Toward establishing structure–activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells

Riveiro, María E.; Maes, Dominick; Vázquez, Ramiro; Vermeulen, Mónica; Mangelinckx, Sven; Jacobs, Jan; Debenedetti, Sílvia; Shayo, Carina; Kimpe, Norbert De; Davio, Carlos

doi:10.1016/j.bmc.2009.08.002

Cited by 48 publications

(23 citation statements)

References 38 publications

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“…The substitution pattern in the B-ring was determined to be 3′,4′-methylenedioxy by its 1 H-NMR and EI-MS spectra by the same manner as 1 and 2. The 1 H-NMR spectrum of 3 (Table 1) was similar to that of 2, except for the presence of signals for the 2,3-dihydroxy-3-methylbutoxy group 21) The EI-MS spectrum showed a peak at m/z 341 that was assigned to the fragment ion produced by the loss of the 2,3-dihydroxy-3-methylbutyl radical from the molecular ion, confirming the presence of the 2,3-dihydroxy-3-methylbutoxy group. 22) It also showed a peak at m/z 425 suggesting a 3,5-dimethoxy substitution pattern.…”

Section: Resultsmentioning

confidence: 87%

Isolation of Five New Flavonoids from Melicope triphylla

Higa

Imamura

Ogihara

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Five new flavonoids, 5,8-dihydroxy-3,7-dimethoxy-3',4'-methylenedioxyflavone (1), 7-hydroxy-3,5-dimethoxy-3',4'-methylenedioxyflavone (2), 7-(2,3-dihydroxy-3-methylbutoxy)-3,5-dimethoxy-3',4'-methylenedioxyflavone (3), 7-(2,3-dihydroxy-3-methylbutoxy)-3,3',4',5-tetramethoxyflavone (4), and 7-(2,3-dihydroxy-3-methylbutoxy)-3,3',4',5,8-pentamethoxyflavone (5), were isolated from the leaves of Melicope triphylla. In addition, six known flavonoids were detected: 3,4',5-trihydroxy-3',7,8-trimethoxyflavone (6), 5,7-dihydroxy-3-methoxy-3',4'-methylenedioxyflavone (7), 4',5,7-trihydroxy-3,3'-dimethoxyflavone (8), 4',7-dihydroxy-3,3',5,8-tetramethoxyflavone (9), 4',7-dihydroxy-3,3',5-trimethoxyflavone (10), and 4',5,7-trihydroxy-3,3',8-trimethoxyflavone (11). The new compound structures were determined by spectroscopic methods. Compounds 1-5 did not exhibit any ichthyotoxic activity against Japanese killifish (medaka in Japanese) (Oryzias latipes var.) at 10 ppm.

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Section: Resultsmentioning

confidence: 87%

Isolation of Five New Flavonoids from Melicope triphylla

Higa

Imamura

Ogihara

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…For example, osthole is a prenylated coumarin, isoimperatorin and oxypeucedanin are linear furanocoumarins, and braylin is an angular pyranocoumarin. However, Riveiro et al proved that alkoxy residue could potentiate the antiproliferative effects of coumarins [39]. Although the tested coumarins were devoid of catechol moiety, which could have contributed to the growth inhibitory activity [40], it is highly likely that the presence of isoprenoid residue in osthole and isoimperatorin has contributed to various pharmacological interactions, which gave rise to the proapoptotic activity [41].…”

Section: Discussionmentioning

confidence: 99%

Comparative Evaluation of Cytotoxic and Apoptogenic Effects of Several Coumarins on Human Cancer Cell Lines: Osthole Induces Apoptosis in p53-Deficient H1299 Cells

Shokoohinia

Hosseinzadeh

Alipour

et al. 2014

Advances in Pharmacological Sciences

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Natural products are excellent resources for finding lead structures for the development of chemotherapeutic agents. Coumarins are a class of natural compounds found in a variety of plants. In this study, we evaluated the cytotoxic potential of coumarins isolated from Prangos ferulacea (L.) Lindl. in PC3, SKNMC, and H1299 (p53 null) human carcinoma cell lines. Osthole proved to be an outstanding potent cytotoxic agent especially against PC3 cells. Isoimperatorin exhibited moderate inhibitory effect against SKNMC and PC3 cell lines. Oxypeucedanin and braylin did not display any cytotoxic activity. In the next set of experiments, the apoptotic potentials of osthole and isoimperatorin were investigated. Induction of apoptosis by isoimperatorin was accompanied by an increase in activation of caspase-3, -8, and -9 in SKNMC cells and caspase-3 and -9 in PC3 cells. Moreover, isoimperatorin induced apoptosis by upregulating Bax and Smac/DIABLO genes in PC3 and SKNMC cells. Osthole induced apoptosis by downregulating antiapoptotic Bcl-2 in only PC3 cells and upregulating the proapoptotic genes Bax and Smac/DIABLO in PC3, SKNMC, and H1299 cells. The effects of osthole on H1299 cells are important because the loss of p53 has been associated with poor clinical prognosis in cancer treatment.

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“…Specifically, in some studies, the significant inhibitory activity of certain coumarins on the proliferation of leukemic cell lines [58,[66][67][68] has been reported. In addition, it has been described that such inhibitory effects could be related to either differentiating [58,66] or proapoptotic activities [67,68] of the compounds, depending on the distribution of their substituents in the coumarin ring.…”

Section: Coumarins and Leukemiamentioning

confidence: 99%

Cytotoxicity and Apoptosis Induction by Coumarins in CLL

Gholami¹

2018

Cytotoxicity

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Chronic lymphocytic leukemia (CLL) is one of the leukemia types. Leukemia is cancer of the body's blood-forming cells. Cancer is a disease that is often characterized by too little apoptosis and uncontrolled duplicate of body cells. Apoptosis, or programmed cell death, is a normal component of the development and health of multicellular organisms. Cells die in response to a variety of stimuli during apoptosis. During cancer, pathophysiology apoptosis of the cancerous cells is disrupted, so one of the strategies for cancer chemotherapy is inducing apoptosis in cancerous cells. Myeloid cell leukemia type 1 (Mcl-1) is one of the antiapoptotic Bcl-2 family proteins. It has been shown that the expression of Mcl-1 in CLL is significantly associated with a failure to achieve complete remission following cytotoxic therapy, so regulation of Mcl-1 expression by coumarins could be one of the mechanisms of CLL chemotherapy. Coumarins consist of a large class of phenolic substances found in plants. Different pharmacologic effects of coumarins were reported. One of these effects is cytotoxicity and apoptosis induction in cancerous cells by coumarins. In this chapter, the cytotoxic activity of coumarins and their role in Mcl-1 regulation are discussed.

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Toward establishing structure–activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells

Cited by 48 publications

References 38 publications

Isolation of Five New Flavonoids from Melicope triphylla

Isolation of Five New Flavonoids from Melicope triphylla

Comparative Evaluation of Cytotoxic and Apoptogenic Effects of Several Coumarins on Human Cancer Cell Lines: Osthole Induces Apoptosis in p53-Deficient H1299 Cells

Cytotoxicity and Apoptosis Induction by Coumarins in CLL

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