Anticancer Activity of Natural and Semi-Synthetic Drimane and Coloratane Sesquiterpenoids.
anticancer activity
mode-of-action
natural products
organic synthesis
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
13 Apr 2022
13 Apr 2022
Historique:
received:
29
03
2022
revised:
09
04
2022
accepted:
11
04
2022
entrez:
23
4
2022
pubmed:
24
4
2022
medline:
27
4
2022
Statut:
epublish
Résumé
Drimane and coloratane sesquiterpenoids are present in several plants, microorganisms, and marine life. Because of their cytotoxic activity, these sesquiterpenoids have received increasing attention as a source for new anticancer drugs and pharmacophores. Natural drimanes and coloratanes, as well as their semi-synthetic derivatives, showed promising results against cancer cell lines with in vitro activities in the low micro- and nanomolar range. Despite their high potential as novel anticancer agents, the mode of action and structure-activity relationships of drimanes and coloratanes have not been completely enlightened nor systematically reviewed. Our review aims to give an overview of known structures and derivatizations of this class of sesquiterpenoids, as well as their activity against cancer cells and potential modes-of-action. The cytotoxic activities of about 40 natural and 25 semi-synthetic drimanes and coloratanes are discussed. In addition to that, we give a summary about the clinical significance of drimane and coloratane sesquiterpenoids.
Identifiants
pubmed: 35458699
pii: molecules27082501
doi: 10.3390/molecules27082501
pmc: PMC9031474
pii:
doi:
Substances chimiques
Antineoplastic Agents
0
Polycyclic Sesquiterpenes
0
Sesquiterpenes
0
drimane
0
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Références
J Nat Prod. 2009 Oct;72(10):1761-7
pubmed: 19769341
J Biol Chem. 2008 Aug 29;283(35):24136-44
pubmed: 18550530
Int J Mol Sci. 2014 Oct 13;15(10):18362-80
pubmed: 25314299
Mitochondrion. 2007 Feb-Apr;7(1-2):106-18
pubmed: 17307400
Molecules. 2014 Nov 18;19(11):18993-9006
pubmed: 25412045
Cancers (Basel). 2010 Apr 08;2(2):376-96
pubmed: 24281075
Leukemia. 2016 Jun;30(6):1290-300
pubmed: 26859075
Phytother Res. 2005 Dec;19(12):1013-7
pubmed: 16372365
Channels (Austin). 2008 Jul-Aug;2(4):287-98
pubmed: 18769139
Glia. 2015 Oct;63(10):1870-82
pubmed: 26010461
ChemMedChem. 2015 Dec;10(12):2014-26
pubmed: 26434977
J Nat Prod. 2009 Sep;72(9):1585-8
pubmed: 19778087
Z Naturforsch C J Biosci. 2008 Mar-Apr;63(3-4):215-20
pubmed: 18533465
Cell Div. 2010 Jan 17;5:2
pubmed: 20180967
J Nat Prod. 2016 Mar 25;79(3):629-61
pubmed: 26852623
J Nat Prod. 2006 Jul;69(7):1101-4
pubmed: 16872156
Breast Cancer (Dove Med Press). 2016 Dec 13;8:243-252
pubmed: 28008282
Apoptosis. 2002 Aug;7(4):321-8
pubmed: 12101391
Proc Natl Acad Sci U S A. 2001 Apr 24;98(9):5043-8
pubmed: 11309491
Cancer Chemother Pharmacol. 2006 May;57(5):545-53
pubmed: 16175394
J Ethnopharmacol. 2000 Nov;73(1-2):171-4
pubmed: 11025153
J Clin Invest. 2007 Oct;117(10):2869-76
pubmed: 17823659
J Am Chem Soc. 2012 Dec 19;134(50):20276-8
pubmed: 23193947
Leukemia. 2021 Oct;35(10):2759-2770
pubmed: 34462526
Biochem Pharmacol. 2006 Apr 14;71(8):1248-54
pubmed: 16457780
Biomed Pharmacother. 2018 Jul;103:1498-1506
pubmed: 29864935
Int J Mol Sci. 2019 May 01;20(9):
pubmed: 31052427
Eur J Pharmacol. 2018 Jun 5;828:154-162
pubmed: 29572068
Oxid Med Cell Longev. 2021 Dec 29;2021:8807676
pubmed: 35003521
Physiol Rev. 2020 Apr 1;100(2):725-803
pubmed: 31670612
J Nat Prod. 1997 Nov;60(11):1115-20
pubmed: 9392880
Int J Mol Sci. 2021 Oct 19;22(20):
pubmed: 34681916
Vet Pathol. 1998 Nov;35(6):461-78
pubmed: 9823588
J Agric Food Chem. 2017 Jul 19;65(28):5700-5712
pubmed: 28657737
J Am Chem Soc. 2010 Aug 4;132(30):10242-4
pubmed: 20614887
Biochem Biophys Res Commun. 2008 Dec 26;377(4):1211-5
pubmed: 18996081
Toxicol Pathol. 2010 Jan;38(1):165-8
pubmed: 19907054
Evid Based Complement Alternat Med. 2014;2014:782830
pubmed: 24834098
Oncogene. 2008 Oct 27;27(50):6434-51
pubmed: 18955971
Histochem Cell Biol. 2005 Jul;124(1):61-8
pubmed: 16041554
Front Physiol. 2017 Jun 09;8:392
pubmed: 28649203
PLoS One. 2013 Jun 14;8(6):e66300
pubmed: 23799090
Front Oncol. 2019 Oct 16;9:1087
pubmed: 31681615
Exp Mol Med. 2020 Feb;52(2):192-203
pubmed: 32060354
Mar Drugs. 2015 Jun 05;13(6):3567-80
pubmed: 26058010
Pharm Biol. 2014 Mar;52(3):378-91
pubmed: 24188508
J Nat Med. 2014 Jul;68(3):513-20
pubmed: 24633883
J Nat Prod. 1980 May-Jun;43(3):365-71
pubmed: 7400822
Org Biomol Chem. 2015 Dec 14;13(46):11200-7
pubmed: 26377594
Life Sci. 2008 May 7;82(19-20):997-1003
pubmed: 18405923
CA Cancer J Clin. 2021 May;71(3):209-249
pubmed: 33538338
Eur J Med Chem. 2015 Oct 20;103:226-37
pubmed: 26360047
J Agric Food Chem. 2001 Mar;49(3):1607-11
pubmed: 11312903
Oncotarget. 2018 Apr 20;9(30):21244-21258
pubmed: 29765535
Naunyn Schmiedebergs Arch Pharmacol. 2016 Jul;389(7):791-7
pubmed: 27095358
Eur J Med Chem. 2021 Nov 15;224:113713
pubmed: 34315042
J Neurophysiol. 2019 Feb 1;121(2):427-443
pubmed: 30485151
J Nat Prod. 2018 Mar 23;81(3):625-629
pubmed: 29406734
Biochem Biophys Res Commun. 2003 May 9;304(3):445-54
pubmed: 12729578
Br J Pharmacol. 1996 Sep;119(2):283-90
pubmed: 8886410
Microb Biotechnol. 2011 Nov;4(6):687-99
pubmed: 21375717
FEBS J. 2021 Nov;288(21):6187-6205
pubmed: 34288422
Talanta. 2011 Oct 15;85(5):2265-89
pubmed: 21962644
Nat Prod Rep. 2013 Sep;30(9):1226-64
pubmed: 23884176
Curr Top Med Chem. 2021;21(12):1027-1036
pubmed: 33655861
J Bioenerg Biomembr. 2020 Oct;52(5):321-342
pubmed: 32715369
J Biochem. 1983 Jul;94(1):149-54
pubmed: 6352692
Angew Chem Int Ed Engl. 2021 Oct 25;60(44):23763-23770
pubmed: 34468074
Proc Natl Acad Sci U S A. 2006 Dec 19;103(51):19564-8
pubmed: 17164327
Genome Biol. 2014;15(6):122
pubmed: 25180339
Beilstein J Org Chem. 2013 Dec 13;9:2866-76
pubmed: 24367452
Insects. 2019 Oct 25;10(11):
pubmed: 31731570
Beilstein J Org Chem. 2019 Nov 5;15:2631-2643
pubmed: 31807198
J Nat Prod. 2018 Jun 22;81(6):1444-1450
pubmed: 29878761
Mol Cancer. 2007 Apr 02;6:24
pubmed: 17407548
Philos Trans R Soc Lond B Biol Sci. 2019 Aug 19;374(1779):20180226
pubmed: 31431182
Biochem Pharmacol. 2013 Feb 1;85(3):426-38
pubmed: 23219522
Nat Rev Cancer. 2008 May;8(5):361-75
pubmed: 18432251
Cell Prolif. 2003 Jun;36(3):131-49
pubmed: 12814430
J Am Heart Assoc. 2016 Sep 26;5(9):
pubmed: 27671317
Autophagy. 2008 May;4(4):487-99
pubmed: 18305408
J Gen Physiol. 2016 Jun;147(6):451-65
pubmed: 27241698
Experientia. 1992 Dec 1;48(11-12):1162-4
pubmed: 1473583
Oncol Rep. 2014 Feb;31(2):581-8
pubmed: 24337105
Int J Mol Sci. 2016 Mar 02;17(3):327
pubmed: 26950115
Nat Rev Cancer. 2005 Jan;5(1):65-72
pubmed: 15630416
Antioxidants (Basel). 2021 Sep 30;10(10):
pubmed: 34679694
Int J Cancer. 2021 Feb 1;148(3):601-608
pubmed: 32706917
Int J Mol Sci. 2020 May 02;21(9):
pubmed: 32370233
Cancer Lett. 2010 Jan 28;287(2):142-9
pubmed: 19570606
J Asian Nat Prod Res. 2015;17(11):1065-72
pubmed: 26123159
Mini Rev Med Chem. 2011 Nov;11(13):1153-64
pubmed: 22353224
Cells. 2019 Sep 18;8(9):
pubmed: 31540530
J Asian Nat Prod Res. 2011 Jun;13(6):561-5
pubmed: 21623521
Drug Discov Today. 2008 Oct;13(19-20):894-901
pubmed: 18691670
Parasitol Res. 2011 Jul;109(1):231-6
pubmed: 21243506
Biomed Res Int. 2019 Apr 30;2019:6712536
pubmed: 31183372
PLoS One. 2017 Oct 10;12(10):e0184360
pubmed: 29016607
Microb Cell. 2020 Mar 12;7(6):146-159
pubmed: 32548177
Br J Pharmacol. 2011 Mar;162(6):1239-49
pubmed: 21091654
Malar J. 2018 Aug 15;17(1):296
pubmed: 30111328
Molecules. 2013 Apr 10;18(4):4192-208
pubmed: 23612472
Mol Cell. 2006 Jul 7;23(1):121-32
pubmed: 16818236
Antimicrob Agents Chemother. 2000 Jul;44(7):1943-53
pubmed: 10858359
Nature. 2007 Feb 1;445(7127):541-5
pubmed: 17237762
J Cancer Res Clin Oncol. 2009 Apr;135(4):507-14
pubmed: 18830626
Nat Prod Rep. 2004 Aug;21(4):449-77
pubmed: 15282630
Biochim Biophys Acta. 2016 Dec;1863(12):2977-2992
pubmed: 27646922
Oncogene. 2003 Nov 24;22(53):8619-27
pubmed: 14634623
Mar Drugs. 2019 Sep 26;17(10):
pubmed: 31561527
Oral Dis. 2009 Jul;15(5):328-35
pubmed: 19320840
Chem Rev. 2009 Jul;109(7):3012-43
pubmed: 19422222
Gut. 2006 Apr;55(4):519-28
pubmed: 16174661
Nat Prod Commun. 2012 Jun;7(6):685-92
pubmed: 22816285
Molecules. 2009 Sep 28;14(10):3844-50
pubmed: 19924033
Exp Hematol. 2003 Jun;31(6):446-54
pubmed: 12829019
J Clin Invest. 2013 Jan;123(1):315-28
pubmed: 23202731
J Biol Chem. 2007 Feb 9;282(6):3799-808
pubmed: 17130121
PLoS Negl Trop Dis. 2016 Dec 30;10(12):e0005268
pubmed: 28036393
J Biol Chem. 2003 Apr 18;278(16):14134-45
pubmed: 12571238
Drug Discov Today. 2010 Aug;15(15-16):668-78
pubmed: 20541036
Cancer Cell. 2018 Jun 11;33(6):985-1003.e7
pubmed: 29805077
J Nat Prod. 2021 Jan 22;84(1):37-45
pubmed: 33346651
Leukemia. 2010 Apr;24(4):679-86
pubmed: 20130602
Hum Exp Toxicol. 2012 Jun;31(6):539-49
pubmed: 21859781
Mem Inst Oswaldo Cruz. 2013 Apr;108(2):140-4
pubmed: 23579790
J Nat Prod. 2001 Jun;64(6):726-31
pubmed: 11421732
Curr Top Med Chem. 2001 Dec;1(6):529-39
pubmed: 11895129
J Clin Invest. 2020 Sep 1;130(9):4999-5010
pubmed: 32584793
Phytochemistry. 2009 Mar;70(4):546-53
pubmed: 19251287
Biochem Pharmacol. 2005 Jul 1;70(1):82-9
pubmed: 15894293
J Nat Prod. 2010 Mar 26;73(3):500-16
pubmed: 20187635
Oncogene. 2004 Apr 12;23(16):2797-808
pubmed: 15077143
J Am Chem Soc. 2018 Mar 28;140(12):4344-4353
pubmed: 29412652
Nat Prod Commun. 2011 Mar;6(3):315-21
pubmed: 21485266
Int J Oncol. 2018 Dec;53(6):2627-2636
pubmed: 30320372
J Biol Chem. 1998 Mar 6;273(10):5858-68
pubmed: 9488723
Chem Biol Interact. 2020 Oct 1;330:109167
pubmed: 32603660
Chem Pharm Bull (Tokyo). 2011;59(6):762-6
pubmed: 21628915
Int J Mol Sci. 2018 Jan 23;19(2):
pubmed: 29360760
Nat Rev Cancer. 2008 Apr;8(4):253-67
pubmed: 18354415