Three undescribed compounds from Diaporthe biguttusis T-24, an endophytic fungus isolated from Ligularia fischeri.

Diaporthpyran A (1), diaporthester E (2) and diaporthester F (3), three new compounds along with four known compounds (4-7) were isolated from the crude extract of Diaporthe biguttusis T-24, an endophytic fungus isolated from Ligularia fischeri. The planar structures of compounds 1-3 including the relative and absolute configurations were elucidated on the basis of HRMS, NMR, J-based coupling constant analysis, CD, and calculated ECD analysis. In addition, compounds 1 and 3 were evaluated for their cytotoxic activities against four human cancer cell lines.

An efficient approach to identify different chemical markers between fibrous root and rhizome of Anemarrhena asphodeloides by ultra high-performance liquid chromatography quadrupole time-of-flight tandem mass spectrometry with multivariate statistical analysis.

An ultra high-performance liquid chromatography quadrupole time-of-flight tandem mass spectrometry approach coupled with multivariate statistical analysis was established and applied to rapidly distinguish the chemical differences between fibrous root and rhizome of Anemarrhena asphodeloides. The datasets of tR-m/z pairs, ion intensity and sample code were processed by principal component analysis and orthogonal partial least squares discriminant analysis. Chemical markers could be identified based on their exact mass data, fragmentation characteristics, and retention times. And the new compounds among chemical markers could be isolated rapidly guided by the ultra high-performance liquid chromatography quadrupole time-of-flight tandem mass spectrometry and their definitive structures would be further elucidated by NMR spectra. Using this approach, twenty-four markers were identified on line including nine new saponins and five new steroidal saponins of them were obtained in pure form. The study validated this proposed approach as a suitable method for identification of the chemical differences between various medicinal parts in order to expand medicinal parts and increase the utilization rate of resources.

Comparison of ultra-high performance supercritical fluid chromatography and ultra-high performance liquid chromatography for the separation of spirostanol saponins.

Spirostanol saponins are important active components of some herb medicines, and their isolation and purification are crucial for the research and development of traditional Chinese medicines. We aimed to compare the separation of spirostanol saponins by ultra-high performance supercritical fluid chromatography (UHPSFC) and ultra-high performance liquid chromatography (UHPLC). Four groups of spirostanol saponins were separated respectively by UHPSFC and UHPLC. After optimization, UHPSFC was performed with a HSS C18 SB column or a Diol column and with methanol as the co-solvent. A BEH C18 column and mobile phase containing water (with 0.1% formic acid) and acetonitrile were used in UHPLC. We found that UHPSFC could be performed automatically and quickly. It is effective in separating the spirostanol saponins which share the same aglycone and vary in sugar chains, and is very sensitive to the number and the position of hydroxyl groups in aglycones. However, the resolution of spirostanol saponins with different aglycones and the same sugar moiety by UHPSFC was not ideal and could be resolved by UHPLC instead. UHPLC is good at differentiating the variation in aglycones, and is influenced by double bonds in aglycones. Therefore, UHPLC and UHPSFC are complementary in separating spirostanol saponins. Considering the naturally produced spirostanol saponins in herb medicines are different both in aglycones and in sugar chains, a better separation can be achieved by combination of UHPLC and UHPSFC. UHPSFC is a powerful technique for improving the resolution when UHPLC cannot resolve a mixture of spirostanol saponins and vice versa.

Pyrrolidine-type iminosugars from leaves of Suregada glomerulata.

Phytochemical investigation of the H2O extract of leaves of Suregada glomerulata led to the isolation of ten pyrrolidine-type iminosugars. The chemical structures of the six new compounds (4-6, 8-10) were elucidated as 2,5-imino-2,4,5-trideoxy-d-manno-heptitol (4-deoxy-homoDMDP) (4), 2,5-imino-2,4,5-trideoxy-d-gulo-heptitol (5), 2,5-imino-2,4,5,6-tetradeoxy-d-gulo-heptitol (6), 6-C-butyl-4-deoxy-DMDP (8), 6-C-(8-hydroxyoctyl)-DMDP (9), and 6-C-(8-hydroxyoctyl)-2,5-dideoxy-2,5-imino-d-galactitol (10), respectively, on the basis of spectroscopic data analysis (NMR and HRESIMS). Compounds 4-6 and 8 were characterized as rarely seen 4-deoxy pyrrolidine-type iminosugars. Pyrrolidine-type iminosugars with a long-side chain have been found in the restrictive plant families Moraceae, Campanulaceae, and Hyacinthaceae. The discovery of compounds 9 and 10 with a C8 side chain from S. glomerulata (Euphorbiaceae) expands the range of distribution for the iminosugars in plants. The 8-hydroxyoctyl side-chain represents a new addition for the molecular diversity of iminosugars. The compounds 1-10 were evaluated for inhibitory activity against rat intestinal α-glucosidase. However, all the test compounds showed no significant inhibitory activities to the glucosidase.

Phenolic glycosides and other constituents from the bark of Magnolia officinalis.

A new phenolic glycoside, syringic acid 4-O-ß-D-glucopyranosyl-(1 → 5)-α-L-rhamnopyranoside (1), together with 12 known compounds consisting of eight phenolic glycosides (2-9), two phenolic acids (10 and 11), and two norsesquiterpenoids (12 and 13), was isolated from the methanol extract of the bark of Magnolia officinalis. Their structures were elucidated on the basis of spectroscopic analysis and chemical methods. Compounds 1-11 were evaluated for their inhibitory activities against fructose-1,6-bisphosphatase, aldose reductase, lipase, dipeptidyl peptidase-IV, α-glucosidase, and three cancer cell lines. However, all the compounds showed weak or no activities in these tests.

α-Glucosidase-inhibitory iminosugars from the leaves of Suregada glomerulata.

A water extract of the leaves of Suregada glomerulata (Euphorbiaceae) was found to inhibit rat small intestinal α-glucosidase. An examination of the extract afforded 20 iminosugars including one pyrrolidine and 19 piperidines. The structures of the 10 new compounds (11-20) were determined by NMR, and MS spectroscopic data analyses, and chemical correlations. The novelty of the identified compounds mainly stems from the loss of a hydroxy at C-4 and the presence of an 8-hydroxyoctyl side chain. Nine N-alkyl derivatives including N-methyl (1a, 8a, and 13a), N-butyl (1b, 2b, and 9b) and N,N-dimethyl (1c, 2c, and 9c) were synthesized. The compounds were tested for rat small intestinal α-glucosidase inhibitory activity. In total, 15 compounds, including compounds 11, 12, 15, and 19 and the three derivatives 8a, 9b, and 13a, showed inhibitory activity with IC50 values less than 40µM. In vivo results showed that total alkaloids of S. glomerulata (10mg/kg) and four major iminosugars 1, 2, 3, and 9 (10mg/kg) can lower the postprandial blood glucose level after sucrose and starch load in healthy male ICR mice.

[Experimental study on anti-atherosclerotic effect of compatibility of active components of danshen and shanzha].

OBJECTIVE: To investigate the effect of active components of Danshen and Shanzha of different matching proportions on atherosclerosis (AS), in the expectation of obtaining the optimum combination method. METHOD: Atherosclerotic rats were fed with high fat diet, and injected with vitamin D3 and ovalbumin. Aqueous extracts of Danshen (DSA) and Shanzha (SZA) and lipophilic extracts of danshen (DSL) were adopted for a low, medium and high-dose orthogonal experiment, to observe the effect of their different matching proportions on lipid level, oxidative stress, endothelial function and inflammatory reaction. The principal component analysis and cluster analysis were adopted for the multi-objective optimization of experimental results. RESULT: Compared with the model group, all of samples with different proportions of DSA, DSL and SZA showed effect in lowering lipid level, scavenging free radicals, reducing endothelial dysfunction and inhibiting inflammation. According to the variance analysis, DSA2-SZA2-DSL1, DSA3-SZA2-DSL1, DSA3-SZA3 -DSL3 and DSA3-SZA1-DSL1 were the optimal proportions for lowering lipid level, scavenging free radicals, reducing endothelial dysfunction and inhibiting inflammation, respectively. According to the results of the multi-objective optimization, DSA2-SZA1-DSL2 was the optimal proportions of anti-AS. CONCLUSION: All of active components of Danshen and Shanzha of different matching proportions show the anti-AS effect in rats to varying degrees, but with different focus in different matching proportions.

[Study on digitization of difference in drug color and odor of Magnoliae Officinalis Cortex before and after perspiration].

OBJECTIVE: To digitalize the changes in characters of Magnoliae Officinalis Cortex after perspiration with colorimeter and electronic nose. METHOD: With perspired and non-perspired Magnoliae Officinalis Cortex as objective, colorimeter and electronic nose were used to detect their color characteristic parameter and odor characteristic parameter. Finally, an identification model was established. RESULT: In terms of drug color, the color characteristic parameter model was established for perspired and non-perspired Magnoliae Officinalis Cortex on the basis of L*, a*, b* color spaces. The range of 90% of reference values of perspired Magnoliae Officinalis Cortex: L* (52.22-59.42), a* (5.36-7.68), b* (22.04-27.05). The range of 90% of reference values of non-perspired Magnoliae Officinalis Cortex: L* (38.42-47.31), a* (9.63-11.85), b* (18.48-25.53). In terms of drug odor, the principal component analysis (PCA) and the partial least squares method (PLS) showed significant difference between perspired and non-perspired Magnoliae Officinalis Cortex. CONCLUSION: The difference in drug color and odor of Magnoliae Officinalis Cortex before and after perspiration can be digitalized according to color and odor characteristic parameters tested with colorimeter and electronic nose.

Bioactive polar compounds from stem bark of Magnolia officinalis.

Two new phenylethanoid glycosides magnoloside D (1) and E (2), together with nine known compounds, were isolated from the polar part of methanol extract of the stem bark of Magnolia officinalis. The structures of the new compounds were established on the basis of spectral analysis. Anti-spasmodic activity of four major constituents (3, 4, 9 and 11) was tested in isolated colon of rat, compounds 3, 4, and 9 showed inhibition against acetylcholine, with the effect similar to that of magnolol and honokiol. At the same time, antioxidant activity of the isolated compounds was investigated using a DPPH and an ORAC assay. All of the compounds, except compound 8 showed potent antioxidant capacity in the ORAC assay, while compounds 1-5 and 11 exhibited potent antioxidant activity in the DPPH assay.

Antioxidant flavonoids from the seed of Oroxylum indicum.

Three new flavonoid glycosides (1-3) and nineteen known compounds (4-22) were isolated from the aqueous ethanolic extract of the seed of Oroxylum indicum. The structures of 1-3 were elucidated on the basis of spectroscopic analysis. Antioxidant activities of all the isolated compounds were evaluated using a DPPH and an ORAC assay. Compounds 3, 5-7, 9 and 12 exhibited potent antioxidant activity in the DPPH assay, while compounds 3-15 showed potent antioxidant capacity in the ORAC assay, and seven antioxidant flavonoids (4-6, 8, 9, 11, 12) were detected as the main ingredients in the methanolic extract of seed of O. indicum using an HPLC analysis.

Three new water-soluble alkaloids from the leaves of Suregada glomerulata (Blume) Baill.

Three new water-soluble alkaloids (1-3) together with twelve known compounds (4-15) have been isolated from the water extract of leaves of Suregada glomerulata. Their structures were determined by spectroscopic analysis and chemical method. Compounds 1-3 were evaluated for their in vitro inhibitory activity against α-glucosidase and HIV-1 replication. However, no significant activities were found.

ent-Abietane and ent-kaurane diterpenoids from the roots of Suregada glomerulata.

Twelve ENT-abietane and ENT-kaurane type diterpenoids, 1- 12, including five new compounds 1- 5, were isolated from the roots of Suregada glomerulata. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR and other spectroscopic studies, and the structures of 1 and 2 were confirmed by X-ray crystallography. Cytotoxic activities against five human tumor cell lines were evaluated.

Wittiorumins A - F, antioxidant diels-alder-type adducts from Morus wittiorum.

Six new Diels-Alder-type adducts, wittiorumins A-F ( 1 - 6) along with the three known compounds chalcomoracin ( 7), mulberrofuran J ( 8), and mongolicin F ( 9), were isolated from the stem bark of Morus wittiorum. Their structures including their absolute configurations were determined on the basis of spectroscopic analysis and chemical methods. Some of the isolated compounds ( 1 - 4) were assayed for their antioxidant activities, among which compounds 1 - 3 were active as antioxidants, with inhibitory ratios of 73.0 %, 82.0 %, and 82.0 %, respectively, at a concentration of 10 ( - 5) M.

Three new compounds from the barks of Morus nigra.

Three new compounds including two flavonoids and a new 2-phenylbenzofuran, named morunigrols A-C (1-3), together with three known compounds albafuran A (4), albafuran B (5), and mulberrofuran L (6), have been isolated from the barks of Morus nigra. Their structures have been elucidated by spectroscopic methods.

A new Diels-Alder type adduct and two new flavones from the stem bark of Morus yunanensis Koidz.

Fractionation of the ethanolic extract of the stem bark of Morus yunanensis resulted in the isolation of a new Diels-Alder type adduct and two new flavones, named yunanensin A (1), yunanensol A (2) and yunanensol B (3), respectively, together with a known flavone (4). Their structures were determined on the basis of spectroscopic analysis and chemical methods. Among them, compound 1 showed moderate antioxidant and significant cytotoxic activities, and compound 2 showed potent anti-inflammatory activity.

Diterpenoids from the roots of Suregada glomerulata.

Six new diterpenoids, 7beta,8alpha-dihydroxy-12-oxo- ent-abietan-16,14-olide ( 1), 3,4,18beta-cyclopropa-7beta,17-dihydroxy- ent-abieta-8(14),13(15)-dien-16,12-olide ( 2), 3alpha,7beta-dihydroxy- ent-abieta-8(14),13(15)-dien-16,12-olide ( 3), 3-oxo-8beta,14beta-epoxy- ent-abieta-11,13(15)-dien-16,12-olide ( 4), 17-hydroxy- ent-pimara-8(14),15-dien-3-one ( 5), and 3alpha,6beta-dihydroxy- ent-kaur-16-ene ( 6), and two known compounds, 7beta-hydroxy- ent-abieta-8(14),13(15)-dien-16,12-olide ( 7) and jolkinolide B, were isolated from roots of Suregada glomerulata. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR and other spectroscopic studies. The structure of compound 1 was confirmed by X-ray crystallography. Cytotoxic activities were evaluated against five human tumor cell lines.

[Studies on chemical constituents of Suregada glomerulata II].

OBJECTIVE: To study the chemical constituents of Suregada glomeruldata. METHOD: Isolation and purification were carried out on silica gel, sephardex LH -20, ODS column chromatography etc. Constituents were identified by physicochemical properties and spectral analysis. RESULT: Nine compounds, Jolkinolide B (1), 8alpha, 14-dihydro-7-oxo-jolkinolide E (2), helioscopinolide B (3), ent-kauran-16beta, 17-diol (4), 7-oxo-beta-sitosterol (5), scopoletin (6), adenosine (7), 1'-sinapoylglucose (8), sucrose (9), were obtained and identified. CONCLUSION: Compounds 2-9 were isolated from S. glomerulata for the first time.