[Research progress on chemical constituents and pharmacological effects of Glechomae Herba and prediction of its Q-markers].

Glechomae Herba, the dried aerial part of Glechoma longituba(Labiatae), has the effects of promoting urination, draining dampness, and relieving stranguria. It has received wide attention in recent years owing to the satisfactory efficacy on lithiasis. Amid the in-depth chemical and pharmacological research, it has been found that Glechomae Herba has antibacterial, anti-inflammatory, antioxidant, antithrombotic, hepatoprotective, cholagogic, antitumor, hypoglycemic, and lipid-lowering effects. The main chemical constituents are volatile oils, flavonoids, terpenoids, phenylpropanoids, and organic acids. This paper summarized the chemical constituents and pharmacological effects of Glechomae Herba. Based on genetic relationship of plants, the characteristics, efficacy, and pharmacokinetics of the chemical constituents, and the potential of these constituents as quality markers(Q-markers), it was summed up that ursolic acid, caffeic acid, rosmarinic acid, luteolin-7-O-diglucuronide, apigenin, apigenin-7-O-diglucuronide, apigetrin, and glechone can be the candidate Q-markers of Glechomae Herba.

New alkaloids from Polygonatum zanlanscianense Pamp.

Sixteen alkaloid compounds were isolated from the dried rhizomes of P. zanlanscianense, including a pair of new enantiomers (R/S)-7'-ethoxy-trans-p-couma-royltyramine (1a/1b) and 14 known compounds (2-14) isolated from this plant for the first time. The structures of new compounds were identified by IR, NMR and MS spectroscopic analysis, and their absolute configurations were determined by comparison of the experimental and calculated ECD data.

Pentacyclic triterpenoids from spikes of Prunella vulgaris L. with thyroid tumour cell cytostatic bioactivities.

Five new triterpenoids, including four ursane types (1-4) and one oleanane type (5), together with 15 known ursane types pentacyclic triterpenoids (6-20) were isolated from the fruit spikes of Prunella vulgaris L., a traditional Chinese herbal medicine. Their structures were elucidated based on IR, HR-ESI-MS, and NMR spectroscopic data. The SW579 cell line was used to evaluate anti-thyroid cancer activities of (1-20). The results indicated that (7-9), (16), and (19) exhibited apparent inhibitory activity with IC50 values of 25.73-71.41 µM (cisplatin as positive control, IC50 14.49 ± 0.97 µM). Network pharmacology and molecular docking were also used for the prediction of the synergistic actions and the underlying mechanisms. Accordingly, four potential targets have been characterized.

Two new stilbenoid diglycosides from the stems of Dendrobium 'Sonia'.

Two undescribed stilbenoid diglycosides, dendrosonside A and dendrosonside B (1 and 2), were isolated from the stems of Dendrobium 'Sonia'. Their structures were elucidated based on 1 D/2D NMR and HRESIMS. The glycosyls contained in the two isolates were determined as D-glucose by acid hydrolysis and GC-MS analyses. In addition, 1 and 2 were further tested for the inhibition of nitric oxide production.

New chlorophenolic glycoside from Curculigo orchioides and their activities on 5α-reductase.

Two new chlorophenolic glucosides curculigines P (1) and Q (2), together with seven known compounds (3-9), were isolated from the dried rhizomes of Curculigo orchioides. Their structures were determined by spectroscopic methods including 1 D, 2 D NMR and MS. All the isolated compounds were evaluated on 5α-reductase activity by a HaCaT-based bioassay. Compounds 1-9 showed varying degrees of inhibiting activity against 5α-reductase, while compound 1 indicated the most potent inhibitory effect.[Formula: see text].

Structures and biological evaluation of phenylpropanoid derivatives from Dendrobium Sonia.

Two new phenylpropanoid derivatives (1-2), together with eight known compounds (3-10) were isolated from the stems of Dendrobium sonia. The structures of these compounds were elucidated on the basis of spectroscopic analyses, including HRESIMS, 1 D and 2 D NMR experiments. All of the isolated compounds were tested for their Nitric Oxide (NO) Inhibitory Activities. The results of bioactive screening showed that compounds 2, 8, 9 and 10 exerted inhibitory effects on NO production with IC50 values in the range of 26.3 to 31.6 µM. Compound 8 and 9 exhibited stronger anti-inflammatory activities with IC50 values 26.3 and 27.7 µM, comparable to that of the positive control.

Microbial Biotransformation of Iridoid Glycosides from Gentiana Rigescens by Penicillium Brasilianum.

This study aimed to investigate the metabolic effects of endophytic fungi in Gentiana rigescens. From the 100 selected morphospecies, strain 7-2 (Penicillium brasilianum) showed a remarkable biocatalytic activity for gentiopicroside and swertiamarin, yielding seven products, including one new compound, 5-ethylidene-8-hydroxy-4,5,6,8-tetrahydropyrano[3,4-c]pyran-1-one (M04), alongside six known compounds. Gentianine (M01) was the only metabolite of swertiamarin in this study, while the remaining ones were all gentiopicroside metabolites. Among these, five compounds: gentianine (M01), (5S,6S)-5-(hydroxymethyl)-6-methyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one (M02), (5R,6S)-5-(hydroxymethyl)-6-methyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one (M03), 2-(3-formyl-2-oxo-3,6-dihydro-2H-pyran-4-yl)but-3-enoic acid (M06), and 2-oxo-4-(1-oxobut-3-en-2-yl)-3,6-dihydro-2H-pyran-3-carboxylic acid (M07) were similar to gentiopicroside metabolites in humans. Screening the metabolic potential of endophytic fungi in Gentiana rigescens provides an outstanding source for assessing the bioactive metabolites of iridoid glycosides. The above findings suggested that the endophytic fungi of G. rigescens possess multi-enzyme systems that mimic metabolic reactions in mammalian organisms.

Antioxidative 2-(2-phenylethyl)chromones in Chinese eaglewood from Aquilaria sinensis.

Two new compounds 6,7-dimethoxy-2-[2-(2'-hydroxyphenyl)ethyl]chromone (1) and 6,7-dimethoxy-2-[2-(4'-hydroxyphenyl)ethenyl]chromone (2), together with ten known 2-(2-phenylethyl)chromones (3-12) were isolated from the resinous wood of Aquilaria sinensis (Lour.) Gilg. Their structures were elucidated by detailed IR, MS, NMR spectroscopic analyses, and comparison with reported. The absolute configuration of 3 was confirmed by Cu Kα X-ray crystallographic experiment, and the X-ray crystallographic data of 3 were firstly reported. Compounds 2, 8, 10, and 11 exhibited strong ABTS•+ radical scavenging activity, with IC50 values of 12.3, 16.5, 12.1, and 34.7 µM, respectively.[Formula: see text].

Four new sesquiterpenoids with anti-inflammatory activity from the stems of Jasminum officinale.

Four new sesquiterpenoids，including three nor-cinalbicane type sesquiterpenoids, named Jasminol A, G, H (1-3) and one eremophilene-type sesquiterpenoid, named Jasminol B (4) together with nine known compounds (5-13) were isolated from the stems of Jasminum officinale L. The structures of new compound were elucidated on the base of IR, HR-ESI-MS, 1D NMR, 2D NMR and DEPT analysis, and the absolute configurations were determined by single-crystal X-ray diffraction analysis. In addition, the anti-inflammatory activity of isolated compounds was evaluated using lipopolysaccharide (LPS)-induced murine macrophage RAW264.7, and compounds 1-4 exhibited a moderate inhibition of LPS-induced nitric oxide (NO) production in RAW264.7 cells with IC50 values of 20.56 ±â€¯1.31, 30.12 ±â€¯0.89, 30.35 ±â€¯2.72 and 31.60 ±â€¯1.69 µM, respectively, and CC50 values >200 uM.

A new ionone derivative from the leaves of Picrasma quassioides.

Nigakialcohol A (1), as unusual cyclization ionone derivative, together with eight known ones (2-9), were isolated from the leaves of Picrasma quassioides (D. Don) Benn (Simaroubaceae). Their structures were elucidated by extensive spectroscopic analyses and comparison with literature data. Compound 2 showed a weak inhibitory effect on NO production at non-cytotoxic concentration (100 µM) with inhibitory rate of 59%, and thus it should be regarded as potential anti-inflammatory agents.

Abietane Diterpenoids from the Roots of Clerodendrum trichotomum and Their Nitric Oxide Inhibitory Activities.

Twelve new abietane diterpenoids (1-12) and 31 known analogues (13-43) were isolated from a medicinal Chinese herb, Clerodendrum trichotomum Thunberg. The absolute configurations of 1-3 were established on the basis of ECD and X-ray crystallography data, whereas that of 4 was elucidated by comparison of experimental and calculated ECD data. Eight diterpenoids, 15,16-dehydroteuvincenone G (1), trichotomin A (4), 2α-hydrocaryopincaolide F (7), villosin C (20), 15-dehydro-17-hydroxycyrtophyllone A (22), demethylcryptojaponol (38), 6ß-hydroxydemethylcryptojaponol (39), and trichotomone (43), exerted inhibitory effects against NO production with IC50 values of 5.6-16.1 µM. The structure-activity relationships of the isolated diterpenoids are also estimated.

Anti-oral common pathogenic bacterial active acetylenic acids from Thesium chinense Turcz.

Discovery of agents for oral infectious diseases is always encouraged in natural products chemistry. A bioassay-guided isolation led to the isolation of two new acetylenic acids (1, 2) along with seven known ones (3-9) from the ethanol extract of Thesium chinense Turcz, a commonly used oral anti-bacterial and anti-inflammatory herb. Their structures were elucidated on the basis of spectroscopic and chemical evidence. Exocarpic acid (3) demonstrated the most promising activity against three tested oral pathogenic bacterial strains, Porphyromonas gingivalis, Fusobacterium nucleatum, and Streptococcus mutans, with minimum inhibitory concentration values of 0.86, 3.43, and 13.70 µg/mL, respectively. Compounds 1, 2, 4, 5 and 7 also showed potential activities against periodontal bacteria (P. gingivalis, F. nucleatum).

[Chemical constituents from hypoglycemic active part of Plantaginis Semen].

The chemical constituents of Plantaginis Semen with hypoglycemic effect was investigated in this paper. The previous results of the in vivo hypoglycemic effect showed that 60% ethanol extract of Plantaginis Semen decreased the levels of FBG and improved the glucose tolerance in high fat diet(HFD)-induced diabetic C57BL/6 mice. Then, in the present study, the above potential bioactive extract was separated and purified by silica gel, ODS, Sephadex LH-20 column chromatography, medium pressure liquid chromatography(MPLC)and preparative HPLC. The structures of isolated compounds were identified by physicochemical properties and spectral analyses. Eight compounds were obtained and identified as 4, 4a, 5, 7a-tetrahydro-7-(hydroxymethyl)cyclopenta[c]pyran-3(1H)-one(1), iridolactone(2), pedicularislacton(3), rehmaglutin C(4), geniposidic acid(5), p-hydroxylphenylglycerol(6), 1, 2-benzenediol-4-(2-hydroxyethyl)(7), and 3-buten-2-one-4-[3-(ß-D-glucopyranosyloxy)-4-hydroxyphenyl](8). Among them, compounds 1-5 were iridoids, and 6-8 were phenolic acids. Compound 1 was a new natural product, and compounds 2-4, 6 and 8 were isolated from the Plantaginaceae family for the first time.

Seventeen steroids from the pith of Tetrapanax papyriferus.

Two new steroidal ketones (1, 2), together with 10 known steroids (3-12) and five known steroidal saponins (13-17), have been obtained from the pitch of Tetrapanax papyrierus. The structures of 1 and 2 were elucidated as 3ß-hydroxystigmast-8, 22-diene-7,11-dione and 3ß-hydroxystigmast-8-ene-7,11-dione by IR, HR-ESI-MS, 1D and 2D NMR techniques. Except for 4, 14, 15, 16, 13 compounds reported in this paper were isolated from Tetrapanax papyriferus for the first time.

Diterpenoids from the Whole Plant of Lagochilus platyacanthus.

Five new diterpenoids, lagoditerpenes A-E (1-3, 5, 6), along with ten known compounds were isolated from the herb of Lagochilus platyacanthus. The absolute structures of 1-4 and 6 were unequivocally elucidated by extensive spectroscopic analyses in association with single-crystal X-ray diffraction, in which compounds 1 and 2 were the epimers at C-13. Furthermore, in in vitro assays, compounds 1, 2 and 6 showed moderate hemostatic activities by shortening the values of activated partial thromboplastin time.

Three new diphenylpropanes from Celastrus hindsii.

Three new diphenylpropanes, Hindsiipropane A-C (1-3), together with one known arylpropyl quinone Griffithane D (4), were isolated from Celastrus hindsii. Their structures were established by 1D and 2D nuclear magnetic resonance spectroscopic analysis, and mass spectroscopy. Compound 4 was firstly obtained in this genus. All the isolated compounds were evaluated in vitro for cytotoxicity against four human tumor cell lines (A549, HCT116, MDA-MB-231, BEL7404) by the MTT assay.

Pseudolarenone, an unusual nortriterpenoid lactone with a fused 5/11/5/6/5 ring system featuring an unprecedented bicyclo[8.2.1]tridecane core from Pseudolarix amabilis.

A phytochemical investigation of the cone of Pseudolarix amabilis led to the isolation of pseudolarenone (), a structurally novel pentacyclic (5/11/5/6/5) nortriterpenoid lactone with an unprecedented carbon skeleton featuring a unique bicyclo[8.2.1]tridecane core. Its structure and absolute configurations were elucidated by spectroscopic analysis and single crystal X-ray diffraction (CuK(α)).

Acylated iridoids from the roots of Valeriana officinalis var. latifolia.

Phytochemical investigation of the roots of Valeriana officinalis var. latifolia resulted in the isolation and characterization of six new acylated iridoids, (5S,7S,8S,9S)-7-hydroxy-8-isovaleroyloxy-Δ4,¹¹-dihyronepetalactone (1), (5S,7S,8S,9S)-7-hydroxy-10-isovaleroyloxy-Δ4,¹¹-dihyronepetalactone (2), (5S,8S,9S)-10-isovaleroyloxy-Δ4,¹¹-dihyronepetalactone (3), (5S,6S,8S,9R)-6-isovaleroyloxy-Δ4,¹¹-1,3-diol (4), (5S,6S,8S,9R)-1,3-isovaleroxy-Δ4,11-1,3-diol (5), and (5S,6S,8S,9R)-3-isovaleroxy-6-isovaleroyloxy-Δ4,¹¹-1,3-diol (6). Their structures were determined mainly by 1D and 2D NMR spectroscopic techniques. We also report herein for the first time the single crystal X-ray structure of compound 1. In addition, the cytotoxic activities of compounds 1-6 were evaluated against A549 (human lung adenocarcinoma), HCT116 (human colon carcinoma), SK-BR-3 (human breast carcinoma), and HepG2 (human hepatoma) cell lines. Compound 6 showed weak cell growth inhibition of A549, HCT116, SK-BR-3, and HepG2 cells.