New oxylipins from Siegesbeckia glabrescens as potential antibacterial agents

Wu, Cong; Zhang, Qianqian; Yang, Fan; Song, Meina; Sun, Yan; Zhang, Yuying; Li, Xiaobin; Liu, Na; Zhang, Hua

doi:10.1016/j.fitote.2020.104613

Cited by 3 publications

(4 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Its structure was elucidated using IR, HR-ESI-MS, and 1-D and 2-D NMR techniques, including 1 H NMR, 13 C NMR, DEPT, 1 H-1 H COSY, HMQC, and HMBC spectra. The remaining compounds were annotated based on mass spectral data and data from previous studies [17][18][19][20][21].…”

Section: Identification Of Compoundsmentioning

confidence: 99%

Rapid identification of chemical compositions from three species of Siegesbeckiae Herba by ultra‐performance liquid chromatography‐electrospray ionization‐quadrupole time of flight‐mass spectrometry in combination with deoxyribonucleic acid barcoding

Tao

et al. 2023

J of Separation Science

View full text Add to dashboard Cite

Siegesbeckiae Herba, a traditional Chinese medicine, originates from Siegesbeckia orientalis, S. glabrescens, and S. pubescens in the Pharmacopoeia of the People's Republic of China. However, accurate identification of decoction pieces from the three plants remains a challenge. In this study, 26 batches of Siegesbeckiae Herba were identified by deoxyribonucleic acid barcoding, and their chemical compositions were determined using ultra-performance liquid chromatographyelectrospray ionization-quadrupole time of flight-mass spectrometry. The results showed that the internal transcribed spacer 2 and internal transcribed spacer 1-5.8 S-internal transcribed spacer 2 sequences could distinguish three species. In total, 48 compounds were identified including 12 marker compounds screened for three species using the partial least square discriminant analysis. Among these, two diterpenoids 16-O-malonylkirenol and 15-O-malonylkirenol, and a novel diterpenoid 15,16-di-O-malonylkirenol were isolated and identified. A convenient method for the identification of Siegesbeckiae Herba was established using kirenol and 16-O-acetlydarutoside as control standards by thin-layer chromatography. Unexpectedly, none of the batches of S. orientalis contained kirenol, which did not meet the quality standards of Siegesbeckiae Herba, suggesting that the rationality of kirenol as a quality marker for S. orientalis should be further investigated. The results of this study will contribute to the quality control of Siegesbeckiae Herba.

show abstract

Section: Identification Of Compoundsmentioning

confidence: 99%

Rapid identification of chemical compositions from three species of Siegesbeckiae Herba by ultra‐performance liquid chromatography‐electrospray ionization‐quadrupole time of flight‐mass spectrometry in combination with deoxyribonucleic acid barcoding

Tao

et al. 2023

J of Separation Science

View full text Add to dashboard Cite

show abstract

“…Our previous studies on S. orientalis and S. glabrescens led to the isolation of sesquiterpenoid lactones and oxylipins, and some of them showed cytotoxic or antibacterial activities [6,12] . S. pubescens is also one of the important plant origins of Sigesbeckiae herba and has been reported to be a rich source of diterpenoids [10] .…”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10][11] Our previous studies on S. orientalis and S. glabrescens led to the isolation of sesquiterpenoid lactones and oxylipins, and some of them showed cytotoxic or antibacterial activities. [6,12] S. pubescens is also one of the important plant origins of Sigesbeckiae herba and has been reported to be a rich source of diterpenoids. [10] The structural diversity and potential biological significance of diterpenoids from Sigesbeckia species prompted us to undertake further phytochemical investigations on S. pubescens.…”

Section: Introductionmentioning

confidence: 99%

“…There are three species S. orientalis , S. glabrescens and S. pubescens growing in China and their aerial parts have been used for centuries to treat arthritis, hypertention, malaria, neurasthenia and snakebite [3] . Phytochemical studies on Siegesbeckia species have been conducted for several decades, and more than 100 compounds have been isolated and characterized, including diterpenoids, [4] sesquiterpenoids, [5] oxylipins, [6] and flavonoids [7] . Among these Siegesbeckia constituents, diterpenoids including ent ‐kaurane and ent ‐pimarane types are the most abundant compounds with diverse bioactivities like antitumor, anti‐inflammatory, antimicrobial, and immunosuppressive effects [8–11] …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

ent‐Pimarane Diterpenes from the Aerial Parts of Siegesbeckia pubescens

Liu

Luo

et al. 2023

Chemistry & Biodiversity

Self Cite

View full text Add to dashboard Cite

Five new ent-pimarane diterpenes (1 -5) and five known analogs (6 -10) were isolated from the aerial parts of Siegesbeckia pubescens. Their structures, including absolute configurations, were determined by comprehensive spectroscopic methods especially 1D and 2D NMR and quantum chemical electronic circular dichroism calculations. All the isolated compounds were evaluated for their cytotoxicity against human BT549, A549 and H157 cancer cell lines. Among them, compounds 1 and 2 showed mild cytotoxicity against lung cancer cell lines H157 with IC 50 values of 16.35 � 2.59 and 18.86 � 4.83 μM, respectively.

show abstract