Part 1: Occurrence of Racemic Natural Products and Their Biological Activities
Keywords:
Natural Products, Racemic mixture, Racemate, Biological activityAbstract
Normally, natural products are optically active compounds with a single enantiomer because they are biosynthesized from enzymatic catalysis. However, there are numbers of natural products isolated as a racemic mixture, i.e., the presence of the two enantiomers. This review provides information of some racemic natural products isolated from bio-resources. Biological activities of racemic natural products are also discussed.
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References
1. Department of Medical Services. Cancer; Thailand Medical Services Profile 2011-2014 First Edition. Ministry of Public Health: Department of Medical Services; 2014. https://www.hiso.or.th/hiso/picture/reportHealth/report/report8_6.pdf.
2. National Cancer Institute. Cancer Registry Unit NCIT, Cancer in Thailand 2018.; 2018.
3. National Cancer Institute, Department of Medical Services. National cancer control programmes (พ.ศ. 2556-2560).Nonthaburi: National Cancer Institute, Department of Medical Services; 2013.
4. Hunter KW, Crawford NP, Alsarraj J. Mechanisms of metastasis. Breast Cancer Res. 2008;10(1):S2. doi:10.1186/bcr1988
5. Otake S, Goto T. Stereotactic Radiotherapy for Oligometastasis. Cancers. 2019;11(2). doi:10.3390/cancers11020133
6. Hellman S, Weichselbaum RR. Oligometastases. J Clin Oncol. 1995;13(1):8-10. doi:10.1200/JCO.1995.13.1.8
7. Milano MT, Katz AW, Zhang H, Okunieff P. Oligometastases treated with stereotactic body radiotherapy: long-term follow-up of prospective study. Int J Radiat Oncol Biol Phys. 2012;83(3):878-886. doi:10.1016/j.ijrobp.2011.08.036
8. Palma DA, Salama JK, Lo SS, et al. The oligometastatic state - separating truth from wishful thinking. Nat Rev Clin Oncol. 2014;11(9):549-557. doi:10.1038/nrclinonc.2014.96
9. Niibe Y, Hayakawa K. Oligometastases and Oligo-recurrence: The New Era of Cancer Therapy. Jpn J Clin Oncol. 2010;40(2):107-111. doi:10.1093/jjco/hyp167
10. Ning MS, Gomez DR, Heymach JV, Swisher SG. Stereotactic ablative body radiation for oligometastatic and oligoprogressive disease. Transl Lung Cancer Res. 2019;8(1):97-106. doi:10.21037/tlcr.2018.09.21
11. Rabassa L, Maria L. Oligometastatic cancer: A curable disease stage. Rep Pract Oncol Radiother. 2013;18:S25-S26. doi:10.1016/j.rpor.2013.04.011
12. Andrews DW, Scott CB, Sperduto PW, et al. Whole brain radiation therapy with or without stereotactic radiosurgery boost for patients with one to three brain metastases: phase III results of the RTOG 9508 randomised trial. The Lancet. 2004;363(9422):1665-1672. doi:10.1016/S0140-6736(04)16250-8
13. Ruers T, Punt C, Van Coevorden F, et al. Radiofrequency ablation combined with systemic treatment versus systemic treatment alone in patients with non-resectable colorectal liver metastases: a randomized EORTC Intergroup phase II study (EORTC 40004). Ann Oncol. 2012;23(10):2619-2626. doi:10.1093/annonc/mds053
14. Ruers T, Van Coevorden F, Punt CJA, et al. Local Treatment of Unresectable Colorectal Liver Metastases: Results of a Randomized Phase II Trial. JNCI J Natl Cancer Inst. 2017;109(9). doi:10.1093/jnci/djx015
15. Gomez DR, Blumenschein GR, Lee JJ, et al. Local consolidative therapy versus maintenance therapy or observation for patients with oligometastatic non-small-cell lung cancer without progression after first-line systemic therapy: a multicentre, randomised, controlled, phase 2 study. Lancet Oncol. 2016;17(12):1672-1682. doi:10.1016/S1470-2045(16)30532-0
16. Gomez D, Tang C, Zhang J, et al. Local consolidative therapy vs. Maintenance therapy or observation for patients with oligometastatic non–small-cell lung cancer: Long-term results of a multi-institutional, phase II, randomized study. J Clin Oncol. 2019;37(18):1558-1565. doi:10.1200/JCO.19.00201
17. Iyengar P, Wardak Z, Gerber DE, et al. Consolidative Radiotherapy for Limited Metastatic Non–Small-Cell Lung Cancer: A Phase 2 Randomized Clinical Trial. JAMA Oncol. 2018;4(1):e173501-e173501. doi:10.1001/jamaoncol.2017.3501
18. Palma DA, Olson R, Harrow S, et al. Stereotactic ablative radiotherapy versus standard of care palliative treatment in patients with oligometastatic cancers (SABR-COMET): a randomised, phase 2, open-label trial. The Lancet. 2019;393(10185):2051-2058. doi:10.1016/S0140-6736(18)32487-5
19. Benson AB III, VAA-HM. NCCN Clinical Practice Guidelines in Oncology: Colon Cancer. Version 3.2019. National Comprehensive Cancer Network. https://www.nccn.org/professionals/physician_gls/pdf/colon.pdf. Published 2019.
20. Folprecht G, Grothey A, Alberts S, Raab H-R, Köhne C-H. Neoadjuvant treatment of unresectable colorectal liver metastases: correlation between tumour response and resection rates. Ann Oncol Off J Eur Soc Med Oncol. 2005;16(8):1311-1319. doi:10.1093/annonc/mdi246
21. van der Pool AEM, Méndez Romero A, Wunderink W, et al. Stereotactic body radiation therapy for colorectal liver metastases. Br J Surg. 2010;97(3):377-382. doi:10.1002/bjs.6895
22. Rusthoven KE, Kavanagh BD, Cardenes H, et al. Multi-institutional phase I/II trial of stereotactic body radiation therapy for liver metastases. J Clin Oncol Off J Am Soc Clin Oncol. 2009;27(10):1572-1578. doi:10.1200/JCO.2008.19.6329
23. Rule W, Timmerman R, Tong L, et al. Phase I dose-escalation study of stereotactic body radiotherapy in patients with hepatic metastases. Ann Surg Oncol. 2011;18(4):1081-1087. doi:10.1245/s10434-010-1405-5
24. Wulf J, Guckenberger M, Haedinger U, et al. Stereotactic radiotherapy of primary liver cancer and hepatic metastases. Acta Oncol Stockh Swed. 2006;45(7):838-847. doi:10.1080/02841860600904821
25. Vautravers-Dewas C, Dewas S, Bonodeau F, et al. Image-guided robotic stereotactic body radiation therapy for liver metastases: is there a dose response relationship? Int J Radiat Oncol Biol Phys. 2011;81(3):e39-47. doi:10.1016/j.ijrobp.2010.12.047
26. Takeda A, Sanuki N, Kunieda E. Role of stereotactic body radiotherapy for oligometastasis from colorectal cancer. World J Gastroenterol WJG. 2014;20(15):4220-4229. doi:10.3748/wjg.v20.i15.4220
27. Welter S, Jacobs J, Krbek T, Krebs B, Stamatis G. Long-term survival after repeated resection of pulmonary metastases from colorectal cancer. Ann Thorac Surg. 2007;84(1):203-210. doi:10.1016/j.athoracsur.2007.03.028
28. De Giacomo T, Rendina EA, Venuta F, Ciccone AM, Coloni GF. Thoracoscopic resection of solitary lung metastases from colorectal cancer is a viable therapeutic option. Chest. 1999;115(5):1441-1443. doi:10.1378/chest.115.5.1441
29. Welter S, Theegarten D, Trarbach T, Maletzki F, Stamatis G, Tötsch M. Safety distance in the resection of colorectal lung metastases: a prospective evaluation of satellite tumor cells with immunohistochemistry. J Thorac Cardiovasc Surg. 2011;141(5):1218-1222. doi:10.1016/j.jtcvs.2010.08.089
30. Norihisa Y, Nagata Y, Takayama K, et al. Stereotactic body radiotherapy for oligometastatic lung tumors. Int J Radiat Oncol Biol Phys. 2008;72(2):398-403. doi:10.1016/j.ijrobp.2008.01.002
31. Guckenberger M, Wulf J, Mueller G, et al. Dose-response relationship for image-guided stereotactic body radiotherapy of pulmonary tumors: relevance of 4D dose calculation. Int J Radiat Oncol Biol Phys. 2009;74(1):47-54. doi:10.1016/j.ijrobp.2008.06.1939
32. Ernst-Stecken A, Lambrecht U, Mueller R, Sauer R, Grabenbauer G. Hypofractionated stereotactic radiotherapy for primary and secondary intrapulmonary tumors: first results of a phase I/II study. Strahlenther Onkol Organ Dtsch Rontgengesellschaft Al. 2006;182(12):696-702. doi:10.1007/s00066-006-1577-x
33. Widder J, Klinkenberg TJ, Ubbels JF, Wiegman EM, Groen HJM, Langendijk JA. Pulmonary oligometastases: metastasectomy or stereotactic ablative radiotherapy? Radiother Oncol J Eur Soc Ther Radiol Oncol. 2013;107(3):409-413. doi:10.1016/j.radonc.2013.05.024
2. National Cancer Institute. Cancer Registry Unit NCIT, Cancer in Thailand 2018.; 2018.
3. National Cancer Institute, Department of Medical Services. National cancer control programmes (พ.ศ. 2556-2560).Nonthaburi: National Cancer Institute, Department of Medical Services; 2013.
4. Hunter KW, Crawford NP, Alsarraj J. Mechanisms of metastasis. Breast Cancer Res. 2008;10(1):S2. doi:10.1186/bcr1988
5. Otake S, Goto T. Stereotactic Radiotherapy for Oligometastasis. Cancers. 2019;11(2). doi:10.3390/cancers11020133
6. Hellman S, Weichselbaum RR. Oligometastases. J Clin Oncol. 1995;13(1):8-10. doi:10.1200/JCO.1995.13.1.8
7. Milano MT, Katz AW, Zhang H, Okunieff P. Oligometastases treated with stereotactic body radiotherapy: long-term follow-up of prospective study. Int J Radiat Oncol Biol Phys. 2012;83(3):878-886. doi:10.1016/j.ijrobp.2011.08.036
8. Palma DA, Salama JK, Lo SS, et al. The oligometastatic state - separating truth from wishful thinking. Nat Rev Clin Oncol. 2014;11(9):549-557. doi:10.1038/nrclinonc.2014.96
9. Niibe Y, Hayakawa K. Oligometastases and Oligo-recurrence: The New Era of Cancer Therapy. Jpn J Clin Oncol. 2010;40(2):107-111. doi:10.1093/jjco/hyp167
10. Ning MS, Gomez DR, Heymach JV, Swisher SG. Stereotactic ablative body radiation for oligometastatic and oligoprogressive disease. Transl Lung Cancer Res. 2019;8(1):97-106. doi:10.21037/tlcr.2018.09.21
11. Rabassa L, Maria L. Oligometastatic cancer: A curable disease stage. Rep Pract Oncol Radiother. 2013;18:S25-S26. doi:10.1016/j.rpor.2013.04.011
12. Andrews DW, Scott CB, Sperduto PW, et al. Whole brain radiation therapy with or without stereotactic radiosurgery boost for patients with one to three brain metastases: phase III results of the RTOG 9508 randomised trial. The Lancet. 2004;363(9422):1665-1672. doi:10.1016/S0140-6736(04)16250-8
13. Ruers T, Punt C, Van Coevorden F, et al. Radiofrequency ablation combined with systemic treatment versus systemic treatment alone in patients with non-resectable colorectal liver metastases: a randomized EORTC Intergroup phase II study (EORTC 40004). Ann Oncol. 2012;23(10):2619-2626. doi:10.1093/annonc/mds053
14. Ruers T, Van Coevorden F, Punt CJA, et al. Local Treatment of Unresectable Colorectal Liver Metastases: Results of a Randomized Phase II Trial. JNCI J Natl Cancer Inst. 2017;109(9). doi:10.1093/jnci/djx015
15. Gomez DR, Blumenschein GR, Lee JJ, et al. Local consolidative therapy versus maintenance therapy or observation for patients with oligometastatic non-small-cell lung cancer without progression after first-line systemic therapy: a multicentre, randomised, controlled, phase 2 study. Lancet Oncol. 2016;17(12):1672-1682. doi:10.1016/S1470-2045(16)30532-0
16. Gomez D, Tang C, Zhang J, et al. Local consolidative therapy vs. Maintenance therapy or observation for patients with oligometastatic non–small-cell lung cancer: Long-term results of a multi-institutional, phase II, randomized study. J Clin Oncol. 2019;37(18):1558-1565. doi:10.1200/JCO.19.00201
17. Iyengar P, Wardak Z, Gerber DE, et al. Consolidative Radiotherapy for Limited Metastatic Non–Small-Cell Lung Cancer: A Phase 2 Randomized Clinical Trial. JAMA Oncol. 2018;4(1):e173501-e173501. doi:10.1001/jamaoncol.2017.3501
18. Palma DA, Olson R, Harrow S, et al. Stereotactic ablative radiotherapy versus standard of care palliative treatment in patients with oligometastatic cancers (SABR-COMET): a randomised, phase 2, open-label trial. The Lancet. 2019;393(10185):2051-2058. doi:10.1016/S0140-6736(18)32487-5
19. Benson AB III, VAA-HM. NCCN Clinical Practice Guidelines in Oncology: Colon Cancer. Version 3.2019. National Comprehensive Cancer Network. https://www.nccn.org/professionals/physician_gls/pdf/colon.pdf. Published 2019.
20. Folprecht G, Grothey A, Alberts S, Raab H-R, Köhne C-H. Neoadjuvant treatment of unresectable colorectal liver metastases: correlation between tumour response and resection rates. Ann Oncol Off J Eur Soc Med Oncol. 2005;16(8):1311-1319. doi:10.1093/annonc/mdi246
21. van der Pool AEM, Méndez Romero A, Wunderink W, et al. Stereotactic body radiation therapy for colorectal liver metastases. Br J Surg. 2010;97(3):377-382. doi:10.1002/bjs.6895
22. Rusthoven KE, Kavanagh BD, Cardenes H, et al. Multi-institutional phase I/II trial of stereotactic body radiation therapy for liver metastases. J Clin Oncol Off J Am Soc Clin Oncol. 2009;27(10):1572-1578. doi:10.1200/JCO.2008.19.6329
23. Rule W, Timmerman R, Tong L, et al. Phase I dose-escalation study of stereotactic body radiotherapy in patients with hepatic metastases. Ann Surg Oncol. 2011;18(4):1081-1087. doi:10.1245/s10434-010-1405-5
24. Wulf J, Guckenberger M, Haedinger U, et al. Stereotactic radiotherapy of primary liver cancer and hepatic metastases. Acta Oncol Stockh Swed. 2006;45(7):838-847. doi:10.1080/02841860600904821
25. Vautravers-Dewas C, Dewas S, Bonodeau F, et al. Image-guided robotic stereotactic body radiation therapy for liver metastases: is there a dose response relationship? Int J Radiat Oncol Biol Phys. 2011;81(3):e39-47. doi:10.1016/j.ijrobp.2010.12.047
26. Takeda A, Sanuki N, Kunieda E. Role of stereotactic body radiotherapy for oligometastasis from colorectal cancer. World J Gastroenterol WJG. 2014;20(15):4220-4229. doi:10.3748/wjg.v20.i15.4220
27. Welter S, Jacobs J, Krbek T, Krebs B, Stamatis G. Long-term survival after repeated resection of pulmonary metastases from colorectal cancer. Ann Thorac Surg. 2007;84(1):203-210. doi:10.1016/j.athoracsur.2007.03.028
28. De Giacomo T, Rendina EA, Venuta F, Ciccone AM, Coloni GF. Thoracoscopic resection of solitary lung metastases from colorectal cancer is a viable therapeutic option. Chest. 1999;115(5):1441-1443. doi:10.1378/chest.115.5.1441
29. Welter S, Theegarten D, Trarbach T, Maletzki F, Stamatis G, Tötsch M. Safety distance in the resection of colorectal lung metastases: a prospective evaluation of satellite tumor cells with immunohistochemistry. J Thorac Cardiovasc Surg. 2011;141(5):1218-1222. doi:10.1016/j.jtcvs.2010.08.089
30. Norihisa Y, Nagata Y, Takayama K, et al. Stereotactic body radiotherapy for oligometastatic lung tumors. Int J Radiat Oncol Biol Phys. 2008;72(2):398-403. doi:10.1016/j.ijrobp.2008.01.002
31. Guckenberger M, Wulf J, Mueller G, et al. Dose-response relationship for image-guided stereotactic body radiotherapy of pulmonary tumors: relevance of 4D dose calculation. Int J Radiat Oncol Biol Phys. 2009;74(1):47-54. doi:10.1016/j.ijrobp.2008.06.1939
32. Ernst-Stecken A, Lambrecht U, Mueller R, Sauer R, Grabenbauer G. Hypofractionated stereotactic radiotherapy for primary and secondary intrapulmonary tumors: first results of a phase I/II study. Strahlenther Onkol Organ Dtsch Rontgengesellschaft Al. 2006;182(12):696-702. doi:10.1007/s00066-006-1577-x
33. Widder J, Klinkenberg TJ, Ubbels JF, Wiegman EM, Groen HJM, Langendijk JA. Pulmonary oligometastases: metastasectomy or stereotactic ablative radiotherapy? Radiother Oncol J Eur Soc Ther Radiol Oncol. 2013;107(3):409-413. doi:10.1016/j.radonc.2013.05.024
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Published
2020-01-02
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Kittakoop P. Part 1: Occurrence of Racemic Natural Products and Their Biological Activities. J Chulabhorn Royal Acad [internet]. 2020 Jan. 2 [cited 2025 Dec. 27];1(2):53-66. available from: https://he02.tci-thaijo.org/index.php/jcra/article/view/225218
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