Chrotacumines G–J, chromone alkaloids from Dysoxylum acutangulum with osteoclast differentiation inhibitory activity

Morita, Hiroshi; Nugroho, Alfarius Eko; Nagakura, Yuta; Hirasawa, Yusuke; Yoshida, Haruka; Kaneda, Toshio; Shirota, Osamu; Ismail, Intan Safinar

doi:10.1016/j.bmcl.2014.04.020

Cited by 18 publications

(9 citation statements)

References 18 publications

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“…In Vietnam, 14 species distributed throughout the country have been described [2]. Study of several species of this genus such as Dysoxylum kuskususense [3], D. richii, D. hainanense, D. acutangulum [4], D. cauliflorum [5], D. variabile [6], D. spectabile [7], etc led to the isolation and structural elucidation of different types of triterpenoids [5,8], diterpenoids [7], sesquiterpenoids [6] and limonoids [7] with many biological activities including osteoclast differentiation inhibitory activity [9], acetylcholinesterase inhibitory activity [10] and cytotoxic effects against different cancer cell lines such as KB cells [6], multidrug-Presented at the Conference RDNP2018, Hanoi, 10/2018. resistant KB cell line KB-C2 (colchicine resistant) [11], leukemia cell line HL-60 [11], liver cancer cell line SMMC-7721 [11] and hepatocarcinoma cell HepG2 [8], breast cancer MCF-7 [11], leukemia K-562 and lung cancer NCI-H522 [3].…”

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confidence: 99%

Terpenoids From the Leaves and Stems of Dysoxylum Tpongense

Khanh

Tài²,

Hương

et al. 2019

JST

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Study on chemical constituents from the leaves and stems of Dysoxylum tpongense Pierre resulted in the isolation of six known compounds (1–6). The chemical structures of isolated compounds were identified as cabraleahydroxylactone (1), cabraleahydroxylactone-3-acetate (2), (+) spathulenol (3), b-sitosterol (4), stigmasterol (5), and stigmast-4-en-3-one (6) by comparison of the physicochemical, interpretation of NMR and mass spectral data with that reported in the literature.

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Section: Introductionmentioning

confidence: 99%

Terpenoids From the Leaves and Stems of Dysoxylum Tpongense

Khanh

Tài²,

Hương

et al. 2019

JST

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“…In our continuous quest to identify novel bioactive compounds of plant origin, many compounds with biological activities have been identified such as cytostatic, vasorelaxation, antilipid droplet accumulation, osteoclast differentiation inhibition, and inhibition of nitric oxide. − We have previously isolated two novel bisindole alkaloids from the leaves of Leuconotis griffithii Hk.f of the Apocynaceae family, leucoridine A N -oxide and bisleucocurine A, which possess antiplasmodial and cytotoxic activity, respectively. , Additionally, investigation of L. griffithii bark led to the isolation of a novel bisindole alkaloid, bisleuconothine A (Bis-A) (Figure ), and three novel indole alkaloids, leucomidines A–C . Although leucomidines A–C are not bioactive, Bis-A, a bisindole alkaloid connecting the C-16 of an eburnane skeleton to C-12′ of an aspidosperma skeleton (Figure ), was found to have cytostatic activity .…”

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confidence: 99%

Bisleuconothine A Induces Autophagosome Formation by Interfering with AKT-mTOR Signaling Pathway

et al. 2015

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We have previously reported that bisleuconothine A (Bis-A), a novel bisindole alkaloid isolated from Leuconotis griffithii, showed cytostatic activity in several cell lines. In this report, the mechanism of Bis-A-induced cytostatic activity was investigated in detail using A549 cells. Bis-A did not cause apoptosis, as indicated by analysis of annexin V and propidium iodide staining. Expression of all tested apoptosis-related proteins was also unaffected by Bis-A treatment. Bis-A was found to increase LC3 lipidation in MCF7 cells as well as A549 cells, suggesting that Bis-A cytostatic activity may be due to induction of autophagy. Subsequent investigation via Western blotting and immunofluorescence staining indicated that Bis-A induced formation but prevented degradation of autophagosomes. Mechanistic studies showed that Bis-A down-regulated phosphorylation of protein kinase B (AKT) and its downstream kinase, PRAS40, which is an mTOR repressor. Moreover, phosphorylation of p70S6K, an mTOR-dependent kinase, was also down-regulated. Down-regulation of these kinases suggests that the increase in LC3 lipidation may be due to mTOR deactivation. Thus, the cytostatic activity shown by Bis-A may be attributed to its induction of autophagosome formation. The Bis-A-induced autophagosome formation was suggested to be caused by its interference with the AKT-mTOR signaling pathway.

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“…Species of the genus Leuconotis are known to produce monoterpene indole alkaloids, , for which skeletons are similar to those found in Alstonia and Kopsia species . In a search for bioactive compounds from tropical plants, − we have reported previously the isolation of several new alkaloids from Leuconotis species. − Recently, an alkaloid isolated from L. griffithii bark, bisleuconothine A, was found to show cytostatic activity against A549 cells by autophagosome formation via inhibition of AKT-mTOR signaling . Many autophagy-inducing compounds have also been reported to induce apoptosis; however, bisleuconothine A did not induce apoptosis even at a high concentration …”

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Bisleuconothines B–D, Modified Eburnane–Aspidosperma Bisindole Alkaloids from Leuconotis griffithii

et al. 2018

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Three new bisindole alkaloids, bisleuconothines B−D (1−3), were isolated from the bark of Leuconotis grif f ithii. Their structures were elucidated by 1D and 2D NMR spectroscopy and DFT calculations. Bisleuconothine B (1) is the first monoterpene indole alkaloid dimer featuring bridges between both C-16−C-10′ and C-2−O−C-9′. All compounds were deemed noncytotoxic (IC 50 > 10 μM) when tested against A549 human lung adenocarcinoma cells.

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Chrotacumines G–J, chromone alkaloids from Dysoxylum acutangulum with osteoclast differentiation inhibitory activity

Cited by 18 publications

References 18 publications

Terpenoids From the Leaves and Stems of Dysoxylum Tpongense

Terpenoids From the Leaves and Stems of Dysoxylum Tpongense

Bisleuconothine A Induces Autophagosome Formation by Interfering with AKT-mTOR Signaling Pathway

Bisleuconothines B–D, Modified Eburnane–Aspidosperma Bisindole Alkaloids from Leuconotis griffithii

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