Tigliane diterpenes isolated from the latex of Euphorbia lucida
Аутори
Savić, DanicaKrstić, Gordana
Jadranin, Milka
Novaković, Miroslav
Lekić, Stefan
Tešević, Vele
Milosavljević, Slobodan
Конференцијски прилог (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
The diversity of plant species from the genus Euphorbia and wide variety of secondary metabolites they produce contributed to their successful use in the traditional medicine all over the world. Therapeutic applications have been attributed to different compounds such as diterpenes and triterpenes. Previous investigations revealed that Euphorbia diterpenes possess a variety of biological activities such as anti-inflammatory, antitumor and antiviral. Some of them showed that tigliane diterpenes, beside other potential pharmaceutical activities, inhibited wild-type HIV-1 and HIV-2 strains as well as drug resistant strains of HIV 1 and that they exhibited low cytotoxicity. Two tigliane diterpenes were
isolated from the latex of E. lucida, using classical and instrumental chromatographic techniques. ESI-HRMS spectra showed that both isolated compounds possess the same molecular formula (C31H38O6). 1D NMR spectra revealed benzoate and isobutanoate ester groups in both molecules, Using HMB...C spectra their position was determined: C-13 for isobutanoate and C-20 for benzoate. Exact configurations were discovered by NOE correlations. It was concluded that these two molecules differ in the way of the binding the five-membered and seven-membered rings, i.e., that these two molecules are C-4-epimers. Compound 1 (20-benzoyloxy-13α-isobutanoyloxy-4,12-dideoxyphorbol) was already described in the literature as a metabolite of E. pannonica [1], while compound 2 (20-benzoyloxy-13α-isobutanoyloxy-4-epi-4,12-dideoxyphorbol) represents a new tigliane derivative.
Кључне речи:
plant species / biologically active compounds / terpenoidsИзвор:
Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria, 2023, 239-239Издавач:
- International Conference on Natural Products Utilization - ICNPU2023
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200168 (Универзитет у Београду, Хемијски факултет) (RS-MESTD-inst-2020-200168)
- Serbian Academy of Sciences and Arts (Strategic Project MilkIng, No. 01-2022)
Институција/група
IHTMTY - CONF AU - Savić, Danica AU - Krstić, Gordana AU - Jadranin, Milka AU - Novaković, Miroslav AU - Lekić, Stefan AU - Tešević, Vele AU - Milosavljević, Slobodan PY - 2023 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/7272 AB - The diversity of plant species from the genus Euphorbia and wide variety of secondary metabolites they produce contributed to their successful use in the traditional medicine all over the world. Therapeutic applications have been attributed to different compounds such as diterpenes and triterpenes. Previous investigations revealed that Euphorbia diterpenes possess a variety of biological activities such as anti-inflammatory, antitumor and antiviral. Some of them showed that tigliane diterpenes, beside other potential pharmaceutical activities, inhibited wild-type HIV-1 and HIV-2 strains as well as drug resistant strains of HIV 1 and that they exhibited low cytotoxicity. Two tigliane diterpenes were isolated from the latex of E. lucida, using classical and instrumental chromatographic techniques. ESI-HRMS spectra showed that both isolated compounds possess the same molecular formula (C31H38O6). 1D NMR spectra revealed benzoate and isobutanoate ester groups in both molecules, Using HMBC spectra their position was determined: C-13 for isobutanoate and C-20 for benzoate. Exact configurations were discovered by NOE correlations. It was concluded that these two molecules differ in the way of the binding the five-membered and seven-membered rings, i.e., that these two molecules are C-4-epimers. Compound 1 (20-benzoyloxy-13α-isobutanoyloxy-4,12-dideoxyphorbol) was already described in the literature as a metabolite of E. pannonica [1], while compound 2 (20-benzoyloxy-13α-isobutanoyloxy-4-epi-4,12-dideoxyphorbol) represents a new tigliane derivative. PB - International Conference on Natural Products Utilization - ICNPU2023 C3 - Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria T1 - Tigliane diterpenes isolated from the latex of Euphorbia lucida SP - 239 EP - 239 UR - https://hdl.handle.net/21.15107/rcub_cer_7272 ER -
@conference{ author = "Savić, Danica and Krstić, Gordana and Jadranin, Milka and Novaković, Miroslav and Lekić, Stefan and Tešević, Vele and Milosavljević, Slobodan", year = "2023", abstract = "The diversity of plant species from the genus Euphorbia and wide variety of secondary metabolites they produce contributed to their successful use in the traditional medicine all over the world. Therapeutic applications have been attributed to different compounds such as diterpenes and triterpenes. Previous investigations revealed that Euphorbia diterpenes possess a variety of biological activities such as anti-inflammatory, antitumor and antiviral. Some of them showed that tigliane diterpenes, beside other potential pharmaceutical activities, inhibited wild-type HIV-1 and HIV-2 strains as well as drug resistant strains of HIV 1 and that they exhibited low cytotoxicity. Two tigliane diterpenes were isolated from the latex of E. lucida, using classical and instrumental chromatographic techniques. ESI-HRMS spectra showed that both isolated compounds possess the same molecular formula (C31H38O6). 1D NMR spectra revealed benzoate and isobutanoate ester groups in both molecules, Using HMBC spectra their position was determined: C-13 for isobutanoate and C-20 for benzoate. Exact configurations were discovered by NOE correlations. It was concluded that these two molecules differ in the way of the binding the five-membered and seven-membered rings, i.e., that these two molecules are C-4-epimers. Compound 1 (20-benzoyloxy-13α-isobutanoyloxy-4,12-dideoxyphorbol) was already described in the literature as a metabolite of E. pannonica [1], while compound 2 (20-benzoyloxy-13α-isobutanoyloxy-4-epi-4,12-dideoxyphorbol) represents a new tigliane derivative.", publisher = "International Conference on Natural Products Utilization - ICNPU2023", journal = "Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria", title = "Tigliane diterpenes isolated from the latex of Euphorbia lucida", pages = "239-239", url = "https://hdl.handle.net/21.15107/rcub_cer_7272" }
Savić, D., Krstić, G., Jadranin, M., Novaković, M., Lekić, S., Tešević, V.,& Milosavljević, S.. (2023). Tigliane diterpenes isolated from the latex of Euphorbia lucida. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria International Conference on Natural Products Utilization - ICNPU2023., 239-239. https://hdl.handle.net/21.15107/rcub_cer_7272
Savić D, Krstić G, Jadranin M, Novaković M, Lekić S, Tešević V, Milosavljević S. Tigliane diterpenes isolated from the latex of Euphorbia lucida. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria. 2023;:239-239. https://hdl.handle.net/21.15107/rcub_cer_7272 .
Savić, Danica, Krstić, Gordana, Jadranin, Milka, Novaković, Miroslav, Lekić, Stefan, Tešević, Vele, Milosavljević, Slobodan, "Tigliane diterpenes isolated from the latex of Euphorbia lucida" in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria (2023):239-239, https://hdl.handle.net/21.15107/rcub_cer_7272 .