Cytotoxicity against cholangiocarcinoma cell lines of zerumbone derivatives

Songsiang, Uraiwan; Pitchuanchom, Siripit; Boonyarat, Chantana; Hahnvajanawong, Chariya; Yenjai, Chavi

doi:10.1016/j.ejmech.2010.05.029

Cited by 31 publications

(21 citation statements)

References 26 publications

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“…However, amine 5 and other ZER derivatives (10, 14, and 20) (Figure 4) showed lesser cytotoxicity toward other CCA cell lines including squamous (KKU-M139) cell carcinoma, moderately differentiated adenocarcinoma (KKU-M156), adenosquamous carcinoma (KKUM213), and moderately differentiated adenocarcinoma (KKU-M214) [92]. …”

Section: Anticancer Properties Of Zerumbonementioning

confidence: 99%

Biomedical Properties of a Natural Dietary Plant Metabolite, Zerumbone, in Cancer Therapy and Chemoprevention Trials

Rahman

Abdullah

Yeap

et al. 2014

BioMed Research International

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Zerumbone (ZER) is a naturally occurring dietary compound, present in many natural foods consumed today. The compound derived from several plant species of the Zingiberaceae family that has been found to possess multiple biomedical properties, such as antiproliferative, antioxidant, anti-inflammatory, and anticancer activities. However, evidence of efficacy is sparse, pointing to the need for a more systematic review for assessing scientific evidence to support therapeutic claims made for ZER and to identify future research needs. This review provides an updated overview of in vitro and in vivo investigations of ZER, its cancer chemopreventive properties, and mechanisms of action. Therapeutic effects of ZER were found to be scientifically plausible and could be explained partially by in vivo and in vitro pharmacological activities. Much of the research outlined in this paper will serve as a foundation to explain ZER anticancer bioactivity, which will open the door for the development of strategies in the treatment of malignancies using ZER.

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Section: Anticancer Properties Of Zerumbonementioning

confidence: 99%

Biomedical Properties of a Natural Dietary Plant Metabolite, Zerumbone, in Cancer Therapy and Chemoprevention Trials

Rahman

Abdullah

Yeap

et al. 2014

BioMed Research International

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“…This effect might have been caused by the hydrogen bonds between two hydrogen groups of zerumbol. In fact, the melting point of zerumbol is higher than that of zerumbone, 9,10) and when the ketone group was replaced with a hydroxyl it weakened the locomotor-reducing effects of THZ.…”

Section: Influence Of Loss Of Double Bond At C6-c7 On Locomotor Activitymentioning

confidence: 99%

Locomotor-Reducing Activity of Sesquiterpenes Related to <i>Zingiber zerumbet</i> Essential Oil and Hexahydrozerumbone Derivatives

Ogawa

Yabe

Kitayama

et al. 2016

Biological & Pharmaceutical Bulletin

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Zerumbone derivatives 1-4 are 11-membered cyclic compounds synthesised from a sesquiterpene zerumbone obtained from the rhizomes of Zingiber zerumbet SMITH (Zingiberaceae). In this study, we investigated the locomotor-reducing effects of hexahydrozerumbone derivatives 1-3 and zerumbol 4, and those of β-caryophyllene 5 and caryophyllene oxide 6, which are present in Z. zerumbet essential oil. The absence of the double bond at C6 weakened the locomotor-reducing effects. β-Caryophyllene 5 and caryophyllene oxide 6 showed locomotor-reducing effects in mice at 4.5 10 3 mg/cage. Moreover, locomotor activity increased significantly at 0.45 mg/cage of caryophyllene oxide 6.Key words hexahydrozerumbone; caryophyllene; locomotor-reducing effect; inhalation Zerumbone obtained from Zingiber zerumbet SMITH (Zingiberaceae) and its derivatives are highly volatile compounds with distinct aromas.1,2) They show locomotorreducing effects when inhaled, and their structure-activity relationships have been investigated.3) The synthesis of hexahydrozerumbone derivatives 1-3, which also have distinct aromas, 1) was achieved by hydrogenation of the C6 double bonds of tetrahydrozerumbone (THZ) derivatives.Takemoto et al. 4) reported locomotor-reducing effects when bicyclic and tricyclic terpenoids are inhaled by mice. Thus, the compounds β-caryophyllene 5 and caryophyllene oxide 6 5) contained in the rhizomes, leaves and flowers of Z. zerumbet, whose structures are similar to zerumbone's structure, could also show locomotor-reducing effects. In this study, the locomotor-reducing effects of the new zerumbone derivatives 1-3 and caryophyllene derivatives 5 and 6 were investigated. Furthermore, the effects of 8-hydroxyl-α-humulene (zerumbol) 4, an expected intermediate in the biosynthesis of zerumbone 6) from α-humulene, were also investigated. MATERIALS AND METHODSMaterials Compounds 1-6 (Fig. 1) were prepared as follows. Hexahydrozerumbone (HHZ) derivatives and zerumbol 1-4 were derived from the starting material zerumbone, which was obtained from the rhizomes of Z. zerumbet SMITH. First, zerumbone was hydrogenated under an H 2 atmosphere using Pd/C in hexane to give 2,3,6,7,10,11-hexahydrozerumbone 1. Compound 1 was reduced with NaBH 4 in ethanol to give hexahydrozerumbol 2. Compound 2 was acetylated with acetic anhydride and pyridine to give hexahydrozerumbyl acetate 3. Racemic zerumbol 4 was obtained by reduction of zerumbone with LiAlH 4 in dry tetrahydrofuran. Compounds 1-4 were each refined to more than 99.9% purity, as evaluated by 1 H-NMR.7) β-Caryophyllene 5 was purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan), and caryophyllene oxide 6 was purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). The odourless solvent triethyl citrate used to dissolve and dilute the fragrant compounds for inhalation was purchased from Merck KGaA (Darmstadt, Germany). The reagents used in this study were of the highest grade available.Animals The animal studies were approved by the Animal Research Committee of Kyoto Univer...

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“…As part of our continued screening program on bioactive substances from natural sources [14][15][16][17][18] , it is expected that C. harmandiana may be the source of many antioxidant and cancer chemopreventive agents with novel structures. Crude hexane, EtOAc and MeOH extracts from the roots of this plant were investigated and 12 compounds were isolated.…”

Section: Introductionmentioning

confidence: 99%

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Songsiang¹,

Thongthoom²,

Zeekpudsa³

et al. 2012

ScienceAsia

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Nine carbazoles and three coumarins were isolated from C. harmandiana. Crude extracts and all isolates were evaluated for antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and lipid peroxidation assay and cytotoxicity against cholangiocarcinoma, KKU-OCA17 and KKU-214 cell lines. 7-Hydroxyheptaphylline and nordentatin showed strong antioxidant activity on lipid peroxidation with IC50 values of 2.95 and 2.90 µM respectively, while the activity on a DPPH assay showed IC50 values of 56.82 and 29.3 µM, respectively. The two compounds exhibited strong cytotoxicity against KKU-OCA17 (IC50=88.7 and 46.1 µM, respectively) and KKU-214 (IC50=43.7 and 39.1 µM, respectively) cell lines. The results show convincingly that these compounds may be the promising leads for the development of cytotoxic agents.

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Cytotoxicity against cholangiocarcinoma cell lines of zerumbone derivatives

Cited by 31 publications

References 26 publications

Biomedical Properties of a Natural Dietary Plant Metabolite, Zerumbone, in Cancer Therapy and Chemoprevention Trials

Biomedical Properties of a Natural Dietary Plant Metabolite, Zerumbone, in Cancer Therapy and Chemoprevention Trials

Locomotor-Reducing Activity of Sesquiterpenes Related to <i>Zingiber zerumbet</i> Essential Oil and Hexahydrozerumbone Derivatives

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