Bioactive Constituents of the Seeds of Brucea javanica

Su, Bao‐Ning; Chang, Leng Chee; Park, Eun Jung; Cuendet, Muriel; Santarsiero, Bernard D.; Mesecar, Andrew D.; Mehta, Rajendra G.; Fong, Harry H. S.; Pezzuto, John M.; Kinghorn, A. Douglas

doi:10.1055/s-2002-33798

Cited by 66 publications

(36 citation statements)

References 12 publications

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“…However, the exact mechanism of HL-60 apoptosis by Flazin must await further study. consistent with those previously reported (Nakatsuka et al, 1986, Shaaban et al, 2007, Su et al, 2002.…”

Section: Comparison Of the Amount Of Flazin In Each Soy Saucesupporting

confidence: 93%

Cellular Effects Of Tamari Soy Sauce-derived 1-[5-(Hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic Acid (Flazin)

Nishio

Yuasa

Okimura

et al. 2012

FSTR

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Keywords: Flazin, soy sauce, HL-60, DNA fragmentation, TUNEL *To whom correspondence should be addressed. E-mail: umekawa@bio.mie-u.ac.jp IntroductionSoy sauce is a representative Japanese seasoning known worldwide. Soy sauce is classified into five (Koikuchi, Usukuchi, Tamari, Sashikomi, and Shiro) according to Japanese Agricultural Standard (Kataoka, 2005). Typical Koikuchi soy sauce involves the fermentation of soybeans and wheat in a 1:1 ratio. A variety of biological functions have been reported for Koikuchi soy sauce, including the blood pressurelowering effect of nicotinamine (Kinoshita et al., 1993) and the arteriosclerosis-controlling activity of polyamine. In contrast, the main raw ingredient of Tamari soy sauce is soybean, with wheat as a minor ingredient (Kataoka, 2005). The physiological effects of Tamari soy sauce are not well understood.Soy sauce is not only a delicious seasoning, characterized by a mellow odor and taste, but exhibits a number of physiological activities, such as an antioxidative effect (Aoshima and Ooshima, 2009), blood pressure-lowering effect, and an action that alleviates allergic symptoms (Kobayashi et al., 2004, Kobayashi, 2005. The aim of the present study was to refine 1-[5-(Hydroxy-methyl)furan-2-yl]-9H-pyrido [3,4-b] indole-3-carboxylic acid (Flazin) from the main body of collected soy sauce (Gessner et al., 1988) and to examine the cellular effects of this compound.Flazin was first separated from sake lees as a crystal during the manufacture of synthetic sake (Gessner et al., 1988) and has been found to exhibit strong fluorescence (Li et al., 2011). Flazin was also discovered as a cluster of dark green microcrystals in rice vinegar during a research study on soy sauce (Gessner et al., 1988). The structure of Flazin was determined by Nakatsuka et al. (1986). Flazin comprises tryptophan and 5-hydroxymethyl-2-furfural, and is generated through processes of oxidation and dehydration. It was later discovered as a metabolic product of a marine microorganism (Shaaban et al., 2007).The aim of this study was to examine the physiological function of Flazin. The results demonstrate that Flazin from Tamari soy sauce inhibits the proliferation of human promyelocytic leukemia cells at least in part due to its apoptotic activity against the cells. Materials and MethodsRegents The soy sauces used in the present study were a gift from Sanjirushi Corp (Japan). HL-60 cells, which are human promyelocytic leukemia cells, were obtained from the three replicates. The concentration of Flazin was 65.1 ± 15.9 μg/mL in Koikuchi soy sauce and 232.0 ± 18.4 μg/mL in Tamari soy sauce (Fig. 1) The cell suspensions were then incubated for 24 h in a CO 2 incubator. Untreated cell suspensions were used as negative controls. Cell proliferation was determined after 3 h using a kit (CCK-8 kit, DOJINDO, Japan) and absorbance was measured at 450 nm using a microplate reader (BIO-RAD, Model-550, Japan). Experiments were performed in triplicate. Preparation of FlazinThe diethyl ether extraction sample from e...

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“…However, the exact mechanism of HL-60 apoptosis by Flazin must await further study. consistent with those previously reported (Nakatsuka et al, 1986, Shaaban et al, 2007, Su et al, 2002.…”

Section: Comparison Of the Amount Of Flazin In Each Soy Saucesupporting

confidence: 93%

Cellular Effects Of Tamari Soy Sauce-derived 1-[5-(Hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic Acid (Flazin)

Nishio

Yuasa

Okimura

et al. 2012

FSTR

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“…For instance, bruceoside A has good efficacy in leukemia and brusatol amarissima exert significant anti-inflammatory activity. 12 The quassinoids contain bruceine A, B, C, D, E, F, G, H, and I (Figure 2), 13,14 brusatol A, 15 dihydrobrusatol B, 16 bruceoside A, B, C, D, E, F, G, I, J, K, L, P, and S (Figure 3), [17][18][19][20][21][22][23] brusatol amarissima E2-glucosidase, 13 brusatol ketoacid, and bruceen.…”

Section: Chemical Ingredientsmentioning

confidence: 99%

Chemical components, pharmacological properties, and nanoparticulate delivery systems of Brucea javanica

Chen

Chen²,

Wang³

et al. 2013

IJN

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Brucea javanica has demonstrated a variety of antitumoral, antimalarial, and anti-inflammatory properties. As a Chinese herbal medicine, Brucea javanica is mainly used in the treatment of lung and gastrointestinal cancers. Pharmacological research has identified the main antitumor components are tetracyclic triterpene quassinoids. However, most of these active components have poor water solubility and low bioavailability, which greatly limit their clinical application. Nanoparticulate delivery systems are urgently needed to improve the bioavailability of Brucea javanica. This paper mainly focuses on the chemical components in Brucea javanica and its pharmacological properties and nanoparticulate formulations, in an attempt to encourage further research on its active components and nanoparticulate drug delivery systems to expand its clinical applications. It is expected to improve the level of pharmaceutical research and provide a strong scientific foundation for further study on the medicinal properties of this plant.

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“…19 Brucea javanica oil (BJO) (ya-dan-zi oil) is an extract of the ripe fruit of the simaroubaceae plant Brucea javanica (L.) Merr., which was first recorded in the Supplement to Compendium of Materia Medica. 20 BJO contains oleic acid, linoleic acid, stearic acid, palmitic acid, arachidonic acid, and other unsaturated fatty acids. A number of clinical studies have suggested that BJO emulsions can be used alone as a conventional treatment for various cancers; [21][22][23] however, the present study can show only that BJO emulsions have synergistic effects when combined with certain anticancer drugs or radiotherapy.…”

Section: Introductionmentioning

confidence: 99%

Intravenous microemulsion of docetaxel containing an anti-tumor synergistic ingredient (Brucea javanica oil): formulation and pharmacokinetics

Shi-lin¹,

Chen²,

Ye³

et al. 2013

IJN

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Bioactive Constituents of the Seeds of Brucea javanica

Cited by 66 publications

References 12 publications

Cellular Effects Of Tamari Soy Sauce-derived 1-[5-(Hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic Acid (Flazin)

Cellular Effects Of Tamari Soy Sauce-derived 1-[5-(Hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic Acid (Flazin)

Chemical components, pharmacological properties, and nanoparticulate delivery systems of Brucea javanica

Intravenous microemulsion of docetaxel containing an anti-tumor synergistic ingredient (Brucea javanica oil): formulation and pharmacokinetics

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