Advance in anti-cancer lead-compounds derived from natural products

WU Shanchao; SHENG Chunquan; ZHANG Wannian

doi:10.3969/j.issn.1006-0111.2014.05.005

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Volume 32 Issue 5

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2014 > 32(5): 337-341,371

WU Shanchao, SHENG Chunquan, ZHANG Wannian. Advance in anti-cancer lead-compounds derived from natural products[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(5): 337-341,371. doi: 10.3969/j.issn.1006-0111.2014.05.005

Citation:

WU Shanchao, SHENG Chunquan, ZHANG Wannian. Advance in anti-cancer lead-compounds derived from natural products[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(5): 337-341,371. doi: 10.3969/j.issn.1006-0111.2014.05.005

Advance in anti-cancer lead-compounds derived from natural products

doi: 10.3969/j.issn.1006-0111.2014.05.005

School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2013-03-11
Rev Recd Date: 2013-06-25

Abstract

Cancer is a serious threat to human life and health. Therefore, there is an emergent need to develop novel anti-cancer agents with new structural type, new mechanism of action and higher efficacy. Natural products had played a key role in the discovery of anticancer agents. The anti-cancer activity, mechanism of action, structure and activity relationship of several lead-compounds which were derived from natural products were summarized in this review.
- natural products,
- anti-cancer lead-compounds,
- anti-cancer activity,
- mechanism of action,
- structure and activity relationship

References

[1]	Newman DJ, Cragg GM. Natural products as sources of new drugs over the last 25 years[J]. J Nat Prod,2007, 70 (3):461-477.
[2]	Kessler JH, Mullauer FB, de Roo GM, et al. Broad in vitro efficacy of plant-derived betulinic acid against cell lines derived from the most prevalent human cancer types[J]. Cancer Lett,2007, 251 (1):132-145.
[3]	Zuco V, Supino R, Righetti SC, et al. Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells[J]. Cancer Lett,2002, 175 (1):17-25.
[4]	Chintharlapalli S, Papineni S, Ramaiah SK, et al. Betulinic acid inhibits prostate cancer growth through inhibition of specificity protein transcription factors[J]. Cancer Res,2007, 67 (6):2816-2823.
[5]	Mertens-Talcitt SU, Noratto GD, Li X, et al. Betulinic acid decreases ER-negative breast cancer cell growth in vitro and in vivo:role of Sp transcription factors and microRNA-27a:ZBTB10[J]. Mol Carcinog, 2012Mar7,doi: 10.1002/mc.21893.
[6]	Eichenmuller M, Hemmerlein B, Von Schweinits D, et al. Betulinic acid induces apoptosis and inhibits hedgehog signalling in rhabdomyosarcoma[J]. Br J Cancer, 2010, 103 (1):43-51.
[7]	Liu X, Jutooru I, Lei P, et al. Betulinic acid targets YY1 and ErbB2 through cannabinoid receptor-dependent disruption of microRNA-27a:ZBTB10 in breast cancer[J]. Mol Cancer Ther, 2012, 11 (7):1421-1431.
[8]	Kama E,Szoka L, Palka JA, et al. Betulinic acid inhibits the expression of hypoxia-inducible factor 1alpha and vascular endothelial growth factor in human endometrial adenocarcinoma cells[J]. Mol Cell Biochem, 2010, 340 (1-2):15-20.
[9]	Pandey MK, Sung B, Aggarwail BB, et al. Betulinic acid suppresses STAT3 activation pathway through induction of protein tyrosine phosphatase SHP-1 in human multiple myeloma cells[J]. Int J Cancer, 2010, 127 (2):282-292.
[10]	Liu Y, Luo W. Betulinic acid induces Bax/Bak-independent cytochrome C release in human nasopharyngeal carcinoma cells[J]. Mol Cells, 2012, 33 (5):517-524.
[11]	Yogeeswari P, Sriram D. Betulinic acid and its derivatives:a review on their biological properties[J]. Curr Med Chem, 2005, 12 (6):657-666.
[12]	Eiznhamer DA, Xu ZQ. Betulinic acid:a promising anticancer candidate[J]. I Drugs, 2004, 7 (4):359-373.
[13]	Chintharlli S, Papineni S, Lei P, et al. Betulinic acid inhibits colon cancer cell and tumor growth and induces proteasome-dependent and-independent downregulation of specificity proteins (Sp) transcription factors[J]. BMC Cancer, 2011, 11:371.
[14]	Mukheijee R, Kumar V, Srivastava SK, et al. Betulinic acid derivatives as anticancer agents:structure activity relationship[J]. Anticancer Agents Med Chem, 2006, 6 (3):271-279.
[15]	Urban M, Vlkm M, Dzubak P, et al. Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid[J]. Bioorg Med Chem, 2012, 20 (11):3666-3674.
[16]	Ahmad FB, Ghaffari Moghaddam M,Basri M, et al. Anticancer activity of 3-O-acylated betulinic acid derivatives obtained by enzymatic synthesis[J]. Biosci Biotechnol Biochem, 2010, 74 (5):1025-1029.
[17]	Kundu JK,Surh YJ. Cancer chemopreventive and therapeutic potential of resveratrol:mechanistic perspectives[J]. Cancer Lett, 2008, 269 (2):243-261.
[18]	Jang M, Cai L, Udeani GO, et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes[J]. Science, 1997, 275 (5297):218-220.
[19]	Kundu JK, Surh YJ. Molecular basis of chemoprevention by resveratrol:NF-kappaB and AP-1 as potential targets[J]. Mutat Res, 2004, 555 (1-2):65-80.
[20]	Garg AK, Buchholz TA, Aggarwal BB. Chemosensitization and radiosensitization of tumors by plant polyphenols[J]. Antioxid Redox Signal, 2005, 7 (11-12):1630-1647.
[21]	Bhardwaj A, Sethi G, Vadhan-Raj S, et al. Resveratrol inhibits proliferation, induces apoptosis, and overcomes chemoresistance through down-regulation of STAT3 and nuclear factor-kappaB-regulated antiapoptotic and cell survival gene products in human multiple myeloma cells[J]. Blood,2007, 109 (6):2293-2302.
[22]	Cai YJ, Wei QY, Fang JG, et al. The 3,4-dihydroxyl groups are important for trans-resveratrol analogs to exhibit enhanced antioxidant and apoptotic activities[J]. Anticancer Res, 2004, 24 (2B):999-1002.
[23]	Hung LM, Su MJ, Chu WK, et al. The protective effect of resveratrols on ischaemia-reperfusion injuries of rat hearts is correlated with antioxidant efficacy[J]. Br J Pharmacol, 2002, 135 (7):1627-1633.
[24]	Saiko P, Szakmary A, Jaeger W, et al. Resveratrol and its analogs:defense against cancer, coronary disease and neurodegenerative maladies or just a fad? [J]. Mutat Res, 2008, 658 (1-2):68-94.
[25]	Jiang GJ, Hu C. Evodiamine:a novel anti-cancer alkaloid from Evodia rutaecarpa[J]. Molecules, 2009, 14 (5):1852-1859.
[26]	Liao CH, Pan SL,Guh JH, et al.Antitumor mechanism of evodiamine, a constituent from Chinese herb Evodiae fructus, in human multiple-drug resistant breast cancer NCI/ADR-RES cells in vitro and in vivo[J]. Carcinogenesis, 2005, 26 (5):968-975.
[27]	Zhang C, Fan X, Xu X, et al. Evodiamine induces caspase-dependent apoptosis and S phase arrest in human colon lovo cells[J]. Anticancer Drugs, 2010, 21 (8):766-776.
[28]	Liao CH, Pan SL, Guh JH, et al. Antitumor mechanism of evodiamine, a constituent from Chinese herb Evodiae fructus, in human multiple-drug resistant breast cancer NCI/ADR-RES cells in vitro and in vivo[J]. Carcinogenesis, 2005, 26 (5):968-975.
[29]	Lee TJ, Kim EJ, Kim S, et al. Caspase-dependent and caspase-independent apoptosis induced by evodiamine in human leukemic U937 cells[J]. Mol Cancer Ther, 2006, 5 (9):2398-2407.
[30]	Takada Y, Kobaysshi Y, Aggarwal BB. Evodiamine abolishes constitutive and inducible NF-kappaB activation by inhibiting IkappaBalpha kinase activation, thereby suppressing NF-kappaB-regulated antiapoptotic and metastatic gene expression, up-regulating apoptosis, and inhibiting invasion[J]. J Biol Chem, 2005, 280 (17):17203-17212.
[31]	Yang ZG, Chen AQ, Liu B. Antiproliferation and apoptosis induced by evodiamine in human colorectal carcinoma cells (COLO-205)[J]. Chem Biodivers, 2009, 6 (6):924-933.
[32]	Huang H, Zhang Y, Liu X, et al. Acid sphingomyelinase contributes to evodiamine-induced apoptosis in human gastric cancer SGC-7901 cells[J]. DNA Cell Biol, 2011, 30 (6):407-412.
[33]	Rasul A, Yu B, Zhong L, et al. Cytotoxic effect of evodiamine in SGC-7901 human gastric adenocarcinoma cells via simultaneous induction of apoptosis and autophagy[J]. Oncol Rep, 2012, 27 (5):1481-1487.
[34]	Wei WT, Chen H, Wang ZH, et al. Enhanced antitumor efficacy of gemcitabine by evodiamine on pancreatic cancer via regulating PI3K/Akt pathway[J]. Int J Biol Sci, 2012, 8 (1):1-14.
[35]	Dong G, Sheng C, Wang S, et al. Selection of evodiamine as a novel topoisomerase I inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents[J]. Med Chem, 2010,53 (21):7521-7531.
[36]	Sheng C, Miao Z, Zhang W. New strategies in the discovery of novel non-camptothecin topoisomerase I inhibitors[J]. Curr Med Chem, 2011, 18(28):4389-4409.
[37]	Anand P, Sundaram C, Jhurani S, et al. Curcumin and cancer:an "old-age" disease with an "age-old" solution[J]. Cancer Lett, 2008, 267 (1):133-164.
[38]	Goel A, Kunnumakkara AB, Aggarwal BB. Curcumin as "Curecumin":from kitchen to clinic[J]. Biochem Pharmacol, 2008, 75 (4):787-809.
[39]	Aggarwal BB, Harikumar KB. Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases[J]. Int J Biochem Cell Biol, 2009, 41 (1):40-59.
[40]	Shishodia S, Singh T, Chaturvedi MM. Modulation of transcription factors by curcumin[J]. Adv Exp Med Biol, 2007, 595:127-148.
[41]	Qiu X, Liu Z, Shao WY, et al. Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors[J]. Bioorg Med Chem, 2008, 16(17):8035-8041.
[42]	Safavy A, Raisch KP, Mantena S, et al. Design and development of water-soluble curcumin conjugates as potential anticancer agents[J]. J Med Chem, 2007, 50(24):6284-6288.
[43]	Raj L, Ide T, Chrkar AU, et al. Selective killing of cancer cells by a small molecule targeting the stress response to ROS[J]. Nature, 2011, 475(7355):231-234.
[44]	Bazerra DP, Castro FO,Alves AP, et al. In vivo growth-inhibition of sarcoma 180 by piplartine and piperine, two alkaloid amides from Piper[J]. Braz J Med Biol Res, 2006, 39(6):801-807.
[45]	Bezerra DP, Militao GC, de Castro FO, et al.Piplartine induces inhibition of leukemia cell proliferation triggering both apoptosis and necrosis pathways[J]. Toxicol In Vitro, 2007, 21(1):1-8.
[46]	Golowine KV, Makhov PB, Teper E, et al. Piperlongumine induces rapid depletion of the androgen receptor in human prostate cancer cells[J]. Prostate, 2013, 73(1):23.
[47]	Bezeera DP, de Castro FO, Alves AP, et al. In vitro and in vivo antitumor effect of 5-FU combined with piplartine and piperine[J]. J Appl Toxicol, 2008, 28(2):156-163.

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通讯作者: 陈斌, [email protected]

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沈阳化工大学材料科学与工程学院沈阳 110142

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Advance in anti-cancer lead-compounds derived from natural products

School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2013-03-11

Rev Recd Date: 2013-06-25

Key words:

Abstract: Cancer is a serious threat to human life and health. Therefore, there is an emergent need to develop novel anti-cancer agents with new structural type, new mechanism of action and higher efficacy. Natural products had played a key role in the discovery of anticancer agents. The anti-cancer activity, mechanism of action, structure and activity relationship of several lead-compounds which were derived from natural products were summarized in this review.

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Reference (47)

[1]	Newman DJ, Cragg GM. Natural products as sources of new drugs over the last 25 years[J]. J Nat Prod,2007, 70 (3):461-477.
[2]	Kessler JH, Mullauer FB, de Roo GM, et al. Broad in vitro efficacy of plant-derived betulinic acid against cell lines derived from the most prevalent human cancer types[J]. Cancer Lett,2007, 251 (1):132-145.
[3]	Zuco V, Supino R, Righetti SC, et al. Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells[J]. Cancer Lett,2002, 175 (1):17-25.
[4]	Chintharlapalli S, Papineni S, Ramaiah SK, et al. Betulinic acid inhibits prostate cancer growth through inhibition of specificity protein transcription factors[J]. Cancer Res,2007, 67 (6):2816-2823.
[5]	Mertens-Talcitt SU, Noratto GD, Li X, et al. Betulinic acid decreases ER-negative breast cancer cell growth in vitro and in vivo:role of Sp transcription factors and microRNA-27a:ZBTB10[J]. Mol Carcinog, 2012Mar7,doi:10.1002/mc.21893.
[6]	Eichenmuller M, Hemmerlein B, Von Schweinits D, et al. Betulinic acid induces apoptosis and inhibits hedgehog signalling in rhabdomyosarcoma[J]. Br J Cancer, 2010, 103 (1):43-51.
[7]	Liu X, Jutooru I, Lei P, et al. Betulinic acid targets YY1 and ErbB2 through cannabinoid receptor-dependent disruption of microRNA-27a:ZBTB10 in breast cancer[J]. Mol Cancer Ther, 2012, 11 (7):1421-1431.
[8]	Kama E,Szoka L, Palka JA, et al. Betulinic acid inhibits the expression of hypoxia-inducible factor 1alpha and vascular endothelial growth factor in human endometrial adenocarcinoma cells[J]. Mol Cell Biochem, 2010, 340 (1-2):15-20.
[9]	Pandey MK, Sung B, Aggarwail BB, et al. Betulinic acid suppresses STAT3 activation pathway through induction of protein tyrosine phosphatase SHP-1 in human multiple myeloma cells[J]. Int J Cancer, 2010, 127 (2):282-292.
[10]	Liu Y, Luo W. Betulinic acid induces Bax/Bak-independent cytochrome C release in human nasopharyngeal carcinoma cells[J]. Mol Cells, 2012, 33 (5):517-524.
[11]	Yogeeswari P, Sriram D. Betulinic acid and its derivatives:a review on their biological properties[J]. Curr Med Chem, 2005, 12 (6):657-666.
[12]	Eiznhamer DA, Xu ZQ. Betulinic acid:a promising anticancer candidate[J]. I Drugs, 2004, 7 (4):359-373.
[13]	Chintharlli S, Papineni S, Lei P, et al. Betulinic acid inhibits colon cancer cell and tumor growth and induces proteasome-dependent and-independent downregulation of specificity proteins (Sp) transcription factors[J]. BMC Cancer, 2011, 11:371.
[14]	Mukheijee R, Kumar V, Srivastava SK, et al. Betulinic acid derivatives as anticancer agents:structure activity relationship[J]. Anticancer Agents Med Chem, 2006, 6 (3):271-279.
[15]	Urban M, Vlkm M, Dzubak P, et al. Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid[J]. Bioorg Med Chem, 2012, 20 (11):3666-3674.
[16]	Ahmad FB, Ghaffari Moghaddam M,Basri M, et al. Anticancer activity of 3-O-acylated betulinic acid derivatives obtained by enzymatic synthesis[J]. Biosci Biotechnol Biochem, 2010, 74 (5):1025-1029.
[17]	Kundu JK,Surh YJ. Cancer chemopreventive and therapeutic potential of resveratrol:mechanistic perspectives[J]. Cancer Lett, 2008, 269 (2):243-261.
[18]	Jang M, Cai L, Udeani GO, et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes[J]. Science, 1997, 275 (5297):218-220.
[19]	Kundu JK, Surh YJ. Molecular basis of chemoprevention by resveratrol:NF-kappaB and AP-1 as potential targets[J]. Mutat Res, 2004, 555 (1-2):65-80.
[20]	Garg AK, Buchholz TA, Aggarwal BB. Chemosensitization and radiosensitization of tumors by plant polyphenols[J]. Antioxid Redox Signal, 2005, 7 (11-12):1630-1647.
[21]	Bhardwaj A, Sethi G, Vadhan-Raj S, et al. Resveratrol inhibits proliferation, induces apoptosis, and overcomes chemoresistance through down-regulation of STAT3 and nuclear factor-kappaB-regulated antiapoptotic and cell survival gene products in human multiple myeloma cells[J]. Blood,2007, 109 (6):2293-2302.
[22]	Cai YJ, Wei QY, Fang JG, et al. The 3,4-dihydroxyl groups are important for trans-resveratrol analogs to exhibit enhanced antioxidant and apoptotic activities[J]. Anticancer Res, 2004, 24 (2B):999-1002.
[23]	Hung LM, Su MJ, Chu WK, et al. The protective effect of resveratrols on ischaemia-reperfusion injuries of rat hearts is correlated with antioxidant efficacy[J]. Br J Pharmacol, 2002, 135 (7):1627-1633.
[24]	Saiko P, Szakmary A, Jaeger W, et al. Resveratrol and its analogs:defense against cancer, coronary disease and neurodegenerative maladies or just a fad? [J]. Mutat Res, 2008, 658 (1-2):68-94.
[25]	Jiang GJ, Hu C. Evodiamine:a novel anti-cancer alkaloid from Evodia rutaecarpa[J]. Molecules, 2009, 14 (5):1852-1859.
[26]	Liao CH, Pan SL,Guh JH, et al.Antitumor mechanism of evodiamine, a constituent from Chinese herb Evodiae fructus, in human multiple-drug resistant breast cancer NCI/ADR-RES cells in vitro and in vivo[J]. Carcinogenesis, 2005, 26 (5):968-975.
[27]	Zhang C, Fan X, Xu X, et al. Evodiamine induces caspase-dependent apoptosis and S phase arrest in human colon lovo cells[J]. Anticancer Drugs, 2010, 21 (8):766-776.
[28]	Liao CH, Pan SL, Guh JH, et al. Antitumor mechanism of evodiamine, a constituent from Chinese herb Evodiae fructus, in human multiple-drug resistant breast cancer NCI/ADR-RES cells in vitro and in vivo[J]. Carcinogenesis, 2005, 26 (5):968-975.
[29]	Lee TJ, Kim EJ, Kim S, et al. Caspase-dependent and caspase-independent apoptosis induced by evodiamine in human leukemic U937 cells[J]. Mol Cancer Ther, 2006, 5 (9):2398-2407.
[30]	Takada Y, Kobaysshi Y, Aggarwal BB. Evodiamine abolishes constitutive and inducible NF-kappaB activation by inhibiting IkappaBalpha kinase activation, thereby suppressing NF-kappaB-regulated antiapoptotic and metastatic gene expression, up-regulating apoptosis, and inhibiting invasion[J]. J Biol Chem, 2005, 280 (17):17203-17212.
[31]	Yang ZG, Chen AQ, Liu B. Antiproliferation and apoptosis induced by evodiamine in human colorectal carcinoma cells (COLO-205)[J]. Chem Biodivers, 2009, 6 (6):924-933.
[32]	Huang H, Zhang Y, Liu X, et al. Acid sphingomyelinase contributes to evodiamine-induced apoptosis in human gastric cancer SGC-7901 cells[J]. DNA Cell Biol, 2011, 30 (6):407-412.
[33]	Rasul A, Yu B, Zhong L, et al. Cytotoxic effect of evodiamine in SGC-7901 human gastric adenocarcinoma cells via simultaneous induction of apoptosis and autophagy[J]. Oncol Rep, 2012, 27 (5):1481-1487.
[34]	Wei WT, Chen H, Wang ZH, et al. Enhanced antitumor efficacy of gemcitabine by evodiamine on pancreatic cancer via regulating PI3K/Akt pathway[J]. Int J Biol Sci, 2012, 8 (1):1-14.
[35]	Dong G, Sheng C, Wang S, et al. Selection of evodiamine as a novel topoisomerase I inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents[J]. Med Chem, 2010,53 (21):7521-7531.
[36]	Sheng C, Miao Z, Zhang W. New strategies in the discovery of novel non-camptothecin topoisomerase I inhibitors[J]. Curr Med Chem, 2011, 18(28):4389-4409.
[37]	Anand P, Sundaram C, Jhurani S, et al. Curcumin and cancer:an "old-age" disease with an "age-old" solution[J]. Cancer Lett, 2008, 267 (1):133-164.
[38]	Goel A, Kunnumakkara AB, Aggarwal BB. Curcumin as "Curecumin":from kitchen to clinic[J]. Biochem Pharmacol, 2008, 75 (4):787-809.
[39]	Aggarwal BB, Harikumar KB. Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases[J]. Int J Biochem Cell Biol, 2009, 41 (1):40-59.
[40]	Shishodia S, Singh T, Chaturvedi MM. Modulation of transcription factors by curcumin[J]. Adv Exp Med Biol, 2007, 595:127-148.
[41]	Qiu X, Liu Z, Shao WY, et al. Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors[J]. Bioorg Med Chem, 2008, 16(17):8035-8041.
[42]	Safavy A, Raisch KP, Mantena S, et al. Design and development of water-soluble curcumin conjugates as potential anticancer agents[J]. J Med Chem, 2007, 50(24):6284-6288.
[43]	Raj L, Ide T, Chrkar AU, et al. Selective killing of cancer cells by a small molecule targeting the stress response to ROS[J]. Nature, 2011, 475(7355):231-234.
[44]	Bazerra DP, Castro FO,Alves AP, et al. In vivo growth-inhibition of sarcoma 180 by piplartine and piperine, two alkaloid amides from Piper[J]. Braz J Med Biol Res, 2006, 39(6):801-807.
[45]	Bezerra DP, Militao GC, de Castro FO, et al.Piplartine induces inhibition of leukemia cell proliferation triggering both apoptosis and necrosis pathways[J]. Toxicol In Vitro, 2007, 21(1):1-8.
[46]	Golowine KV, Makhov PB, Teper E, et al. Piperlongumine induces rapid depletion of the androgen receptor in human prostate cancer cells[J]. Prostate, 2013, 73(1):23.
[47]	Bezeera DP, de Castro FO, Alves AP, et al. In vitro and in vivo antitumor effect of 5-FU combined with piplartine and piperine[J]. J Appl Toxicol, 2008, 28(2):156-163.

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Advance in anti-cancer lead-compounds derived from natural products

doi: 10.3969/j.issn.1006-0111.2014.05.005

Abstract

References

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通讯作者: 陈斌, [email protected]

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