Distribution of Phytoestrogenic Diarylheptanoids and Sesquiterpenoids Components in Curcuma Comosa Rhizomes and Its Related Spec
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Revista Brasileira de Farmacognosia 27 (2017) 290–296 ww w.elsevier.com/locate/bjp Original Article Distribution of phytoestrogenic diarylheptanoids and sesquiterpenoids components in Curcuma comosa rhizomes and its related species a,b,∗ c,∗ Vichien Keeratinijakal , Sumet Kongkiatpaiboon a Department of Agronomy, Faculty of Agriculture, Kasetsart University, Bangkok, Thailand b National Center for Agricultural Biotechnology, Kasetsart University, Bangkok, Thailand c Drug Discovery and Development Center, Thammasat University (Rangsit Campus), Pathumthani, Thailand a b s t r a c t a r t i c l e i n f o Article history: Curcuma comosa Roxb., Zingiberaceae, a phytoestrogen-producing herb with vernacularly named “Wan Received 30 August 2016 Chak Mod Loog” in Thailand, has been traditionally used for treatment of gynecologic diseases and sold Accepted 16 December 2016 as food supplement in the market. However, similar rhizomes of its related species may lead to the Available online 21 March 2017 confusion in the uses of this plant. This study was aimed to investigate the phytochemical constituents of different Curcuma spp. that used as “Wan Chak Mod Loog”. Characteristic major compounds were isolated Keywords: and identified. Phytochemical analysis of 45 Curcuma samples representing Curcuma sp., C. latifolia, and C. Wan Chak Mod Loog comosa were analyzed and compared with their phylogenetic relationship inferred by Amplified Fragment Phytochemicals Length Polymorphism analysis. Phytoestrogen diarylheptanoids were found in all samples of C. comosa Phytoestrogen-producing herb Diarylheptanoids while sesquiterpenoids including hepatoxic zederone were found in C. latifolia and Curcuma sp. samples. Sesquiterpenoids © 2017 Sociedade Brasileira de Farmacognosia. Published by Elsevier Editora Ltda. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). Introduction 1999b), plasma cholesterol reduction (Piyachaturawat et al., 1999a), anti-inflammatory (Jantaratnotai et al., 2006; Sodsai et al., Curcuma comosa Roxb., an indigenous medicinal herb vernac- 2007), and anti-oxidant effect (Niumsakul et al., 2007). More- ularly named “Wan Chak Mod Loog” in Thailand, is recognized over, in ovariectomized rats with estrogen deficiency, this plant as a phytoestrogen-producing plant belonging to family Zingib- could protect bone loss and accelerate human osteoblast pro- eraceae (Phupatanapong et al., 2001; Soontornchainaksaeng and liferation and differentiation (Tantikanlayaporn et al., 2013a,b; Jenjittikul, 2010). Its roots have been used for the treatment Weerachayaphorn et al., 2011), enhance vascular relaxation of fluatalence and gynecologic diseases such as premenstrual (Intapad et al., 2009, 2012), prevent neuron loss and improve learn- syndrome (PMS), abnormal menstruation and uterine pain. This ing and memory function (Su et al., 2010, 2011, 2012a,b). plant is considered as an active constituent in various traditional Phytochemical investigation of C. comosa revealed the pres- woman drug preparation in South East Asian countries. It has ence of sesquiterpenoids (Xu et al., 2008; Qu et al., 2009) and estrogenic-like activity (Piyachaturawat et al., 1995a,b) and has diarylheptanoids (Suksamrarn et al., 2008). Diarylheptanoids are been extensively used among menopausal women (Winuthayanon of interest since they exerted estrogenic-like activity (Suksamrarn et al., 2009a). Various pharmacological activities have also been et al., 2008; Winuthayanon et al., 2009a,b). However, its C. comosa reported, e.g. anti-lipidemic (Piyachaturawat et al., 1995c, 1999a), related species (e.g. C. latifolia and C. elata) available in the market choleretic (Suksamrarn et al., 1997), estrogenic (Winuthayanon also has similar shape of rhizomes and may lead to the confusion in et al., 2009a,b; Bhukkhai et al., 2012), uterotroic (Piyachaturawat the uses of this plant. The inconsistency of raw materials hampered et al., 1995a), growth suppressing on male reproductive organs the usage, development, and scientific research of these plants. (Piyachaturawat et al., 1998), male fertility (Piyachaturawat et al., Therefore, a special consideration is needed when purchasing the samples from the market. In general, sesquiterpenoids may exert a variety of pharma- ∗ cological properties. However, hexane extract of rhizomes from Corresponding authors. C. elata containing high proportion of sesquiterpene zederone (5) E-mails: [email protected] (V. Keeratinijakal), sumet [email protected] (S. Kongkiatpaiboon). caused liver enlargement and scattered white foci over the organs http://dx.doi.org/10.1016/j.bjp.2016.12.003 0102-695X/© 2017 Sociedade Brasileira de Farmacognosia. Published by Elsevier Editora Ltda. This is an open access article under the CC BY-NC-ND license (http:// creativecommons.org/licenses/by-nc-nd/4.0/). V. Keeratinijakal, S. Kongkiatpaiboon / Revista Brasileira de Farmacognosia 27 (2017) 290–296 291 at autopsy (Pimkaew et al., 2013). Zederone (5) and was found to be Fresh rhizomes of mixed Curcuma sp. and C. latifolia (75 kg) hepatotoxic in mice. However, it was also isolated from C. comosa yielded 6.5 kg of dried course powder. Successive extraction using (Qu et al., 2009). While there is a very large variation in rhizome Soxhlet extractor yielded the hexane, ethyl acetate, and ethanol morphology of “Wan Chak Mod Loog” in cultivation, the pheno- extracts of 150.32, 210.75 and 375.69 g, respectively. Hexane typic plasticity of vegetative parts of “Wan Chak Mod Loog” can extract was subjected to column chromatography (Merck silica gel lead to the wrong taxonomic assignment (Soontornchainaksaeng 60 No. 107734, particle size 0.063–0.20 mm) with solvent mixtures and Jenjittikul, 2010). Therefore, this study utilized Amplified Frag- of hexane–ethyl acetate (ratio from 10:0 to 0:10) with increas- ment Length Polymorphism (AFLP) markers technique to examine ing polarity, yielding seven fractions (CLH1–CLH7) of 2.35 mg, Curcuma samples (Keeratinijakal et al., 2010) together with their 1.87 g, 25.98 g, 34.56 g, 12.85 g, 28.14 g, and 47.96 g, respectively. morphological characteristics and investigated the bioactive con- Ethyl acetate extract was subjected to column chromatogra- stituents of different Curcuma species that are used as “Wan Chak phy with solvent mixtures of hexane–ethyl acetate (ratio from Mod Loog”. 10:0 to 0:10), and ethyl acetate–methanol (ratio from 10:0 to In the course of identifying the genetic diversity of C. comosa 0:10), with increasing polarity, yielding five fractions (CLA1–CLA5) and its related species, the samples were collected from dif- of 1.45, 15.68, 35.84, 49.70, and 67.73 g, respectively. Ethanol ferent provenances of Thailand (Keeratinijakal et al., 2010). extract was subjected to column chromatography with solvent Additional samples were collected and 118 accessions were mixtures of hexane–ethyl acetate (ratio from 10:0 to 0:10), and used to elucidate the phylogenetic relationships. Correspond- ethyl acetate–methanol (ratio from 10:0 to 0:10) with increas- ing plant materials were cultivated under field conditions in ing polarity, yielding six fractions (CLE1–CLE6) of 3.45, 26.78, the National Corn and Sorghum Research Center of Kasetsart 28.40, 32.50, 69.25, and 56.76 g, respectively. Further purifica- University in the east of Thailand. Major constituents were iso- tion was done using column chromatography (Merck silica gel lated and identified. After being cultivated in the same condition 60 No. 107734, particle size 0.063–0.20 mm). Fraction CLH-3 and harvested in the same age, the chemical constituents phy- using hexane–ethyl acetate (95:5) as an eluent yielded germa- toestrogen diarylheptanoids and sesquiterpenoids of different crone (1) (20 mg). Fraction CLH-4 using hexane–ethyl acetate Curcuma sample were analyzed. The results could identify the most (9:1) as an eluent yielded furanodienone (2) (35 mg) and curz- productive plant with high contents of active phytoestrogen con- erenone (3) (44 mg). Fraction CLH-4 using hexane–ethyl acetate stituents with non-toxic compounds. The present paper should (85:15) as an eluent yielded curdione (4) (75 mg). Fraction CLH- provide a basis for further pharmaceutical development of this 5 using hexane–ethyl acetate (8:2) as an eluent yielded zederone plant. (5) (7.8 mg). Fresh rhizomes of mixed C. comosa (10 kg) yielded dried course powder of 2 kg. Successive extraction using Soxhlet extractor Materials and methods yielded the hexane, ethyl acetate, and ethanol extracts of 95.30, 150.10 and 275 g, respectively. Hexane extract was subjected to Plant materials column chromatography (Merck silica gel 60 No. 107734, parti- cle size 0.063–0.20 mm) with solvent mixtures of hexane–ethyl A total of 118 accessions of Curcuma spp., locally called “Wan acetate (ratio from 10:0 to 0:10) with increasing polarity, yield- Chak Mod Loog”, was collected in our previous study (Keeratinijakal ing five fractions (CCH1–CCH5) of 2.25 mg, 0.97 g, 30.15 g, 28.45 g, et al., 2010) together with some additional collections from culti- and 10.55 g, respectively. Ethyl acetate extract was subjected to vated sites throughout Thailand. All samples were grown at the column chromatography with solvent mixtures of hexane–ethyl National Corn and Sorghum Research Center of Kasetsart Uni- acetate (ratio from 10:0 to 0:10), and ethyl acetate–methanol (ratio versity, Pakchong, Nakhon-Ratchasima province, Thailand. AFLP from 10:0 to 0:10) with increasing polarity, yielded five fractions analysis