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Antiproliferative Activity Of Abietane Diterpenoids Against Human Tumor Cells.

O. Burmistrova, M. Simões, P. Rijo, J. Quintana, J. Bermejo, F. Estévez
Published 2013 · Biology, Medicine

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In the present study, the cytotoxicity of 30 diterpenoids with an abietane or a halimane skeleton was determined against five human tumor cell lines (HL-60, U937, Molt-3, SK-MEL-1, and MCF-7). Diterpenoids containing an abietane skeleton including taxodone (1) and taxodione (2), as well as the semisynthetic derivatives 12, 14, 15, 17, and 22, were the most cytotoxic compounds for human leukemia cells. Overexpression of the protective mitochondrial proteins Bcl-2 and Bcl-x(L) did not confer resistance to abietane diterpene-induced cytotoxicity. Studies performed on HL-60 cells indicated that growth inhibition triggered by compounds 1, 12, 14, and 15 was caused by induction of apoptosis. This was prevented by the nonspecific caspase inhibitor Z-VAD-FMK and, in the case of compounds 14 and 15, reduced by the selective caspase-8 inhibitor Z-IETD-FMK. Cell death induced by these abietane diterpenes was found to be associated with the release of mitochondrial proteins, including cytochrome c, Smac/DIABLO, and AIF (apoptosis-inducing factor), accompanied by dissipation of the mitochondrial membrane potential (ΔΨ), and modulated by inhibition of extracellular signal-regulated kinases signaling and the p38 mitogen-activated protein kinase pathway.
This paper references
10.1007/s10495-008-0202-0
Trifolin acetate-induced cell death in human leukemia cells is dependent on caspase-6 and activates the MAPK pathway
F. Torres (2008)
10.1038/81343
Deficiency in caspase-9 or caspase-3 induces compensatory caspase activation
T. Zheng (2000)
10.1016/0031-9422(83)80033-8
Abietane diterpenoids from the root of Salvia phlomoides
Juan A. Hueso-Rodríguez (1983)
10.1002/mc.20574
Betuletol 3‐methyl ether induces G2‐M phase arrest and activates the sphingomyelin and MAPK pathways in human leukemia cells
S. Rubio (2010)
10.1016/S0031-9422(00)94547-3
Abietane diterpenoids from the root of Salvia lavandulaefolia
A. Michavila (1985)
10.1002/MED.20077
New developments in the chemistry and biology of the bioactive constituents of tanshen
Xihong Wang (2007)
10.1016/j.canlet.2011.02.005
Carnosol: a promising anti-cancer and anti-inflammatory agent.
J. Johnson (2011)
10.1126/SCIENCE.275.5303.1129
Prevention of Apoptosis by Bcl-2: Release of Cytochrome c from Mitochondria Blocked
J. Yang (1997)
10.1074/jbc.272.11.7223
Substrate and Inhibitor Specificity of Interleukin-1β-converting Enzyme and Related Caspases*
N. Margolin (1997)
10.1016/S0031-9422(97)00251-3
Modified abietane diterpenoids and a methoxylupane derivative from Salvia palaestina
A. A. Hussein (1997)
10.1016/S0040-4020(01)81367-3
Rearranged abietane diterpenoids from the root of teucrium polium subsp. vincentinum
M. C. Carreiras (1990)
10.1016/J.BSE.2006.10.011
Further diterpenoids from Plectranthus ornatus and P. grandidentatus
P. Rijo (2007)
10.1016/J.FCT.2007.08.013
Cytotoxicity of major tanshinones isolated from Danshen (Salvia miltiorrhiza) on HepG2 cells in relation to glutathione perturbation.
W. Y. Lee (2008)
10.1158/1535-7163.MCT-07-0073
Phytochemistry and pharmacogenomics of natural products derived from traditional chinese medicine and chinese materia medica with activity against tumor cells
T. Efferth (2008)
10.1093/CARCIN/BGM131
Acetyl derivative of quercetin 3-methyl ether-induced cell death in human leukemia cells is amplified by the inhibition of ERK.
S. Rubio (2007)
10.1016/J.BMC.2006.03.047
Cytotoxicity of abietane diterpenoids from Perovskia abrotanoides and of their semisynthetic analogues.
Y. Aoyagi (2006)
10.1016/j.canlet.2011.05.018
Astragalin heptaacetate-induced cell death in human leukemia cells is dependent on caspases and activates the MAPK pathway.
O. Burmistrova (2011)
10.1016/j.phytochem.2012.02.015
Abietane diterpenes induce cytotoxic effects in human pancreatic cancer cell line MIA PaCa-2 through different modes of action.
M. Fronza (2012)
10.1002/cbdv.200900099
Antimycobacterial Metabolites from Plectranthus: Royleanone Derivatives against Mycobacterium tuberculosis Strains
P. Rijo (2010)
An informatics approach identifying markers of chemosensitivity in human cancer cell lines.
S. Amundson (2000)
10.1016/J.COI.2007.05.004
Bcl-2-regulated apoptosis: mechanism and therapeutic potential.
J. Adams (2007)
10.1182/BLOOD-2002-12-3647
Map kinase signaling pathways and hematologic malignancies.
L. Platanias (2003)
10.1016/j.bmc.2011.06.067
In vitro cytotoxic activity of abietane diterpenes from Peltodon longipes as well as Salvia miltiorrhiza and Salvia sahendica.
M. Fronza (2011)
10.1038/nrm2308
The BCL-2 protein family: opposing activities that mediate cell death
R. Youle (2008)
10.1021/NP060279I
Abietane diterpenoids from Salvia pachyphylla and S. clevelandii with cytotoxic activity against human cancer cell lines.
I. C. Guerrero (2006)
10.1021/np200906s
Natural products as sources of new drugs over the 30 years from 1981 to 2010.
D. Newman (2012)
10.4161/cbt.4.1.1371
Prognostic role of bcl-xL and p53 in childhood acute lymphoblastic leukemia
R. Addeo (2005)
10.1038/onc.2008.297
Caspases in apoptosis and beyond
J. Li (2008)
10.1016/J.PHYMED.2005.06.002
Abietanes from Plectranthus grandidentatus and P. hereroensis against methicillin- and vancomycin-resistant bacteria.
C. Gaspar-Marques (2006)
10.1074/JBC.M001185200
p38 Mitogen-activated Protein Kinase Mediates Bid Cleavage, Mitochondrial Dysfunction, and Caspase-3 Activation during Apoptosis Induced by Singlet Oxygen but Not by Hydrogen Peroxide*
S. Zhuang (2000)



This paper is referenced by
10.1107/S205698901700946X
Crystal structure of taxodione isolated from Taxodium ascendens (B.)
Rui-Fang Ke (2017)
ytotoxic diterpenoids from the roots of Salvia lachnocalyx ossein
Hadavand Mirzaeia (2017)
10.4155/tde-2016-0027
Functionalized diterpene parvifloron D-loaded hybrid nanoparticles for targeted delivery in melanoma therapy.
C. Silva (2016)
10.1016/j.phymed.2015.06.013
The abietane diterpenoid parvifloron D from Plectranthus ecklonii is a potent apoptotic inducer in human leukemia cells.
O. Burmistrova (2015)
10.1021/acs.orglett.6b03597
Taxodikaloids A and B, Two Dimeric Abietane-Type Diterpenoids from Taxodium ascendens Possessing an Oxazoline Ring Linkage.
Xinghao Huang (2017)
10.1016/j.fitote.2018.05.005
Cytotoxic diterpene quinones from Salvia tebesana Bunge.
Samira Eghbaliferiz (2018)
10.1080/10799893.2019.1710847
Study of the mechanism of action, molecular docking, and dynamics of anticancer terpenoids from Salvia lachnocalyx
Hossein Hadavand Mirzaei (2020)
10.1016/j.ejmech.2019.111687
Recent advances in α,β-unsaturated carbonyl compounds as mitochondrial toxins.
M. Hossain (2019)
10.4236/ABC.2014.42015
Pharmacological Prospects of Oxygenated Abietane-Type Diterpenoids from Taxodium distichum Cones
Norihisa Kusumoto (2014)
10.1016/J.BJP.2017.01.009
Cytotoxic diterpenoids from the roots of Salvia lachnocalyx
H. Mirzaei (2017)
10.2147/OTT.S211933
14-Deoxycoleon U-induced endoplasmic reticulum stress-mediated apoptosis, autophagy, and cell cycle arrest in lung adenocarcinoma
Xiaozhi Peng (2019)
10.3390/molecules25071707
Antibacterial Natural Halimanes: Potential Source of Novel Antibiofilm Agents
Ignacio E Tobal (2020)
10.1016/j.jksus.2019.11.021
Inhibition of nasopharyngeal cells mediated via G2/M cell cycle arrest, blocking PI3K/AKT/mTOR signalling pathway and suppression of cell migration and invasion
Hao-jie Wen (2020)
10.1021/jo401606q
Protection-group-free semisyntheses of parthenolide and its cyclopropyl analogue.
J. Long (2013)
10.1002/cbdv.201500071
Structure Elucidation, Antimicrobial and Cytotoxic Activities of a Halimane Isolated from Vellozia kolbekii Alves (Velloziaceae)
Carmelita G. Silva (2015)
Secondary Metabolites from Bolivian Plants- Isolation and Characterization
Marcelo Dávila (2014)
10.1055/s-0042-115646
Antiparasitic Activity of Diterpenoids Against Trypanosoma cruzi.
Sergio Alegre-Gómez (2017)
10.1039/c8np00016f
Halimane diterpenoids: sources, structures, nomenclature and biological activities.
A. Roncero (2018)
10.3390/cancers11111733
Development and Mechanistic Insight into the Enhanced Cytotoxic Potential of Parvifloron D Albumin Nanoparticles in EGFR-Overexpressing Pancreatic Cancer Cells
Ana Santos-Rebelo (2019)
10.1016/B978-0-444-63749-9.00002-5
Chapter 2 - Natural Products as Lead Protein Kinase C Modulators for Cancer Therapy
Diogo Matias (2016)
10.1007/s00210-020-01967-2
4,5-Seco-5,10-friedo-abietane-type diterpenoids with anticancer activity from Salvia atropatana Bunge.
Abolfazl Shakeri (2020)
10.1007/978-981-10-8064-7_8
Terpenes of the Genus Salvia: Cytotoxicity and Antitumoral Effects
Nimsi Campos-Xolalpa (2018)
Isolation, modeling and phytosome forms of antimicrobial and antiproliferative compounds from plectranthus spp.
Diogo Matias (2016)
10.1073/pnas.1409061111
Taxodione and arenarone inhibit farnesyl diphosphate synthase by binding to the isopentenyl diphosphate site
Y. Liu (2014)
10.3390/biom10020194
Insight the Biological Activities of Selected Abietane Diterpenes Isolated from Plectranthus spp.
Przemysław Sitarek (2020)
10.1002/ptr.5800
Diterpenes and Their Derivatives as Potential Anticancer Agents
M. T. Islam (2017)
10.1186/s40064-016-2652-0
Abietane and nor-abitane diterpenoids from the roots of Salvia rhytidea
Farrokh Eghtesadi (2016)
10.12659/MSM.914348
Ferruginol Diterpenoid Selectively Inhibits Human Thyroid Cancer Growth by Inducing Mitochondrial Dependent Apoptosis, Endogenous Reactive Oxygen Species (ROS) Production, Mitochondrial Membrane Potential Loss and Suppression of Mitogen-Activated Protein Kinase (MAPK) and PI3K/AKT Signaling Pathways
Guoqing Luo (2019)
10.1007/978-3-030-44921-6_4
Natural Products and Nanopharmaceuticals
Ana Santos-Rebelo (2021)
10.1016/J.TETLET.2014.10.030
Holophyllin A, a rearranged abietane-type diterpenoid from the trunk of Abies holophylla
C. S. Kim (2014)
10.1107/S2056989017011987
Crystal structure of 7β-hydroxyroyleanone isolated from Taxodium ascendens (B.)
Shicheng Xu (2017)
10.1021/acsomega.9b00512
Cytotoxic Activity of Royleanone Diterpenes from Plectranthus madagascariensis Benth
Diogo Matias (2019)
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