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Boesenbergia Pandurata Roxb., an Indonesian Medicinal Plant: Phytochemistry, Biological Activity, Plant Biotechnology

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Boesenbergia Pandurata Roxb., an Indonesian Medicinal Plant: Phytochemistry, Biological Activity, Plant Biotechnology Available online at www.sciencedirect.com ScienceDirect Procedia Chemistry 13 ( 2014 ) 13 – 37 International Seminar on Natural Product Medicines, ISNPM 2012 Boesenbergia pandurata Roxb., An Indonesian Medicinal Plant: Phytochemistry, Biological Activity, Plant Biotechnology Agus Chahyadi a,b, Rika Hartatia, Komar Ruslan Wirasutisnaa, Elfahmia* aPharmaceutical Biology Research Group, School of Pharmacy, Bandung Institute of Technology, Jl. Ganesha 10 Bandung, Indonesia, 40132 bPharmacy Department, Faculty of Pharmacy, Universitas Haluoleo, Kendari, 93231, Indonesia Abstract Boesenbergia pandurata Roxb. (Zingiberaceae), known as “temu kunci”, is one of the Indonesian medicinal plants. Its rhizome has been traditionally used in folk medicine for treatment of several diseases. Rhizome of B. pandurata contains essential oils and many flavonoid compounds that showed many interesting pharmacological activities, such as antifungal, antibacterial, antioxidant, etc. Interestingly, this plant has several prenylated flavonoid compounds, panduratins, that showed very promising of biological activities, especially as strong antifungal and antibacterial, anti-inflammatory, and anti-cancer. This paper aims to review chemical constituents of this plant and their pharmacological activities and also to give a brief view through biotechnological perspective concerning the several possibilities to produce several valuable prenylated flavonoids from this plant. ©© 2014 2014 The The Authors. Authors. Published Published by Elsevier by Elsevier B.V. ThisB.V. is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/). Peer-review under responsibility of the School of Pharmacy, Bandung Institute of Technology. Peer-review under responsibility of the School of Pharmacy, Bandung Institute of Technology Keywords: Boesenbergia pandurata, Essential oil, Prenylated flavonoid, Panduratin, Antibacterial * Corresponding author. Tel.: +62-22-2504852 fax: +62-22-2504852 E-mail address:[email protected] 1. Introduction Boesenbergia pandurata Roxb. Schlecht. (Zingiberaceae) is one of the ginger plants that is found in South East Asia. In Indonesia, this geophytic plant is known as “temu kunci”, grows wildly in teak forests, and is cultivated everywhere. This plant has many synonymously botanical names, such as Gastrochilus panduratum RIDL., Kaempferia pandurata Roxb., Curcuma rotunda L., and Boesenbergia rotunda Linn. Mansft 1-3. According to the Indonesian medicinal plants literatures, fresh rhizome of B. pandurata has been long time utilized as spice, particularly, the young rhizome was very popular for seasoning vegetables. It was strongly believed that its efficacy could strengthen the stomach. As a traditional medicine, the sliced rhizomes which are chewed together with areca 1876-6196 © 2014 The Authors. Published by Elsevier B.V. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/). Peer-review under responsibility of the School of Pharmacy, Bandung Institute of Technology doi: 10.1016/j.proche.2014.12.003 14 Agus Chahyadi et al. / Procedia Chemistry 13 ( 2014 ) 13 – 37 nut (Areca catechu) could treat dry cough and aphtha1,2. As food, in the form of porridge, combination between rhizome and Pimpinella anisum was used to treat stomach distended and as a diuretic for children, while combination with coconut milk was used as anti-anthelmintic. Rhizome of B. pandurata was also used as a traditional medicine for treatment inflammation in women uterus and in combination with other spices, for treatment vaginal infection 2. The rhizome of this plant is a one of the components of herbal medicine “jamu” in Indonesia 4. In the references of herbal preparations published by The National Agency of Drug and Food Control (NA-DFC or BPOM Republik Indonesia), herbal preparation from rhizome of B. pandurata is utilized as an anti-inflammatory 5 and an anti-cancer 6. This plant has been identified to contain various essential oils (EOs) and also several flavonoid compounds that have demonstrated many biological activities. Most of its flavonoids have unique features with some prenyl substituents integrated in their main structures 7,8. A panduratin derivative are prenylated flavonoids from B. pandurata that showed broad range of biological activities, such as strong antibacterial acitivity9-11, anti- inflammatory 12, and anti-cancer 13. The aim of this paper is to present information of the chemical constituents and also to compile various pharmacological studies that is well established from this plant. A second aim is to give a brief view concerning the possibility to produce biological active compounds from B. pandurata through biotechnological approach. All of literatures have been cited from both offline and online media. Offline literatures were based on Handbooks of Indonesian Medicinal Plants, Indonesian Herbal Pharmacopeia, and Herbal Preparations of NA-DFC. Whereas ISI Web, Scopus, Pubmed, and other online media were used to regain any online publications such as scientific journals, patents, etc. All of them were used to compile this paper. 2. Phytochemistry 2.1. Flavonoid Flavonoids are large secondary metabolites found in rhizome of B. pandurata. More than 51 flavonoid compounds from B. pandurata have been isolated and their structure was confirmed. However, only three classes of flavonoid have been reported exist in B. pandurata rhizome. The main flavonoids are chalcones, flavanones, and flavones, classified according to their skeletons (Fig. 1). However some of these flavonoids also exist in other plants. Most of them showed a unique structure with some prenyl substituents integrated in their main skeleton. Interestingly, more than half of total flavonoids isolated from B. pandurata are prenylated flavonoids. But only two classes of flavonoids have prenylated derivative, namely prenylated chalcones and prenylated flavanones. Flavones, however, there is no report that showed the existence of their prenylated derivative in B. pandurata. Fig. 1 Typical class of regular flavonoids in B. pandurata 2.1.1. Unprenylated flavonoids Several known flavonoid chalcones, flavanones, and flavones have been isolated and identified from rhizome extract of B. pandurata. In our review, there are five chalcones and two hydrochalcones, due to the difference of their oxygenation pattern, have been reported (Fig. 2). They are cardamonin (1), a known 2’,4’-dihydroxy-6’- Agus Chahyadi et al. / Procedia Chemistry 13 ( 2014 ) 13 – 37 15 methoxy chalcone 14 and a major chalcone in B. pandurata rhizome 15; pinocembrin chalcone (2), a known 2’,4’,6’- trihydroxychalcone 15; helichrysetin (3), a known 2’,4’,4-trihydroxy-6’-methoxychalcone 16; 2’,6’-dihydroxy-4’- methoxychalcone (4) 14; flavokawain C (5), a known chalcone possessing a 4-oxygenated pattern of A-ring namely 2’,4-hydroxy-4’,6’-dimethoxychalcone 17; and also two known hydrochalcones, namely 2’,4’,6’-trihydroxychalcone (6) and uvangoletin (7) 12. Structural analysis showed that oxygenation pattern in most of these chalcones, except compound 3 and 5, only occurred at B-ring. Fig. 2 Regular chalcones in B. pandurata Flavanones are isomerized products from chalcones. The isomerise of chalcones to form flavanones are naturally due to the presence of chalcone isomerase and also this process still occurs spontaneously even in the absence of this enzyme. Six known flavanones have been isolated from B. pandurata, namely pinostrobin (8), the major flavanone in B. pandurata; pinocembrin (9) 14; 5,7-dimethoxyflavanone (10) 18; alpinetin (11) 19; sakuranetin (12) 7; and 7,4’- dihydroxy-5-methoxyflavanone (13) 17 (Fig. 3). In the Indonesian Herbal Pharmacopeia, compound 8 is used as a marker compound in examination of metabolite profile from botany, extract and herbal preparations of B. pandurata rhizomes 20. Fig. 3 Regular flavanones in B. pandurata Some flavones are also found in black rhizome, another variety of B. pandurata with yellow rhizomes. They are formed through the dehydrogenation and followed by the formation of double bound in C2-C3 of flavanones. There are eight known flavones contained in black rhizome of B. pandurata 18. Tectochrysin (14), 5,7-dimethoxyflavone (15 ), and 5-hydroxy-3,7-dimethoxyflavone (16) are flavones with no oxygenated pattern in A-ring, while the others, 16 Agus Chahyadi et al. / Procedia Chemistry 13 ( 2014 ) 13 – 37 namely 5,7,4’-trimethoxyflavone (17), 5-hydroxy-7,4’-dimethoxyflavone (18), 5,7,3’,4’-tetramethoxyflavone (19), 5-hydroxy-3,7,4’-trimethoxyflavone (20), and 5-hydroxy-3,7,3’,4’-tetramethoxyflavone (21), have oxygenated pattern in their A-ring. However, only compounds 16, 20, and 21 have methoxy constituents in C3 position (Fig. 4). According to this report, the chemical constituents in black rhizome differ substantially to B. pandurata with yellow/red rhizomes, the main plant that is reported in this review. So far, only compound 14 that was successfully isolated again in yellow rhizomes 17, the rest, there is no more report that showed these flavones were isolated again. Fig. 4 Regular flavones in B. pandurata 2.1.2. Prenylated flavonoids Unlike the other Zingiberaceae plants, most of the flavonoids from B. pandurata are very distinctive due to the prenyl substituents in their main skeleton. More than 31 prenylated flavonoids have been isolated from rhizome of B. pandurata (Fig. 5). Boesenbergin A (22) is a first prenylated flavonoid isolated from this plant by Tuntiwachwuttikul’s
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