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1.
Fitoterapia ; 175: 105905, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38479616

ABSTRACT

Six new dimeric 2-(2-phenylethyl)chromones (1-6) were successfully isolated from the ethanol extract of agarwood of Aquilaria filaria from Philippines under HPLC-MS guidance. Compounds 1-6 are all dimers formed by linking 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone and flindersia 2-(2-phenylethyl)chromone via a single ether bond, and the linkage site (C5-O-C8'') of compound 2 is extremely rare. A variety of spectroscopic methods were used to ascertain their structures, including extensive 1D and 2D NMR spectroscopic analysis, HRESIMS, and comparison with literature. The in vitro tyrosinase inhibitory and anti-inflammatory activities of each isolate were assessed. Among these compounds, compound 2 had a tyrosinase inhibition effect with an IC50 value of 27.71 ± 2.60 µM, and compound 4 exhibited moderate inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with an IC50 value of 35.40 ± 1.04 µM.


Subject(s)
Anti-Inflammatory Agents , Monophenol Monooxygenase , Nitric Oxide , Thymelaeaceae , Wood , RAW 264.7 Cells , Animals , Thymelaeaceae/chemistry , Mice , Molecular Structure , Wood/chemistry , Nitric Oxide/metabolism , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/chemistry , Monophenol Monooxygenase/antagonists & inhibitors , Philippines , Chromones/isolation & purification , Chromones/pharmacology , Chromones/chemistry , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Flavonoids
2.
Fitoterapia ; 173: 105814, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38163447

ABSTRACT

Four new ansamycin derivatives, named 1,19-epithio-geldanamycin A (1), 17-demethoxylherbimycin H (2), herbimycin M (3), and seco-geldanamycin B (4), together with eight known ansamycin analogues (5-12) were isolated from the solid fermentation of marine-derived actinomycete Streptomyces sp. ZYX-F-97. The structures of new compounds were elucidated by extensive spectroscopic analysis as well as nuclear magnetic resonance (NMR) and electronic circular dichroism (ECD) calculations. All the compounds were assayed for their antibacterial activity. Among them, compounds 4, 8, and 12 exhibited remarkable inhibition against Listeria monocytogenes with minimum inhibitory concentrations (MIC) values ranging from 8 µg·mL-1 to 64 µg·mL-1, and displayed moderate inhibition against methicillin-resistant Staphylococcus aureus (MRSA) with MIC value of 64 µg·mL-1. Compounds 4, 8, 9, and 12 showed moderate inhibition activities against both Staphylococcus aureus and Bacillus subtilis with MIC values ranging from 32 µg·mL-1 to 128 µg·mL-1.


Subject(s)
Benzoquinones , Methicillin-Resistant Staphylococcus aureus , Streptomyces , Lactams, Macrocyclic , Streptomyces/chemistry , Molecular Structure , Anti-Bacterial Agents , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests
3.
Fitoterapia ; 172: 105748, 2024 Jan.
Article in English | MEDLINE | ID: mdl-37967770

ABSTRACT

Three new sesquiterpenoids, dendrohercoglin A - C (1-3), and one new bibenzyl derivative, dendronbiline D (4), together with nine known sesquiterpenoids (5-13) were isolated from Dendrobium hercoglossum. The structures of the new compounds were elucidated by extensive spectroscopic analysis as well as NMR and ECD calculations. All the compounds were evaluated for their neuroprotective and anti-inflammatory activities. Compounds 2 and 3 increased the H2O2-damaged SH-SY5Y cell viabilities from 43.3% to 58.6% and 68.4%, respectively. Compound 4 exhibited pronounced anti-inflammatory activity with IC50 value of 9.5 ± 0.45 µM which was superior to the reference compound quercetin (IC50: 15.7 ± 0.89 µM).


Subject(s)
Bibenzyls , Dendrobium , Neuroblastoma , Sesquiterpenes , Humans , Dendrobium/chemistry , Molecular Structure , Hydrogen Peroxide , Magnetic Resonance Spectroscopy , Sesquiterpenes/pharmacology , Bibenzyls/pharmacology , Bibenzyls/chemistry , Anti-Inflammatory Agents/pharmacology
4.
Front Plant Sci ; 14: 1243323, 2023.
Article in English | MEDLINE | ID: mdl-37719219

ABSTRACT

Introduction: Agarwood, the dark-brown resin produced by Aquilaria trees, has been widely used as incense, spice, perfume or traditional medicine and 2-(2-phenethyl) chromones (PECs) are the key markers responsible for agarwood formation. But the biosynthesis and regulatory mechanism of PECs were still not illuminated. The transcription factor of basic leucine zipper (bZIP) presented the pivotal regulatory roles in various secondary metabolites biosynthesis in plants, which might also contribute to regulate PECs biosynthesis. However, molecular evolution and function of bZIP are rarely reported in Malvales plants, especially in Aquilaria trees. Methods and results: Here, 1,150 bZIPs were comprehensively identified from twelve Malvales and model species genomes and the evolutionary process were subsequently analyzed. Duplication types and collinearity indicated that bZIP is an ancient or conserved TF family and recent whole genome duplication drove its evolution. Interesting is that fewer bZIPs in A. sinensis than that species also experienced two genome duplication events in Malvales. 62 AsbZIPs were divided into 13 subfamilies and gene structures, conservative domains, motifs, cis-elements, and nearby genes of AsbZIPs were further characterized. Seven AsbZIPs in subfamily D were significantly regulated by ethylene and agarwood inducer. As the typical representation of subfamily D, AsbZIP14 and AsbZIP41 were localized in nuclear and potentially regulated PECs biosynthesis by activating or suppressing type III polyketide synthases (PKSs) genes expression via interaction with the AsPKS promoters. Discussion: Our results provide a basis for molecular evolution of bZIP gene family in Malvales and facilitate the understanding the potential functions of AsbZIP in regulating 2-(2-phenethyl) chromone biosynthesis and agarwood formation.

5.
Fitoterapia ; 169: 105582, 2023 Sep.
Article in English | MEDLINE | ID: mdl-37331407

ABSTRACT

Four new compounds ((±)-1-3), including one pair of enantiomers ((±)-1), along with 11 known bibenzyls (4-14) were isolated from Dendrobium nobile. The structures of the new compounds were elucidated by spectroscopic methods including 1D and 2D NMR as well as HRESIMS. The configurations of (±)-1 were established via the electronic circular dichroism (ECD) calculations. Compounds (+)-1 and 13 displayed pronounced α-glucosidase inhibitory activities with IC50 values of 16.7 ± 2.3 and 13.4 ± 0.2 µM, respectively, which were comparable to that of genistein (IC50, 8.54 ± 0.69 µM). Kinetic studies revealed that (+)-1 and 13 were non-competitive inhibitors against α-glucosidase and molecular docking simulations illuminated their interactions with α-glucosidase. All the isolates were also evaluated for their anti-inflammatory activities. Compounds 4, 5, and 11 exhibited superior inhibition activity with IC50 values ranging from 9.2 to 13.8 µM to that of quercetin (IC50, 16.3 ± 1.1 µM).


Subject(s)
Dendrobium , alpha-Glucosidases , Molecular Structure , Dendrobium/chemistry , Molecular Docking Simulation , Kinetics , Glycoside Hydrolase Inhibitors/pharmacology
6.
Front Pharmacol ; 14: 1079539, 2023.
Article in English | MEDLINE | ID: mdl-36937875

ABSTRACT

Background: Dendrobium nobile (D. nobile), a traditional Chinese medicine, has received attention as an anti-tumor drug, but its mechanism is still unclear. In this study, we applied network pharmacology, bioinformatics, and in vitro experiments to explore the effect and mechanism of Dendrobin A, the active ingredient of D. nobile, against pancreatic ductal adenocarcinoma (PDAC). Methods: The databases of SwissTargetPrediction and PharmMapper were used to obtain the potential targets of Dendrobin A, and the differentially expressed genes (DEGs) between PDAC and normal pancreatic tissues were obtained from The Cancer Genome Atlas and Genotype-Tissue Expression databases. The protein-protein interaction (PPI) network for Dendrobin A anti-PDAC targets was constructed based on the STRING database. Molecular docking was used to assess Dendrobin A anti-PDAC targets. PLAU, one of the key targets of Dendrobin A anti-PDAC, was immunohistochemically stained in clinical tissue arrays. Finally, in vitro experiments were used to validate the effects of Dendrobin A on PLAU expression and the proliferation, apoptosis, cell cycle, migration, and invasion of PDAC cells. Results: A total of 90 genes for Dendrobin A anti-PDAC were screened, and a PPI network for Dendrobin A anti-PDAC targets was constructed. Notably, a scale-free module with 19 genes in the PPI indicated that the PPI is highly credible. Among these 19 genes, PLAU was positively correlated with the cachexia status while negatively correlated with the overall survival of PDAC patients. Through molecular docking, Dendrobin A was found to bind to PLAU, and the Dendrobin A treatment led to an attenuated PLAU expression in PDAC cells. Based on clinical tissue arrays, PLAU protein was highly expressed in PDAC cells compared to normal controls, and PLAU protein levels were associated with the differentiation and lymph node metastatic status of PDAC. In vitro experiments further showed that Dendrobin A treatment significantly inhibited the proliferation, migration, and invasion, inducing apoptosis and arresting the cell cycle of PDAC cells at the G2/M phase. Conclusion: Dendrobin A, a representative active ingredient of D. nobile, can effectively fight against PDAC by targeting PLAU. Our results provide the foundation for future PDAC treatment based on D. nobile.

7.
Zhongguo Zhong Yao Za Zhi ; 48(3): 707-714, 2023 Feb.
Article in Chinese | MEDLINE | ID: mdl-36872234

ABSTRACT

Chemical constituents in soft coral Sarcophyton glaucum were separated and purified by various chromatographic methods. Based on the spectral data, physicochemical properties, and comparison with the data reported in the literature, nine cembranoids, including a new cembranoid named sefsarcophinolide(1) together with eight known cembranoids, namely(+)-isosarcophine(2), sarcomilitatin D(3), sarcophytonolide J(4),(1S,3E,7E,13S)-11,12-epoxycembra-3,7,15-triene-13-ol(5), sarcophytonin B(6),(-)-eunicenone(7), lobophytin B(8), and arbolide C(9), were identified. As revealed by biological activity experiment results, compounds 2-6 had weak acetylcholinesterase inhibitory activity, and compound 5 displayed weak cytotoxicity against K562 tumor cell line.


Subject(s)
Anthozoa , Animals , Acetylcholinesterase , Cell Line, Tumor
8.
Fitoterapia ; 165: 105422, 2023 Mar.
Article in English | MEDLINE | ID: mdl-36592638

ABSTRACT

Four new 2-(2-phenethyl)chromone dimers (1-4) were isolated from EtOAc extract of agarwood originating from Aquilaria filaria from Philippines. Their structures were elucidated by spectroscopic analysis (1D and 2D NMR, and HRESIMS) and comparison of the experimental and computed ECD curves. Compounds 1-4 exhibited inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with IC50 values in the range from 33.94 to 57.53 µM.


Subject(s)
Chromones , Thymelaeaceae , Chromones/pharmacology , Molecular Structure , Thymelaeaceae/chemistry , Magnetic Resonance Spectroscopy , Lipopolysaccharides , Flavonoids/chemistry
9.
Fitoterapia ; 165: 105421, 2023 Mar.
Article in English | MEDLINE | ID: mdl-36587748

ABSTRACT

Two rare flavonoid-2-(2-phenylethyl)chromones and five new dimeric 2-(2-phenylethyl)chromones were isolated from ethanol extract of agarwood of Aquilaria walla by LC-MS-guided fractionation procedure. Their structures were established based on extensive spectroscopic methods including HRESIMS, 1D and 2D NMR, as well as by comparison with the literature. Compound 1 showed cytotoxic activity against five human cancer cell lines with IC50 values ranging from 13.40 to 28.96 µM with cisplatin as the positive control.


Subject(s)
Chromones , Thymelaeaceae , Humans , Chromones/pharmacology , Thymelaeaceae/chemistry , Molecular Structure , Flavonoids/chemistry , Mass Spectrometry , Wood/chemistry
10.
Org Lett ; 24(50): 9275-9280, 2022 12 23.
Article in English | MEDLINE | ID: mdl-36512336

ABSTRACT

Chalcane-containing dimers are major compounds identified from dragon's blood, the red resin that accumulates in Dracaena trees after injury. The key step for the formation of these dimers was a p-quinone methide (p-QM, 3) mediated nonenzymatic Michael addition. Compound 3 is derived from the spontaneous dehydration of chalcane alcohol-M274 (2). Two dihydroflavonol-4-reductases, discovered in D. cambodiana, reduce dihydrochalcone-M272 (7) to 2. Moreover, the application potential of p-QMs was demonstrated using a 3-like p-QM to synthesize diverse dimeric derivatives.


Subject(s)
Dracaena , Indolequinones , Plant Extracts , Resins, Plant
11.
Molecules ; 27(20)2022 Oct 18.
Article in English | MEDLINE | ID: mdl-36296582

ABSTRACT

Macrofungus Ganoderma luteomarginatum is one of the main species of Ganoderma fungi distributed in Hainan province of China, the fruiting bodies of which have been widely used in folk as a healthy food to prevent tumors. To explore the potential cytotoxic constituents from G. luteomarginatum, the phytochemical investigation on the ethyl acetate soluble fraction of 95% ethanolic extract from the fruiting bodies of this fungus led to the isolation of twenty-six lanostane triterpenoids (1-26), including three undescribed ones (1-3), together with eight ergostane steroids (27-34). The structures of three new lanostane triterpenoids were elucidated as lanosta-7,9(11)-dien-3ß-acetyloxy-24,25-diol (1), lanosta-7,9(11)-dien-3-oxo-24,26-diol-25-methoxy (2), and lanosta-8,20(22)-dien-3,11,23-trioxo-7ß,15ß-diol-26-oic acid methyl ester (3) by the analysis of 1D, 2D NMR, and HRESIMS spectroscopic data. All isolates were assayed for their cytotoxic activities using three human cancer cell lines (K562, BEL-7402, and SGC-7901) and seven lanostane triterpenoids (1, 2, 7, 13, 18, 22, and 24), and one ergostane steroid (34) showed definite cytotoxicity with IC50 values that ranged from 6.64 to 47.63 µg/mL. Among these cytotoxic lanostane triterpenoids, compounds 2 and 13 showed general cytotoxicity against three human cancer cell lines, while compounds 1 and 18 exhibited significant selective cytotoxicity against K562 cells with IC50 values of 8.59 and 8.82 µg/mL, respectively. Furthermore, the preliminary structure-cytotoxicity relationships was proposed.


Subject(s)
Antineoplastic Agents , Ganoderma , Triterpenes , Humans , Triterpenes/chemistry , Fruiting Bodies, Fungal/chemistry , Molecular Structure , Ganoderma/chemistry , Steroids/chemistry , Antineoplastic Agents/chemistry , Esters/analysis , Plant Extracts/analysis
12.
J Ethnopharmacol ; 298: 115574, 2022 Nov 15.
Article in English | MEDLINE | ID: mdl-35944737

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: Euphorbia is one of the major genera in angiosperms, which is widely distributed all over the world, including Asia, Africa and Central and South America. The roots or tubers of Euphorbia are famous for medicinal purposes, especially in China. Many of them, such as Euphorbia pekinensis Rupr, Euphorbia fischeriana Steud and Euphorbia Kansui S.L.Liou ex S.B.Ho. . are used as Chinese herbal medicines. AIM OF THE STUDY: This paper reviews the diterpenoids isolated from the genus Euphorbia species and the pharmacological activities of these compounds to evaluate its traditional use and potential future development. MATERIALS AND METHODS: Information on the studies of the genus Euphorbia Linn was collected from scientific journals, books and reports via library and electronic data search (Scifinder, Web of Science, PubMed, Elsevier, Scopus, Google Scholar, Springer, Science Direct, Wiley, ACS, CNKI and Kew Plants of the Word Online). Meanwhile, it was also obtained from published works of material medica, folk records, ethnophmacological literatures, Ph.D. and Masters dissertations. RESULTS: Known as the main constituents of the genus Euphorbia Linn, Diterpenoids possess many pharmacological properties such as anti-inflammation, antiviral activities and cytotoxicity. To date, various types of diterpenoids were identified from this genus, including isopimarane, rosane, abietane, ent-kaurane, ent-atisane. cembrane, casbane, lathyrane, myrsinane, jatropholane, tigliane, ingenane, jatrophane, paraliane, pepluane, and euphoractin. CONCLUSIONS: This review describes 14 types of diterpenoid isolated from 45 Euphorbia species from 2012 to 2021, a total of 615 compounds. Among them, mainly include jatrophane (171), lathyrane (92), myrsinane (62), abietane (70), ent-atisane (36), ent-kaurane (7), tigliane (26) and ingenane (19). The possible biological pathways of these compounds were presumed. At the same time, more than 10 biological activities of these compounds were summarized, such as anti-inflammation, antiviral activities and cytotoxicity.


Subject(s)
Diterpenes, Kaurane , Diterpenes , Euphorbia , Phorbols , Abietanes , Antiviral Agents , Euphorbia/chemistry , Phytochemicals/pharmacology
13.
Fish Shellfish Immunol ; 127: 280-294, 2022 Aug.
Article in English | MEDLINE | ID: mdl-35752371

ABSTRACT

This study aimed to investigate the effects of Elephantopus scaber extract on the GIFT (genetic improvement of farmed tilapia) strain of Nile tilapia Oreochromis niloticus. A total of 800 tilapia with an initial body weight of 1.34 ± 0.09 g each were randomly divided into five groups. The tilapia in the control group (E0 group) were fed on a basal diet only. Meanwhile, tilapia in the four experimental groups were fed on a basal diet supplemented with 1 g/kg (E1 group), 3 g/kg (E2 group), 5 g/kg (E3 group), and 7 g/kg (E4 group) of E. scaber extract for 10 weeks. Results showed that the survival rate was higher in the experimental groups than in the control group. Compared with the control group, some growth parameters (FW, WGR, SGR, VSI, and HSI) were significantly improved in the E1 group and E2 group. The crude lipid content in the dorsal muscle and liver was lower in the E1 group than in the control group. After E. scaber extract supplementation, activities of immunity-related enzymes (ACP, AKP, T-AOC, SOD, CAT, GSH-Px and LZM) in plasma, liver, spleen and head kidney, and expressions of immunity-related genes (IL-1ß, IFN-γ, TNF-α, and CCL-3) in liver, spleen and head kidney showed various degrees of improvement, while MDA content and Hsp70 expression level were decreased. The survival rate of tilapia increased in all the supplementation groups after Streptococcus agalactiae treatment. E. scaber extract addition changed the species composition, abundance, and diversity of intestinal microbiota in tilapia. These results demonstrate that E. scaber extract supplementation in diet can improve the growth, immunity, and disease resistance of GIFT against S. agalactiae. E. scaber extract supplementation can also change intestinal microbiota and reduce crude lipid content in dorsal muscle and liver. The above indicators show that the optimal dose of E. scaber extract for GIFT is 1 g/kg.


Subject(s)
Asteraceae , Cichlids , Fish Diseases , Gastrointestinal Microbiome , Streptococcal Infections , Tilapia , Animal Feed/analysis , Animals , Diet/veterinary , Dietary Supplements/analysis , Lipids , Plant Extracts/metabolism , Plant Extracts/pharmacology , Streptococcal Infections/veterinary , Streptococcus agalactiae/physiology , Tilapia/metabolism
14.
J Nat Prod ; 85(5): 1193-1200, 2022 05 27.
Article in English | MEDLINE | ID: mdl-35512012

ABSTRACT

Eight new phenethoxy derivatives, trichoasperellins A-H (1-8), were isolated from the endophytic fungus Trichoderma asperellum G10 isolated from the medicinal plant Areca catechu L. The structures of these compounds were elucidated from spectroscopic data, J-based configurational analysis, and Mosher's methods. Compounds 1-4 and 6-8 bear one or two multioxidized C7 moieties with the same carbon skeleton. The carbon skeletons of compounds 6-8 are new, all containing three moieties connected via two acetal carbons similar to those of disaccharide glycosides. Compound 4 inhibited nitric oxide production with an IC50 value of 48.3 µM, comparable to that of the positive control indomethacin (IC50, 42.3 µM).


Subject(s)
Hypocreales , Trichoderma , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Areca , Carbon , Molecular Structure , Trichoderma/chemistry
15.
Fitoterapia ; 158: 105162, 2022 Apr.
Article in English | MEDLINE | ID: mdl-35217119

ABSTRACT

Six new 2-(2-phenylethyl)chromone dimers (1-6) were isolated from ethyl ether extract of red soil agarwood of Aquilaria crassna from Vietnam by LC-MS-guided fractionation procedure. Their structures were unambiguously elucidated based on HRESIMS, 1D and 2D NMR spectra. The absolute configuration of 2-(2-phenylethyl)chromone dimers was determined by comparison of the experimental and computed ECD spectra. Compound 6 displayed cytotoxicity against the human myeloid leukemia cell line (K562) with an IC50 value of 39.49 µM.


Subject(s)
Chromones , Thymelaeaceae , Chromatography, Liquid , Chromones/chemistry , Flavonoids/chemistry , Humans , Molecular Structure , Soil , Tandem Mass Spectrometry , Thymelaeaceae/chemistry , Wood/chemistry
16.
Front Vet Sci ; 8: 753546, 2021.
Article in English | MEDLINE | ID: mdl-34722710

ABSTRACT

Didancao (Elephantopus scaber L.) has been used as a traditional herbal medicine and has exhibited a beneficial role in animal health. This study aimed to investigate the effects of dietary supplementation with E. scaber on growth performance, meat quality, intestinal morphology, and microbiota composition in ducks. A total of 480 Jiaji ducks (42 days old, male:female ratio = 1:1) were randomly assigned to one of four treatments. There were six replicates per treatment, with 20 ducks per replicate. The ducks in the control group (Con) were fed a basal diet; the three experimental groups were fed a basal diet supplementation with 30 (T1), 80 (T2), and 130 mg/kg (T3) of E. scaber. After a 48-day period of supplementation, growth performance, meat quality, intestinal morphology, and microbiota composition were evaluated. The results showed that no differences were observed in the final body weight, average daily feed intake, and average daily gain among the four groups. Compared with that in the Con group, the feed conversion in the T1 and T2 groups was increased significantly; the T2 group was shown to decrease the concentration of alanine aminotransferase in serum; the T3 group was lower than the Con group in the concentration of aspartate aminotransferase and was higher than the Con group in the concentration of high-density lipoprotein-cholesterol. The highest concentration of creatinine was observed in the T1 group. The T2 group was higher than the Con group in the contents of Phe, Ala, Gly, Glu, Arg, Lys, Tyr, Leu, Ser, Thr, Asp, and total amino acids in the breast muscle. Moreover, the T2 group was higher than the Con group in the contents of meat C18:2n-6 and polyunsaturated fatty acid. The concentration of inosinic acid in the T1, T2, and T3 groups was significantly higher than that in the Con group. However, the Con group was higher than the T2 or T3 group in the Zn content. The T2 group was lower than the Con group in the jejunal crypt depth. The T3 group was higher than the Con group in the ileal villus height and the ratio of villus height to crypt depth. In addition, the T3 group had a trend to significantly increase the abundance of Fusobacteria. Compared with the Con group, the T1 and T2 groups displayed a higher abundance of Subdoligranulum. Collectively, dietary supplementation with 80 mg/kg of E. scaber improves meat quality and intestinal development in ducks.

17.
Zhongguo Zhong Yao Za Zhi ; 46(7): 1783-1789, 2021 Apr.
Article in Chinese | MEDLINE | ID: mdl-33982482

ABSTRACT

Chemical constituents were isolated and purified from fruiting bodies of Ganoderma calidophilum by various column chromatographic techniques, and their chemical structures were identified through combined analysis of physicochemical properties and spectral data. As a result, 11 compounds were isolated and identified as(24E)-lanosta-8,24-dien-3,11-dione-26-al(1), ganoderone A(2), 3-oxo-15α-acetoxy-lanosta-7,9(11), 24-trien-26-oleic acid(3),(23E)-27-nor-lanosta-8,23-diene-3,7,25-trione(4), ganodecanone B(5), ganoderic aldehyde A(6), 11ß-hydroxy-lucidadiol(7), 3,4-dihydroxyacetophenone(8), methyl gentiate(9), ganoleucin C(10), ganotheaecolumol H(11). Among them, compound 1 is a new triterpenoid. The cytotoxic activities of all of the compounds against tumor cell lines were evaluated. The results showed that compounds 1, 3, 4 and 6 showed cytotoxic activity against BEL-7402, with IC_(50) values of 26.55, 11.35, 23.23, 18.66 µmol·L~(-1); compounds 1 and 3-6 showed cytotoxic activity against K562, with IC_(50) values of 5.79, 22.16, 12.16, 35.32, and 5.59 µmol·L~(-1), and compound 4 showed cytotoxic activity against A549, with IC_(50) value of 42.50 µmol·L~(-1).


Subject(s)
Ganoderma , Triterpenes , Cell Line, Tumor , Fruiting Bodies, Fungal , Molecular Structure , Triterpenes/pharmacology
18.
Molecules ; 26(2)2021 Jan 15.
Article in English | MEDLINE | ID: mdl-33467706

ABSTRACT

Recently, cultivated "Qi-Nan" (CQN) agarwood has emerged as a new high-quality agarwood in the agarwood market owing to its similar characteristics, such as high content of resin and richness in two 2-(2-phenylethyl)chromone derivatives, 2-(2-phenylethyl)chromone (59) and 2-[2-(4-methoxyphenyl)ethyl]chromone (60), to the wild harvested "Qi-Nan" (WQN) agarwood. In this study, we compared the chemical constituents and fragrant components of two types of WQN agarwood from A. agallocha Roxb. and A. sinensis, respectively, with CQN agarwood and ordinary agarwood varieties. Additionally, we analyzed different samples of WQN agarwood and CQN agarwood by GC-MS, which revealed several noteworthy differences between WQN and CQN agarwood. The chemical diversity of WQN was greater than that of CQN agarwood. The content of (59) and (60) was higher in CQN agarwood than in WQN agarwood. For the sesquiterpenes, the richness and diversity of sesquiterpenes in WQN agarwood, particularly guaiane and agarofuran sesquiterpenes, were higher than those in CQN. Moreover, guaiane-furans sesquiterpenes were only detected by GC-MS in WQN agarwood of A. sinensis and could be a chemical marker for the WQN agarwood of A. sinensis. In addition, we summarized the odor descriptions of the constituents and established the correlation of scents and chemical constituents in the agarwood.


Subject(s)
Flavonoids/chemistry , Sesquiterpenes/chemistry , Thymelaeaceae/chemistry , Wood/chemistry , Flavonoids/analysis , Molecular Structure , Odorants/analysis , Perfume/analysis , Perfume/chemistry , Sesquiterpenes/analysis
19.
Front Vet Sci ; 8: 793698, 2021.
Article in English | MEDLINE | ID: mdl-35174238

ABSTRACT

Yizhi (Alpiniae Oxyphyllae, A. oxyphylla) has been widely used as an important traditional Chinese medicinal herb for centuries. Existing studies have shown that A. oxyphylla has numerous benefits in human and animal health. We hypothesized that extract from the stems and leaves of A. oxyphylla (AOE) as a feed additive may have positive effects on animal health and products. Thus, this study was conducted to evaluate the effects of AOE as a feed additive on growth performance, serum biochemical parameters, intestinal morphology, microbial composition, and meat quality in Jiaji ducks. A total of 240 Jiaji ducks of 42 days old (1675.8 ± 44.2 g, male: female ratio = 1:1) were blocked based on body weight and randomly allocated into four dietary treatments with three replicates that each had 20 duck individuals. The dietary treatments included: basal diet, control group (CK); basal diet supplementation with 30 mg/kg (Y1), 80 mg/kg (Y2), and 130 mg/kg (Y3) AOE, respectively, and lasted for 49 days. The results showed that average daily feed intake from day 42 to day 60 was decreased with the increasing level of AOE (P < 0.05). Compared with the CK group, the groups with AOE supplementation decreased serum LDL-C level (P < 0.05), the addition of 30 mg/kg AOE increased total amino acids, essential amino acids, branched-chain amino acids, nonessential amino acids, and umami taste amino acids (P < 0.05), but decreased selenium and zinc concentrations in breast muscle (P < 0.05). In addition, the supplementation of 30 or 130 mg/kg AOE significantly increased jejunal villus height (P < 0.05) and tended to increase the ratio of villus height to crypt depth in the jejunum (P = 0.092) compared to the CK group. Moreover, the addition of 30 mg/kg AOE showed a higher abundance of genus unclassified Bacteroidales and genus unclassified Ruminococcaceae than the CK group (P < 0.05). Therefore, dietary supplementation with 30 mg/kg AOE increased meat nutrition profile and flavor through promoting amino acid contents in breast muscle, as well as maintained intestine integrity and modulated the microbial composition. In conclusion, AOE as an antibiotic alternative displayed potential in maintaining intestinal health and improving meat quality.

20.
Nat Prod Rep ; 38(3): 528-565, 2021 03 01.
Article in English | MEDLINE | ID: mdl-32990292

ABSTRACT

Covering: Up to the end of 2019.Agarwood is a resinous portion of Aquilaria trees, which is formed in response to environmental stress factors such as physical injury or microbial attack. It is very sought-after among the natural incenses, as well as for its medicinal properties in traditional Chinese and Ayurvedic medicine. Interestingly, the chemical constituents of agarwood and healthy Aquilaria trees are quite different. Sesquiterpenes and 2-(2-phenethyl)chromones with diverse scaffolds commonly accumulate in agarwood. Similar structures have rarely been reported from the original trees that mainly contain flavonoids, benzophenones, xanthones, lignans, simple phenolic compounds, megastigmanes, diterpenoids, triterpenoids, steroids, alkaloids, etc. This review summarizes the chemical constituents and biological activities both in agarwood and Aquilaria trees, and their biosynthesis is discussed in order to give a comprehensive overview of the research progress on agarwood.


Subject(s)
Biological Products/chemistry , Biological Products/pharmacology , Thymelaeaceae/chemistry , Wood/chemistry , Alkaloids/chemistry , Alkaloids/pharmacology , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Biological Products/metabolism , Flavonoids/chemistry , Flavonoids/pharmacology , Humans , Hypoglycemic Agents/chemistry , Hypoglycemic Agents/pharmacology , Phenols/chemistry , Phenols/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Thymelaeaceae/metabolism , Wood/metabolism
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