Comparative Study of the Structural Characteristics and Bioactivity of Polysaccharides Extracted from Aspidopterys obcordata Hemsl. Using Different Solvents.

The polysaccharides extracted from Aspidopterys obcordata are thought to have anti-urolithiasis activity in Drosophila kidney stones. This study aimed to assess the effects of different extraction solvents on the yield, chemical composition, and bioactivity of polysaccharides from A. obcordata. A. obcordata polysaccharides were extracted by using four solutions: hot water, HCl solution, NaOH solution, and 0.1 M NaCl. The results revealed that the extraction solvents significantly influenced the extraction yields, molecular weight distribution, monosaccharide compositions, preliminary structural characteristics, and microstructures of polysaccharides. The NaOH solution's extraction yield was significantly higher than the other extraction methods. Vitro antioxidant activity assays revealed that the NaOH solution extracted exhibited superior scavenging abilities towards DPPH and ABTS radicals and higher FRAP values than other polysaccharides. The vitro assays conducted for calcium oxalate crystallization demonstrated that four polysaccharides exhibited inhibitory effects on the nucleation and aggregation of calcium oxalate crystals, impeded calcium oxalate monohydrate growth, and induced calcium oxalate dihydrate formation. The NaOH solution extracted exhibited the most pronounced inhibition of calcium oxalate crystal nucleation, while the hot water extracted demonstrated the most significant suppression of calcium oxalate crystal aggregation. Therefore, it can be inferred that polysaccharides extracted with NaOH solution exhibited significant potential as a viable approach for extracting polysaccharides from stems due to their superior yield and the remarkable bioactivity of the resulting products.

Chemical Composition and Antifungal, Anti-Inflammatory, Antiviral, and Larvicidal Activities of the Essential Oils of Zanthoxylum acanthopodium DC. from China and Myanmar.

Zanthoxylum acanthopodium DC. is a widely used traditional medicinal plant to treat fever, flu, stomachache, traumatic injury, and mosquito bite in tropical and subtropical Asia. This study aimed to investigate the antifungal, anti-inflammatory, antiviral, and larvicidal activities of its fruit essential oil. The essential oil sample from China (EOZC) was mainly composed of limonene (29.78%) and ß-myrcene (26.65%), while the sample from Myanmar (EOZM) was dominated by Terpinen-4-ol (43.35%). Both essential oils showed antifungal activity, with 90% minimum inhibitory concentration (MIC90) values ranging from 26.3 to 499 µg/mL. By obviously inhibiting nitric oxide (NO) in RAW 264.7 cells, EOZC (IC50, 16 µg/mL) showed comparable anti-inflammatory activity to the positive control L-NMMA (IC50, 12.2 µg/mL). EOZM showed significant antiviral activity against the dengue virus with an IC50 value of 13 µg/mL. Additionally, both EOZC and EOZM demonstrated dose-dependent larvicidal activity against Aedes albopictus, with LC50 and LC90 values ranging from 45.8 to 144.0 µg/mL. Our results contribute a theoretical foundation for the further application of Zanthoxylum acanthopodium DC. as an antifungal and anti-inflammatory ingredient in the pharmaceutical industry and further indicate that it has the potential to be developed as a new source of natural and eco-friendly medicine for the prevention and treatment of dengue virus.

Croargoids A-G, Eudesmane Sesquiterpenes from the Bark of Croton argyratus.

Seven new sesquiterpenes, named croargoid A-G (1-7), were isolated from the bark of Croton argyratus. Compounds 1-4 were the first examples of eudesmane sesquiterpene lactones containing C5-OH group. Compound 7 was a highly degraded eudesmane sesquiterpene possessing a rare eleven-carbon skeleton. Their structures with stereochemistry were mainly elucidated by NMR analyses in combination with MS and ECD data. Cytotoxicities and NO inhibitions of all isolates were evaluated and only compound 5 showed moderate NO inhibitory activity.

Cryptoyunnanones A-H, Complex Flavanones from Cryptocarya yunnanensis.

Eight new complex flavanones with a novel linkage, cryptoyunnanones A-H (1-8), together with four known α-pyrones, were isolated from the leaves and twigs of Cryptocarya yunnanensis. The structures of 1-8 including their absolute configurations were characterized by spectroscopic data analysis and single-crystal X-ray crystallography. Plausible biosynthetic pathways for the formation of compounds 1-8 were proposed. Compounds 1-4 exhibited cytotoxicity against HCT-116, MDA-MB-231, and PC-3 cancer cells with IC50 values from 6.4 to 9.1 µM.

Neolignans and Sesquiterpenoid from Piper yunnanense.

Two biphenyl-type neolignans with a rare dibenzofuran skeleton, including a new one piyunneolignan A (1) and a known one piperneolignan D (2), together with a new sesquiterpenoid piyunin A (3), were isolated from the leaves and twigs of Piper yunnanense. Their structures were established on the basis of comprehensive spectroscopic data analysis and electronic circular dichroism (ECD) calculation. Piyunneolignan A (1) featured a rare C-2-C-2'/C-3-O-C-3' linkage. Compounds 1-3 were evaluated for their antimicrobial and cytotoxic activities against a panel of bacteria, fungi, and human cancer cell lines, respectively.

Chemical Composition and the Cytotoxic, Antimicrobial, and Anti-Inflammatory Activities of the Fruit Peel Essential Oil from Spondias pinnata (Anacardiaceae) in Xishuangbanna, Southwest China.

Spondias pinnata (Linn. f.) Kurz (Anacardiaceae) is widely distributed in tropical Asia, where it is commonly used as a vegetable and fruit, and is attracting increasing research attention. In this study, we investigated the chemical composition and the cytotoxic, antimicrobial, and anti-inflammatory activities of the fruit peel essential oil of S. pinnata (EOSP), which has been consumed as a medicine and condiment in Xishuangbanna, southwest China. A total of 40 components were identified by Gas Chromatography/Mass spectrometry (GC-MS), representing 95.19% of the EOSP, with furfural (17.14%), α-terpineol (13.09%), and ethyl benzoate (9.05%) as the main constituents. EOSP has moderate cytotoxic activity against five cancer cells and obvious antimicrobial activity against five pathogenic strains. In particular, EOSP (Minimal Inhibitory and Fungicidal Concentration, MIC and MFC, 16‒32 µg/mL) showed a 32-times higher inhibition effect against Aspergillus fumigatus than the positive control Tigecycline (MIC and MBC 512‒1024 µg/mL). EOSP also showed strong anti-inflammatory activity by significantly inhibiting nitric oxide (NO) production induced by lipopolysaccharide (LPS) in RAW 264.7 cell lines at 0.08‱, with no effect on cell viability. These bioactivities of S. pinnata fruit peel validate its traditional uses and suggest that it could be a new source of natural antimicrobial and anti-inflammatory agents for food or medical industries.

Aspidoptoids A-D: Four New Diterpenoids from Aspidopterys obcordata Vine.

Four new diterpenoids, named aspidoptoids A-D (1-4), together with two known analogues (5-6) were isolated from Aspidopterys obcordata vine. Aspidoptoids A-B (1-2) are the first examples of phenylethylene-bearing 20-nor-diterpenoids of which aspidoptoid B (2) possesses a rare 3,10-oxybridge. Their structures and absolute configuration were determined by extensive spectroscopic analyses (IR, HRESIMS, 1D and 2D NMR) and electronic circular dichroism (ECD) calculation. In addition, all the isolates were evaluated for their cytotoxic activities and inhibitory effects on the nitric oxide (NO) production.

Maximumins A-D, Rearranged Labdane-Type Diterpenoids with Four Different Carbon Skeletons from Amomum maximum.

Four highly rearranged labdane-type diterpenoids, maximumins A-D (1-4) possessing different new carbon skeletons, together with a biosynthetically related known analog 5 were isolated from Amomum maximum. The structures of new compounds with absolute configurations were characterized by spectroscopic and computational approaches. The plausible biogenetic pathways for 1-4 were proposed. These compounds showed moderate to weak activities against nuclear factor kappa B (NF-κB).

(±)-Meliviticines A and B: Rearranged prenylated acetophenone derivatives from Melicope viticina and their antimicrobial activity.

Two new prenylated acetophenone derivatives racemates, meliviticines A (1) and B (2) with unprecedented rearranged skeletons, were isolated from Melicope viticina. Subsequent chiral resolution led to the separation of two pairs of enantiomers, (±)-meliviticines A (1a/1b) and (±)-meliviticines B (2a/2b). Their structures including absolute configurations were elucidated by extensive spectroscopic data, electronic circular dichroism analysis, and X-ray crystallography. A plausible biosynthetic pathway of 1 and 2, involving ring cleavage and rearrangement of the prenylated acetophenone backbone was proposed. All the isolates showed moderate antimicrobial activities with MIC values of 25-50 µg/mL against several bacterial and fungal strains.

A new selaginellin derivative and a new triarylbenzophenone analog from the whole plant of Selaginella pulvinata.

Five selaginellin derivatives (1 and 3-6) including a new one, selaginellin T (1), and a new triarylbenzophenone analog, selagibenzophenone A (2), were isolated from the whole plants of Selaginella pulvinata. Their structures were determined by 1D- and 2D-NMR and HR-ESI-MS data. Selagibenzophenone A (2) is the first example of naturally occurring triarylbenzophenone. The results of the phosphodiesterase-4 (PDE4) inhibitory screening assays showed that compounds 1-6 exhibited potent activities with the IC50 values in the range of 1.04-9.35 µM.

Quick method for separating target compounds from the bark of Maqian (Zanthoxylum myriacanthum var. pubescens) by high-performance countercurrent chromatography.

Choosing a suitable solvent system for a countercurrent chromatography separation presents a challenge for many researchers. In this study, we introduce a quick method of separating a target compound from the bark of Zanthoxylum myriacanthum var. pubescens by countercurrent chromatography. This method relies on the thin-layer chromatography based generally useful estimation of solvent systems. This paper will present how to quickly choose a suitable solvent system with a thin-layer chromatography based generally useful estimation of solvent systems working chart. O-Methyltembamide (1) was enriched by countercurrent chromatography using n-hexane/ethyl acetate/methanol/water (6:4:6:4) as the solvent system. Further purification was achieved by high-performance liquid chromatography with purities of 98.2% from Z. myriacanthum var. pubescens bark.

Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans.

Nine new alkaloids of the koumine (1-4), humantenine (5-7), and yohimbane (8, 9) types as well as 12 known analogues were isolated from the leaves and vine stems of Gelsemium elegans. Compound 1 is the first N-4-demethyl alkaloid of the koumine type, compound 7 is the first nor-humantenine alkaloid, and compounds 8 and 9 are the first N-1-oxide and the first seco-E-ring alkaloids, respectively, of the yohimbane type. Compounds 1 and 7 exhibited moderate cytotoxicity against five human tumor cell lines with IC50 values in the range 4.6-9.3 µM.

Limonoids from the Leaves and Twigs of Walsura yunnanensis.

Nine new cedrelone limonoids, namely, walsuranolide B (1), 11ß-hydroxy-23-O-methylwalsuranolide (2), yunnanolide A (3), yunnanol A (4), 11ß-hydroxyisowalsuranolide (5), 11ß-hydroxy-1,2-dihydroisowalsuranolide (6), 1α,11ß-dihydroxy-1,2-dihydroisowalsuranolide (7), 11ß-hydroxy-1α-methoxy-1,2-dihydroisowalsuranolide (8), and yunnanolide B (9), together with a new cycloartane triterpenoid, (24S*,25R*)-cycloartane-3ß,24,25,26-tetrol (10), were isolated from the leaves and twigs of Walsura yunnanensis. Their structures were elucidated on the basis of spectroscopic analysis and by comparison with literature data. Compounds 3 and 5 exhibited potent cytotoxicity against five human tumor cell lines with IC50 values in the range 2.2-4.2 µM.

Limonoids from the fruits of Khaya ivorensis.

Two new limonoids, namely 14,15-didehydroruageanin A (1) and 3-O-methyl- butyrylseneganolide A (2), were isolated from the fruits of Khaya ivorensis along with six known limonoids: seneganolide A (3), 1,3-dideacetylkhivorin (4), 7-deacetylkhivorin (5), 3-deacetylkhivorin (6), 1-deacetylkhivorin (7), and 3-deacetyl-7-oxokhivorin (8). All the compounds were evaluated for their cytotoxicity against five tumor cell lines.

Targeting urinary calcium oxalate crystallization with inulin-type AOFOS from Aspidopterys obcordata Hemsl. for the management of rat urolithiasis.

ETHNOPHARMACOLOGICAL RELEVANCE: Calcium oxalate crystals play a key role in the development and recurrence of kidney stones (also known as urolithiasis); thus, inhibiting the formation of these crystals is a central focus of urolithiasis prevention and treatment. Previously, we reported the noteworthy in vitro inhibitory effects of Aspidopterys obcordata fructo oligosaccharide (AOFOS), an active polysaccharide of the traditional Dai medicine Aspidopterys obcordata Hemsl. (commonly known as Hei Gai Guan), on the growth of calcium oxalate crystals. AIM OF THE STUDY: To investigated the effectiveness and mechanism of AOFOS in treating kidney stones. MATERIALS AND METHODS: A kidney stones rats model was developed, followed by examining AOFOS transport dynamics and effectiveness in live rats. Additionally, a correlation between the polysaccharide and calcium oxalate crystals was studied by combining crystallization experiments with density functional theory calculations. RESULTS: The results showed that the polysaccharide was transported to the urinary system. Furthermore, their accumulation was inhibited by controlling their crystallization and modulating calcium ion and oxalate properties in the urine. Consequently, this approach helped effectively prevent kidney stone formation in the rats. CONCLUSIONS: The present study emphasized the role of the polysaccharide AOFOS in modulating crystal properties and controlling crystal growth, providing valuable insights into their potential therapeutic use in managing kidney stone formation.

Uncarilic acid and secouncarilic acid, two new triterpenoids from Uucaria sessilifructus.

Two new compounds, the 6-oxo oleanane-type triterpenoid uncarilic acid, and its 5,6-secotriterpenoid derivative, secouncarilic acid, were isolated from the hooks and stems of Uucaria sessilifructus together with seven known ursane-type triterpenoids. Uncarilic acid is the second 6-oxo oleanane-type triterpenoid ever reported, while secouncarilic acid is the first oleanane-type 5,6-secotriterpenoid. A plausible biosynthetic pathway from uncarilic acid to secouncarilic acid was also postulated. The inhibitory activities of all the nine compounds against LPS-induced nitric oxide production in RAW264.7 macrophages were evaluated.

[Chemical constituents from stems of Dysoxylum laxiracemosum].

Twelve compounds were separated from stems of Dysoxylum laxiracemosum and their structures were identified by spectrum analysis as shoreic acid (1), cabraleahydroxylactone (2), cabralealactone (3), cinchonain (5), catechin (6), scopoletin (7), vanillic acid (8), p-hydroxybenzoic acid (9), docosanol (10), beta-sitosterol (11), daucosterol (12). Of them, compounds 1-6,8-12 were separated from this plant for the first time, and compounds 4-6 were reported from this plant genus for the first time.

Geranyl phenyl ethers from Illicium micranthum and their anti-HBV activity.

Fourteen new geranyl phenyl ethers (1-14) along with three known compounds (15-17) were isolated from Illicium micranthum, and their structures were elucidated by comprehensive spectroscopic methods. Illimicranins A-H (1-8) were characterized as geranyl vanillin ethers, while 9 and 10 were dimethyl acetal derivatives. Illimicranins I and J (11 and 12) were rare geranyl isoeugenol ethers. Illimicranins K and L (13 and 14) represented the first example of geranyl guaiacylacetone ether and geranyl zingerone ether, respectively. Compounds 1, 2 and 15 exhibited anti-HBV (hepatitis B virus) activity against HBsAg (hepatitis B surface antigen) and HBeAg (hepatitis B e antigen) secretion, and HBV DNA replication.

Cytotoxic α-pyrone derivatives from Cryptocarya yunnanensis.

Five new α-pyrone derivatives, cryptoyunnanes A - E (1 - 5), together with four known analogues, were isolated from the leaves and twigs of Cryptocarya yunnanensis. Their structures including absolute configurations were elucidated by extensive spectroscopic data and electronic circular dichroism (ECD) analyses. Compounds 4 and 6 showed significant cytotoxicity against A549, HCT-116, MDA-MB-231, PC-3 and HeLa with IC50 values from 2.25 to 8.97 µM. Compounds 1, 2 and 7 also displayed good cytotoxicity against HCT-116, MDA-MB-231 and PC-3 with IC50 values from 1.26 to 8.32 µM. This is the first time to report the isolation and bioactivity evaluation of chemical constituents from C. yunnanensis.

Alpinia hainanensis Rhizome Extract Ameliorates Dextran Sulfate Sodium-Induced Ulcerative Colitis: Active Ingredient Investigation and Evaluation.

Alpinia hainanensis is an important food spice and ethnic medicine in Southwest China. In this study, we found that the EtOAc-soluble fraction (AHE) of the A. hainanensis rhizome ethanol extract could ameliorate dextran sulfate sodium-induced ulcerative colitis (UC). To explore active constituents, five pairs of previously unreported enantiomers (1-5), together with nine known ones (6-14), were obtained. Structural characterization was achieved by comprehensive spectroscopic methods. Compounds 1 and 2 were new curcumin-butyrovanillone hybrids featuring a rare structural fragment of 2,3-dihyrofuran. The anti-inflammatory activities of isolates were evaluated, and the results indicated that compounds (-)-1, (-)-3, 6, 9, 11, and 12 significantly inhibited the nuclear factor-κB signaling pathway. These findings indicate the major active fraction of the A. hainanensis rhizome ethanol extract enriched with diarylheptanoids, flavonoids, phenolics, and their hybrid mixtures, which could be developed as a nutritional and dietary supplement for treating UC.