Eight undescribed metabolites (1-8), including three sesquiterpenoids (1-3) and five 2-(2-phenylethyl)chromones (4-8), and 28 known compounds (8-35) were isolated by bioassay-guided fractionation of A. sinensis extract. Their structures were elucidated by analyses of NMR and MS data, as well as single-crystal X-ray diffraction and ECD calculations. All the isolated compounds were systematically evaluated cytotoxic and anti-inflammatory activity. Four compounds including one eudesmane-type sesquiterpenoid (-)-(5R,7R,10R)-12,15-dioxo-α-selinene (9) and three 5,6:7,8-diepoxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromones, namely (5R,6R,7R,8R)-oxidoagarochromone A (11), (5S,6S,7S,8S)-oxidoagarochromone B (12), and (5S,6S,7S,8S)-oxidoagarochromone C (13), were the most cytotoxic against eleven cancer cell lines (HL-60, K562, A549, MDA-MB-231, SW480, HepG2, HCT116, Caco2, SK-OV-3, MG-63, and U251), with IC50 values of 0.18-6.35 μM. Moreover, compounds 9 (IC50 = 0.19 μM), 11 (IC50 = 0.60 μM), and 12 (IC50 = 1.01 μM), and (5R,6S,7S,8S)-7,8-dihydroxy-5,6-epoxy-2-[2-(4-methoxyphenyl)ethyl]-5,6,7,8-tetrahydrochrome (16; IC50 = 3.55 μM) exhibited the strongest inhibition of the NO production. The absolute configurations of compounds 11-13 were determined by X-ray diffraction for the first time. These dual anticancer/anti-inflammatory compounds (9, 11, and 12) may serve as promising candidates for future mechanistic and in vivo studies.
Ethnopharmacological relevance Ethnoveterinary practices have supported livestock healthcare around the world. Global demand for plant-based products as alternatives to antimicrobial feed additives in livestock production industry is rising. Detailed documentation of ethnoveterinary knowledge could shorten the bioprospecting process for veterinary applications, while supporting evidence-based ethnopharmacological studies which improve local veterinary practices. Aim of the study Systematically investigating ethnoveterinary knowledge in northeast Yunnan of China to identify species and formulars for further bioprospection on veterinary medicines and antimicrobial feed additives. Materials and methods In 2022-2024, we carried out five surveys in 24 villages with 64 dialog partners who are local veterinary healers, knowledgeable farmers, and local veterinary technicians. We employed Use Report, Frequency of Citation, informant consensus factor and Apriori algorithm for data analysis. Results We documented 218 species (82 families) and 220 formulars for 16 categories of local veterinary use. The most treated veterinary diseases are digestive, musculoskeletal and respiratory disorders. Three frequently mentioned species (Dipsacus asper, Taraxacum sinicum, Bupleurum longicaule var. amplexicaule) were newly reported for ethnoveterinary uses for the first time in Eurasia. Bistorta vivipara and Argentina lineata, Plantago asiatica and Rumex nepalensis, Berberis wilsoniae and Rumex nepalensis were often used together to treat digestive, respiratory and skin disorders respectively. Argentina lineata, Rumex nepalensis, Dipsacus asper have high potential as antimicrobial feed additives, promoting livestock growth and health with little drug resistance and ecological damage. Conclusions Pharmaceutical studies could be designed based on these findings to develop effective, safe and user-friendly plant-derived veterinary medicines and antimicrobial feed additives. Local government agencies should recognize and promote ethnoveterinary knowledge transmission and support local conservation initiatives for sustainable use of the plant species.
Gastrodia elata (Orchidaceae) is a material used for medicine, food, and cosmetics in China. Two new alkaloids, 1,7-bis(4-hydroxybenzyl)-1,7-dihydro-6H-purin-6-one (1) and 1,9-bis(4-hydroxybenzyl)-1,9-dihydro-6H-purin-6-one (2), five known alkaloids, (–)-(R)-4-(2-hydroxy-2-quinolin-4-ylethyl)phenol ((–)-3), (+)-(S)-4-(2-hydroxy-2-quinolin-4-ylethyl)phenol ((+)-3), 1-(4-hydroxyphenyl)-β-carboline (4), p-topolin riboside (5), and cannabisin F (6), and nine other compounds (7–15), were isolated from the rhizomes, peduncles, and inflorescences of Gastrodia elata, a waste collected after seed harvesting. The chemical structures of these new compounds were determined by MS and NMR spectroscopic data. These isolated alkaloids were evaluated for their cholinesterase inhibitory activity and collagen I secretion-promoting activity. Compound 2 inhibited acetylcholinesterase (AChE) with an IC50 value of 19.8 ± 1.8 μM, whereas compound 4 exhibited an inhibitory effect on AChE with an IC50 value of 24.7 ± 3.2 μM, and on butyrylcholinesterase (BuChE) with an IC50 value of 0.84 ± 0.06 μM. At a concentration of 0.1 μM, compounds (–)-3, (+)-3, and 5 exhibited significant collagen I secretion-promoting activity in human dermal fibroblast adults (HDFa). These active compounds have potential for the development of neuroprotective drugs or antiaging cosmetics.
Developing highly efficient and stable catalysts for hydroxylamine nitrate (HAN) decomposition is challenged by their tendency to sinter and suffer a sharp loss in specific surface area at high temperatures. Herein, a series of manganese-substituted lanthanum hexaaluminate (LM(x)A, x = 0, 0.5, 1, 2, 3) nanomaterials were prepared by coprecipitation-decarbonization templating method, and the effect of manganese doping on structure and the catalytic activity for HAN decomposition were systematically investigated. XRD and BET characterization revealed that the manganese substitution significantly regulated the structural properties of hexaaluminate nanomaterials, among which pure-phase LaMnAl11O19 (denoted as LM(1)A) exhibited excellent high-temperature structural stability. After calcination at 1400 degrees C for 12 h, the grain size increased only slightly from 24.1 to 28.7 nm, and the specific surface area retained at 15.8 m(2)& centerdot;g(-1), indicating outstanding resistance to nanoparticle sintering. Notably, LM(1)A served dual roles as both a catalytic support and an active component, exhibiting a stable catalytic efficiency for HAN decomposition, which could significantly reduce the initial decomposition temperature from 162.0 degrees C (thermal decomposition) to 120.4 degrees C. Manganese doping lowers the reaction energy barrier, as confirmed by critical kinetic parameters. Rational nanoscale regulation of manganese doping in hexaaluminate significantly enhances the high-temperature stability, providing an important reference for the development of highly efficient and long-life HAN decomposition catalysts.
Thirteen compounds (1–13), including two new amides, piperunnamides E (1) and F (2), were isolated from the aerial parts of Piper yunnanense collected from Myanmar. (7R,7′R,8R,8′R)-1 and (7S,7′S,8S,8′S)-1 were obtained by the chiral separation of 1 and their absolute configurations were determined by electronic circular dichroism (ECD) calculations. Sarmentomicine (5) and lutein A (13) significantly suppressed nitric oxide (NO) production (IC50 = 8.97 ± 0.38 μM and 30.48 ± 0.48 μM, respectively) in mouse monocyte RAW264.7 macrophages induced by lipopolysaccharide (LPS). This anti-inflammatory activity of sarmentomicine is being reported for the first time.
A pair of amide enantiomers, (+)-magenamide B [(+)-1] and (-)-magenamide B [(-)-1], and six undescribed alkaloids, magenamides CF (2-5), along with 2-nonyl-3,5-dioctylpyridine (6) and 3-decyl-2-nonyl-5-octylpyridine (7), together with 19 known compounds (8-26) were isolated from the stems of Piper magen (Piperaceae). The chemical structures of all the new compounds were elucidated using NMR and MS data. Magenamide C and 5,6-dihydro-1-[(2E)-3-(4-methoxyphenyl)-1-oxo-2-propen-1-yl]-2(1H)-pyridinone (15) strongly inhibited NO production, with IC50 values of 30.09 μM and 3.16 μM, respectively (positive control: L-NMMA, IC50 = 42.24 μM). Moreover, corydalisin C (24) showed DPPH radical scavenging activity, with an IC50 value of 26.10 μM (positive control: Trolox, IC50 = 21.38 μM). Compound 15 and magenamide A demonstrated protective effects against corticosterone-induced neuronal injury at a concentration of 2 μM (P < 0.001). 1-(m-Methoxycinnamoyl)pyrrolidine (16) exhibited BACE1 inhibitory activity, with an IC50 value of 8.73 μM (positive control: LY2886721, IC50 = 31.80 nM).
The stem bark of Aquilaria yunnanensis(Thymelaeaceae) is traditionally used to treat cough and asthma in folk medicine. However, its active components have not been reported. In the present study, the chemical constituents of A. yunnanensis stem bark were isolated and identified, and their inhibitory activities against nitric oxide(NO) production in RAW264.7 cells induced by lipopolysaccharide(LPS) were evaluated to clarify the anti-inflammatory components in the stem bark of A. yunnanensis. A total of 22 compounds, including a new norlignan [(±)-1], were isolated from the ethanolic extract of A. yunnanensis stem bark by column chromatography, high-performance liquid chromatography(HPLC), recrystallization, etc. Through chiral separation of(±)-1,(-)-1 and(+)-1 were obtained. Based on electronic circular dichroism(ECD) calculations, the absolute configurations of(-)-1 and(+)-1 were determined to be(-)-(7R,8S,8'S)-4-O-(1,3-dihydroxypropan-2-yl)zhebeiresinol and(+)-(7S,8R,8'R)-4-O-(1,3-dihydroxypropan-2-yl)zhebeiresinol. The known compounds included(±)-zhebeiresinol(2),(+)-syringaresinol(3),(+)-episyringaresinol(4), orcinol(5), orsellinic acid(6), methyl orsellinate(7), 3,4-dihydroxybenzoic acid(8), lecanoric acid(9), barbatic acid(10), 7β-hydroxy-β-sitosterol(11), β-sitosterol(12), stigmasterol(13), ergosterol peroxide(14), genkwanin(15), pilloin(16), 5-hydroxy-3',4',7-trimethoxyflavone(17),(-)-epicatechin(18),(-)-epicatechin gallate(19), tectorigenin 2-O-α-L-rhamnopyranoside(20), 2,3-dihydroxypropyl docosanoate(21), and 1-O-linolenoylglycerol(22). According to the bioassay testing results, compounds 4 and 22 which inhibited NO production with IC_(50) values of(32.82±1.04) and(18.50±0.95) μmol·L~(-1), respectively, exhibited anti-inflammatory activities.
Twenty-six compounds, including one new 2-(2-phenylethyl)chromone derivative, (R)-2-(1-hydroxy-2- phenylethyl)chromone (1), and one new resorcylic acid lactone, (S)-de-O-methylhispidulactone A (2), were isolated from the nonresinous heartwood of Aqualaria sinensis (Lour.) Spreng. Among these compounds, (S)-de-O-methylhispidulactone A (2), 2-(2-phenylethyl)chromone (4), 2-[2-(4-hydroxyphenyl)ethyl]chromone (7), 6-methoxy-2-(2-phenylethyl)chromone (8), 6-methoxy-2-[2-(3-methoxyphenyl)ethyl]chromone (9), 2-[2-(3-methoxyphenyl)ethyl]chromone (10), 6,7-dimethoxy-2-(2-phenylethyl)chromone (11), 8-chloro-6- hydroxy-2-[2-(4-methoxyphenyl)ethyl]chromon-4-one (13), (+)-(R)-de-O-methyllasiodiplodin (14), lasiodiplodin (15), and (3R)-(–)-melliein (20) exhibited antifungal activity against Epidermophyton floccosum, Trichophyton rubrum, and Microsporum gypseum, with MIC values ranging from 5.8 to 51.6 μM. Furthermore, (R)-2-(2-hydroxy-2-phenylethyl)chromone (3b), 7, 8, 9, 14, 15, 5-hydroxy-7,3′,4′- trimethoxyflavone (17), and velutin (18) demonstrated antibacterial effects against Staphylococcus aureus, with MIC values ranging from 20.2 to 96.0 μM.
This study first integrates genomic and chemical analyses of Botryosphaeria dothidea isolated from Aquilaria sinensis to investigate its role in agarwood formation. Whole-genome sequencing revealed a 44.33 Mb assembly encoding 69 biosynthetic gene clusters (BGCs). antiSMASH analysis revealed that 37 of these BGCs (53.6
This study systematically explored the secondary metabolites of an endophytic fungus, Penicillium polonicum, isolated from Emmenopterys henryi. Advanced separation techniques, including silica gel column chromatography, Sephadex LH-20 column chromatography, and semi-preparative liquid chromatography, were combined for compound isolation. Seven compounds were successfully isolated from the rice fermentation products of P. polonicum. Their structures were elucidated by nuclear magnetic resonance spectroscopy, high resolution mass spectrometry, ultraviolet spectrometry, and circular dichroism spectroscopy. The identified compounds were penicimolide A(1), penicimenolide E(2),(3S)-cis-resorcylide(3),(R)-7-hydroxydihydroresorcylide(4),(S)-7-hydroxydihydroresorcylide(5), communesin A(6), and chaetoglobosin C(7). Notably, compound 1 represents a new 12-membered benzenediol lactone. The antifungal activities of these compounds against phytopathogenic fungi was evaluated. The results indicated that compound 1 exhibited weak antifungal activity against Alternaria alternata, with a minimum inhibitory concentration(MIC) of 100 μg·mL~(-1). Compound 6 exhibited moderate antifungal activity against Fusarium graminearum with an MIC value of 25 μg·mL~(-1). Compound 7 demonstrated strong antifungal activity against A. solani and Geotrichum candidum, with MICs of 12.5 μg·mL~(-1).
The role of fungi in agarwood resin formation remains incompletely understood. This study investigated the metabolic effects of Botryosphaeria dothidea strain ket49 on the nonresinous heartwood of Aquilaria sinensis. HPLC analysis revealed that, compared with the control treatment, fermentation with ket49 induced a time-dependent metabolic shift, markedly increasing the accumulation of agarotetrol, a pharmacopeial marker, by 4.5-fold. UPLCQTOFMS/MS analysis of the fermented extract tentatively revealed 14 2-(2-phenylethyl)chromones. Subsequent isolation yielded 11 compounds, including the new (R)-2-[2-hydroxy-2-(2-hydroxyphenyl)ethyl]chromone (1). These findings revealed the possibility that 2-(2-phenylethyl)chromones are hydroxylated by this fungus. The increase in agarotetrol production by fungi may be a sustainable strategy for high-quality agarwood induction.
The global rise in animal protein consumption has significantly amplified the demand for fodder. A comprehensive understanding of the diversity and characteristics of existing fodder resources is essential for balanced nutritional fodder production. This study investigates the diversity and composition of fodder plants and identifies key species for cattle in Zhaotong City, Yunnan, China, while documenting indigenous knowledge on their usage and selection criteria. Ethnobotanical surveys were conducted in 19 villages across seven townships with 140 informants. Data were collected through semi-structured interviews, free listing, and participatory observation, and analyzed using Relative Frequency Citation. A total of 125 taxa (including 106 wild and 19 cultivated) were reported. The most cited family is Poaceae (27 taxa, 21.43%), followed by Asteraceae (17 taxa, 13.49%), Fabaceae (14 taxa, 11.11%), Polygonaceae (9 taxa, 7.14%) and Lamiaceae (4 taxa, 3.17%). The whole plant (66.04%) and herbaceous plants (84.80%) were the most used parts and life forms. The most cited species were Zea mays, Brassica rapa, Solanum tuberosum, Eragrostis nigra, and Artemisia dubia. Usage of diverse fodder resources reflects local wisdom in managing resource availability and achieving balanced nutrition while coping with environmental and climatic risks. Preferences for certain taxonomic groups are due to their quality as premier fodder resources. To promote integrated crop-livestock farming, we suggest further research into highly preferred fodder species, focusing on nutritional assessment, digestibility, meat quality impacts, and potential as antibiotic alternatives. Establishing germplasm and gene banks for fodder resources is also recommended.
Three new polyhydroxylated spirostanol steroidal saponins, dulongenosides B-D (2-4), along with 14 known compounds, dulongenoside A (1), padelaoside B (5), parisyunnanoside G (6), polyphyllin D (7), ophiopogonin C' (8), formosanin C (9), dioscin (10), paris saponin VII (11), paris H (12), parisyunnanoside I (13), protodioscin (14), proprotogracillin (15), crustecdysone (16), and stigmasterol-3-O-β-d-glucopyranoside (17), were isolated from the rhizomes of Paris dulongensis (Melanthiaceae). Their chemical structures were elucidated based on extensive analyses of NMR and MS data and acidic hydrolyses. The isolates were evaluated for their cytotoxicity to five human cancer cell lines (HL-60, SW480, MDA-MB-231, A549, and A549/Taxol) and the normal human bronchial epithelial cell line BEAS-2B by the MTS test. Compounds 7-12 and 14 showed cytotoxic activity, with IC50 values ranging from 0.20 to 4.35 μM. Proprotogracillin selectively inhibited A549 (IC50=0.58 μM) and A549/Taxol (IC50=0.74 μM) cells, with no significant cytotoxic activity against HL-60, SW480, MDA-MB-231, or BEAS-2B cells, with IC50 values greater than 40 μM.
Hyperforin is the compound responsible for the effectiveness of St. John's wort (Hypericum perforatum) as an antidepressant, but its complete biosynthetic pathway remains unknown. Gene discovery based on co- expression analysis of bulk RNA-sequencing data or genome mining failed to discover the missing steps in hyperforin biosynthesis. In this study, we sequenced the 1.54-Gb tetraploid H. perforatum genome assembled into 32 chromosomes with the scaffold N50 value of 42.44 Mb. By single-cell RNA sequencing, we identified a type of cell, "Hyper cells", wherein hyperforin biosynthesis de novo takes place in both the leaves and flowers. Through pathway reconstitution in yeast and tobacco, we identified and characterized four transmembrane prenyltransferases (HpPT1-4) that are localized at the plastid envelope and complete the hyperforin biosynthetic pathway. The hyperforin polycyclic scaffold is created by a reaction cascade involving an irregular isoprenoid coupling and a tandem cyclization. Our findings reveal how and where hyperforin is biosynthesized, enabling synthetic-biology reconstitution of the complete pathway. Thus, this study not only deepens our comprehension of specialized metabolism at the cellular level but also provides strategic guidance for elucidation of the biosynthetic pathways of other specializied metabolites in plants.
The stem bark of Aquilaria sinensis(Thymelaeaceae), with the local name of "Li-Wa-Zi-Xing", is used in traditional Yi medicine for treating chronic gastritis and other diseases. However, its active ingredients remain currently unknown. In this study, Helicobacter pylori(Hp) is used in anti-bacterial experiments to test the active compounds derived from A. sinensis stem bark. Nineteen compounds were isolated from the stem bark of A. sinensis by column chromatography, high-performance liquid chromatography, recrystallization, etc. Aquilaridiester(1) is a new lignan. The other eighteen compounds were reported before, including docosyl caffeate(2), 6-hydroxy-2-[2-(4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one(3), qinanone A(4), 6-hydroxy-2-(2-phenylethyl)chromone(5), 6-hydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one(6), 6-hydroxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]-4H-1-benzopyran-4-one(7), 6-hydroxy-2-[2-(3,4-dimethoxyphenyl)ethyl]chromone(8), 6-hydroxy-2-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-4H-1-benzopyran-4-one(9), genkwanin(10), 5-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one(11), 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(12),(+)-syringaresinol(13), zhebeiresinol(14), aquilarin A(15), caruilignan D(16),(-)-ficusal(17), pistaciamide(18), and protocatechuic acid(19). The anti-bacterial results show that compounds 2-7, 10-11, and 13 have inhibitory activity against Hp. Among them, 6-hydroxy-2-(2-phenylethyl)chromone(5) and 6-hydroxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]-4H-benzopyran-4-one(7) have superior inhibitory effects on Hp to others, with the same minimum inhibitory concentration(MIC) of 6.25 μmol·L~(-1). The 2-(2-phenylethyl)chromones are the major active ingredients in A. sinensis stem bark.
Two previously undescribed steroidal saponins, rugosarosides A (1) and B (2), as well as 16 known compounds (3-18), were isolated from the rhizomes of Paris rugosa H. Li & S. Kurita (Melanthiaceae). Their chemical structures were elucidated based on extensive analyses of NMR and MS data and acidic hydrolyses. These isolates were evaluated for their cytotoxicity to five human cancer cell lines (HL-60, SW480, MDA-MB-231, A549, and A549/Taxol) and the normal human bronchial epithelial cell line BEAS-2B using the MTS test. Spirostanol saponins 6-12 and furostanol saponin 16 showed cytotoxic activity, with IC50 values ranging from 0.13 to 3.88 mu M. The furostanol saponins 14, 15, and 17 selectively inhibited HL-60, A549, and A549/Taxol cells (IC50: 3.45-9.51 mu M), with no cytotoxicity to SW480 and MDA-MB-231 cells (IC50 > 40 mu M).
Five new steroidal saponins, xuefengshanosides A-E; one new stilbene trimer, xuefengshansin; and 16 known compounds were isolated from the rhizomes of Paris xuefengshanensis (Melanthiaceae). The chemical structures of the compounds were elucidated by MS and NMR data analyses, ECD calculations, and acidic hydrolysis experiments. The cytotoxicity and antimicrobial activities of the selected compounds were evaluated. Ophiopogonin C', paris saponin I, paris saponin H, and paris saponin VII showed the most inhibitory activity against five human cancer cell lines and one normal cell line. Xuefengshansin showed weak cytotoxic and antibacterial activities. Paris saponin I was the most active compound against the five tested fungal strains. This species contains structurally diverse compounds that exhibit significant anticancer and antimicrobial activities, suggesting its potential for future development and utilization.
Paris xuefengshanensis, a new species collected from Hunan, China, is described and illustrated here based on phylogenetic and morphological evidence. Morphologically, it resembles P. thibetica and P. qiliangiana but can be distinguished by the shape of the leaf and sepal, the type of placenta and fruit. The phylogenetic analysis of the chloroplast genome revealed that P. xuefengshanensis does not belong to any section of the latest infrageneric taxonomy system, but form a well-supported independent monophyletic clade. Combined with morphology, we speculate that its distinctive phylogenetic position is related to the type of placenta (the transitional type between the parietal placenta and axile placenta).