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Comparative Study on the Chemical Constituents of Curcuma Drugs (NISHIDONO, CHIYOMATSU, SAIFUDIN, DEEVANHXAY, TANAKA)

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Comparative Study on the Chemical Constituents of Curcuma Drugs (NISHIDONO, CHIYOMATSU, SAIFUDIN, DEEVANHXAY, TANAKA) Comparative Study on the Chemical Constituents of Curcuma Drugs (NISHIDONO, CHIYOMATSU, SAIFUDIN, DEEVANHXAY, TANAKA) Comparative Study on the Chemical Constituents of Curcuma Drugs Yuto NISHIDONO*1, Takahiro CHIYOMATSU*2, Azis SAIFUDIN*3, Phengxay DEEVANHXAY*4, Ken TANAKA*5 Abstract: Curcuma drugs are derived from the rhizomes of Curcuma plants, such as C. aeruginosa, C. aromatica, C. heyneana, C. longa, C. mangga, C. phaeocaulis, C. xanthorrhiza and C. zedoaria. They have been used as a spice, as a dye for textiles, as a major ingredient of curry powder and as a drug in traditional medicine, in many Asian countries. In Japan, Curcuma drugs derived from C. longa have been used to strengthen and tone the stomach, and the drug derived from C. zedoaria has been used to relieve the symptoms of “Oketsu” (various syndromes caused by the obstruction of blood circulation such as arthralgia, psychataxia and dysmenorrhea). In Indonesia, many Curcuma plants, such as C. xanthorrhiza (Temulawak), C. longa (Kunyit), are more commonly used in traditional Jamu medicine. The composition of the chemical constituents of Curcuma drugs often varies depending on the species, the geographical location, the cultivation conditions, and the post-harvest processing. In the present study, to evaluate the qualities of the Curcuma drugs produced in several countries in Asia, the chemical profiles of their constituents were investigated. As a result, it was shown that C. longa produced in Indonesia has the highest concentration of curcumin, which is one of the major active constituents in Curcuma drugs. Concerning the volatile constituents, C. longa and C. xanthorrhiza were characterized by high contents of bisabolane-type sesquiterpenes. Characteristic distributions of the sesquiterpenes, curzerenone, curdione, curcumenol and γ-bicyclohomofarnesal appeared in the chemical profiles of C. aeruginosa, C. heyneana, C. mangga, C. zedoaria, C. phaeocaulis, and C. aromatica. The following *1 Doctoral Student, Graduate School of Pharmacy, Ritsumeikan University *2 Student, College of Pharmaceutical Sciences, Ritsumeikan University *3 Dean, Faculty of Pharmacy, Universitas Muhammadiyah Surakarta *4 Lecturer, Department of Chemistry, Faculty of Natural Sciences, National University of Laos *5 Professor, College of Pharmaceutical Sciences, Ritsumeikan University E-mail: *1 [email protected] *2 [email protected] *3 [email protected] *4 [email protected] *5 [email protected] Received on 2020/1/31, accepted after peer reviews on 2020/7/3. ©Asia-Japan Research Institute of Ritsumeikan University: Journal of the Asia-Japan Research Institute of Ritsumeikan University, 2020. PRINT ISSN 2435-0184 ONLINE ISSN 2435-0192, Vol.2, pp.15-33. 15 Journal of the Asia-Japan Research Institute of Ritsumeikan University Volume 2 • October 2020 marker compounds of C. heyneana were identified; curcumanolide A and B, procurcumenol, 15, 16-bisnorlabda-8 (17),11-diene-13-one, zedoarondiol, isozedoarondiol and aerugidiol. Keywords: Curcuma drugs, Zingiberaceae, Volatile constituents, Gas chromatography- mass spectrometry (GC-MS). 1. Introduction Curcuma is a genus in the family Zingiberaceae with 93 species accepted in the Plants List organized by the Royal Botanical Gardens at Kew and the Mississippi Botanical Garden. Curcuma plants are distributed predominantly in South and Southeast Asia and many species, such as C. aeruginosa, C. aromatica, C. heyneana, C. longa, C. mangga, C. phaeocaulis, C. xanthorrhiza and C. zedoaria, have been used as a spice, as a dye for textiles, as a major ingredient of curry powder and as a drug in traditional medicine in Asian countries as shown in Photos 1 and 2. For example, in the Japanese traditional medicine, Kampo, “Ukon” (dried rhizome of C. longa) and “Gajyutsu” (dried rhizome of C. zedoaria or C. phaeocaulis or C. kwangsiensis) have been used to prevent or to cure diseases. In Chinese traditional medicine, rhizomes of C. longa are used as “Jianghuang”, and rhizomes of C. phaeocaulis, C. wenyujin and C. kwangsiensis are used as “Ezhu” (Komatsu et al., 2007). In Indonesia, many Curcuma plants, such as C. xanthorrhiza (Temulawak), C. longa (Kunyit), are more commonly used in Jamu medicine (Widyowati and Agil, 2018). Photo 1. Indonesia, Beringharjo Crude Drugs Market Photo 2. Lao PDR, Crude Drugs Morning Market 16 Comparative Study on the Chemical Constituents of Curcuma Drugs (NISHIDONO, CHIYOMATSU, SAIFUDIN, DEEVANHXAY, TANAKA) Curcuma drugs are derived from the rhizomes of different Curcuma plants, and the morphological appearances of the crude drugs are very similar, making identification of the botanical source very difficult. Many attempts to develop an identification methodology for Curcuma drugs using molecular analysis have been reported (Cao et al., 2001; Komatsu et al., 2007). However, Curcuma plants consist of a diverse range of polyploid complexes (2x-15x) and their ploidy level coupled with the mode of vegetative propagation make numerous intra-individual polymorphisms (Záveská et al., 2012). Therefore, identifying the species of a Curcuma plant by molecular analysis is considered to be relatively difficult. Záveská et al. reported that there is a broad range of variation of the internal transcribed spacer (ITS) region of ribosomal DNA in Curcuma plants, ranging from 0 to 87 polymorphic sites within intra-individual alignments (Záveská et al., 2012). Moreover, the sequence of the ITS region for most individuals is unreadable by direct sequencing, so cloning was employed to uncover the ITS polymorphism in these individuals. To clarify the phylogenetic relationships of Curcuma, Hayakawa et al. reported on the determination of nucleotide sequences of the chloroplast DNA matK region (Hayakawa et al., 2011). They found that two haplotypes are shared within C. longa. Recently, Duan et al. has reported that molecular analysis using the ITS-LSU D1/D3 region showed sufficient discriminatory power to precisely identify all of the market samples as C. longa (Duan et al., 2017). However, they also reported that chemical composition differences do not correspond well with genetic variations among Curcuma drugs derived from C. longa. There have been several reports on a variety of pharmacological activities of the respective Curcuma drugs. Rajkumari and Sanatombi indicated the following biological activities of Curcuma drugs (Rajkumari and Sanatombi, 2017); 1. C. longa: anti-inflammatory, anti-allergic, anti-obesity, antimicrobial, antioxidant, antidiabetic, hypoglycemic, immunomodulating, insecticidal, antifungal, neuroprotective; 2. C. aeruginosa: antimicrobial, cytotoxicity, antioxidant, inhibition of nitric oxide production, anti-inflammatory; 3. C. aromatica: anti-Alzheimer, antioxidant, cytotoxicity, insecticidal, anti-inflammatory, anti-bacterial, inhibition of nitric oxide production, gastroprotective; 4. C. xanthorrhiza: antimicrobial, anticandidal, anti-mycotic, chemopreventive, hepatoprotective, antinociceptive, antioxidant, anti-inflammatory, anti-ulcerogenic, gastroprotective, cytotoxicity; 5. C. zedoaria: antimicrobial, anti-allergic, antioxidant, antifungal, cytotoxicity, anti- inflammatory, antinociceptive. Regarding the bioactive constituents of Curcuma drugs, the contributions of curcuminoids and sesquiterpenes have been identified (Ravindran et al., 2007). Curcuminoids, comprising curcumin, demethoxycurcumin and bisdemethoxycurcumin, are one of the major constituents in C. aromatica, C. longa and C. xanthorrhiza. The following biological activities of curcuminoids have been reported by Amalraj et al; antioxidant, antimicrobial, antimalarial, anti-inflammatory, anti-tumor and anti-aging activities (Amalraj et al., 2017). So far, almost 100 terpenoids, including sesquiterpenoids and monoterpenoids, have been identified from Zingiberaceae (Afzal et al., 2013; Dosoky and Setzer, 2018). Afzal et al. reported on the chemistry and bioactivities of comprehensive terpenoids from Curcuma plants up to the year 2012, indicating that they have anti-inflammatory, antioxidant, anti- bacterial, and antifungal activities (Afzal et al., 2013). The composition of the chemical constituents in Curcuma drugs often varies depending on the species, the part of the plant, the geographical location, the cultivation conditions and the post-harvest 17 Journal of the Asia-Japan Research Institute of Ritsumeikan University Volume 2 • October 2020 processing. Therefore, an investigation into the different chemical constituents in Curcuma drugs produced in Asian countries is important for quality control. In this study, we investigated the chemical profiles of the constituents in Curcuma drugs produced in Indonesia, Lao PDR, China and Japan in order to evaluate the quality of each drug. 2. Material and Methods (1) Crude Drug Samples Sixteen samples from eight different Curcuma species were examined. The eight species were as follows: C. aeruginosa, C. aromatica, C. heyneana, C. longa, C. mangga, C. phaeocaulis, C. xanthorrhiza and C. zedoaria. The crude drugs used in this study were authenticated by Professor Dr. Azis Saifudin (Muhammadiyah University of Surakarta, Indonesia) based on the morphological characteristics of each rhizome. The collection data is summarized in Table 1, along with the voucher numbers. All the crude drugs were stored in the Museum of Materia Medica, Ritsumeikan University (RIN). Table 1. Curcuma Drug Samples Used in This Study Sample No. Botanical source Market Date collected RIN No. 1 Curcuma aeruginosa
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