New Macrocyclic Diterpenes From Euphorbia Connata Boiss. With Cytotoxic Activities on Human Breast Cancer Cell Lines

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):

Share this content! On (X network) By

New Macrocyclic Diterpenes From Euphorbia Connata Boiss. With Cytotoxic Activities on Human Breast Cancer Cell Lines Publisher Pubmed

Shadi S¹ ; Saeidi H¹ ; Ghanadian M^{2, 3} ; Rahimnejad MR¹ ; Aghaei M³ ; Ayatollahi SM⁴ ; Iqbal Choudhary M^{5, 6}

Show Affiliations

1. Department of Biology, Faculty of Science, University of Isfahan, Isfahan, Iran
2. Isfahan Pharmaceutical Sciences Research Center, Isfahan University of Medical Sciences, Isfahan, Iran
3. Isfahan Faculty of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Hezar Jerib Ave., P.O. Box 81746-73461, Isfahan, Iran
4. Phytochemistry Research Center and School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran
5. Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
6. Department of Biochemistry, Faculty of Science, King Abdulaziz University, Jeddah, 214421, Saudi Arabia

Source: Natural Product Research Published:2016

Abstract

Acetone:chloroform (1:2) extract of the aerial parts of Euphorbia connata Boiss. (Euphorbiaceae) was investigated for its diterpenoids. This led to the isolation of one known and two new diterpenes, belonging to the pentahydroxy-13(17)-epoxy-8,10(18)-myrsinadiene and tetrahydroxy-5,6-epoxy-14-oxo-jatropha-11(E)-ene classes. The structures were elucidated based on 13C and 1H NMR as well as 2D NMR, IR and MS spectra and the cytotoxicity for compounds 1-3 were evaluated by using MTT assay against two human breast cancer cell lines. Myrsinane-type compounds - 3,7,14,15-tetraacetyl-5-propanoyl-13(17)-epoxy-8,10(18)-myrsinadiene (1) and 3,7,10,14,15-pentaacetyl-5-butanoyl-13,17-epoxy-8-myrsinene (2) - exhibited moderate inhibitory effects, with IC50 values of 24.53 ± 3.39 and 26.67 ± 1.41 μM against the MDA-MB cell line, and 37.73 ± 3.41 and 34.57 ± 2.12 μM against the MCF-7 cell line, respectively. Jatrophane-type diterpene - 5,6-epoxy-8,9,15-triacetyl-3-benzoyl-14-oxo-jatropha-11(E)-ene (3) - showed weak cytotoxicity, with IC50 values of 55.67 ± 7.09 μM against MDA-MB, and moderate cytotoxicity with IC50 values of 24.33 ± 3.21 μM against MCF-7 cell line. © 2014 Taylor & Francis.

Related Docs

View other Related Docs

1. New Jatrophane Diterpenes From Euphorbia Osyridea With Proapoptotic Effects on Ovarian Cancer Cells, Phytochemistry Letters (2015)

2. Diterpenoids From Euphorbia Gedrosiaca As Potential Anti-Proliferative Agents Against Breast Cancer Cells, Metabolites (2023)

3. 6(17)-Epoxylathyrane Diterpenes From Euphorbia Sogdiana Popov With Cytotoxic Activity, Fitoterapia (2016)

4. Unusual Ingenoids From Euphorbia Erythradenia Bioss. With Pro-Apoptotic Effects, Fitoterapia (2013)

5. Discovery of New 13(17)-Epoxymyrsinane Diterpenes From Aerial Flowering Parts of Euphorbia Spinidens Bornm. Ex Prokh. With Proapoptotic Activities Against Human Bladder Cancer Ej138 Cells, Natural Product Research (2024)

6. Cytotoxicity and Apoptosis Assay of Novel Cyclomyrsinol Diterpenes Against Breast Cancer Cell Lines, World Journal of Traditional Chinese Medicine (2022)

7. Malleatin a and B: New Premyrsine-Type Diterpenes From Euphorbia Malleata With Cytotoxic Effects Against A2780 Wild and A2780 R-Cis Ovarian Cancer Cell Lines in Mono or Combination Treatment With Cisplatin, Iranian Journal of Pharmaceutical Research (2024)

8. Jatrophane and Rearranged Jatrophane-Type Diterpenes: Biogenesis, Structure, Isolation, Biological Activity and Sars (1984–2019), Phytochemistry Reviews (2020)

Experts (# of related papers)

View all Related Experts

Mustafa Ghanadian (48)

Mahmoud Aghaei (22)

Other Related Docs

9. Kopetdaghinanes, Pro-Apoptotic Hemiacetialic Cyclomyrsinanes From Euphorbia Kopetdaghi, Fitoterapia (2020)

10. New Tigliane-Type Diterpenoids From Euphorbia Aellenii Rech. F. With Immunomodulatory Activity, Research in Pharmaceutical Sciences (2011)

11. New Cyclomyrsinol Diterpenes From Euphorbia Aellenii With Their Immunomodulatory Effects, Journal of Asian Natural Products Research (2013)

12. Myrsinane-Type Diterpenes From Euphorbia Gedrosiaca With Cell Growth Inhibitory Activity and Apoptotic Effects on Melanoma Cancer Cells, Fitoterapia (2022)

13. New Immunosuppressive Cyclomyrsinol Diterpenes From Euphorbia Kopetdaghi Prokh, Natural Product Research (2013)

14. Cytotoxic Activities of Euphorbia Kopetdaghi Against Ovcar-3 and Ej-138 Cell Lines, Journal of HerbMed Pharmacology (2015)

15. A New Taraxastane Triterpene From Euphorbia Denticulata With Cytotoxic Activity Against Prostate Cancer Cells, Iranian Journal of Pharmaceutical Research (2018)

16. New Cytotoxic Premyrsinane-Type Diterpenes From Euphorbia Aleppica Against Breast Cancer Cells, Iranian Journal of Pharmaceutical Research (2022)

17. Cytotoxicity and Apoptosis Inducing Effects of Some Lathyrane and Tigliane Diterpenes Against Breast Cancer Cell Lines, Traditional and Integrative Medicine (2021)

18. New Diterpene Compound From Euphorbia Connate Boiss., 3,7,14,15-Tetraacetyl-5-Propanoyl-13(17)-Epoxy-8,10(18)-Myrsinadiene, Inhibits the Growth of Ovarian Cancer Cells by Promoting Mitochondrial-Mediated Apoptosis, Nutrition and Cancer (2021)

19. New Mirsinane-Type Diterpenes From Euphorbia Microsciadia Boiss. With Inhibitory Effect on Vegf-Induced Angiogenesis, Journal of Natural Medicines (2013)

20. Pentacyclic Triterpenes in Euphorbia Microsciadia With Their T-Cell Proliferation Activity, Iranian Journal of Pharmaceutical Research (2011)

21. Obtusifoliol Related Steroids From Euphorbia Sogdiana With Cell Growth Inhibitory Activity and Apoptotic Effects on Breast Cancer Cells (Mcf-7 and Mda-Mb231), Steroids (2016)

22. New Myrsinane-Type Diterpenoids From Euphorbia Aellenii Rech. F. With Their Immunomodulatory Activity, Journal of Asian Natural Products Research (2010)

23. Phytochemical Study of Euphorbia Turcomanica Boiss., Metabolites (2022)

24. Macrocyclic Diterpenoids From the Iranian Plant Euphorbia Bungei Boiss., Fitoterapia (2011)

25. Cyclomyrsinane and Premyrsinane Diterpenes From Euphorbia Sogdiana Popov, Tetrahedron (2016)

26. Sesquiterpenes and Flavonoids of Anthemis Odontostephana Var. Odontostephana, Chemistry of Natural Compounds (2015)

27. Triterpenes and Steroids From Euphorbia Denticulata Lam. With Anti-Herpes Symplex Virus Activity, Iranian Journal of Pharmaceutical Research (2013)

28. Cycloartanes From Euphorbia Aellenii Rech. F. and Their Antiproliferative Activity, Iranian Journal of Pharmaceutical Research (2011)

29. Bioactivity-Guided Isolation of New Antiproliferative Compounds From Juniperus Foetidissima Willd, Natural Product Research (2016)

30. Phytochemical Analysis of Holothuria Leucospilota, a Sea Cucumber From Persian Gulf, Research in Pharmaceutical Sciences (2019)

31. Tamec: A New Analogue of Cyclomyrsinol Diterpenes Decreases Anxiety- and Depression-Like Behaviors in a Mouse Model of Multiple Sclerosis, Neurological Research (2017)

32. Two New Lathyrane Type Diterpenoids From Euphorbia Aellenii, Fitoterapia (2010)

33. Phytochemical Study of Seriphidium Khorassanicum (Syn. Artemisia Khorassanica) Aerial Parts: Sesquiterpene Lactones With Anti-Protozoal Activity, Natural Product Research (2022)

34. Neuropharmacological Potential of Diterpenoid Alkaloids, Pharmaceuticals (2023)

35. Triterpene Constituents of Euphorbia Erythradenia Bioss. and Their Anti-Hiv Activity, Iranian Journal of Pharmaceutical Research (2016)

36. Cytotoxic Effects of Chloroform and Hydroalcoholic Extracts of Aerial Parts of Cuscuta Chinensis and Cuscuta Epithymum on Hela, Ht29 and Mda-Mb-468 Tumor Cells, Research in Pharmaceutical Sciences (2014)

37. Two New Dammarane Triterpenes Isolated From Cleome Khorassanica Bunge & Bien With Cytotoxicity Against Du-145 and Lncap Prostate Cancer Cell Lines, Journal of Asian Natural Products Research (2020)

38. Biological Screening of Euphorbia Aellenii, Iranian Journal of Pharmaceutical Research (2010)

39. Main Phenolic Compound of Petals of Echium Amoenum Fisch. and C.A. Mey., a Famous Medicinal Plant of Iran, Daru (2005)

40. Pimpinelol, a Novel Atypical Sesquiterpene Lactone From Pimpinella Haussknechtii Fruits With Evaluation of Endoplasmic Reticulum Stress in Breast Cancer Cells, Fitoterapia (2018)

41. Evaluation of the Anti-Tuberculosis and Cytotoxic Potential of the Seaweed Padina Australis, Iranian Journal of Pharmaceutical Sciences (2020)

42. Novel 16,17-Epoxy-23-Methylergostane Derivative From Sinularia Variabilis, a Soft Coral From the Persian Gulf, With Apoptotic Activities Against Breast Cancer Cell Lines, Natural Product Research (2022)

43. Suppressive Role of Viola Odorata Extract on Malignant Characters of Mammosphere-Derived Breast Cancer Stem Cells, Clinical and Translational Oncology (2020)

44. Phytochemical Analysis of Daphne Pontica L. Stems With Their Pro-Apoptotic Properties Against Du-145 and Lncap Prostate Cancer Cells, DARU, Journal of Pharmaceutical Sciences (2022)

45. Flavonol Glycosides From Euphorbia Microsciadia Bioss. With Their Immunomodulatory Activities, Iranian Journal of Pharmaceutical Research (2012)

46. Sesquiterpene Lactones From Shoot Culture of Artemisia Aucheri With Cytotoxicity Against Prostate and Breast Cancer Cells, Research in Pharmaceutical Sciences (2019)

47. Jatropha-6(17),11 E -Diene Class Derivatives Induce Apoptosis Effects in Ovcar-3 and Caov-4 Ovarian Cancer Cell Lines Via a Mitochondrial Pathway, Biochemistry and Cell Biology (2017)

48. Cycloartane Triterpenoids From Euphorbia Macrostegia With Their Cytotoxicity Against Mda-Mb48 and Mcf-7 Cancer Cell Lines, Iranian Journal of Pharmaceutical Research (2014)

49. New 6(17)-Epoxylathyrane Diterpene: Aellinane From Euphorbia Aellenii Induces Apoptosis Via Mitochondrial Pathway in Ovarian Cancer Cell Line, Toxicology Mechanisms and Methods (2017)

50. The Cytotoxic and Pro-Apoptotic Effects of Various Extracts of Allium Giganteum on Mcf-7 and Hela Cell Lines, Journal of Isfahan Medical School (2021)

Style	Citing Format
MLA	Shadi S, et al.. "New Macrocyclic Diterpenes From Euphorbia Connata Boiss. With Cytotoxic Activities on Human Breast Cancer Cell Lines." Natural Product Research, vol. 29, no. 7, 2016, pp. 607-614.
APA	Shadi S, Saeidi H, Ghanadian M, Rahimnejad MR, Aghaei M, Ayatollahi SM, Iqbal Choudhary M (2016). New Macrocyclic Diterpenes From Euphorbia Connata Boiss. With Cytotoxic Activities on Human Breast Cancer Cell Lines. Natural Product Research, 29(7), 607-614.
Chicago	Shadi S, Saeidi H, Ghanadian M, Rahimnejad MR, Aghaei M, Ayatollahi SM, Iqbal Choudhary M. "New Macrocyclic Diterpenes From Euphorbia Connata Boiss. With Cytotoxic Activities on Human Breast Cancer Cell Lines." Natural Product Research 29, no. 7 (2016): 607-614.
Harvard	Shadi S et al. (2016) 'New Macrocyclic Diterpenes From Euphorbia Connata Boiss. With Cytotoxic Activities on Human Breast Cancer Cell Lines', Natural Product Research, 29(7), pp. 607-614.
Vancouver	Shadi S, Saeidi H, Ghanadian M, Rahimnejad MR, Aghaei M, Ayatollahi SM, et al.. New Macrocyclic Diterpenes From Euphorbia Connata Boiss. With Cytotoxic Activities on Human Breast Cancer Cell Lines. Natural Product Research. 2016;29(7):607-614.
BibTex	@article{ author = {Shadi S and Saeidi H and Ghanadian M and Rahimnejad MR and Aghaei M and Ayatollahi SM and Iqbal Choudhary M}, title = {New Macrocyclic Diterpenes From Euphorbia Connata Boiss. With Cytotoxic Activities on Human Breast Cancer Cell Lines}, journal = {Natural Product Research}, volume = {29}, number = {7}, pages = {607-614}, year = {2016} }
RIS	TY - JOUR AU - Shadi S AU - Saeidi H AU - Ghanadian M AU - Rahimnejad MR AU - Aghaei M AU - Ayatollahi SM AU - Iqbal Choudhary M TI - New Macrocyclic Diterpenes From Euphorbia Connata Boiss. With Cytotoxic Activities on Human Breast Cancer Cell Lines JO - Natural Product Research VL - 29 IS - 7 SP - 607 EP - 614 PY - 2016 ER -

Science Communicator Platform

Authors

Authors Affiliations

Abstract