities [16]. Recent in vitro and in vivo studies and clinical trials in China and USA suggest that curcumin might be one of the most promising compounds for the development of Alzheimer's disease therapies [37]. Accumulating evidences suggest that curcumin (1) may regulate lipid metabolism, which plays a central role in the development of obesity and its complications [38]. Recently, it was found that curcumin (1) and demethoxycurcumin (2) can reduce lead-induced memory deficits in rates [39]. Turmeric oils/oleoresin or a major compound ar-turmerone (99) have shown antimicrobial [40-43], larvicidal [44], and antioxidant activities [45]. Essential oils of Curcuma also exerts triglyceride-lowering activity on serum as well as liver triglycerides [46]. Curcuma longa is often cultivated to harvest rhizomes (Fig. 1) for ground turmeric powder as a spice and food col- oring agent (used alone or in mustard paste or curry powder). The plant has also been recognized as a pharmaceutical crop for production of standardized therapeutic extracts (STEs) or small therapeutic molecules (STMs) [47]. India is the largest producer of turmeric supplying over 90% of the world’s de- mand [48]. The country produced about 716,900 Mt of tur- Fig. (1). Curcuma longa is primarily cultivated for turmeric rhi- meric from approximately 161,300 hectares of crops during zomes and their products (The upper picture shows the plants culti- 2004-2005 [49]. China also has cultivated turmeric for both vated at the SFA Mast Arboretum, Stephen F. Austin State Univer- domestic use and export. There are about 70 cultivars or va- sity in Nacogdoches, Texas, USA and the lower picture shows rhi- rieties of C. longa cultivated in India, some important re- zomes and ground turmeric as well as curry powder. Photos by S.Y. gional trade varieties of turmeric are ‘Rajapuri’, ‘Duggirala’, Li). ‘Cuddappah’, ‘Berhampur’, ‘Erode’, ‘Nizamabad’, ‘Ko- raput’, ‘Kasturi’, ‘Chaya’, ‘Kodur’, ‘Salem’, ‘Waigon’, ‘Alleppey’, ‘Karur’, ‘Tekurpeta’ [2]. Turmeric is valued Phenolic Compounds primarily for curcumin (1). Thus, curcumin (1) content has Diarylheptanoids and Diarylpentanoids been an important factor in developing and selecting