Pseudoguaianelactones A-C: three unusual sesquiterpenoids from Lindera glauca with anti-inflammatory activities by inhibiting the LPS-induced expression of iNOS and COX-2.

Published on Feb 4, 2020in Chemical Communications5.996
· DOI :10.1039/C9CC09159A
Qingfeng Ruan6
Estimated H-index: 6
(Guangzhou University of Chinese Medicine),
Shiqin Jiang4
Estimated H-index: 4
(Guangzhou University of Chinese Medicine)
+ 6 AuthorsZhongxiang Zhao13
Estimated H-index: 13
(Guangzhou University of Chinese Medicine)
Pseudoguaianelactones A (1) and B (2), two novel sesquiterpene lactones with an unprecedented [5, 7, 7] ring system featuring a α-methylene-γ-lactone moiety, together with new pseudoguaianelactone C (3), were isolated from the roots of Lindera glauca. Pseudoguaianelactones A–C (1–3) inhibited NO production with IC50 values ranging from 1.38 to 4.00 μM. Moreover, all compounds suppressed significantly the production of proinflammatory mediator (TNF-α, IL-6, IL-1β and PGE2) and the enzyme expression (iNOS and COX-2) in protein levels.
📖 Papers frequently viewed together
6 Authors (Lan Liu, ..., Mi Zhang)
4 Citations
12 Citations
58 Citations
#1Yena Liu (SYSU: Sun Yat-sen University)H-Index: 8
#2Qingfeng Ruan (Guangzhou University of Chinese Medicine)H-Index: 6
Last. Hui Cui (Guangzhou University of Chinese Medicine)H-Index: 6
view all 10 authors...
Abstract Four new compounds: diaporthichalasins A-C (1–3) and biatriosporin N (7), along with six known compounds (4–6 and 8–10) were separated from the culture of the fungus Diaporthe sp. GZU-1021. The absolute configurations of 1–3 were determined by quantum chemical calculations, X-ray diffraction, and spectroscopic analysis. The structure of 4 was analyzed by X-ray crystallography analysis for the first time. All of the isolates were evaluated on the production of nitric oxide in lipopolysac...
11 CitationsSource
#1Qingfeng Ruan (Guangzhou University of Chinese Medicine)H-Index: 6
#2Xing-Hong Zhou (Guangzhou University of Chinese Medicine)H-Index: 5
Last. Zhongxiang Zhao (Guangzhou University of Chinese Medicine)H-Index: 13
view all 7 authors...
Abstract Six previously undescribed cassane diterpenoids, named caesalminaxins O-T (1–6), together with 28 known compounds (7–34), were isolated from the seeds of Caesalpinia minax Hance. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, X-ray diffraction, and quantum chemical calculations. Among the undescribed diterpenoids, compound 6 that possessed an unusual enol group at C-7 with a highly deshielded 1H NMR signal was the first exa...
8 CitationsSource
#1Wei Li (SCUN/SCUEC: South Central University for Nationalities)H-Index: 2
#2Juan He (SCUN/SCUEC: South Central University for Nationalities)H-Index: 9
Last. Ji-Kai Liu (SCUN/SCUEC: South Central University for Nationalities)H-Index: 35
view all 7 authors...
Antroalbocin A (1), a sesquiterpenoid possessing a bridged tricyclic system, was isolated from cultures of the higher fungus Antrodiella albocinnamomea (Basidiomycota). The structure with the absolute configuration was determined by extensive spectroscopic methods and single-crystal X-ray diffraction. A plausible biosynthetic pathway for 1 was proposed. Compound 1 was found to inhibit Staphylococcus aureus with an MIC value of 169 μM.
5 CitationsSource
#1Qin-Mei ZhouH-Index: 11
#2Minghua Chen (Peking Union Medical College)H-Index: 17
Last. Liang XiongH-Index: 15
view all 8 authors...
Seven novel guaiane sesquiterpenoids (1–7) and three known seco-guaianes were isolated from the volatile oil of Pogostemon cablin. Their structures including absolute configurations were determined by spectroscopic analyses, a modified Mosher’s method, and X-ray diffraction and ECD data. The results indicated that the ECD Cotton effects arising from one or two nonconjugated olefinic chromophores could be applied to define the absolute configurations of guaiane sesquiterpenoids. Compounds 3 and 6...
19 CitationsSource
#1Hui Cui (Guangzhou University of Chinese Medicine)H-Index: 13
#2Yena Liu (SYSU: Sun Yat-sen University)H-Index: 8
Last. Zhigang She (SYSU: Sun Yat-sen University)H-Index: 30
view all 9 authors...
Diaporindenes A–D (1–4), four unusual 2,3-dihydro-1H-indene isomers, a novel isoprenylisobenzofuran A (5), two new isoprenylisoindole alkaloids diaporisoindoles D and E (6 and 7), and a new benzophenone derivative tenellone D (11), together with four known biogenetic agents (8–10 and 12), were all separated from the endophytic fungus Diaporthe sp. SYSU-HQ3 guided by ultraperformance liquid chromatography high-resolution mass spectrometry. The absolute configurations of 1–7 and 11 were defined by...
35 CitationsSource
#1Zhang Chen (PKU: Peking University)H-Index: 1
#2Shu WangH-Index: 76
Last. Peng-Fei Tu (PKU: Peking University)H-Index: 54
view all 8 authors...
Abstract Six new guaiane sesquiterpenoids, rupestonic acids B–G ( 1 – 6 ), have been isolated from the whole plants of Artemisia rupestris together with six known compounds ( 7 – 12 ). The structures of the new isolates ( 1 – 6 ) were elucidated on the basis of extensive 1D and 2D NMR analysis, and the absolute configurations were established by electronic circular dichroism (ECD) in combination with density functional theory calculations. In in vitro bioassays, compounds 2 and 6 exhibited signi...
13 CitationsSource
#1Yue Liu (SPU: Shenyang Pharmaceutical University)H-Index: 8
#2Jiang-Hao MaH-Index: 2
Last. Feng QiuH-Index: 29
view all 8 authors...
: Ten new guaiane-type sesquiterpenes (1-10), phaeocaulisins A-J, and 18 known guaiane derivatives were isolated from rhizomes of Curcuma phaeocaulis. Their structures were established on the basis of extensive spectroscopic analyses, X-ray crystallographic analysis, and comparison with literature data. Compound 10 is the first example of a norsesquiterpene with this unusual skeleton isolated from the genus Curcuma. All of the isolated compounds were tested for inhibitory activity against LPS-in...
54 CitationsSource
#1Zhi‐Yong XieH-Index: 1
#2Ting-Ting LinH-Index: 5
Last. Sheng YinH-Index: 17
view all 5 authors...
Two new guaiane sesquiterpenoids, (1β,5β)-1-hydroxyguaia-4(15),11(13)-dieno-12,5-lactone (1) and 1,5-epoxy-4-hydroxyguai-11(13)-en-12-oic acid (2), together with five known compounds, rupestonic acid (3), strobilactone A (4), antiquorin (5), isosclerone (6), and 5-hydroxy-2′,3′,4′,7,8-pentamethoxyflavone (7), were isolated from a 95% EtOH extract of Artemisia rupestris. Compounds 1 and 2 are rare examples of guaiane sesquiterpenoids, incorporating a 12,5-lactone group or featuring a 1,5-epoxy ri...
8 CitationsSource
#1María-Carmen Recio (University of Valencia)H-Index: 27
#2Isabel AndújarH-Index: 22
Last. J. L. RíosH-Index: 2
view all 3 authors...
The identification of substances that can promote the resolution of inflammation in a way that is homeostatic, modulatory, efficient, and well-tolerated by the body is of fundamental importance. Traditional medicines have long provided front-line pharmacotherapy for many millions of people worldwide. Medicinal extracts are a rich source of therapeutic leads for the pharmaceutical industry. The use of medicinal plant therapies to treat chronic illness, including rheumatoid arthritis (RA) and infl...
125 CitationsSource
#1Akram Ghantous (AUB: American University of Beirut)H-Index: 20
#2Hala Gali-Muhtasib (AUB: American University of Beirut)H-Index: 32
Last. Nadine Darwiche (AUB: American University of Beirut)H-Index: 27
view all 5 authors...
Sesquiterpene lactones (SLs) are plant-derived compounds often used in traditional medicine against inflammation and cancer. This review focuses on the chemical and biological properties of SLs that lead to enhanced anticancer and anti-inflammatory effects. The chemical properties comprise alkylating center reactivity, lipophilicity, and molecular geometry and electronic features. SLs in clinical trials are artemisinin, thapsigargin and parthenolide and many of their synthetic derivatives. These...
405 CitationsSource
Cited By2
#1Qingfeng RuanH-Index: 6
#2Wencong PanH-Index: 1
Last. Zhongxiang ZhaoH-Index: 13
view all 9 authors...
Abstract Nine previously undescribed butyrolactone and sesquiterpene derivatives, named cyclopentanone A (1), subamolides F and G (2 and 3), secosubamolide F (4), rupestonic acids J − L (5–7), linderaguaianols A and B (8 and 9), together with six known ones 10–15 were isolated from the roots of Lindera glauca. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, quantum chemical calculations, and Mo2(AcO)4-induced circular dichroism. Comp...
#1Mohamed Mroueh (Lebanese American University)H-Index: 2
#2Wissam H. Faour (Lebanese American University)H-Index: 9
Last. Hanan M. Ragab (Alexandria University)H-Index: 6
view all 6 authors...
Abstract New tetrahydro-1H-pyrazolo[3,4-b]quinoline derivatives were designed, synthesized and characterized as dual anticholinestrase and cyclooxygenase-2 inhibitors. The in vitro and in vivo anti-cholinesterase evaluation exhibited promising activities with lower hepatotoxicity for many candidates compared to tacrine as a reference. Furthermore, their anti-inflammatory activity using in vitro (COX-1/COX-2) inhibitory assay demonstrated superior activity to celecoxib with higher selectivity ind...
7 CitationsSource