Phenolic and flavonoid compounds from the fruit shell of Camellia oleifera.

A new phenolic compound oleiphenol (1), and a new dihydrochalcone oleifechalcone (2) along with seven known compounds (3-9) were isolated from the fruit shell of Camellia oleifera Abel. The planar structures of compounds 1 and 2 were determined on the basis of extensive spectroscopic analyses (IR, UV, NMR, and HR-ESI-MS) and comparison with literature data. The absolute configurations of the new structures were determined by ECD calculations and chemical methods. In addition, compounds 1-9 underwent a series of pharmacological activity tests, including cytotoxic, anti-inflammatory, anti-RSV and antioxidant activities.

Two new chemical constituents from the stem and branch of Tripterygium wilfordii.

A chemical investigation of 95% ethanol extract from the stem and branch of Tripterygium wilfordii has resulted in the isolation and characterization of two new compounds, one neolignan (1) and one phenylalanine derivative (2), as well as four known compounds (3-6). The structures of the new compounds were determined based on extensive spectroscopic analyses. The absolute configuration of compound 1 was defined by X-ray crystallographic analyses and electronic circular dichroism calculation. In addition, compounds 2 and 4-6 exhibited inhibitory effects against NO production in LPS-induced RAW 264.7 macrophages with the IC50 value ranging from 3.51 µM to 30.40 µM.

Two new pregnane glycosides from the root of Cynanchum auriculatum.

Two new pregnane glycosides (1 and 2), together with four known ones (3- 6), were isolated from the roots of Cynanchum auriculatum Royle ex Wight (Asclepiadaceae). On the basis of detailed spectroscopic analysis and chemical method, the structures of new compounds were characterized to be metaplexigenin 3-O-ß-D-cymaropyranosyl- (1→4)-α-L-diginopyranosyl-(1→4)-ß-D-cymaropyranoside (1), metaplexigenin 3-O-α-L-diginopyranosyl-(1→4)-ß-D-cymaropyranoside (2). All the isolated compounds (1-6) were tested for their in vitro inhibitory activity against the growth of human colon cancer cell lines HCT-116. Compounds 5 and 6 showed significant cytoxicities with IC50 values of 43.58 µM and 52.21 µM.

One pair of new enantiomeric trinorsesquiterpenes from the aerial parts of Justicia gendarussa.

A pair of new enantiomeric trinorsesquiterpenes, (+)-genpenterpene A (1a) and (-)-genpenterpene A (1b), together with seven known compounds (2-8), were isolated from the aerial parts of Justicia gendarussa Burm.f.. All of these known compounds were isolated from this plant for the first time. Racemic genpenterpene A was separated by chiral HPLC column. Their chemical structures were elucidated based on extensive spectroscopic analysis, single crystal X-ray diffraction, and ECD calculations. (+)-genpenterpene A (1a) exhibited potent inhibitory effect against nitric oxide production in lipopolysaccharide-activated RAW 264.7 mouse macrophage cells with an IC50 value of 9.54 ± 1.02 µM.

Barbaram, a bicyclic neolactam from the root and stem of Lycium barbarum.

Barbaram (1), a neolactam together with other five known compunds (2-6) was isolated from the EtOAc-soluble fraction of an EtOH extract of the root and stem of Lycium barbarum by using silica gel, Sephadex LH-20 column chromatography and semi-preparative RP-C18 HPLC. Based on HR-TOF-MS, NMR spectral data, quantum chemistry ECD calculations and referencing to the data reported earlier, the structures of these compounds (1-6) were determined, specially including the absolute configuration of the neolactam (1). Compounds 2 and 4 showed significant anti-inflammatory activity in LPS-induced RAW 264.7 macrophages with the IC50 values of 8.98 ± 0.57 µM, 6.68 ± 0.77 µM.

[Chemical constituents from Xanthii Fructus].

This study was carried out to investigate the chemical constituents from Xanthii Fructus(the fruits of Xanthium sibiricum). The compounds were separated and purified by silica gel column chromatography, Sephadex LH-20 and ODS chromatography and semi-preparative HPLC. Base on HR-ESI-MS, NMR and other spectral data, their structures were identified. The anti-inflammatory activity of the isolated compounds was evaluated by lipopolysaccharide(LPS)-induced macrophage RAW264.7 as a screening model. A total of twenty-one compounds were isolated from the EtOAc fraction of 95% ethanol extract and identified as uracil(1), thymine(2), uridine(3), indole-3-carbaldehyde(4), indole-3-carboxylic acid(5), 2'-O-methyluridine(6), guanosine(7), 2,4(1H,3H)-quinazolinedione(8), 3-hydroxy-3-(2-hydroxyethyl)indolin-2-one(9), nicotinamide(10), N-acetyl-L-phenylalaninol(11), heliolactam(12), terresoxazine(13), caudatin(14), qingyangshengenin(15), caudatin-3-O-ß-D-oleandropyranosyl-(1→4)-ß-D-cymaropyranosyl-(1→4)-ß-D-cymaropyranoside(16), caudatin-3-O-ß-D-cymaropyranosyl-(1→4)-ß-D-oleandropyranosyl-(1→4)-ß-D-cymaropyranosyl-(1→4)-ß-D-cymaropyranoside(17), caudatin-3-O-α-L-cymaropyranosyl-(1→4)-ß-D-cymaropyranosyl-(1→4)-ß-D-cymaropyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-ß-D-oleandropyranosyl-(1→4)-ß-D-cymaropyranoside(18), qinyangshengenin-3-O-ß-D-oleandropyranosyl-(1→4)-ß-D-oleandropyranosyl-(1→4)-ß-D-cymaropyranoside(19), qinyangshengenin-3-O-ß-D-oleandropyranosyl-(1→4)-ß-D-cymaropyranosyl-(1→4)-ß-D-digitoxopyranoside(20), rostratamine-3-O-ß-D-oleandropyranosyl-(1→4)-ß-D-cymaropyranosyl-(1→4)-ß-D-cymaropyranoside(21). Compounds 5-21 are obtained from genus Xanthium for the first time. Compounds 12 and 13 indirectly exhibited anti-inflammatory activity by suppressing LPS-induced NO production in RAW264.7 cells with IC_(50) values of(15.45±0.56) and(20.14±0.78) µmol·L~(-1), respectively.

Anticandidal Potential of Stem Bark Extract from Schima superba and the Identification of Its Major Anticandidal Compound.

Plant-derived extracts are a promising source of new drugs. Schima superba is traditionally used in China for heat clearing, detoxification, and treatment of furuncles. In this study, the anticandidal properties and mechanism of action of S. superba (SSE) were explored using a stem bark extract. SSE possessed high polyphenol and saponin contents of 256.6 ± 5.1 and 357.8 ± 31.5 µg/mg, respectively. A clear inhibition zone was observed for C. albicans growth through the disc diffusion method and the 50% inhibition of C. albicans by SSE was 415.2 µg/mL. Transcriptomic analysis in C. albicans treated with different doses of SSE was conducted through RNA-seq. Average values of 6068 genes and 20,842,500 clean reads were identified from each sample. Among these samples, 1680 and 1956 genes were differentially expressed genes (DEGs) from the SSE treatments of 0.2 and 0.4 mg/mL, respectively. C. albicans growth was inhibited by the changes in gene expression associated with the cell wall and membrane composition including the regulation of chitin degradation and ergosterol biosynthesis. This result could be reflected in the irregularly wrinkled morphology of the ruptured cell as revealed through SEM analysis. ESI-MS and NMR analyses revealed that the major compound purified from SSE was sasanquasaponin III and the 50% inhibition of C. albicans was 93.1 µg/mL. In summary, the traditional Chinese medicine S. superba can be applied as an anticandidal agent in complementary and alternative medicine.

A new secondary metabolite from the fermented mycelia of Streptomyces antibiotic H41-55.

An actinomycete strain, H41-55 from sea sediment was identified as Streptomyces antibiotic on the basis of its morphological, physiological and biochemical characteristics as well as 16S rDNA data. A new secondary metabolite, (2S,3R)-N-[3-(formylamino)-2-hydroxybenzoyl]-l-threonine propyl ester (1), together with five known compounds was isolated from fermentation product by use of silica gel and Sephadex LH-20 column chromatography, and preparative RP-C18 HPLC, and identified by HR-TOF-MS and NMR spectra. The cytotoxicities of these isolates against three cancer cell lines and their antifungal activities on Candida albicans were tested. Compounds 1, 3, 5, and 6 displayed moderate cytotoxicity. 5 and 6 showed inhibitory activity on C. albicans.

A New Lignanamide from the Root of Lycium yunnanense Kuang and Its Antioxidant Activity.

A new lignanamide (1), lyciumamide K, together with four known analogues (2-5), was isolated from the root of Lycium yunnanense Kuang. Based on HR-ESI-MS, NMR spectral data and quantum chemistry ECD calculations, the structure of this new compound was confirmed, including its absolute configuration. Evaluation of the antioxidant activity of compounds 1-5 in the oxygen radical absorption capacity (ORAC) assay showed that they all exhibited significant antioxidant activities. Particularly, compound 1 showed the best activity with ORAC values (U/mol) of 7.90 ± 0.52. Thus, the new lignanamide may be a good source of bioavtive and protective compounds.

Anandins A and B, Two Rare Steroidal Alkaloids from a Marine Streptomyces anandii H41-59.

Anandins A (1) and B (2), two rare steroidal alkaloids, were isolated from the fermentative broth of a marine actinobacteria Streptomyces anandii H41-59. The gross structures of the two alkaloids were elucidated by spectroscopic methods including HR-ESI-MS, and NMR. Their absolute configurations were confirmed by single-crystal X-ray diffraction analysis and comparison of their experimental and calculated electronic circular dichroism spectra, respectively. Anandin A exhibited a moderate inhibitory effect against three human cancer cell lines MCF-7, SF-268, and NCI-H460 with IC50 values of 7.5, 7.9, 7.8 µg/mL, respectively.

Neoantimycins A and B, Two Unusual Benzamido Nine-Membered Dilactones from Marine-Derived Streptomyces antibioticus H12-15.

An actinomycete strain (H12-15) isolated from a sea sediment in a mangrove district was identified as Streptomycesantibioticus on the basis of 16S rDNA gene sequence analysis as well as the investigation of its morphological, physiological, and biochemical characteristics. Two novel benzamido nonacyclic dilactones, namely neoantimycins A (1) and B (2), together with the known antimycins A1ab (3a,b), A2a (4), and A9 (5), were isolated from the culture broth of this strain. Compounds 1 and 2 are the first natural modified ATNs with an unusual benzamide unit. The structures of these new compounds, including their absolute configuration, were established on the basis of HRMS, NMR spectroscopic data, and quantum chemical ECD calculations. Their cytotoxicities against human breast adenocarcinoma cell line MCF-7, the human glioblastoma cell line SF-268, and the human lung cancer cell line NCI-H460 were also tested. All compounds exhibited mild cytotoxic activity. However, Compounds 1 and 2 showed no activity against C. albicans at the test concentration of 1 mg/mL via paper disc diffusion, while the known antimycins showed obvious antifungal activity.

Ergosterols from the Culture Broth of Marine Streptomyces anandii H41-59.

An actinomycete strain, H41-59, isolated from sea sediment in a mangrove district, was identified as Streptomyces anandii on the basis of 16S rDNA gene sequence analysis as well as the investigation of its morphological, physiological and biochemical characteristics. Three new ergosterols, ananstreps A-C (1-3), along with ten known ones (4-13), were isolated from the culture broth of this strain. The gross structures of these new compounds were elucidated on the basis of extensive analysis of spectroscopic data, including HR-ESI-MS, and NMR. The cytotoxicities of these isolates against human breast adenocarcinoma cell line MCF-7, human glioblastoma cell line SF-268, and human lung cancer cell line NCI-H460 and their antibacterial activities in inhibiting the growth of Candida albicans and some other pathogenic microorganisms were tested. Compounds 3-8, 10 and 11 displayed cytotoxicity with IC50 values in a range from 13.0 to 27.8 µg/mL. However, all the tested compounds showed no activity on C. albicans and other bacteria at the test concentration of 1 mg/mL with the paper disc diffusion method.

[Non-alkaloid Chemical Constituents from Macleaya cordata].

Objective: To study the non-alkaloid chemical constituents of Macleaya cordata. Methods: Alcohol extraction and liquidliquid partitionmethods were used to extract the chemical constituents. Silica gel,reverse-phase octadecylsilyl( ODS), and Sephadex LH-20 column chromatographic methods were applied for isolation and purification. Spectroscopic methods including MS and NMR were used to determine their structures. Results: Eleven non-alkaloid compounds were isolated from the fruits of Macleaya cordata, and their structures were identified as 3-( 3,4-dihydroxy) phenylpropanoic acid methyl ester( 1),ferulic acid( 2),1-octacosanol( 3),syringic acid( 4),p-hydroxy-benzoic acid( 5),p-coumaric acid( 6),quercetin-3-O-ß-D-glucoside( 7),N-p-coumaroyl tyramine( 8),10-eicosenoic acid( 9) and ß-sitosterol( 10) and daucosterol( 11). Conclusion: Compounds 1,3 ~9 are isolated from Macleaya cordata for the first time.

A new flavonoid glucoside from Rhododendron seniavinii.

The leaves of Rhododendron seniavinii Maxim with little phytochemical information are used as folk remedies for the treatment of acute and chronic bronchitis in China. In our pursuing for the biologically active chemical constituents in the leaves, a new flavonoid glycoside 5,7,3'-trimethoxy-quercetin-3-O-ß-D-glucopyranoside (1) was isolated from the water extract of its leaves, together with two known compounds 5,7,3'-trimethoxy-quercetin (2) and ovafolinin B-9'-O-ß-D-glucopyranoside (3). The structures of the new flavonoid glucoside as well as two known compounds were elucidated by spectroscopic and chemical methods.

A new cytotoxic benzophenanthridine isoquinoline alkaloid from the fruits of Macleaya cordata.

A new cytotoxic benzophenanthridine isoquinoline alkaloid, named cordatine (1), together with one known alkaloid 8-methoxydihydrochelerythrine (2), was isolated from the fruits of Macleaya cordata. The structure of the new compound was elucidated by spectroscopic methods including 1D and 2D NMR, HR-ESI-MS. Both compounds indicated significant cytotoxicity against MCF-7 and SF-268 cell lines.

New Ent-Kaurane-Type Diterpene Glycosides and Benzophenone from Ranunculus muricatus Linn.

Two new ent-kaurane diterpene glycosides, ranunculosides A (1) and B (2), and a new benzophenone, ranunculone C (3), were isolated from the aerial part of Ranunculus muricatus Linn. The chemical structures of compounds 1-3 were established to be (2S)-ent-kauran-2ß-ol-15-en-14-O-ß-d-glucopyranoside, (2S,4S)-ent-kauran-2ß,18-diol-15-en-14-O-ß-d-glucopyranoside, and (R)-3-[2-(3,4-dihydroxybenzoyl)-4,5-dihydroxy-phenyl]-2-hydroxylpropanoic acid, respectively, by spectroscopic data and chemical methods. The absolute configuration of 1 was determined by the combinational application of RP-HPLC analysis and Mosher's method.

[Alkaloids from Macleaya cordata and their cytotoxicity assay].

OBJECTIVE: To study the alkaloids of Macleaya cordata and their anti-tumor activities. METHOD: Alcohol and liquid-liquid extraction were used methods were used to extract the alkaloids constituents, and silica gel, reverse-phase octadecylsilyl (ODS), sephadex LH-20 chromatographic methods and HPLC were applied to isolate and purify compounds. MS, NMR spectroscopic methods were used to determine their structures. Furthermore, the cytotoxicity of these chemical components for MCF-7 and SF-268 cell lines was measured by MTT method. RESULT: Twelve alkaloids were isolated from the fruits of M. cordata, and their structures were identified as: maclekarpine E (1), 6-acetonyldihyrochelerythrine (2), cavidilinine (3), 6-acetonyldihyrosanguinnarine (4), O-methylzanthoxyline (5), 6-methoxy-dihydrosanguinarine (6), spallidamine (7), 6-hydroxyldihydrochelerythrine (8), arnotianamida (9), dihydrosanguinarine (10), protopine (11), and cryptopine (12). CONCLUSION: Compounds 1, 3, 7-9 were isolated from M. cordata for the first time, and compound 5 is a new natural product. The results of cytotoxic assay indicated that compound 6 showed strong cytotoxicity against MCF-7 and SF-268 cell lines with IC50 values of 0.61 µmol · L(-1) and 0.54 µmol · L(-1), respectively.

Desacetyluvaricin induces S phase arrest in SW480 colorectal cancer cells through superoxide overproduction.

Annonaceous acetogenins (ACGs) are a group of fatty acid-derivatives with potent anticancer effects. In the present study, we found desacetyluvaricin (Dau) exhibited notable in vitro antiproliferative effect on SW480 human colorectal carcinoma cells with IC50 value of 14 nM. The studies on the underlying mechanisms revealed that Dau inhibited the cancer cell growth through induction of S phase cell cycle arrest from 11.3% (control) to 33.2% (160 nM Dau), which was evidenced by the decreased protein expression of cyclin A Overproduction of superoxide, intracellular DNA damage, and inhibition of MEK/ERK signaling pathway, were also found involved in cells exposed to Dau. Moreover, pre-treatment of the cells with ascorbic acid significantly prevented the Dau-induced overproduction of superoxide, DNA damage and cell cycle arrest. Taken together, our results suggest that Dau induces S phase arrest in cancer cells by firstly superoxide overproduction and subsequently the involvement of various signaling pathways.

[Chemical constituents of flavonoids and their glycosides in Melastoma dodecandrum].

The chemical constituents of 95% ethanol extract of Melastoma dodecandrum were isolated and purified by chromatography on silica gel, Sephadex LH-20, and HPLC, to obtain thirteen compounds eventually. On the basis of their physico-chemical properties and spectroscopic data, these compounds were identified as quercetin (1), quercetin-3-O-ß-D-glucopyranoside (2), quercetin-3-O-(6"-O-p-coumaroyl) -ß-D-glucopyranoside (3), kaempferol (4), kaempferol-3-O-ß-D-glucopyranoside (5), kaempferol-3-O- [2",6"-di-O-(E)-coumaroyl]-ß-D-glucopyra-noside (6), luteolin (7), luteolin-7-O-(6"-p-coumaroyl) -ß-D-glucopyranoside (8), apigenin (9), apigenin-7-(6"-acetyl-glucopyranoside) (10) , naringenin (11), isovitexin (12), and epicatechin-[8,7-e] -4ß-(4-hydroxyphenyl)-3,4-dyhydroxyl-2(3H)-pyranone (13). Eight compounds(3,5,6,8-11 and 13) were obtained from M. dodecandrum for the first time.

Two new chemical constituents from the aerial parts of Tripterygium wilfordii.

Tripterygium wilfordii has been historically employed as a conventional botanical insecticide and a plant of medicinal significance. A new dihydroagarofuran sesquiterpene (1) and a new acyclic compound (2), along with seven known compounds (3-9), have been isolated from the aerial parts of Tripterygium wilfordii. The identification of the structures of novel compounds were accomplished through comprehensive spectroscopic analyses, encompassing HRESIMS, NMR, UV, IR, and a comparative analysis with spectroscopic data from compounds previously characterised. In in-vitro bioassay, compound 8 exhibited significant inhibitory activity for NO release in LPS-induced RAW 264.7 cells, with an IC50 value of 15.7 µM.