Structures of yadanziolides A, B, and C, new bitter principles from Brucea javanica.

Yoshimura, Shin; Sakaki, Toshiro; Ishibashi, Masami; Tsuyuki, Takahiko; Takahashi, Takeyoshi; Matsushita, Kazuhiro; Honda, Tadashi

doi:10.1248/cpb.32.4698

Cited by 22 publications

(14 citation statements)

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“…Absorbance was measured using a Synergy™ MX microplate reader (BioTek Instruments, Inc., Winooski, VT, USA). A Bruker AMX 500 instrument (Bruker BioSpin K.K., Bruker Instruments, Billerica, MA, USA) was used to obtain nuclear magnetic resonance (NMR) spectra and residual solvents were used as internal standards (pyridine-d5: 1 H 7.22 ppm, 13 C 135.91 ppm).…”

Section: Materials and Equipmentmentioning

confidence: 99%

“…Various chemical compounds have been isolated from B. javanica, including alkaloids [5], lignans, terpenoids [6], and alkaloid glycosides [7], but the most extensively studied are the triterpene lactones, known as "quassinoids". Quassinoids are triterpenes that are unique to the Simaroubaceae family, and nearly 50 have been identified in B. javanica extracts, including bruceins A-C, bruceantinol, javanicolides A-D, javanicosides A-F [8][9][10][11][12], and their glycosides (bruceosides and yadanziosides) [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

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Quassinoids in Brucea javanica are potent stimulators of lipolysis in adipocytes

et al. 2019

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Obesity is associated with a number of metabolic disorders. Lipolysis is the initial step in the metabolism of lipids stored in adipocytes and is therefore considered a therapeutic target for obesity. Quassinoids are unique terpenes found in plants of the Simaroubaceae family, which were recently reported to have lipolytic activity and to suppress weight gain. Brucea javanica is a plant employed in traditional medicines in Asia, which is known to contain various quassinoids. Here, we investigated the lipolytic activity of B. javanica extracts, and identified six quassinoids: brucein A, brucein B, brucein C, 3'hydroxybrucein A, brusatol, and bruceantinol, which represent the bioactive principals. The quassinoids contained in B. javanica demonstrated lipolytic activity at nanomolar concentrations, which were an order of magnitude lower than those of the previously reported quassinoids, suggesting that they may be useful for the treatment of obesity.

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Section: Materials and Equipmentmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Quassinoids in Brucea javanica are potent stimulators of lipolysis in adipocytes

et al. 2019

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“…The seeds from the Asian species have been previously investigated for its various biological activities such as antimalarial [10][11][12][13][14][15][16], cytotoxic and antileukemic [5,[17][18][19][20][21][22][23], antiprotozoal against amoeba [24,25], Toxoplama gondii, Giardia intestinal [25], Trypanosoma brucei brucei and Leishmania donovani [14], Blastocystis hominis [26], Trypanosoma evansi [27] and Babesia gibsoni [3,28], and anti-inflammatory [29] activities. Different chemical constituents including quassinoids [11,12,17,19,30,31], alkaloids from cell suspension cultures of B. javanica seeds [5,32] and lignans [20] had been reported to be present in the seeds and recognized to be responsible for different biological activities according to the case.…”

Section: Introductionmentioning

confidence: 99%

In Vitro Antiprotozoal and Cytotoxic Activity of the Aqueous Extract, the 80% Methanol Extract and Its Fractions from the Seeds of Brucea sumatrana Roxb. (Simaroubaceae) Growing in Democratic Republic of Congo

Ehata¹,

Phuati²,

Lumpu³

et al. 2012

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The in vitro antiprotozoal and cytotoxic activity of the aqueous extract, the 80% methanol extract, and its different soluble fractions and subfractions from Brucea sumatrana seeds were assessed against two Trypanosoma (T. cruzi and T. brucei brucei), Leishmania infantum and chloroquine and pyrimethanine-resistant K1strain of P. falciparum and against MRC-5 cell-lines respectively. Results indicated that the 80% methanol extract showed a cytotoxic effect against MRC-5 cell lines with CC50 value of 0.54 µg/ml. It however exhibited pronounced and non selective activity against T. cruzi (IC50 = 1.52 µg/ml, SI = 0.03) and L. infantum (IC50 = 2.41 µg/ml, SI = 0.22). It however displayed pronounced and selective effect against T. brucei brucei (IC50 < 0.25, SI > 2.16) and chloroquine and pyrimethamine-resistant K1 strain of P. falciparum (IC50 < 0.25 µg/ml, SI > 2.16). All soluble fractions and subfractions from the partition of the 80% methanol extract were found to exhibit an antiprotozoal activity with IC50 values ranging from <0.25 to 30 µg/ml. The most active was the alkaline aqueous soluble fraction exhibiting pronounced antiprotozoal activity against T .cruzi, T. b. brucei, L. infantum and chloroquine and pyrimethamine-resistant K1 strain of P. falciparum with IC50 values of 0.33, <0.25, 0.25, <0.25 µg/ml respectively resulting in high selective index values of 61.36, > 81, 81 and >81 respectively. The chloroform soluble fraction rich in alkaloid was cytotoxic against MRC-5 cell lines (CC50 = 27.09 µg/ml) and showed good activity against T. b. brucei (IC50 = 8.36 and SI = 3.24) and moderate activity against T. cruzi, L. infantum and chloroquine-pyrimethane-resistant K1 strain of P. falciparum (20 < IC50 < 30 µg/ml). Although the aqueous extract (decoction) and the total alkaloids extract showed a cytotoxic effect against MRC-5 cell lines (CC50 = 1.55 and 0.43 µg/ml respectively), they however displayed pronounced antiprotozoal activity against T. cruzi, T. b. brucei and chloroquine and pyrimethamine-resistant K1 strain of P. falciparum with IC50 values ranging from < 0.25 to 0.6 µg/ml with only a selective action against chloroquine and pyrimethamine-resistant K1 strain of P. falciparum (SI = >6.2 and >1.72 respectively). These extracts however showed good and low activity respectively against L. infantum (IC...

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“…NMR Spectroscopic Data (500 MHz, C 5 D 5 N) for Javanic Acids A (4) and B(5) and Javanicolide H(6) a Data assignments are based on HSQC and HMBC experiments. b Not assigned.…”

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confidence: 99%

Bioactive Quassinoids from the Seeds of Brucea javanica

et al. 2012

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Six new quassinoids (1-6) and eight known compounds of this type (7-14) were isolated from the seeds of Brucea javanica. Their structures were elucidated by analysis of their spectroscopic data and from chemical evidence. Compounds 1-5 were found to be unusual quassinoids with a 2,3-seco A ring. The configurations at C-4 in 4 and 5 were determined by a difference circular dichroism method. In in vitro bioassays, 8 and 10 showed inhibitory activities for nitric oxide production in LPS-activated macrophages, with IC(50) values of 1.9 and 5.0 μM, respectively, while compounds 6, 8-11, 13, and 14 exhibited cytotoxicity against five human tumor cell lines (HCT-8, HepG2, BGC-823, A549, and SKVO3), having IC(50) values in the range 0.12-9.3 μM.

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Structures of yadanziolides A, B, and C, new bitter principles from Brucea javanica.

Cited by 22 publications

References 1 publication

Quassinoids in Brucea javanica are potent stimulators of lipolysis in adipocytes

Quassinoids in Brucea javanica are potent stimulators of lipolysis in adipocytes

<i>In Vitro</i> Antiprotozoal and Cytotoxic Activity of the Aqueous Extract, the 80% Methanol Extract and Its Fractions from the Seeds of <i>Brucea sumatrana</i> Roxb. (Simaroubaceae) Growing in Democratic Republic of Congo

Bioactive Quassinoids from the Seeds of Brucea javanica

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Structures of yadanziolides A, B, and C, new bitter principles from Brucea javanica.

Cited by 22 publications

References 1 publication

Quassinoids in Brucea javanica are potent stimulators of lipolysis in adipocytes

Quassinoids in Brucea javanica are potent stimulators of lipolysis in adipocytes

&lt;i&gt;In Vitro&lt;/i&gt; Antiprotozoal and Cytotoxic Activity of the Aqueous Extract, the 80% Methanol Extract and Its Fractions from the Seeds of &lt;i&gt;Brucea sumatrana&lt;/i&gt; Roxb. (Simaroubaceae) Growing in Democratic Republic of Congo

Bioactive Quassinoids from the Seeds of Brucea javanica

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<i>In Vitro</i> Antiprotozoal and Cytotoxic Activity of the Aqueous Extract, the 80% Methanol Extract and Its Fractions from the Seeds of <i>Brucea sumatrana</i> Roxb. (Simaroubaceae) Growing in Democratic Republic of Congo