Constituents of Seeds of <i>Brucea javanica</i>. Structures of New Bitter Principles, Yadanziolides A, B, C, Yadanziosides F, I, J, and L.

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

doi:10.1246/bcsj.58.2673

Cited by 36 publications

(20 citation statements)

References 12 publications

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“…of this approach for the determination of the configuration at C-20.8 The reaction of dammaranes with m-chloroperbenzoic acid introduces hydroxyl groups in several positions, including 120, which is a position that is of interest for the preparation of ginseng sapogenins. 82 Tirucallanes that have recently been reported include tirucalla-8,23-dien-3P-ol (1 18) from the seeds of Aesculus hippo~astanurn,~~ aphananin (1 19) from Aphanamixis polysta-~h y a , ~, and piscidinols A (120) and B ( 121…”

Section: Ziziphus J O a ~E I R O ~~ And Alnus Pendula8qmentioning

confidence: 99%

Triterpenoids

Connolly¹,

Hill²

1986

Nat. Prod. Rep.

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Section: Ziziphus J O a ~E I R O ~~ And Alnus Pendula8qmentioning

confidence: 99%

Triterpenoids

Connolly¹,

Hill²

1986

Nat. Prod. Rep.

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“…To understand the pharmacology activities of this plant in controlling the blood pressure, molecular analysis of specific protein binding in the cell is required to be deeply investigated. The several active compounds derived from Brucea javanica , such as Javanicin, Javanicoside B, Yadanzioside B, Yadanziolide A, Macedonic acid, have been experimentally identified [12–16] . However, it is not easy to determine which compounds that correspond to decreased blood pressure.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Active Compounds of Brucea Javanica In Treating Hypertension Using A Network Pharmacology‐Based Analysis Combined with Homology Modeling, Molecular Docking and Molecular Dynamics Simulation

et al. 2022

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Hypertension is a disease that can increase the risk of stroke, cardiovascular, and heart failure. In this letter, we investigated the potency of active compounds of Brucea javanica (BJ) in treating hypertension by using network pharmacology combined with several in silico approaches, including molecular docking, homology modeling and molecular dynamics (MD) simulations. Twenty protein targets at the intersection of BJ and hypertension were identified by using network pharmacology. We found that peroxisome proliferator‐activated receptor gamma (PPARG) was the first‐degree rank that might strongly connect with the disease. Therefore, the tertiary structure of PPARG, generated using homology modeling, was assigned as a receptor. In docking analysis, two ligands, i. e., Javanicin and Yadanziolide A, could be potential inhibitors for PPARG due to the higher binding energy score than the control (Hydrochlorothiazide). To confirm the stability of the ligand‐receptor complex in water solvent, MD simulation was performed. We found that complexes 1 and 2 reached stable structures during the simulation indicated by no significant fluctuation in the validation parameters. Furthermore, based on the binding energies calculated by Molecular Mechanics‐Generalized Born Surface Area (MM‐GBSA), we confirm that the ligands of these complexes strongly bind to the catalytic site of the receptor. This points out the potency of these complexes as promising drugs against hypertension targeting PPARG.

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“…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%

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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Constituents of Seeds of Brucea javanica. Structures of New Bitter Principles, Yadanziolides A, B, C, Yadanziosides F, I, J, and L.

Cited by 36 publications

References 12 publications

Triterpenoids

Triterpenoids

Investigation of Active Compounds of Brucea Javanica In Treating Hypertension Using A Network Pharmacology‐Based Analysis Combined with Homology Modeling, Molecular Docking and Molecular Dynamics Simulation

Quassinoids in Brucea javanica are potent stimulators of lipolysis in adipocytes

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