scholarly journals Clerodane Diterpenoids from Callicarpa hypoleucophylla and Their Anti-Inflammatory Activity

Molecules ◽  
2020 ◽  
Vol 25 (10) ◽  
pp. 2288 ◽  
Author(s):  
Yu-Chi Lin ◽  
Jue-Jun Lin ◽  
Shu-Rong Chen ◽  
Tsong-Long Hwang ◽  
Shu-Yen Fang ◽  
...  

Plants of the genus Callicarpa are known to possess several medicinal effects. The constituents of the Taiwan endemic plant Callicarpa hypoleucophylla have never been studied. Therefore, C. hypoleucophylla was selected for our phytochemical investigation. Two new clerodane-type diterpenoids, named callihypolins A (1) and B (2), along with seven known compounds were isolated from the leaves and twigs of the Lamiaceae plant C. hypoleucophylla and then characterized. The structures of compounds 1 and 2 were elucidated by spectroscopic data analysis, specifically, two-dimension nuclear magnetic resonance (NMR). The anti-inflammatory activity of compounds 1–9 based on the suppression of superoxide anion generation and elastase release was evaluated. Among the isolates, compounds 2–4 showed anti-inflammatory activity (9.52−32.48% inhibition at the concentration 10 μm) by suppressing superoxide anion generation and elastase release. Our findings not only expand the description of the structural diversity of the compounds present in plants of the genus Callicarpa but also highlight the possibility of developing anti-inflammatory agents from Callicarpa endemic species.

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4149
Author(s):  
Shiou-Ling Li ◽  
Ho-Cheng Wu ◽  
Tsong-Long Hwang ◽  
Chu-Hung Lin ◽  
Shuen-Shin Yang ◽  
...  

In a series of anti-inflammatory screenings of lauraceous plants, the methanolic extract of the leaves of Machilus japonica var. kusanoi (Hayata) J.C. Liao showed potent inhibition on both superoxide anion generation and elastase release in human neutrophils. Bioassay-guided fractionation of the leaves of M. japonica var. kusanoi led to the isolation of twenty compounds, including six new butanolides, machinolides A–F (1–6), and fourteen known compounds (7–20). Their structures were characterized by 1D and 2D NMR, UV, IR, CD, and MS data. The absolute configuration of the new compounds were unambiguously confirmed by single-crystal X-ray diffraction analyses (1, 2, and 3) and Mosher’s method (4, 5, and 6). In addition, lignans, (+)-eudesmin (11), (+)-methylpiperitol (12), (+)-pinoresinol (13), and (+)-galbelgin (16) exhibited inhibitory effects on N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation in human neutrophils with IC50 values of 8.71 ± 0.74 μM, 2.23 ± 0.92 μM, 6.81 ± 1.07 μM, and 7.15 ± 2.26 μM, respectively. The results revealed the anti-inflammatory potentials of Formosan Machilus japonica var. kusanoi.


2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110445
Author(s):  
Yunqing Li ◽  
Xiaoyong Zhu ◽  
Liuyan Mo ◽  
Cailan Liu ◽  
Jun Li ◽  
...  

Phytochemical investigation of the folk medicinal plant Argyreia acuta Lour. has led to the isolation of a pair of new 3-alkylated coumarin enantiomers, (±)-acutamarin [(±)-1] and 3 known structurally related coumarins (2-4), along with 4 known flavonoids (5-8). The structures of these compounds were elucidated on the basis of extensive spectroscopic (including one-dimensional and two-dimensional nuclear magnetic resonance) analyses and by comparison of their spectral data with those reported in the literature. The absolute configurations of ( − )-1 and ( + )-1 were proposed by comparison of experimental and calculated electronic circular dichroism data. Compounds 5 and 7 exhibited in vitro anti-inflammatory activity by inhibiting the production of nitric oxide with IC50 values of 24.54 ± 0.36 μM and 10.60 ± 0.15 μM, respectively.


Pharmaceutics ◽  
2021 ◽  
Vol 13 (5) ◽  
pp. 743
Author(s):  
Geovana F. G. Silvestre ◽  
Renally P. Lucena ◽  
Genil D. Oliveira ◽  
Helimarcos N. Pereira ◽  
Jhonatta A. B. Dias ◽  
...  

This work aimed to carry out a study of Apodanthera congestiflora by investigating its chemical composition and pharmacological potential. From the dichloromethane phase (Dic-Ac) of the A. congestiflora stems, three compounds were identified: cayaponoside C5b (Ac-1), cabenoside C (Ac-2) and fevicordin C2 glucoside (Ac-3), being last identified for the first time as a natural product. These compounds were obtained by chromatographic methods and their structures were elucidated by means of spectroscopic analysis of IR, MS and NMR. In the quantification of Dic-Ac, it was possible to observe the presence of 7% of cayaponoside C5b. Dic-Ac showed significant toxicity for in vivo tests, with macroscopic and biochemical changes. The anti-inflammatory activity of Dic-Ac was investigated using the paw edema model. A decrease in inflammatory signs was observed in the first 5 h and the most effective dose in reducing edema with was 7.5 mg kg−1 (66.6%). Anti-tumor activity of Dic-Ac was evaluated by Ehrlich’s carcinoma model, which showed inhibition rate of 78.46% at 15 mg kg−1 dosage. The phytochemical investigation, together with the biological tests carried out in this study, demonstrated that A. congestiflora is a promising species in the search for therapeutics, since it contains substances with high pharmacological potential in its composition.


Marine Drugs ◽  
2021 ◽  
Vol 19 (1) ◽  
pp. 38
Author(s):  
Chi-Jen Tai ◽  
Chiung-Yao Huang ◽  
Atallah F. Ahmed ◽  
Raha S. Orfali ◽  
Walied M. Alarif ◽  
...  

Chemical investigation of a Red Sea Spongia sp. led to the isolation of four new compounds, i.e., 17-dehydroxysponalactone (1), a carboxylic acid, spongiafuranic acid A (2), one hydroxamic acid, spongiafuranohydroxamic acid A (3), and a furanyl trinorsesterpenoid 16-epi-irciformonin G (4), along with three known metabolites (−)-sponalisolide B (5), 18-nor- 3,17-dihydroxy-spongia-3,13(16),14-trien-2-one (6), and cholesta-7-ene-3β,5α-diol-6-one (7). The biosynthetic pathway for the molecular skeleton of 1 and related compounds was postulated for the first time. Anti-inflammatory activity of these metabolites to inhibit superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophil cells and cytotoxicity of these compounds toward three cancer cell lines and one human dermal fibroblast cell line were assayed. Compound 1 was found to significantly reduce the superoxide anion generation and elastase release at a concentration of 10 μM, and compound 5 was also found to display strong inhibitory activity against superoxide anion generation at the same concentration. Due to the noncytotoxic activity and the potent inhibitory effect toward the superoxide anion generation and elastase release, 1 and 5 can be considered to be promising anti-inflammatory agents.


2019 ◽  
Vol 193 ◽  
pp. 100-108 ◽  
Author(s):  
Manuel I. Azócar ◽  
Romina Alarcón ◽  
Antonio Castillo ◽  
Jenny M. Blamey ◽  
Mariana Walter ◽  
...  

2014 ◽  
Vol 38 (4) ◽  
pp. 494-504 ◽  
Author(s):  
Renata M. Martinez ◽  
Daniela T. Longhi-Balbinot ◽  
Ana C. Zarpelon ◽  
Larissa Staurengo-Ferrari ◽  
Marcela M. Baracat ◽  
...  

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5430
Author(s):  
Maria Elaine Araruna ◽  
Catarina Serafim ◽  
Edvaldo Alves Júnior ◽  
Clelia Hiruma-Lima ◽  
Margareth Diniz ◽  
...  

Inflammatory bowel diseases (IBDs) refer to a group of disorders characterized by inflammation in the mucosa of the gastrointestinal tract, which mainly comprises Crohn’s disease (CD) and ulcerative colitis (UC). IBDs are characterized by inflammation of the intestinal mucosa, are highly debilitating, and are without a definitive cure. Their pathogenesis has not yet been fully elucidated; however, it is assumed that genetic, immunological, and environmental factors are involved. People affected by IBDs have relapses, and therapeutic regimens are not always able to keep symptoms in remission over the long term. Natural products emerge as an alternative for the development of new drugs; bioactive compounds are promising in the treatment of several disorders, among them those that affect the gastrointestinal tract, due to their wide structural diversity and biological activities. This review compiles 12 terpenes with intestinal anti-inflammatory activity evaluated in animal models and in vitro studies. The therapeutic approach to IBDs using terpenes acts basically to prevent oxidative stress, combat dysbiosis, restore intestinal permeability, and improve the inflammation process in different signaling pathways.


2021 ◽  
Vol 50 (1) ◽  
pp. 101-107
Author(s):  
Shean-Yeaw Ng ◽  
Lee-Ping Ang ◽  
Vui-Lun Hau ◽  
Monica Suleiman ◽  
Charles Santhanaraju Vairappan ◽  
...  

Two terpenes; cneorubin X (1), (-)-gymnomitr-3(15)-en-4β-ol (2) as well as one benzoic compound; caffeic acid (3) were isolated from Bazzania harpago collected from Mt. Trus Madi, Sabah, Malaysia. The structures of these secondary metabolites were elucidated based on spectroscopic data (Infra-Red (IR), 1D and 2D Nuclear Magnetic Resonance (NMR), and Mass Spectrum (MS)). This is the first record that cneorubin X (1) was isolated from non-vascular plants and it exhibited active anti-fungal activity against Haliphthoros sabahensis and Haliphthoros milfordensis. Chemosystematics finding suggests that the Marchantiophyta (liverworts) genus Bazzania might have a closer chemical relationship to its sister group Bryophyta (mosses) genus Brachythecium, Kindbergia and Mnium, as well as Anthocerophyta (hornworts) genus Anthocerosin their evolutionary history.


Marine Drugs ◽  
2022 ◽  
Vol 20 (1) ◽  
pp. 44
Author(s):  
Hee Jae Shin ◽  
Chang-Su Heo ◽  
Cao Van Anh ◽  
Yeo Dae Yoon ◽  
Jong Soon Kang

Four new streptoglycerides E–H (1–4), with a rare 6/5/5/-membered ring system, were isolated from a marine-derived actinomycete Streptomyces specialis. The structures of 1–4 were elucidated by detailed analysis of HRESIMS, 1D and 2D NMR data and ECD spectra as well as comparison of their spectroscopic data with those reported in literature. Compounds 1–4 showed significant anti-inflammatory activity by inhibiting lipopolysaccharide (LPS)-induced nitric oxide (NO) production in Raw 264.7 cells with IC50 values ranging from 3.5 to 10.9 µM. Especially, 2 suppressed mRNA expression levels of iNOS and IL-6 without cytotoxicity.


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