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1.
Phytomedicine ; 128: 155523, 2024 Jun.
Article En | MEDLINE | ID: mdl-38489893

Callicarpa nudiflora Hook (C. nudiflora) is an anti-inflammatory, antimicrobial, antioxidant, and hemostatic ethnomedicine. To date, little has been reported regarding the activity of C. nudiflora against ulcerative colitis (UC). In this study, we investigated the effect of a flavonoid extract of C. nudiflora on Dextran Sulfate Sodium (DSS)-induced ulcerative colitis in mice. Mice in the treatment group (CNLF+DSS group) and drug-only (CNLF group) groups were administered 400 mg/kg of flavonoid extract of C. nudiflora leaf (CNLF), and drinking water containing 2.5 % DSS was given to the model and treatment groups. The symptoms of colitis were detected, relevant indicators were verified, intestinal barrier function was assessed, and the contents of the cecum were analyzed for intestinal microorganisms. The results showed that CNLF significantly alleviated the clinical symptoms and histological morphology of colitis in mice, inhibited the increase in pro-inflammatory factors (TNF-α, IL-6, IL-1ß, and IFN-γ), and increased the level of IL-10. The expression of NF-κB and MAPK inflammatory signal pathway-related proteins (p-p65, p-p38, p-ERK, p-JNK) was regulated. The expression of tight junction proteins (ZO-1, OCLDN, and CLDN1) was increased, while the content of D-LA, DAO, and LPS was decreased. In addition, 16S rRNA sequencing showed that CNLF restored the gut microbial composition, and increased the relative abundance of Prevotellaceae, Intestinimonas butyriciproducens, and Barnesiella_intestinihominis. In conclusion, CNLF alleviated colitis by suppressing inflammation levels, improving intestinal barrier integrity, and modulating the intestinal microbiota, and therefore has promising future applications in the treatment of UC.


Callicarpa , Dextran Sulfate , Flavonoids , Plant Extracts , Animals , Plant Extracts/pharmacology , Flavonoids/pharmacology , Male , Mice , Callicarpa/chemistry , Colitis, Ulcerative/drug therapy , Colitis, Ulcerative/chemically induced , Gastrointestinal Microbiome/drug effects , Anti-Inflammatory Agents/pharmacology , Cytokines/metabolism , Plant Leaves/chemistry , NF-kappa B/metabolism , Mice, Inbred C57BL , Disease Models, Animal
2.
Fitoterapia ; 174: 105878, 2024 Apr.
Article En | MEDLINE | ID: mdl-38417683

Six previously undescribed clerodane diterpenes, cardorubellas A-F (1-6), along with seven known ones (7-13), were isolated from the aerial parts of Callicarpa pseudorubella. Their chemical structures were established by analysis of 1D and 2D NMR, HR-ESI-MS, X-ray diffraction, and electronic circular dichroism (ECD) data. Notably, cardorubella B (2) represented the first examples of naturally occurring succinic anhydride-containing clerodane diterpenes derivatives. The anti-proliferative activities of these compounds were assessed. Remarkably, compound 2 exhibited comparable inhibitory activity against HEL cell lines, surpassing the positive control with an IC50 value of 14.01 ± 0.77 µM, compared to 17.02 ± 4.70 µM for 5-fluorouracil.


Callicarpa , Diterpenes, Clerodane , Diterpenes , Diterpenes, Clerodane/pharmacology , Diterpenes, Clerodane/chemistry , Callicarpa/chemistry , Molecular Structure , Cell Line , Magnetic Resonance Spectroscopy , Diterpenes/pharmacology
3.
Phytomedicine ; 123: 155240, 2024 Jan.
Article En | MEDLINE | ID: mdl-38056143

BACKGROUND: In our preliminary research on screening traditional Chinese medicine extracts for anti-H1N1 activity, we discovered that the 75 % ethanol extract of Callicarpa nudiflora Hook. & Arn (C. nudiflora) exhibited promising anti-H1N1 infection activity. However, the underlying active components and mechanism of action remain to be elucidated. AIM OF THE STUDY: This experiment further explores the potential active components and mechanisms of action of C. nudiflora against H1N1. METHODS: In this study, the composition of the C. nudiflora was determined using UPLC-Q-Orbitrap-MS/MS. The inhibitory effect of C. nudiflora on H1N1 was investigated using a Madin-Darby canine kidney (MDCK) cell model infected with H1N1, and the protective effect of C. nudiflora on H1N1-infected mice was examined using a Balb/c mouse model infected with H1N1. The potential mechanisms of action were demonstrated at the mRNA and protein levels. RESULTS: A total of 21 compounds were detected in C. nudiflora, which was found to act on the replication stages of H1N1. Moreover, C. nudiflora improved the survival rate of H1N1-infected mice, enhanced the organ index, alleviated the trend of weight loss, reduced lung viral load, mitigated lung tissue damage, and regulated CD4/CD8 and Th1/Th2 immune balance. Molecular mechanism studies revealed that C. nudiflora can regulate the expression of key genes in the toll-like receptor and STAT signaling pathway. CONCLUSION: C. nudiflora can inhibit H1N1 replication. It also can exert a regulatory effect on the immune response of H1N1-infected mice, and mitigate inflammatory damage by modulating the expression of key genes in the toll-like receptor and STAT signaling pathways, indicating its potential for development as an anti-H1N1 drug.


Callicarpa , Influenza A Virus, H1N1 Subtype , Influenza A virus , Animals , Dogs , Mice , Tandem Mass Spectrometry , Toll-Like Receptors , Antiviral Agents/pharmacology
4.
Int J Biol Macromol ; 258(Pt 1): 128887, 2024 Feb.
Article En | MEDLINE | ID: mdl-38118262

Ulcerative colitis (UC) is a type of inflammatory bowel disease (IBD) that cannot be completely cured by current treatments. C. nudiflora Hook has antibacterial, anti-inflammatory, and hemostatic biological functions; however, the therapeutic role of C. nudiflora Hook or its extracts in IBD remains poorly understood. In this study, we extracted and purified three fractions of C. nudiflora Hook polysaccharides by hydroalcohol precipitation method, which were named as CNLP-1, CNLP-2 and CNLP-3, respectively. CNLP-2, the main component of the polysaccharides of C. nudiflora Hook is an pyranose type acidic polysaccharide composed of Fuc, Rha, Ara, Gal, Glc, Xyl, Man, Gal-UA and Glc-UA, with an Mn of 15.624 kDa; Mw of 31.375 kDa. CNLP-2 was found to have a smooth lamellar structure as observed by scanning electron microscopy. To investigate the effect of CNLP-2 (abbreviated to CNLP) on dextran sodium sulfate (DSS)-induced UC mice and its mechanism of action, we treated DSS-induced UC mice by administering CNLP at a dose of 100 mg/kg every other day. The results of the study showed that CNLP alleviated the clinical symptoms such as body weight (BW) loss, pathological damage, and systemic inflammation. The mechanism may be through the regulation of intestinal flora and its metabolism, which in turn affects the expression of NF-κB/MAPK pathway-related proteins through the metabolites of intestinal flora to further alleviate inflammation and ultimately improve the intestinal barrier function in UC mice. In conclusion, CNLP has great potential for the treatment of IBD.


Callicarpa , Colitis, Ulcerative , Colitis , Gastrointestinal Microbiome , Inflammatory Bowel Diseases , Humans , Male , Animals , Mice , Colitis, Ulcerative/drug therapy , Inflammatory Bowel Diseases/pathology , Inflammation/pathology , Polysaccharides/pharmacology , Dextran Sulfate/adverse effects , Disease Models, Animal , Colon , Colitis/pathology , Mice, Inbred C57BL
5.
Chem Biodivers ; 20(12): e202301628, 2023 Dec.
Article En | MEDLINE | ID: mdl-37964626

Two new prostaglandin-like compounds callicarboric acids A-B (1-2), along with six known compounds (3-8) were isolated from the stems of Callicarpa arborea Roxb. Their structures were determined with the help of modern spectroscopic techniques such as NMR, UV, IR, HR-ESI-MS, ECD, and ORD with the assistance of quantum chemical calculations. Compound 1 exhibited remarkable anti-NLRP3 inflammasome activation potential, demonstrating an IC50 value of 0.74 µM. Additionally, by reducing GSDMD-NT production, inhibiting caspase-1 activation, and suppressing IL-1ß secretion, it effectively mitigated NLRP3 inflammasome-induced pyroptosis in J774A.1 cells. These findings indicate that compound 1 possesses the capability to be a valuable candidate for further research and development as an NLRP3 inflammasome inhibitor.


Callicarpa , Inflammasomes , NLR Family, Pyrin Domain-Containing 3 Protein , Prostaglandins/pharmacology , Pyroptosis
6.
Chem Biodivers ; 20(12): e202301676, 2023 Dec.
Article En | MEDLINE | ID: mdl-37971960

Three new compounds callicarpenoids A-C (1-3), were isolated from the stems of Callicarpa arborea Roxb together with fifteen known compounds (4-18). The structures of these compounds were elucidated using advanced spectroscopic techniques, including 1D and 2D NMR, UV, IR, HR-ESI-MS, ECD, ORD, and quantum chemical calculations. Compound 3, a rare rearranged diterpenoid with a fused 5/6-ring system demonstrated strong potential as an inhibitor of the NLRP3 inflammasome activation with an IC50 value of 3.153 µM. It effectively reduced GSDMD-NT production, inhibited caspase-1 activation, and suppressed IL-1ß secretion, thereby mitigating NLRP3 inflammasome-induced pyroptosis in J774A.1 cells. These findings suggest that compound 3 warrants further research and development as a promising NLRP3 inflammasome inhibitor.


Callicarpa , Diterpenes, Clerodane , Inflammasomes , NLR Family, Pyrin Domain-Containing 3 Protein , Diterpenes, Clerodane/pharmacology , Callicarpa/chemistry , Magnetic Resonance Spectroscopy
7.
Phytochemistry ; 214: 113825, 2023 Oct.
Article En | MEDLINE | ID: mdl-37591440

Nine undescribed abietane diterpenoids (1-9) and eleven known abietane analogs (10-20) were isolated from Callicarpa bodinieri. Their structures were characterized by interpreting spectroscopic data, X-ray crystallography, and ECD analysis. The anti-inflammatory activities of these compounds were tested by evaluation of their inhibitory effect on NO production by lipopolysaccharide in RAW 264.7 macrophages, and compounds 3 and 8 exhibited potent anti-inflammatory activities with IC50 values of 36.35 ± 1.12 and 37.21 ± 0.92 µM. The western blotting studies demonstrated that compound 3 inhibited the expression of nitric oxide synthase and p65 that involved in the NF-κB pathway.


Callicarpa , Abietanes/pharmacology , Anti-Inflammatory Agents/pharmacology , Crystallography, X-Ray , Lipopolysaccharides/pharmacology
8.
Fitoterapia ; 170: 105629, 2023 Oct.
Article En | MEDLINE | ID: mdl-37524125

A phytochemical investigation of the medicinal plant Callicarpa macrophylla resulted in the characterization of two rare rearrangement abietane-type diterpenoids, macrophypene F-G (1-2), and three abietane diterpenoids, named macrophypene H-J (3-5). Additionally, five known diterpenoids (6-10) were identified. The structures of the newly discovered compounds were fully established through extensive analysis of HRESIMS, 1D and 2D NMR data. The absolute configurations of the isolated compounds were determined using CD comparison, chemical methods, and X-ray crystal diffraction experiments. Subsequently, all isolated diterpenoids were evaluated for their inhibitory effects on extracellular PCSK9 protein levels by PCSK9 AlphaLISA screening. Jiadfenoic acid B (6, 56.80% inhibition at 20 µM) and holophyllin F (10, 43.18% inhibition at 20 µM) significantly decreased PCSK9 protein levels in medium of HepG2 cells.


Callicarpa , Diterpenes , Abietanes , Proprotein Convertase 9 , Callicarpa/chemistry , Molecular Structure , Plant Leaves/chemistry
9.
Zhongguo Zhong Yao Za Zhi ; 48(14): 3815-3825, 2023 Jul.
Article Zh | MEDLINE | ID: mdl-37475073

This study aims to identify the chemical constituents from Callicarpa kwangtungensis and determine their activities. MCI, ODS, and Sephadex LH-20 chromatography and semi-preparative HPLC were employed to separate the chemical constituents. A total of 15 compounds were separated, and their structures were identified on the basis of spectroscopic analysis and comparison with the data in relevant literature. Specifically, the 15 compounds were 3-O-α-L-rhamnopyranosyl-6-O-ß-D-apiofuranosyl-4-O-E-caffeoyl-D-glucopyranoside(1), 3,6-O-α-L-dirhamnopyranosyl-4-O-E-caffeoyl-D-glucopyranoside(2), ß-OH-forsythoside B(3), ß-OH-poliumoside(4),(+)-lyoniresinol-3α-O-ß-D-apiofuranosyl-(1→2)-ß-D-glucopyranoside(5),(+)-lyoniresinol-3α-O-ß-D-glucopyranoside(6),(-)-lyoniresinol-3α-O-ß-D-glucopyranoside(7), kelampayoside A(8), descaffeoylpoliumoside(9), acteoside(10), alyssonoside(11), poliumoside(12), isacteoside(13), acetyl forsythoside B(14), and forsythoside B(15). Compounds 1 and 2 were novel, and the NMR data of compounds 3 and 4 were reported here for the first time. Furthermore, the hemostatic activities of the extract and abundant ingredients(compounds 12 and 15) of C. kwangtungensis were determined with Yunnan Baiyao as the positive control and normal saline as the negative control. The extract and compounds 12 and 15 significantly shortened the tail tip bleeding time in mice.


Callicarpa , Hemostatics , Animals , Mice , China , Glycosides/chemistry
10.
Phytochemistry ; 213: 113748, 2023 Sep.
Article En | MEDLINE | ID: mdl-37286023

Ten undescribed diterpenoids namely rubellawus E-N of structural types pimarane (1, 3-4), nor-abietane (2), nor-pimarane (5-6), isopimarane (7-9), and nor-isopimarane (10), along with eleven known compounds, were isolated and identified from the aerial parts of Callicarpa rubella Lindl. The structures of the isolated compounds were confirmed by comprehensive spectroscopic analyses and quantum chemical computations. Pharmacologically, almost all the compounds exhibited a potential inhibitory effect on oxidized low-density lipoprotein-induced macrophage foam cell formation, which suggests that these compounds may be promising candidates in the treatment of atherosclerosis.


Callicarpa , Diterpenes , Rubella , Abietanes/chemistry , Callicarpa/chemistry , Foam Cells , Molecular Structure , Plant Leaves/chemistry , Diterpenes/chemistry , Macrophages , Rubella/metabolism
11.
Phytochemistry ; 213: 113773, 2023 Sep.
Article En | MEDLINE | ID: mdl-37385362

Twenty-one previously undescribed compounds, including nineteen 3,4-seco-labdanes (nudiflopenes P-W, Y, AI-JI), one 3,4-seco-pimarane (nudiflopene X), and one labdane (nudiflopene Z), along with nine known compounds (one 3,4-seco-pimarane and eight 3,4-seco-labdanes) were isolated from the leaves of Callicarpa nudiflora Hook. Et Arn. The structures of these compounds were elucidated by high-resolution electrospray ionization mass spectrometry and one- and two-dimensional nuclear magnetic resonance spectroscopy. In addition, configurations of the isolated compounds were determined by electronic circular dichroism, DP4+ probability analysis, and single-crystal X-ray diffraction experiments. All undescribed compounds were evaluated for their cytotoxicity against HepG2 cells in vitro, among which compound 12 exhibited a moderate activity with an IC50 value of 27.8 µM.


Callicarpa , Diterpenes , Drugs, Chinese Herbal , Humans , Abietanes , Hep G2 Cells , Callicarpa/chemistry , Diterpenes/pharmacology , Diterpenes/chemistry , Drugs, Chinese Herbal/chemistry , Molecular Structure
12.
Phytochemistry ; 210: 113665, 2023 Jun.
Article En | MEDLINE | ID: mdl-37044361

Fourteen undescribed seco-type diterpenoids, named nudifloids A-N, together with ten known analogs, were isolated from the leaves of Callicarpa nudiflora. Nudifloids A-N had a characteristic 3,4-seco-labdane-type diterpenoid skeleton, whereas nudifloids A-C and K-N were 3,4-seco-norditerpenoids. Nudifloid A was the first example of a 3,4-seco-12,13,14,15,16-quartnor-labdane diterpenoid, with a seven-membered lactone ring formed through esterification between C-3 and C-11. Nudifloids B and C were a pair of highly modified 3,4-seco-labdane nor-diterpenoid epimers, of which C-2 and C-18 were cyclized together to form a cyclohexene fragment. The structures of these undescribed diterpenoids were established by spectroscopic analysis and reference data. The anti-inflammatory activity of diterpenoids in rich yield was evaluated by analyzing the inhibition of lipopolysaccharide plus nigericin-induced pyroptosis in J774A.1 cells. Nudifloids D and E exhibited prominent anti-NLRP3 inflammasome activity, with IC50 values of 1.80 and 1.59 µM, respectively. Cell permeability assays revealed that nudifloid D inhibited pyroptosis, which could ameliorate inflammation by blocking the activation of the NLRP3 inflammasome.


Callicarpa , Diterpenes , Drugs, Chinese Herbal , Callicarpa/chemistry , Inflammasomes , Molecular Structure , Drugs, Chinese Herbal/chemistry , Diterpenes/pharmacology , Diterpenes/chemistry
13.
J Nat Med ; 77(3): 496-507, 2023 Jun.
Article En | MEDLINE | ID: mdl-37002508

Five new phenylethanoid glycosides integerrima A-E (1-5) were isolated from the stem of Callicarpa integerrima for the first time. Their structures were elucidated by extensive spectroscopic analyses. In addition, cytotoxicity, anti-adipogenic and antioxidant activities were evaluated. All the phenylethanoid glycosides would be nontoxic to the normal human hepatocytes LO-2 and pre-adipocytes 3T3-L1 cell lines, significantly promote the proliferation of normal hepatocytes, thus displaying the potential for hepatoprotective. Integerrima A (1), C (3) and D (4) exhibited selectively moderate cytotoxic activity against the hepatoma cell lines Bel-7402, with the IC50 value at 72.66, 80.43 and 84.88 µmol/L, respectively. Moreover, integerrima D (4) had significant activities on reducing lipid droplet formation, with the inhibition rate of 48.02% on the concentration of 200 µg/mL. Finally, the result of FRAP assays exhibited remarkable antioxidant activity in integerrima E (5), which was close to the positive control ascorbic acid with the concentration of 100 µg/mL.


Antineoplastic Agents , Callicarpa , Humans , Glycosides/pharmacology , Glycosides/chemistry , Callicarpa/chemistry , Molecular Structure
14.
Chem Biodivers ; 20(3): e202200210, 2023 Mar.
Article En | MEDLINE | ID: mdl-36732885

There is an ongoing interest to identify alternative pesticidal agents to avoid the chronic problems associated with synthetic pesticides. Essential oils have shown promise as botanical pest control agents. In the present study, the essential oils of four members of the Lamiaceae (Callicarpa candicans, C. erioclona, C. macrophylla, and Karomia fragrans; Vietnamese names: Nàng nàng, Tu châu lông mem, Tu châu lá to and Cà dien, respectively), obtained from wild populations in Vietnam, have been obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry. The essential oils were formulated into microemulsions and the essential oils and their microemulsions were screened for mosquito larvicidal activity against Aedes aegypti, Aedes albopictus, Culex quinquefasciatus, and for molluscicidal activity against Pomacea canaliculata. Atractylone and (E)-caryophyllene dominated the volatiles of C. candicans (CCEO) and C. erioclona (CEEO), while the major component in C. macrophylla (CMEO) and K. fragrans (KFEO) was (E)-caryophyllene. The essential oils and microemulsions of both C. candicans and C. erioclona exhibited excellent larvicidal activity against all three mosquito species (Ae. aegypti, Ae. albopictus, and Cx. quinquefasciatus) with LC50 values <10 µg/mL. Additionally, the larvicidal activity of the microemulsions were significantly improved compared with their free essential oils, especially for C. candicans and C. erioclona. All four essential oils and their microemulsions showed excellent molluscicidal activity with LC50 <10 µg/mL. In most cases, the essential oils and microemulsions showed greater pesticidal activity against target organisms than the non-target freshwater fish, Oreochromis niloticus. The in silico studies on physicochemical and ADMET properties of the major components in the studied essential oils were also investigated and most of the compounds possessed a favorable ADMET profile. Computational modeling studies of the studied compounds demonstrated a favorable binding interaction with the mosquito odorant-binding protein target and support atractylone, ß-selinene, and caryophyllene oxide as potential inhibitors. Based on the observed pesticidal activities of the essential oils and their microemulsions, the Callicarpa species and K. fragrans should be considered for potential cultivation and further exploration as botanical pesticidal agents.


Aedes , Callicarpa , Insecticides , Lamiaceae , Oils, Volatile , Pesticides , Animals , Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Pesticides/pharmacology , Vietnam , Insecticides/pharmacology , Insecticides/chemistry , Larva
15.
J Ethnopharmacol ; 305: 116124, 2023 Apr 06.
Article En | MEDLINE | ID: mdl-36587880

ETHNOPHARMACOLOGICAL RELEVANCE: Callicarpa longissima is a typical Yao ethnomedicine that has been used to treat arthritis in China. Our previous study found that the dichloromethane extract (DCME) of C. longissima showed anti-inflammatory activity in vitro. However, the anti-inflammatory mechanism and detailed chemical composition of DCME remain unclear, which lead to the original interest of this study. AIM OF THE STUDY: The study aimed to evaluate the anti-inflammatory properties of the DCME from C. longissima and further explore the accurate chemical components responsible for this active extract. MATERIALS AND METHODS: The anti-inflammatory activity of DCME in vivo was tested with carrageenan-induced mice paw edema model. Its anti-inflammatory mechanism was explored with LPS-stimulated RAW264.7 macrophages model. The compounds in DCME were isolated by repeated column chromatography and their structures were identified on the basis of nuclear magnetic resonance spectroscopy. The anti-inflammatory activities of the isolates in vitro were also tested by suppressing releases of inflammatory mediators (NO, IL-6 and TNF-α) in RAW264.7 macrophages model. In addition, the molecular docking analysis, which evaluated the potential interaction between the compounds and Toll-like receptor 4 (TLR4) and nuclear factor κB (NF-κB), was performed. RESULTS: DCME effectively alleviated the mice paw edema induced by carrageenan. In LPS-stimulated RAW264.7 cells, DCME significantly decreased the production of interleukin (IL)-6 and tumor necrosis factor α (TNF-α) via inhibiting their mRNA transcription, down-regulated the expression of TLR4 and myeloid differentiation factor 88, inhibited the phosphorylation of alpha inhibitor of NF-κB (IκBα), NF-κB p65, and degradation of IκBα. Twelve diterpenoid phenols were identified from DCME, and they not only showed different inhibitory effects on the production of NO, IL-6 and TNF-α in LPS-stimulated RAW264.7 cells, but also could bind to TLR4 and NF-κB as analyzed by molecular docking. CONCLUSIONS: Taken together, DCME from C. longissima could inhibit inflammatory response both in vitro and in vivo, which is mainly attributed to the synergistic effect of abundant diterpenoid phenols through inhibiting the TLR4/NF-κB signaling pathway, and might be a promising agent for the treatment of inflammatory diseases.


Callicarpa , Diterpenes , Animals , Mice , NF-kappa B/metabolism , NF-KappaB Inhibitor alpha/metabolism , Methylene Chloride/adverse effects , Interleukin-6/metabolism , Carrageenan/pharmacology , Tumor Necrosis Factor-alpha/metabolism , Toll-Like Receptor 4/metabolism , Lipopolysaccharides/pharmacology , Molecular Docking Simulation , Signal Transduction , Anti-Inflammatory Agents/adverse effects , Diterpenes/pharmacology , Edema/chemically induced , Edema/drug therapy
16.
Fitoterapia ; 165: 105394, 2023 Mar.
Article En | MEDLINE | ID: mdl-36526220

Callicarpa rubella is a characteristic folk herb in the genus Callicarpa, and has abundant ethnobotanical usage as indigenous medicine in Lingnan area of P. R. China. However, the phytochemical and pharmacological properties of C. rubella was rarely investigated. Now, three new diterpenoids, named rubellapene A-C (1-3), along with five known analogues (4-8), were isolated from C. rubella. Their structures were determined by spectroscopic methods, quantum chemical electronic circular dichroism calculations and single-crystal X-ray diffraction analysis. Notably, the norditerpenoids C18 of clerodane type (rubellapene B) was rarely found in the genus Callicarpa. The liver protective effects of all of the isolates (1-8) were evaluated by the changes of cell viability and transaminase content of AST and ALT in H2O2-induced BRL cells. Compound 1, 3-8 exhibited that potent liver protective effects at different levels.


Callicarpa , Diterpenes, Clerodane , Diterpenes , Callicarpa/chemistry , Hydrogen Peroxide/analysis , Molecular Structure , Plant Leaves/chemistry , Diterpenes/pharmacology , Diterpenes/chemistry , Diterpenes, Clerodane/pharmacology , Liver
17.
Chem Biodivers ; 20(1): e202200985, 2023 Jan.
Article En | MEDLINE | ID: mdl-36433761

Twelve new clerodane diterpenoids named callicarpanes A-L (1-12), together with eight known compounds (13-20), were isolated from Callicarpa integerrima. Their structures were determined by comprehensive spectroscopic data. The calculated chemical shifts were used to identify relative configurations using DP4+ analysis. The absolute configurations (AC) were assigned based on quantum chemical calculations and X-ray single-crystal diffraction methods. Compounds 1, 3, 5, 9, 10, 12, 15, 16, and 19 showed significant inhibitory activity for NLRP3 inflammasome activation, with the IC50 against lactate dehydrogenase (LDH) release ranging from 0.08 to 4.78 µM. Further study revealed that compound 10 repressed IL-1ß secretion and caspase-1 maturation in J774A.1 cell as well as blocked macrophage pyroptosis.


Callicarpa , Diterpenes, Clerodane , Diterpenes, Clerodane/pharmacology , Diterpenes, Clerodane/chemistry , Inflammasomes , NLR Family, Pyrin Domain-Containing 3 Protein , Callicarpa/chemistry , Macrophages
18.
Nat Prod Res ; 37(10): 1662-1667, 2023 May.
Article En | MEDLINE | ID: mdl-35875993

Callicarpa kwangtungensis (C. Kw), C. macrophylla (C. Ma), C. nudiflora (C. Nu), C. formosana (C. Fo), and C. kochiana (C. Ko) were medicinal plant resource in China. In this study, the UPLC/Q-TOF-MS analysis was performed and 151 compounds were identified. PCA analysis metabolic profiles of C. Nu, C. Ko and C. Kw leaves differ significantly from the other two Callicarpa species, while C. Fo and C. Ma share similar chemical constituents. OPLS-DA highlight with an S-plot indicated that there are 14 robust known chemical markers enabling the differentiation between these five Callicarpa plants. C. Ma, C. Nu, and C. Fo leaves extracts treatment effectively reversed the body weight loss, uric acid and creatinine content, hepatic XOD activity, kidney, liver, and ankle tissues injury and inflammation induced by potassium oxonate in hyperuricemia mice. While Ko and C. Kw leaves extracts treatment showed less improvement in hyperuricemia mice.


Callicarpa , Hyperuricemia , Plants, Medicinal , Animals , Mice , Callicarpa/chemistry , Hyperuricemia/drug therapy , Inflammation , Metabolome , Plants, Medicinal/chemistry , Chromatography, High Pressure Liquid , Mass Spectrometry
19.
J Ethnopharmacol ; 300: 115757, 2023 Jan 10.
Article En | MEDLINE | ID: mdl-36167233

ETHNOPHARMACOLOGICAL RELEVANCE: Callicarpa arborea Roxb. is widely used as traditional medicine especially by the tribal people of Bangladesh in the management of wide range of ailments. In addition to Bangladesh, the leaves of this plant is utilized as a remedy to various painful and inflammatory conditions including rheumatism, toothache and stomachache in other countries of Indian subcontinent. AIM OF THE STUDY: Depending on the ethnomedicinal uses, we undertook this study to investigate the in-vivo analgesic and anti-inflammatory activities of the methanolic extract of C. arborea Roxb. leaves in Swiss albino mice as well as its chemical composition. MATERIALS AND METHODS: We evaluated the analgesic activity of Callicarpa arborea Roxb. leaves by the acetic acid induced writhing test, the hot plate test, and the formalin test. We undertook the egg albumin induced paw edema test to determine the anti-inflammatory activity of the plant. Furthermore, we conducted the phytochemical profiling by gas chromatography-mass spectrometry (GC-MS). RESULTS: In acute toxicity test, no mortality was observed at the highest dose of 2000 mg/kg b.w. Significant (p < 0.005) inhibition of acetic acid induced writhing was observed at both doses of the extract. A dose dependent increase in the response time was seen in the hot-plate test. In the formalin test, the extract significantly inhibited pain response in both early and late phase. We observed marked anti-inflammatory activity manifested by a significant (p < 0.005) reduction in egg albumin induced paw edema. We identified a total of twenty one compounds in the extract of by GC-MS analysis. CONCLUSION: Taken all into consideration we conclude that the leaves of C. arborea Roxb. possesses potent analgesic and anti-inflammatory activity, thus justifying its's ethnomedicinal use against painful and inflammatory pathological conditions.


Callicarpa , Acetic Acid/therapeutic use , Albumins/analysis , Analgesics/pharmacology , Analgesics/therapeutic use , Animals , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/therapeutic use , Edema/chemically induced , Edema/drug therapy , Humans , Methanol/therapeutic use , Mice , Pain/chemically induced , Pain/drug therapy , Pain/pathology , Plant Extracts/therapeutic use , Plant Extracts/toxicity , Plant Leaves/chemistry
20.
Article Zh | WPRIM | ID: wpr-981514

This study aims to identify the chemical constituents from Callicarpa kwangtungensis and determine their activities. MCI, ODS, and Sephadex LH-20 chromatography and semi-preparative HPLC were employed to separate the chemical constituents. A total of 15 compounds were separated, and their structures were identified on the basis of spectroscopic analysis and comparison with the data in relevant literature. Specifically, the 15 compounds were 3-O-α-L-rhamnopyranosyl-6-O-β-D-apiofuranosyl-4-O-E-caffeoyl-D-glucopyranoside(1), 3,6-O-α-L-dirhamnopyranosyl-4-O-E-caffeoyl-D-glucopyranoside(2), β-OH-forsythoside B(3), β-OH-poliumoside(4),(+)-lyoniresinol-3α-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside(5),(+)-lyoniresinol-3α-O-β-D-glucopyranoside(6),(-)-lyoniresinol-3α-O-β-D-glucopyranoside(7), kelampayoside A(8), descaffeoylpoliumoside(9), acteoside(10), alyssonoside(11), poliumoside(12), isacteoside(13), acetyl forsythoside B(14), and forsythoside B(15). Compounds 1 and 2 were novel, and the NMR data of compounds 3 and 4 were reported here for the first time. Furthermore, the hemostatic activities of the extract and abundant ingredients(compounds 12 and 15) of C. kwangtungensis were determined with Yunnan Baiyao as the positive control and normal saline as the negative control. The extract and compounds 12 and 15 significantly shortened the tail tip bleeding time in mice.


Animals , Mice , Callicarpa , Hemostatics , China , Glycosides/chemistry
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