The chemistry of zerumbone. Part 5: Structural transformation of the dimethylamine derivatives

Kitayama, Takashi; Yokoi, Taketo; Kawai, Yasushi; Hill, Richard K.; Morita, Masanori; Okamoto, Tadashi; Yamamoto, Yukio; Fokin, Valery V.; Sharpless, K. Barry; Sawada, Seiji

doi:10.1016/s0040-4020(03)00667-7

Cited by 47 publications

(35 citation statements)

References 23 publications

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“…1,2 Zerumbone has been shown to possess antitumor, anti-inflammatory, antioxidant, antimicrobial, antinociceptive, hepatoprotective, and immunomodulatory activity. This compound also significantly suppresses tumor promoter 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus activation in Raji cells and free radical (superoxide anion) generation in cancer cell lines, and strongly inhibits platelet aggregation induced by arachidonic acid, collagen, and adenosine diphosphate.…”

Section: Introductionmentioning

confidence: 99%

Zerumbone-loaded nanostructured lipid carriers: preparation, characterization, and antileukemic effect

Rahman¹,

Abdullah²,

How³

et al. 2013

IJN

133

121

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Zerumbone, a natural dietary lipophilic compound with low water solubility (1.296 mg/L at 25°C) was used in this investigation. The zerumbone was loaded into nanostructured lipid carriers using a hot, high-pressure homogenization technique. The physicochemical properties of the zerumbone-loaded nanostructured lipid carriers (ZER-NLC) were determined. The ZER-NLC particles had an average size of 52.68 ± 0.1 nm and a polydispersity index of 0.29 ± 0.004 µm. Transmission electron microscopy showed that the particles were spherical in shape. The zeta potential of the ZER-NLC was −25.03 ± 1.24 mV, entrapment efficiency was 99.03%, and drug loading was 7.92%. In vitro drug release of zerumbone from ZER-NLC was 46.7%, and for a pure zerumbone dispersion was 90.5% over 48 hours, following a zero equation. Using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay in human T-cell acute lymphoblastic leukemia (Jurkat) cells, the half maximal inhibitory concentration (IC 50 ) of ZER-NLC was 5.64 ± 0.38 µg/mL, and for free zerumbone was 5.39 ± 0.43 µg/mL after 72 hours of treatment. This study strongly suggests that ZER-NLC have potential as a sustainedrelease drug carrier system for the treatment of leukemia.

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Section: Introductionmentioning

confidence: 99%

Zerumbone-loaded nanostructured lipid carriers: preparation, characterization, and antileukemic effect

Rahman¹,

Abdullah²,

How³

et al. 2013

IJN

133

121

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“…7) Common primary and secondary amines reacted with 1 and 6,7-epoxide (4), which was prepared from 1 and MCPBA, at or below room temperature to give conjugate-added products at C3, and sometimes at C3 and C10 of the substrates. 8) In a tightly sealed container, 1 was stirred with excess concentrated aqueous ammonia in acetonitrile at room temperature to yield monoamine 5. The same reaction with 4 yielded crystalline 6.…”

Section: Conjugate Additionmentioning

confidence: 99%

“…The stereochemistry of 6, 7, 8, and 9 was determined unambiguously by X-ray diffraction. 8) II. Transannular Reaction…”

Section: Conjugate Additionmentioning

confidence: 99%

“…We built the foundations for the industrial use of 1 by establishing novel methods, including conjugate addition, 7) transannular reaction, 7,8) ring cleavage, [8][9][10] ring expansion, 11) and asymmetric induction. [12][13][14][15][16][17] For example, since many useful polycyclic compounds exist in nature, the development of the transannular reaction and the construction of various transannular products are very important in organic and material chemistry.…”

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confidence: 99%

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Attractive Reactivity of a Natural Product, Zerumbone

Kitayama

2011

Bioscience, Biotechnology, and Biochemistry

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Zerumbone is a cyclic seaquiterpene and, a potential resource for natural materials-related diversityoriented synthesis (NMRDOS). Zerumbone, the main component of the essential oil of a wild ginger, Zingiber zerumbet Smith, showed strong reactivity with good chemo-, regio-, and stereoselectivity. To build the foundations for the industrial use of zerumbone, we examined conjugate addition, transannular reactions, ring cleavage, ring expansion, and asymmetric induction. The biological activity of zerumbone derivatives was also studied.

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“…Zerumbone 1 exhibits a variety of interesting reactions, such as transannular ring contraction and cyclization, [3][4][5] regio-and stereoselective conjugate additions, 3 and various regioselective ring cleavage reactions. 4,6 However, much of its chemistry still remains to be explored in order to fully exploit the ready availability and versatility of this substance as a starting material for conversion to other useful compounds.…”

Section: Introductionmentioning

confidence: 99%