Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae)
Апстракт
Stachys annua (L.) L. (annual yellow-woundwort) is an arrable weed and melliferous archaeophyte, with the native range in Europe to Siberia and Iran [1]. The aim of this work is to implement simple chromatographic technique for isolation of flavonoids from crude methanol extract of S. annua aerial flowering parts (herb).
Plant material collected in NW Serbia (Mt Sokolske planine) was air-dried, powdered, and then extracted by bimaceration with chloroform and methanol. Dry methanol extract of S. annua herb was applied on preparative TLC plates of silica gel. After developing of chromatogram in methylene chloride:methanol:water (40:10:1, V/V/V), and spraying with NP/PEG reagent, in ultraviolet light at 365 nm three clearly separated fluorescence-quenching zones were observed. Zones were eluted with mixture of methylene chloride and methanol (1:1, V/V), and using LC-MS analysis one dominant compound was detected in each of these fractions. According to their UV, MS and 1H-NMR spectral ...data, as well as using flavonoids previously isolated from S. alpina subsp. dinarica [2], these compounds (1-3) were identified as 8-hydroxyflavone glycosides, namely: isoscutellarein-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 1), 3'-hydroxy-4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 2) and 4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 3).
It could be concluded that the developed preparative TLC method is suitable for rapid isolation of the mentioned flavonoid biosides from the crude methanol extract of S. annua without prior fractionation by other chromatographic techniques.
Кључне речи:
Stachys annua / flavonoids / NMRИзвор:
5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts, 2023, 194-195Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200161 (Универзитет у Београду, Фармацеутски факултет) (RS-MESTD-inst-2020-200161)
Напомена:
- 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023, Sts. Constantine & Helena, Bulgaria, 30th May to 2nd June 2023
- Saopštenje sa međunarodnog skupa štampano u izvodu
Институција/група
PharmacyTY - CONF AU - Kukić-Marković, Jelena AU - Petković, Miloš AU - Niketić, Marjan AU - Petrović, Silvana PY - 2023 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4987 AB - Stachys annua (L.) L. (annual yellow-woundwort) is an arrable weed and melliferous archaeophyte, with the native range in Europe to Siberia and Iran [1]. The aim of this work is to implement simple chromatographic technique for isolation of flavonoids from crude methanol extract of S. annua aerial flowering parts (herb). Plant material collected in NW Serbia (Mt Sokolske planine) was air-dried, powdered, and then extracted by bimaceration with chloroform and methanol. Dry methanol extract of S. annua herb was applied on preparative TLC plates of silica gel. After developing of chromatogram in methylene chloride:methanol:water (40:10:1, V/V/V), and spraying with NP/PEG reagent, in ultraviolet light at 365 nm three clearly separated fluorescence-quenching zones were observed. Zones were eluted with mixture of methylene chloride and methanol (1:1, V/V), and using LC-MS analysis one dominant compound was detected in each of these fractions. According to their UV, MS and 1H-NMR spectral data, as well as using flavonoids previously isolated from S. alpina subsp. dinarica [2], these compounds (1-3) were identified as 8-hydroxyflavone glycosides, namely: isoscutellarein-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 1), 3'-hydroxy-4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 2) and 4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 3). It could be concluded that the developed preparative TLC method is suitable for rapid isolation of the mentioned flavonoid biosides from the crude methanol extract of S. annua without prior fractionation by other chromatographic techniques. C3 - 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts T1 - Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae) SP - 194 EP - 195 UR - https://hdl.handle.net/21.15107/rcub_farfar_4987 ER -
@conference{ author = "Kukić-Marković, Jelena and Petković, Miloš and Niketić, Marjan and Petrović, Silvana", year = "2023", abstract = "Stachys annua (L.) L. (annual yellow-woundwort) is an arrable weed and melliferous archaeophyte, with the native range in Europe to Siberia and Iran [1]. The aim of this work is to implement simple chromatographic technique for isolation of flavonoids from crude methanol extract of S. annua aerial flowering parts (herb). Plant material collected in NW Serbia (Mt Sokolske planine) was air-dried, powdered, and then extracted by bimaceration with chloroform and methanol. Dry methanol extract of S. annua herb was applied on preparative TLC plates of silica gel. After developing of chromatogram in methylene chloride:methanol:water (40:10:1, V/V/V), and spraying with NP/PEG reagent, in ultraviolet light at 365 nm three clearly separated fluorescence-quenching zones were observed. Zones were eluted with mixture of methylene chloride and methanol (1:1, V/V), and using LC-MS analysis one dominant compound was detected in each of these fractions. According to their UV, MS and 1H-NMR spectral data, as well as using flavonoids previously isolated from S. alpina subsp. dinarica [2], these compounds (1-3) were identified as 8-hydroxyflavone glycosides, namely: isoscutellarein-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 1), 3'-hydroxy-4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 2) and 4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 3). It could be concluded that the developed preparative TLC method is suitable for rapid isolation of the mentioned flavonoid biosides from the crude methanol extract of S. annua without prior fractionation by other chromatographic techniques.", journal = "5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts", title = "Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae)", pages = "194-195", url = "https://hdl.handle.net/21.15107/rcub_farfar_4987" }
Kukić-Marković, J., Petković, M., Niketić, M.,& Petrović, S.. (2023). Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae). in 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts, 194-195. https://hdl.handle.net/21.15107/rcub_farfar_4987
Kukić-Marković J, Petković M, Niketić M, Petrović S. Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae). in 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts. 2023;:194-195. https://hdl.handle.net/21.15107/rcub_farfar_4987 .
Kukić-Marković, Jelena, Petković, Miloš, Niketić, Marjan, Petrović, Silvana, "Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae)" in 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts (2023):194-195, https://hdl.handle.net/21.15107/rcub_farfar_4987 .