Polygonatone H,a new homoisoflavanone with cytotoxicity from Polygonatum Cyrtonema Hua.

A new homoisoflavonoid, (3R)-5,7-dihydroxy-6-methyl-3-(2′-hydroxy-4′-methoxybenzyl)-chroman-4-one (1), namely polygonatone H, in addition to fourteen known homoisoflavones (2–15) were isolated from the rhizome of Polygonatum Cyrtonema Hua. The structures were identified with the aid of 1D/2D NMR spectroscopic technologies. Compounds 2, 6, 8, 10, 11, 13, and 15 were isolated from P. Cyrtonema for the first time. Compound 1 showed cytotoxicities to human cancer cell lines with IC₅₀ values to comparable those of cisplatin.     

Structural Characterization of a Polygonatum cyrtonema Hua Tuber Polysaccharide and Its Contribution to Moisture Retention and Moisture-Proofing of Porous Carbohydrate Material

Porous carbohydrate materials such as tobacco shreds readily absorb moisture and become damp during processing, storage, and consumption (smoking). Traditional humectants have the ability of moisture retention but moisture-proofing is poor. Polygonatum cyrtonema Hua polysaccharide (PCP 85−1−1) was separated by fractional precipitation and was purified by anion exchange and gel permeation chromatography. The average molecular weight (Mw) of PCP 85−1−1 was 2.88 × 10³ Da. The monosaccharide composition implied that PCP 85−1−1 consisted of fucose, glucose, and fructose, and the molar ratio was 22.73:33.63:43.65. When 2% PCP 85−1−1 was added to tobacco shreds, the ability of moisture retention and moisture-proofing were significantly enhanced. The moisture retention index (MRI) and moisture-proofing index (MPI) increased from 1.95 and 1.67 to 2.11 and 2.14, respectively. Additionally, the effects of PCP 85−1−1 on the aroma and taste of tobacco shreds were evaluated by electronic tongue and gas chromatography–mass spectrometry (GC-MS). These results indicated that PCP 85−1−1 had the characteristics of preventing water absorption under high relative humidity and moisturizing under dry conditions. The problem that traditional humectants are poorly moisture-proof was solved. PCP 85−1−1 can be utilized as a natural humectant on porous carbohydrates, which provides a reference for its development and utilization.     

Extraction and identification of steroidal saponins from Polygonatum cyrtonema Hua using natural deep eutectic solvent-synergistic quartz sand-assisted extraction method

In this study, quartz sand with particularly sharp nanoscale edges acted like a nanoscale knife physically cut cells of Polygonatum cyrtonema Hua into nanosized particles and was synergized with natural deep eutectic solvent to extract steroidal saponins of Polygonatum cyrtonema Hua. The natural deep eutectic solvent (choline chloride-lactic acid)-synergistic quartz sand-assisted extraction was optimized using response surface methodology. The steroidal saponins purified with AB-8 macroporous resin were identified using ultra-high-performance liquid chromatography-triple time of flight mass spectrometry. The results showed that the experimental total saponins content value (36.97 ± 0.12 mg dioscin equivalent/g dry weight) at optimal extraction conditions with a temperature of 68°C, a rotational speed of 20 400 rpm, shear time of 4.3 min, the liquid-solid ratio of 38 ml/g, was close to the maximum possible theoretical value (36.64 mg dioscin equivalent/g dry weight). A total of 20 steroidal saponins were identified, among which the content of (25R)-Kingianoside E was the highest (102.66 ± 3.47 mg/g). Furthermore, a new steroid saponin (3β,25S)-26-(β-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl 4-O-β-D-glucopyranosyl-β-D-galactopyranoside+Glc was found for the first time. These results revealed that natural deep eutectic solvent-synergistic quartz sand-assisted extraction was an efficient and green method to extract a variety of steroidal saponins.     

Chemical constituents,anticancer, antimicrobial and antioxidant activities of essential oil from Anaphalis lacteal grown in Qinghai-Tibet Plateau

The chemical constituent of the essential oil from Anaphalis lacteal was determined; 31 compounds, representing 93.91% of the total oil, were identified by gas chromatography–mass spectrometry analysis. Three Gram-positive bacteria species, three Gram-negative bacteria species and four fungi were used to determine antimicrobial activity; the results revealed that the essential oil had a remarkable antimicrobial effect against bacteria and a susceptive effect against fungus. The oil also possessed more efficient free-radical scavenging activities than butylated hydroxytoluene (BHT) with 50% inhibitory concentration (IC₅₀) value 31 μg/mL (40 μg/mL for BHT). MTT assay illustrated that the oil expressed certain effect in inhibiting the growth of HeLa and Hep-6 cancer cells.     

New chemical constituents from the Piper betle Linn. (Piperaceae)

The phytochemical investigation of chloroform extract from Piper betle var. haldia, Piperaceae, leaves has resulted in the isolation of two new chemical constituents which were identified as 1-n-dodecanyloxy resorcinol (H1) and desmethylenesqualenyl deoxy-cepharadione-A (H4), on the basis of spectroscopic data 1D NMR (¹H and ¹³C) and 2D NMR (¹H-¹H COSY and HMBC) as well as ESI-MS, FT-IR and HR-ESI-MS analyses. Compounds H1 and H4 showed excellent antioxidant DPPH free radical scavenging activity with IC₅₀ values of 7.14 μg/mL and 8.08 μg/mL compared to ascorbic acid as a standard antioxidant drug with IC₅₀ value of 2.52 μg/mL, respectively. Evaluation of cytotoxic activity against human hepatoma cell line (PLC-PRF-5) showed moderate effect with the GI₅₀ values of 35.12 μg/mL for H1, 31.01 μg/mL for H4, compared to Doxorubicin^® as a standard cytotoxic drug with GI₅₀ value of 18.80 μg/mL.     

Chemical constituents,cytotoxic and antioxidant activities of extract from the rhizomes of Osmunda japonica Thunb

Abstract

Thirty-three compounds (1–33) were isolated from the rhizomes of Osmunda japonica. Their structures were elucidated on the basis of spectral analysis and identified as ent-kaurene terpenoids (1–3), anthraquinones (4–8), flavonoids (9–12), steroids (13–15), and other compounds (16–33). Compound 1–14, 19–27 were isolated from the genus osmunda for the first time. Compound 28–29 were isolated from the plant for the first time. Cytotoxicities of all compounds against Hela, HepG2 and A549 cell lines were measured by MTT assay, and their antioxidant activities were determined by DPPH and ABTS radical scavenging assays. Compound 2 exhibited potent cytotoxicity against Hela, HepG2 cell lines with IC₅₀ values of 9.31 and 9.66?μM, respectively. Compound 9 showed good antioxidant activity. The Trolox-equivalent antioxidant capacity (TEAC) value was 0.95?mM in ABTS assay, and the IC₅₀ value was 18.63?μM in DPPH assay.     

New cytotoxic constituents in the water-soluble fraction from Momordicae Semen

Abstract

Two new lignans mubezhisol (1) and mubezhisal (2), together with twenty six known compounds (3–28) were isolated from water-soluble fraction from the semens of Momordica cochinchinensis. In the subsequent action evaluation, four saponins (4, 6, 13, 27), six lignans (1, 2, 16, 17, 22, 23), and one naphthoquinone (24) exhibited the significant cytotoxicity. The results indicated that various saponins and lignans were mainly responsible for the antitumor activities of Momordicae Semen.     

红树林真菌Penicillium sp．No．ZZF33发酵液化学成分的研究

海洋微生物是寻找药物先导化合物的一个新的源泉,人类已从海洋微生物的次级代谢产物中发现了许多有生物活性的结构新颖的化合物[1]。近几年,本研究组对来自南中国海红树林的海洋真菌的代谢产物进行了系统的研究,从中发现大量有生物活性的化合物,揭示了红树林真菌的巨大应用潜力     

Chemical constituents from the rhizomes of Polygonatum sibiricum Red. and anti-inflammatory activity in RAW264.7 macrophage cells

Chemical investigation of the rhizomes of Polygonatum sibiricum Red. led to the identification of 27 constituents. Among them, a total of 16 compounds were obtained from Polygonatum for the first time, in which, 3 and 4 were also firstly isolated as natural products. Anti-inflammatory activity studies on 13 isolated compounds showed that β-carboline constituents, especially compounds 1 and 2, significantly inhibited the expression of NO, TNF-α, IL-6 and IL-1β in lipopolysaccharide (LPS)-treated RAW264.7 macrophage cells. Moreover, western blotting analysis demonstrated that compound 1 significantly inhibited the expression of COX-2, iNOS and the activation of NF-κB, suggesting that β-carboline structures may play an important role in inhibition of NF-κB signaling pathway, which thereby inhibits the production of inflammatory factors. The present research may not only help further elucidation of the anti-inflammatory mechanism of P. sibiricum Red., but also provide the potential bioactive molecules for inflammatory diseases research.     

崖县风车子茎化学成分研究

研究崖县风车子茎的化学成分。用硅胶柱层析法、制备薄层色谱法、重结晶法和高效液相色谱法进行分离,并根据理化性质和光谱数据对分离化合物进行结构鉴定。分离并鉴定了10个化合物,分别为:3,3',4'-tri-O-methylellagic acid(1),3,3'-di-O-methylellagic acid(2),hederagenin(3),白桦脂酸(4),6R,9R-blumenol B(5),6S,9R-blumenol B(6),2α,3β,23-trihydroxyolean-12-en-28-oic(7),4-hydroxycinnamic acid(8),咖啡酸(9),evofolin B(10)。化合物5、6、9和10为首次从该属植物中分离得到,所有化合物均为首次从该植物中分离得到。     

A new rearranged abietane diterpene from Clerodendrum inerme with antioxidant and cytotoxic activities

Eight compounds were isolated from the leaves of Clerodendrum inerme, including one new rearranged abietane diterpene, crolerodendrum B (1). Their structures were determined by means of spectroscopic methods including one-dimensional and two-dimensional nuclear magnetic resonance (1-D and 2-DNMR), high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) and circular dichroism (CD). The DPPH radical scavenging and cytotoxic activities of isolated compounds against MCF7 (breast), HCT116 (colon) and B16F10 (melanoma) cancer cell lines were evaluated. Compounds 1, 3 and 4 exhibited strong DPPH radical-scavenging effects (ED₅₀ values of 17.6 ± 2.1, 10.1 ± 0.8 and 11.3 ± 0.3 μM, respectively) and 4 showed strong cytotoxicity against the HCT116 cell line (IC₅₀ = 3.46 ± 0.01 μM).     

大叶鱼骨木茎的化学成分研究

Chemical constituents of the stems of Canthium simile were studied.Seven compounds were isolated from ethyl acetate extract of the stem,and their structures were elucidated by various spectroscopic methods.They were identified as syringic acid (Ⅰ),isovanillic acid (Ⅱ),Caruilignan D (Ⅲ),(3β)-28-Norlup-20(29)-ene-3,17-diol(Ⅳ),3,4-dimethoxy-2,4-hexadienedioic acid (Ⅴ),dibutyl phthalate (Ⅵ) and diisobutyl phthalate(Ⅶ).The seven compounds were isolated from this genus for the first time.     

Phytochemical,cytotoxic and chemotaxonomic study on Ajuga forrestii Diels (Labiatae)

A phytochemical investigation of Ajuga forrestii Diels led to the isolation of 14 compounds, including eight neo-clerodane diterpenes (1–8), two phytoecdysteroids (9, 11), one stigmastane sterol (10) and three iridoid glycosides (12–14). The structures of these compounds were identified by spectroscopic methods and a comparison of their data with those reported in the literature. This is the first report of compounds 1–14 from A. forrestii. The cytotoxic activities of the aqueous extract of A. forrestii and several compounds have been studied and the chemotaxonomic significance of isolated compounds has also been summarised.     

UHPLC-Q-Orbitrap-MS-Based Metabolomics Reveals Chemical Variations of Two Types of Rhizomes of Polygonatum sibiricum

The rhizomes of Polygonatum sibiricum are commonly consumed as food and also used as medicine. However, the metabolic profile of P. sibiricum has not been fully revealed yet. Recently, we developed a novel evergreen species of P. sibiricum. The objectives of this study were to compare the metabolic profiles of two types of P. sibiricum, i.e., the newly developed evergreen type (Gtype) and a wide-type (Wtype), by using UHPLC-Q-Orbitrap-MS-based untargeted metabolomics approach. A total of 263 and 258 compounds in the positive and negative modes of the mass spectra were tentatively identified. Distinctively different metabolomic profiles of these two types of P. sibiricum were also revealed by principal component analysis (PCA) and principal coordinates analysis (PCoA). Furthermore, by using partial least squares discriminant analysis (PLS-DA) modeling, it was found that, as compared with Wtype, Gtype samples had significantly higher content of oxyberberine, proliferin, alpinetin, and grandisin. On the other hand, 15 compounds, including herniarin, kaempferol 7-neohesperidoside, benzyl beta-primeveroside, vanillic acid, biochanin A, neoschaftoside, benzyl gentiobioside, cornuside, hydroxytyrosol-glucuronide, apigenin-pentosyl-glucoside, obacunone, 13-alpha-(21)-epoxyeurycomanone, vulgarin, digitonin, and 3-formylindole, were discovered to have higher abundance in Wtype samples. These distinguishing metabolites suggest the different beneficial health potentials and flavor attributes of the two types of P. sibiricum rhizomes.     

Chemical constituents from rhizomes of Cautleya spicata (Sm.) Baker (Zingiberaceae)

The chemical investigation of ethanolic extract from rhizomes of Cautleya spicata (Sm.) Baker (Zingiberaceae) has resulted in the isolation of eight compounds which were characterised as β-sitosterol (1), β-sitosterol β-D-glucoside (2), bergapten (3), zerumin A (4), (E)-labda-8(17),12-diene-15,16-dial (5), kaempferol (6), quercetin (7) and astragalin (8). All compounds were identified by spectroscopic and chemical methods. This paper describes the first phytochemical work on C. spicata.     

Heliotropium bacciferum Forssk. (Boraginaceae) extracts: chemical constituents,antioxidant activity and cytotoxic effect in human cancer cell lines

Heliotropium bacciferum (Boraginaceae) is a perennial herb, growing in the Bechar region of Algeria, where it is traditionally used for skin diseases and tonsillitis. Herein, we report the isolation and characterization of sixteen secondary metabolites from the aerial part extracts. They include a sterol (1), megastigman type nor-isoprenoids (2, 3, 4, 6, 8, 10), C-11 terpene lactones (5 and 9), and a monoterpene (7) from the chloroform extract (HB-C); monoterpene glucoside (14), and phenolic compounds (11–13, 15, 16) from the methanol one (HB-M). Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments, and ESIMS analysis. HB-M showed a significant and concentration dependent scavenging activity in vitro against the radicals DPPH and ABTS, related to the phenol derivatives (11–13, and 15–16), and HB-C inhibited the growth of colon cancer cell lines, mainly for the presence of the antiproliferative C-11 terpene lactones (5 and 9).     

Antimicrobial and inhibition on heat-induced protein denaturation of constituents isolated from Polygonatum verticillatum rhizomes

This study was designed to assess the susceptibility of various microorganisms and inhibition on heat-induced protein denaturation against diosgenin and santonin, isolated from Polygonatum verticillatum rhizomes. Both diosgenin and santonin showed significant zone of inhibition when studied against various Gram-positive (Bacillus subtilis, Bacillus cereus, Staphylococcus aureus and Staphylococcus epidermidis) and Gram-negative bacteria (Escherichia coli and Salmonella typhi). In antifungal assay, only santonin exhibited profound sensitivity against various fungi (Aspergillus flavus, Aspergillus niger, Trichoderma harzianum and Fusarium oxysporum) used in the test. Both diosgenin and santonin also exhibited marked attenuation on heat-induced protein denaturation in a concentration-dependent manner with EC₅₀ values of 375 and 310 μg/mL, respectively. In conclusion, both the isolated compounds have antimicrobial potential supported by strong inhibition on protein denaturation and thus support the antimicrobial uses of plant in traditional system of treatment.     

Research on Processing-Induced Chemical Variations in Polygonatum Cyrtonema Rhizome by Integrating Metabolomics and Glycomics

Polygonatum cyrtonema rhizome (PCR), the dried sweet rhizome of Polygonatum cyrtonema Hua, is commonly used as a tonic remedy and a functional food in Asia, Europe, and North America. Multiple components, including secondary metabolites, monosaccharides, oligosaccharides, and polysaccharides, collectively contribute to the therapeutic effects of PCR. Processing time exerts a significant influence on the quality of PCR, but the various processing stages have not been comprehensively chemically profiled. It is urgent to study processing-induced chemical variations in PCR to control the processing degree. In this study, multiple chromatographic and mass spectrometric techniques were used in combination with multivariate statistical analysis to perform qualitative and quantitative research on secondary metabolites and carbohydrates in PCR during processing. The results demonstrated that PCR processing can be divided into three stages, namely the raw stage (0 h), the middle stage (1–6 h), and the late stage (8–18 h). Twenty differential compounds were screened from secondary metabolites and oligosaccharides to distinguish PCR in different processing stages. Furthermore, the chemical variations of Polygonatum cyrtonema polysaccharides (PCP) also entered a new stage after processing for 6 h. Multiple chemical mechanisms, including hydrolysis, oxidative decomposition, dehydration, Maillard reaction, and polymerization were involved in the processing. This work provides a scientific basis to reveal the relationship between processing stage and chemical variations.     

Chemical constituents of Lycoris albiflora and their cytotoxic activities

An alcoholic extract of Lycoris albiflora (Amaryllidaceae) showed potent cytotoxic activity against HL-60 cells with an IC50 value of 1.7 microg/mL. Phytochemical examination of the extract resulted in the isolation of 15 alkaloids, including two phenanthridine-type alkaloids (1, 2), one benzylphenethylamine-type alkaloid (3), two crinane-type alkaloids (4, 5), one pyrrolophenanthridine-type alkaloid (6), six lycorenan-type alkaloids (7-12), and three galanthamine-type alkaloids (13-15), together with three neolignans (16-18), two flavans (19, 20), and two acetophenone derivatives (21, 22). Compound 3 (hostasinine A) has not been isolated from Amaryllidaceae plants, and 1, 2, 4, 5, 7-9, 11, 12 and 14-22 are the first isolation and identification from L. albiflora. The phenanthridine-type alkaloids (1, 2), as well as the alkaloids (3-5), exhibited potent cytotoxic activities against not only HL-60 cells but also HSC-2 cells, thus leading to the conclusion that these alkaloids are mainly responsible for the cytotoxicity of the L. albiflora extract. Compound 1 (lycoricidinol), with the most potent cytotoxic activities, induced apoptosis in both HL-60 cells and HSC-2 cells. It is notable that 1 induced transient autophagy and morphological changes in mitochondria in the early stages of the apoptotic cell death process in HSC-2 cells.     

Chemical constituents and cytotoxic activity from the wood-decaying fungus Xylaria sp. SWUF08-37

Abstract

A new cyclic pentapeptide, pentaminolarin (1), and a new cytochalasin, xylochalasin (2), along with thirteen known compounds (3–15) were isolated from the wood-decaying fungus Xylaria sp. SWUF08-37. The absolute configurations of 1 were determined by a combination of Marfey’s method and TDDFT ECD calculation and the absolute configurations of 2 were established by TDDFT ECD calculation. Compound 12 showed moderate cytotoxicity against HeLa (IC₅₀?=?19.60?µg/mL), HT29 (IC₅₀?=?17.31?µg/mL), HCT116 (IC₅₀?=?14.28?µg/mL), MCF-7 (IC₅₀?=?15.38?µg/mL), and Vero (IC₅₀?=?24.97?µg/mL) cell lines by MTT assay. Compounds 1 and 2 showed slight cytotoxicity against all tested cancer cell lines.