Anti-inflammatory constituents of Zingiber zerumbet

Chien, Ting Yi; Chen, L.G.; Lee, C.J.; Lee, F.Y.; Wang, C.C.

doi:10.1016/j.foodchem.2008.02.038

Cited by 81 publications

(57 citation statements)

References 20 publications

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“…Zerumbone 1 was extracted from Z. zerumbet rhizome, and the extract was refined. 2,3,10,11-Tetrahydrozerumbone (THZ) stereoisomers (3)(4)(5) and tetrahydrozerumbone derivatives (6-9) were synthesised from compound 1. First, 1 was reduced with H 2 on Pd/C to give racemic THZ 5.…”

Section: Methodsmentioning

confidence: 99%

“…Furthermore, zerumbone 1 is a valuable natural raw material for medicinal compounds, because of its high reactivity. [4][5][6] Terpenoids, in particular monoterpenes and sesquiterpenes, often have characteristic odors, and are used in incense. In European countries, essential oils that contain odorant terpenoids are used in home remedies and medical treatments for conditions such as anxiety.…”

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confidence: 99%

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Locomotor-Reducing Effects and Structural Characteristics of Inhaled Zerumbone and Tetrahydrozerumbone Derivatives

Ogawa

Miyoshi

Kitayama

et al. 2014

Biological & Pharmaceutical Bulletin

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Zerumbone 1 is an 11-membered cyclic sesquiterpene obtained from the rhizomes of Zingiber zerumbet SMITH (Zingiberaceae). In this study, we investigated the structure-activity relationship of 1, α-humulene (2), tetrahydrozerumbone stereoisomers (3-5), and tetrahydrozerumbone derivatives (6-9). The oxygen-containing functional groups and the configurations at C1 and C2 contributed to the spontaneous locomotor activity reduction of zerumbone 1 and derivatives 2-9.Key words zerumbone; tetrahydrozerumbone; sedative effect; inhalation; structure-activity relationship Zingiber zerumbet SMITH is a member of the ginger family (Zingiberaceae) and is native to India. This plant grows widely from India and Southeast Asia to the Hawaiian Islands.1) Z. zerumbet, which has a flowery scape, is cultivated in Europe and the United States mainly as a garden plant. In contrast, the rhizome of Z. zerumbet is used as a traditional folk medicine for pain in Southeast Asia.2) Zerumbone 1 is a main component of the essential oil obtained from Z. zerumbet rhizome, and has antinociceptive, 3) antiviral, and antiinflammatory effects. Furthermore, zerumbone 1 is a valuable natural raw material for medicinal compounds, because of its high reactivity. [4][5][6] Terpenoids, in particular monoterpenes and sesquiterpenes, often have characteristic odors, and are used in incense. In European countries, essential oils that contain odorant terpenoids are used in home remedies and medical treatments for conditions such as anxiety.7,8) Zerumbone, a highly volatile compound with a distinct odor, 6) may show biological activity when inhaled. In this study, the reduction of locomotor activity in mice given zerumbone and its derivatives by inhalation was examined. The structure-activity relationship among the compounds was also investigated. MATERIALS AND METHODS MaterialsCompounds 1-9 shown in Fig. 1 were prepared as below. Zerumbone 1 was extracted from Z. zerumbet rhizome, and the extract was refined. 2,3,10,11-Tetrahydrozerumbone (THZ) stereoisomers (3-5) and tetrahydrozerumbone derivatives (6-9) were synthesised from compound 1. First, 1 was reduced with H 2 on Pd/C to give racemic THZ 5. Then, 5 was reduced with LiAlH 4 to give 6 and 7, which were acetylated with acetic anhydride in pyridine solution to obtain 8 and 9. Furthermore, 6 and 7 were treated with lipase and isopropenyl acetate to obtain (2S)-tetrahydrozerumbyl acetate and (2R)-tetrahydrozerumbol in order to resolve the racemic THZ into 3 and 4 by oxidisation following deacylation. 9,10) Compounds 1, 3, 4, and 7-9 were refined to more than 99.9% purity, as evaluated by 1 H-NMR, and 3 and 4 were obtained with 97% and 95% e.e., respectively. The purity of 6 was 85%. α-Humulene (2) was purchased from Sigma-Aldrich (St. Louis, MO, U.S.A.). The odorless solvent triethyl citrate used to dissolve and dilute the odorant compounds for inhalation was purchased from Merck KGaA (Darmstadt, Germany). The reagents used in this study were of the highest grade available.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Locomotor-Reducing Effects and Structural Characteristics of Inhaled Zerumbone and Tetrahydrozerumbone Derivatives

Ogawa

Miyoshi

Kitayama

et al. 2014

Biological & Pharmaceutical Bulletin

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“…A possible regulatory role of NO on cytokine production by macrophages is partly controversial. Inhibition of NO lead to decreased TNF levels in RAW 264.7 after activation by LPS+ INF-γ (Chien et al, 2008;Levy and Simon, 2009). In contrast, Eigler et al (1995) reported that TNF-α production was increased after inhibition of iNOS.…”

Section: Bucida Bucerasmentioning

confidence: 99%

Anti-inflammatory activity and modulate oxidative stress of Bucida buceras in lipopolysaccharide-stimulated RAW 264.7 macrophages and Carrageenan-induced acute paw edema in rats

Assanga¹,

LujÃ¡n²,

Gil-Salido³

et al. 2017

J. Med. Plants Res.

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Since oxidative stress is an important mediator that lead or maintain inflammatory processes, the aim of this work is to evaluate the effects of Bucida buceras on inflammatory response in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and anti-inflammatory effect and redox biomarkers in carrageenan-induced paw edema in rats. B. buceras also known as "black-olive" belongs to the Combretaceae family and it is used as an ornamental evergreen tree in many city streets. This plant is widely distributed in tropical regions of Caribbean, Central America and northern South America. In a continuous effort to find more potent, non-toxic natural product inhibitors that suppress inflammation, the present study was carried out to analyzed the influence of aqueous extract on nitric oxide (NO), tumor necrosis factor (TNF-α), interleukin (IL)-6 and IL-1β in LPS-induced murine macrophages and paw thickness, NO, C-reactive protein (CPR), organoperoxide, oxidation protein and reducing power antioxidant in paw edema in rats. Results revealed that treatment with B. buceras aqueous extract inhibited not only the protein (albumin) denaturation but also, in LPS-induced inflammatory response, including increased secretion of pro-inflammatory cytokines (IL-6 and IL-1β) and NO were inhibited by aqueous extract in a concentration-dependent manner. Furthermore, B. buceras suppressed significantly edema in a dose-dependent fashion in inflamed rat paws; decrease the C-reactive protein, lipid peroxidation levels (OT) and oxidation protein product and exerted strong reducing antioxidant power. Thus, these results suggest that antioxidative properties of B. buceras attenuate inflammatory changes and support the application in complementary and alternative medicine.

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“…It has been demonstrated that the active herbs in the SFD formula have a wide range of biological activities, including anti-inflammatory, analgesic, antioxidant, immunomodulatory, and anticoagulant activities (Chien et al, 2008;Zhang et al, 2008;Du et al, 2007;Lantz et al, 2007;Tognolini et al, 2006). However, there are few reports on the pharmacological actions and active components of whole-formula SFD related to primary dysmenorrhea.…”

Section: Research Articlementioning

confidence: 99%

Evaluation of the analgesic activities of the crude aqueous extract and fractions of Shao Fu Zhu Yu decoction

Duan

et al. 2010

Pharmaceutical Biology

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Anti-inflammatory constituents of Zingiber zerumbet

Cited by 81 publications

References 20 publications

Locomotor-Reducing Effects and Structural Characteristics of Inhaled Zerumbone and Tetrahydrozerumbone Derivatives

Locomotor-Reducing Effects and Structural Characteristics of Inhaled Zerumbone and Tetrahydrozerumbone Derivatives

Anti-inflammatory activity and modulate oxidative stress of Bucida buceras in lipopolysaccharide-stimulated RAW 264.7 macrophages and Carrageenan-induced acute paw edema in rats

Evaluation of the analgesic activities of the crude aqueous extract and fractions of Shao Fu Zhu Yu decoction

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