Antiangiogenic activity of lupeol from <i>Bombax ceiba</i>

You, Youngjae; Nam, Nguyen Hai; Kim, Yong; Bae, Ki Hwan; Ahn, Byung Zun

doi:10.1002/ptr.1140

Cited by 116 publications

(76 citation statements)

References 17 publications

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“…Compound 5, which was identified as lupane-type triterpenoid, was the most potent agent against the panel of three cell lines tested and rewardingly the compound exhibited selectivity Bagalkotkar et al 187 towards MCF-7 cells (IC 50 17.1 µM). Search of the literature revealed that lupane-type triterpenoids such as lupeol possess in vitro antitumour, antiangiogenic and apoptosis inducing properties in cancer cells (Moriarty et al, 1998;You et al, 2003;Aratanechemuge et al, 2004) which is in accordance with our findings. Interestingly, betulinic acid, another lupane-type triterpenoid with good in vitro anticancer activity was reported to be less cytotoxic to normal cells such as normal human astrocytes and melanocytes (Cichewicz and Kouzi, 2004) Basing on the above evidences, we propose that compound 5 would be less toxic against normal tissues.…”

Section: Resultssupporting

confidence: 91%

Isolation and cytotoxicity of triterpenes from the roots of Phyllanthus pulcher Wall. ex Mll. Arg. (Euphorbiaceae)

Bagalkotkar

Chuan

Khalivulla

et al. 2011

Afr. J. Pharm. Pharmacol.

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The dried powdered roots of Phyllanthus pulcher Wall. ex Müll. Arg. (Euphorbiaceae), were sequentially extracted with dichloromethane (DCM), ethyl acetate (EtOAc) and methanol (MeOH). The extracts were tested for cytotoxic activity against three human cancer cell lines: MCF-7 (breast), NCI-H460 (lung) and DU-145 (prostate). The DCM extract exhibited the strongest cytotoxic activity compared with EtOAc and MeOH extracts. Hence from the DCM extract, five pentacyclic triterpenes, 3α-acetoxyl-25-hydroxyolean-12-en-28-oic acid (1), glochidone (2), 12(13)-dehydro-3α-acetoxyolean-28-oic acid (3), lupanyl acetate (4) and glochidonol (5) were isolated and identified by spectroscopic analyses ( 1 H NMR, C NMR, FT-IR, UV, DEPT, HMQC, HMBC and HREIMS). This is the first report on the isolation of 4 from a natural source, whereas 1 and 3 have already been isolated from the families Hamamelidaceae and Compositae (Asteraceae), respectively. However this is the first study reporting the presence of 1 and 3 in the Euphorbiaceae family. The isolated tritepenes 1-5 were tested against the three human tumour cell lines as stated above. Only compounds 1 and 5 exhibited cytotoxic activity, 5 being most potent with IC 50 values ranging 7.5-13.4 µg/mL (17.1-30.5 µM).

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Section: Resultssupporting

confidence: 91%

Isolation and cytotoxicity of triterpenes from the roots of Phyllanthus pulcher Wall. ex Mll. Arg. (Euphorbiaceae)

Bagalkotkar

Chuan

Khalivulla

et al. 2011

Afr. J. Pharm. Pharmacol.

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“…Recently, it was shown that compound 1 exhibits an anti-angiogenic effect through the inhibition of HUVEC tube formation (You et al 2003). In this study, we demonstrated the anti-migration activity of compound 1 against melanoma and neuroblastoma cells.…”

Section: Melanoma Cell Motilitysupporting

confidence: 52%

Differentiation-inducing activity of lupane triterpenes on a mouse melanoma cell line

et al. 2006

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Lupane triterpenes were found to promote melanogenesis, a hallmark of B16 2F2 mouse melanoma cell differentiation. Studies of the structureactivity relationships demonstrated that the keto function at C-3 of the lupane skeleton played important roles in the melanogenic activities of lupane triterpenes on melanoma cells. The carbonyl group at C-17 of lupane triterpenes was essential against their apoptosis-inducing activity against human cancer cells via the inhibition of topoisomerase I. We investigated whether signaling mechanisms were involved in the stimulative effects of lupane triterpenes on the melanogenesis of B16 2F2 cells. In experiments using selective inhibitors against various signal transduction molecules and Western blotting analysis, it was suggested that p38 MAPK was involved in melanoma cell differentiation as a downstream effector of PKA. Lupeol (compound 1), a lupane triterpene, induced dendrite formations, a morphological hallmark of B16 2F2 cell differentiation by rearrangement of the actin cytoskeleton.The activation of cofilin, an actin depolymerizing factor, by compound 1 caused actin fiber disassembly in B16 2F2 cells. Furthermore, compound 1 was shown to inhibit the cell motilities of human melanoma and neuroblastoma in vitro.

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“…With the discovery of the role of angiogenesis in tumor growth and progression, considerable efforts have been directed towards antiangiogenic therapy as a new modality to treat human cancers. In recent years, attention has been given to identifying non-toxic, endothelial cell specific, diet-derived compounds as antiangiogenic agents for cancer therapy, in an effort to reduce the toxic side effects [3][4][5][6].…”

mentioning

confidence: 99%

Butyrate-induced proapoptotic and antiangiogenic pathways in EAT cells require activation of CAD and downregulation of VEGF

Belakavadi

Prabhakar

Salimath

2005

Biochemical and Biophysical Research Communications

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Antiangiogenic activity of lupeol from Bombax ceiba

Cited by 116 publications

References 17 publications

Isolation and cytotoxicity of triterpenes from the roots of Phyllanthus pulcher Wall. ex Mll. Arg. (Euphorbiaceae)

Isolation and cytotoxicity of triterpenes from the roots of Phyllanthus pulcher Wall. ex Mll. Arg. (Euphorbiaceae)

Differentiation-inducing activity of lupane triterpenes on a mouse melanoma cell line

Butyrate-induced proapoptotic and antiangiogenic pathways in EAT cells require activation of CAD and downregulation of VEGF

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