Diarylheptanoids from Alnus glutinosa Bark and Their Chemoprotective Effect on Human Lymphocytes DNA
Само за регистроване кориснике
2013
Аутори
Novaković, Miroslav M.Stanković, Miroslava
Vučković, Ivan M.
Todorović, Nina
Trifunović, Snežana S.
Tešević, Vele
Vajs, Vlatka
Milosavljević, Slobodan M.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
A study of secondary metabolites from the bark of Alnus glutinosa led to the isolation of fourteen diarylheptanoids: oregonin (1), platyphylloside (2), rubranoside A (3), rubranoside B (4), hirsutanonol (5), hirsutenone (6), hirsutanonol-5-O-β-D-glucopyranoside (7), platyphyllonol-5-O-β-D- xylopyranoside (8), aceroside VII (9), alnuside A (10), alnuside B (11), 1,7-bis-(3,4-dihydoxyphenyl)-5-hydroxy-heptane-3-O-β-D-xylopyranoside (12), (5S)-1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)-5-O-β-D-glucopyranosyl- heptan-3-one (13), and (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-O-β-D-[6-(3,4- dimethoxycinnamoylglucopyranosyl)]-heptan-3-one (14). All of the diarylheptanoids, except 1 and 5, were found in A. glutinosa for the first time, while 13 and 14 were new compounds. The structures were determined by spectroscopic techniques: 1D and 2D NMR, HR-ESI-MS, FTIR, UV, and CD. All isolated compounds were analyzed for an in vitro protective effect on chromosome aberrations in peripheral human lymphocyt...es using the cytokinesis-block micronucleus assay. The majority of them, including the new compounds 13 and 14, exerted a pronounced effect in decreasing DNA damage in human lymphocytes. Diarylheptanoids 1, 2, 5, 13, and 14 at a concentration of 1 g/mL decreased the frequency of micronuclei by 52.8 %, 43.8 %, 63.6 %, 44.4 %, and 56.0 %, respectively, exerting a much stronger effect than the synthetic protector amifostine (17.2 %, c = 1 g/mL).
Кључне речи:
Alnus glutinosa / Betulaceae / diarylheptanoids / HPLC-DAD / NMR analysis / protective effect / CBMN assayИзвор:
Planta Medica, 2013, 79, 6, 499-505Издавач:
- Georg Thieme Verlag Kg, Stuttgart
Финансирање / пројекти:
- Биоактивни природни производи самониклих, гајених и јестивих биљака: одређивање структура и активности (RS-MESTD-Basic Research (BR or ON)-172053)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-FP7-256716)
Напомена:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3484
DOI: 10.1055/s-0032-1328301
ISSN: 0032-0943
PubMed: 23512500
WoS: 000317814300012
Scopus: 2-s2.0-84876680636
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Novaković, Miroslav M. AU - Stanković, Miroslava AU - Vučković, Ivan M. AU - Todorović, Nina AU - Trifunović, Snežana S. AU - Tešević, Vele AU - Vajs, Vlatka AU - Milosavljević, Slobodan M. PY - 2013 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1630 AB - A study of secondary metabolites from the bark of Alnus glutinosa led to the isolation of fourteen diarylheptanoids: oregonin (1), platyphylloside (2), rubranoside A (3), rubranoside B (4), hirsutanonol (5), hirsutenone (6), hirsutanonol-5-O-β-D-glucopyranoside (7), platyphyllonol-5-O-β-D- xylopyranoside (8), aceroside VII (9), alnuside A (10), alnuside B (11), 1,7-bis-(3,4-dihydoxyphenyl)-5-hydroxy-heptane-3-O-β-D-xylopyranoside (12), (5S)-1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)-5-O-β-D-glucopyranosyl- heptan-3-one (13), and (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-O-β-D-[6-(3,4- dimethoxycinnamoylglucopyranosyl)]-heptan-3-one (14). All of the diarylheptanoids, except 1 and 5, were found in A. glutinosa for the first time, while 13 and 14 were new compounds. The structures were determined by spectroscopic techniques: 1D and 2D NMR, HR-ESI-MS, FTIR, UV, and CD. All isolated compounds were analyzed for an in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using the cytokinesis-block micronucleus assay. The majority of them, including the new compounds 13 and 14, exerted a pronounced effect in decreasing DNA damage in human lymphocytes. Diarylheptanoids 1, 2, 5, 13, and 14 at a concentration of 1 g/mL decreased the frequency of micronuclei by 52.8 %, 43.8 %, 63.6 %, 44.4 %, and 56.0 %, respectively, exerting a much stronger effect than the synthetic protector amifostine (17.2 %, c = 1 g/mL). PB - Georg Thieme Verlag Kg, Stuttgart T2 - Planta Medica T1 - Diarylheptanoids from Alnus glutinosa Bark and Their Chemoprotective Effect on Human Lymphocytes DNA VL - 79 IS - 6 SP - 499 EP - 505 DO - 10.1055/s-0032-1328301 ER -
@article{ author = "Novaković, Miroslav M. and Stanković, Miroslava and Vučković, Ivan M. and Todorović, Nina and Trifunović, Snežana S. and Tešević, Vele and Vajs, Vlatka and Milosavljević, Slobodan M.", year = "2013", abstract = "A study of secondary metabolites from the bark of Alnus glutinosa led to the isolation of fourteen diarylheptanoids: oregonin (1), platyphylloside (2), rubranoside A (3), rubranoside B (4), hirsutanonol (5), hirsutenone (6), hirsutanonol-5-O-β-D-glucopyranoside (7), platyphyllonol-5-O-β-D- xylopyranoside (8), aceroside VII (9), alnuside A (10), alnuside B (11), 1,7-bis-(3,4-dihydoxyphenyl)-5-hydroxy-heptane-3-O-β-D-xylopyranoside (12), (5S)-1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)-5-O-β-D-glucopyranosyl- heptan-3-one (13), and (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-O-β-D-[6-(3,4- dimethoxycinnamoylglucopyranosyl)]-heptan-3-one (14). All of the diarylheptanoids, except 1 and 5, were found in A. glutinosa for the first time, while 13 and 14 were new compounds. The structures were determined by spectroscopic techniques: 1D and 2D NMR, HR-ESI-MS, FTIR, UV, and CD. All isolated compounds were analyzed for an in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using the cytokinesis-block micronucleus assay. The majority of them, including the new compounds 13 and 14, exerted a pronounced effect in decreasing DNA damage in human lymphocytes. Diarylheptanoids 1, 2, 5, 13, and 14 at a concentration of 1 g/mL decreased the frequency of micronuclei by 52.8 %, 43.8 %, 63.6 %, 44.4 %, and 56.0 %, respectively, exerting a much stronger effect than the synthetic protector amifostine (17.2 %, c = 1 g/mL).", publisher = "Georg Thieme Verlag Kg, Stuttgart", journal = "Planta Medica", title = "Diarylheptanoids from Alnus glutinosa Bark and Their Chemoprotective Effect on Human Lymphocytes DNA", volume = "79", number = "6", pages = "499-505", doi = "10.1055/s-0032-1328301" }
Novaković, M. M., Stanković, M., Vučković, I. M., Todorović, N., Trifunović, S. S., Tešević, V., Vajs, V.,& Milosavljević, S. M.. (2013). Diarylheptanoids from Alnus glutinosa Bark and Their Chemoprotective Effect on Human Lymphocytes DNA. in Planta Medica Georg Thieme Verlag Kg, Stuttgart., 79(6), 499-505. https://doi.org/10.1055/s-0032-1328301
Novaković MM, Stanković M, Vučković IM, Todorović N, Trifunović SS, Tešević V, Vajs V, Milosavljević SM. Diarylheptanoids from Alnus glutinosa Bark and Their Chemoprotective Effect on Human Lymphocytes DNA. in Planta Medica. 2013;79(6):499-505. doi:10.1055/s-0032-1328301 .
Novaković, Miroslav M., Stanković, Miroslava, Vučković, Ivan M., Todorović, Nina, Trifunović, Snežana S., Tešević, Vele, Vajs, Vlatka, Milosavljević, Slobodan M., "Diarylheptanoids from Alnus glutinosa Bark and Their Chemoprotective Effect on Human Lymphocytes DNA" in Planta Medica, 79, no. 6 (2013):499-505, https://doi.org/10.1055/s-0032-1328301 . .