Polyketone metabolites isolated from Rhodiola tibetica endohytic fungus Alternaria sp. HJT-Y7 and their SARS-CoV-2 virus inhibitory activitives.

Six new polyketone metabolites, compounds (1-6) and seven known polyketone compounds (7-13) were isolated from Rhodiola tibetica endophytic fungus Alternaria sp. The structural elucidation of five new polyketone metabolites were elucidated on the basis of spectroscopic including 2D NMR and HRMS and spectrometric analysis. Inhibition rate evaluation revealed that compounds 1(EC50 = 0.02 mM), 3(EC50 = 0.3 mM), 6(EC50 = 0.07 mM), 8(EC50 = 0.1 mM) and 9(EC50 = 0.04 mM) had inhibitory effect on the SARS-CoV-2 virus.

Two isopentenyl resorcinols from Peperomia tetraphylla.

Two isopentenyl resorcinols, peperobtusin B and peperobtusin C, have been isolated from Peperomia tetraphylla. Their structures were determined on the basis of spectroscopic methods, especially 1H NMR, 13C NMR, 2D NMR, and HR-TOF-MS. Two compounds were evaluated for cytostatic activity against G2, A 549, Hela and HCT 116 cells, but cytostatic activity of both compounds is weak.

[Preliminary study of dihydroartemisin in inhibiting invasion and metastasis of hepatoma cells].

It is reported that dihydroartemisinin could reduce the expression of phosphorylated adhesion kinase and matrix metalloproteinase-2, inhibit the growth, migration and invasion of ovarian cancer cells, promote the formation of Treg cells through TGF-beta/Smad signaling pathway, and play an immunosuppressive role; dihydroartemisinin could also inhibit the growth of lung cancer cells by inhibiting the expression of vascular endothelial growth factor(VEGF) receptor KDR. However, there are few studies on dihydroartemisinin in hepatocellular carcinoma cells. In order to preliminarily explore the effect of dihydroartemisinin on invasion and metastasis of hepatocellular carcinoma cells, CCK-8 method and crystal violet staining were used to detect the effect of dihydroartemisinin on the growth of hepatocellular carcinoma cell 7402 and highly metastatic hepatocellular carcinoma cell MHCC97 H. The effects of dihydroartemisinin on the invasion and metastasis of hepatocellular carcinoma cell 7402 and highly metastatic hepatocellular carcinoma cell MHCC97 H were studied by using cell wound healing and Transwell. Western blot was used to detect the protein expression of epidermal growth factor receptor(EGFR) and its downstream signaling pathway in cells treated with dihydroartemisinin for 48 hours. The results showed that dihydroartemisinin could inhibit the growth of hepatocellular carcinoma cell 7402 and highly metastatic hepatocellular carcinoma cell MHCC97 H at 25 µmol·L~(-1). As compared with the control group, the number of cell clones was significantly reduced, and the ability of cell migration and invasion was weakened. Western blot results showed that as compared with the control group, dihydroartemisinin group could down-regulate the protein expression of EGFR and its downstream signaling pathways p-AKT, p-ERK, N-cadherin, Snail and Slug, and up-regulate the expression of E-cadherin protein, thus affecting the migration, invasion and metastasis of hepatocellular carcinoma cells 7402 and MHCC97 H.

Two new secolignans from the roots of Urtica fissa.

Two new secolignans, 3,4-trans-3-hydroxymethyl-4-[bis(4-hydroxy-3- methoxyphenyl)methyl]butyrolactone (1) and 3,4-trans-3-hydroxymethyl-4- [bis(3,4-dimethoxyphenyl)methyl]butyrolactone (2) have been isolated from the roots of Urtica fissa E.Pritz. Their structures were determined on the basis of spectroscopic methods, especially 1H NMR, 13C NMR, 2D NMR, and HR-ESI-MS. The inhibitory effects on N1 and N2, two subtypes of neuraminidases (NAs), of these two compounds were assayed.

Triterpenoids from Euphorbia maculata and Their Anti-Inflammatory Effects.

Euphorbia maculata is a medicinal plant of the Euphorbiaceae family, which can produce anti-inflammatory and cancer chemopreventive agents of triterpenoids. The present study reports on the bioactive triterpenoids of this plant. Two new lanostane-type triterpenoids, named (3S,4S,7S,9R)-4-methyl-3,7-dihydroxy-7(8→9) abeo-lanost-24(28)-en-8-one (1) and 24-hydroperoxylanost-7,25-dien-3ß-ol (2), together with 15 known triterpene derivatives, were isolated from Euphorbia maculata. The structures of the new compounds were determined on the basis of extensive spectroscopic data (UV, MS, ¹H and 13C-NMR, and 2D NMR) analysis. All tetracyclic triterpenoids (1⁻11) were evaluated for their anti-inflammatory effects in the test of TPA-induced inflammation (1 µg/ear) in mice. The triterpenes exhibited significant anti-inflammatory activities.

Three new amino acid derivatives from edible mushroom Pleurotus ostreatus.

Three new amino acid derivatives, oxalamido-L-phenylalanine methyl ester (1), oxalamido-L-leucine methyl ester (2), and lumichrome hydrolyzate (3), together with nine known compounds (4-12), were isolated from the solid culture of edible mushroom Pleurotus ostreatus. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configurations of 1 and 2 were established by the chiral synthesis and confirmed by circular dichroism (CD) analysis of their total synthesis products and natural isolates. All new compounds were evaluated for their antioxidant effects, antimicrobial activities, and cytotoxic activity. Compounds 1-3 showed weak antifungal activities against Candida albicans with minimum inhibitory concentration (MIC) value of 500 µg/ml.

Polyketide butenolide, diphenyl ether, and benzophenone derivatives from the fungus Aspergillus flavipes PJ03-11.

Five new polyketides including three new butenolides (1-3), one new diphenyl ether (4), and one new benzophenone (5), together with eleven known compounds (6-16) were isolated from a wetland fungus Aspergillus flavipes PJ03-11. Their structures were elucidated on the basis of detailed spectroscopic analysis. All the isolated compounds were tested for their α-glucosidase inhibitory activities. The results showed that compounds 1-3, 6, 7, 11, 15 and 16 exhibited stronger inhibitory activities than acarbose. And the preliminary structure-activity relationships of aspulvinone and diphenyl ether compounds on the α-glucosidase inhibitory activity were reported.

Two new asterriquinols from Aspergillus sp. CBS-P-2 with anti-inflammatory activity.

Two new bisindolylbenzenoid alkaloids asterriquinol E (1) and asterriquinol F (2), together with four known compounds (3-6) were isolated from the fermentation products of the fungus Aspergillus sp. CBS-P-2. Their structures were established on the basis of extensive spectroscopic analysis, including HR-ESI-MS, UV, IR, 1D, and 2D NMR (HSQC, HMBC, and NOESY) methods. The stereochemical structure of 2 was confirmed via the CD data of the in situ formed [Rh2(OCOCF3)4] complex method. All of the isolated compounds were tested for inhibitory activity against LPS (lipopolysaccharide)-induced nitric oxide production in microglia.

Three new secolignans from Peperomia blanda (Jacq.) Kunth.

Three new secolignans were found in the detailed chemical study of Peperomia blanda (Jacq.) Kunth collected from China. Detailed NMR data analysis, especially 1H NMR, 13C NMR and 2 D NMR, elucidates the structures of the three new secolignans.

Polyketides with anti-inflammatory activity isolated from Rhodiola tibetica endophytic fungus Penicillium sp. HJT-A-10.

Seven undescribed polyketide compounds (1-4, 9-11) and six known polyketide compounds (5-8,12, 13) were isolated from Rhodiola tibetica endophytic Penicillium sp. HJT-A-10. The structural of seven undescribed polyketides metabolites were established on the basis of spectroscopic methods. The results of anti-inflammatory activity showed that compounds 1-8，10-13 had significant inhibitory effects on LPS-induced NO production in RAW 264.7 cells.

A new acylated flavonoid glycoside from the flowers of Camellia nitidissima and its effect on the induction of apoptosis in human lymphoma U937 cells.

From the EtOH extract of the flowers of Camellia nitidissima Chi, a new acylated flavonoid glycoside, quercetin 7-O-(6"-O-E-caffeoyl)-ß-D-glucopyranoside (1), has been isolated, together with three known flavonoids: quercetin (2), quercetin 3-O-ß-D-glucopyranoside (3), and quercetin 7-O-ß-D-glucopyranoside (4). Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was shown to inhibit proliferation and to induce apoptosis of human lymphoma U937 cells.

[Synthesis of seven sinapine analogs and their effects on the tension of smooth muscle of intestines isolated from rabbit].

Seven sinapine analogs (6a-6g) were synthesized using cinnamon acid or benzoic acid and their derivatives as starting materials, which obtained from substituted benzaldehyde and malonate. The structures of target compounds were characterized by IR, 1H NMR and elemental analysis. The effects of compounds 6a-6g on the smooth muscle of intestine isolated from rabbit were studied, and the experimental results showed that compounds 6a, 6d and 6g had diastolic action, while 6f had contractile action.

Aging affects artemisinin synthesis in Artemisia annua.

Artemisinin (ART) is the most effective component in malaria treatment, however, the extremely low content restricts its clinical application. Therefore, it is urgent to increase the yield of ART. ART gradually accumulates with aging, small RNA (sRNA) and transcriptome analysis were applied on the leaves of 2-week-old (2 w) and 3-month-old (3 m) A. annua respectively. Among all the annotated sRNAs, 125 were upregulated and 128 downregulated in the 3 m sample compared to the 2 w one. Whereas 2183 genes were upregulated and 2156 downregulated. Notably, the level of miR156 and several annotated miRNAs gradually decreased while SPLs increased. In addition, the genes on ART biosynthesis pathway were significantly upregulated including ADS, CYP71AV1, ADH1, DBR2 and ALDH1, and so were the positive transcription factors like AaERF1, AaORA and AaWRKY1 indicating that age influences the ART biosynthesis by activating the expression of the synthesizing genes as well as positive transcription factors. This study contributes to reveal the regulatory effects of age on ART biosynthesis both in sRNA and transcription levels.

Two diketopiperazines from Acanthopanax senticosus Harms.

From the dried aerial parts of Acanthopanax senticosus, two new diketopiperazines, eleutherazines A (1) and B (2), were isolated. Their structures were elucidated on the basis of chemical and spectroscopic methods.

Three new compounds from the marine fungus Penicillium sp.

Continuous research on the ethyl acetate extract of the fermentation broth of the marine fungus Y26-02 (Penicillium sp.) led to the purification of one known and three new compounds. Their structures were elucidated, respectively, as butyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (1), 4-hydroxyphenethyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (2), 3-hydroxybenzyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (3), and desoxypatulinic acid (4) on the basis of their spectroscopic and physico-chemical properties.

[Studies on phenolic compounds from Stellera chamaejasme].

OBJECTIVE: To study the chemical constituents of the roots of Stellera chamaejasme. METHOD: The chemical constituents were separated and purified by chromatographic method after solvent extraction and were identified by spectroscopic analysis. RESULT: Two phenolic compounds were obtained and determined as stelleranol (1) and umbelliferone-7-O-glucoside (2). CONCLUSION: Compound 1 was a new compound, and compound 2 was isolated from this plant for the first time.

[Study on the theraputic effect of plants of Camellia genus on osteoporosis].

OBJECTIVE: To observe anti-osteoporotic effect of Plants of Camelia genus induced by retinoic acid in rats, in adqulis crude drug dosage, and to compare activities of them. METHODS: Extracts of Camellia japonica and Camellia oleifera were given to rats with osteoporosis induced by retinoic acid, some indexes of rats were measured and compared with those of modle group, control group and positive control group, including weight/length (G/L), bone density, earth and calcium content of bone, morphology change and serum calcium, tartrate-resistant acid phosphatase and alkaline phosphatase. We also compared effective intensity between different groups in adqulis crude drug dosage. RESULTS: Ethanol extracts of seed from Camellia japonica 0.51 g/kg could markedly enhance weight/length (G/L), bone density of femur, serum calcium and alkaline phosphatase level, with the decreasing of anti-tartaric acid tartrate-resistant acid phosphatase level. Meanwhile, they were accompanied by a significant increase of morphologic observed sclerotomal cell and by a significant decrease of osteoclast. Moreover, it was observed greatly that bone trabecula transformateed to normal morphous. The results of this study indicated that effects of ethanol extracts of seed from Camellia japonica on anti-osteoporosis with retinoic acid were the strongest. Ethanol extracts of seed from Camellia japonica , ethanol extracts of leaves from Camellia Oleifera, and aqueous extracts of leaves from Camellia Oleifera were stronger than positive control drug. The other extracts didnt show obvious anti-osteoporotic effects. Eventually the strength order of each group on anti-osteoporosis was as following: ethanol extracts of seed from Camellia japonica > ethanol extracts of leaves from Camellia Oleifera > aqueous extracts of leaves from Camellia Oleifera > aqueous extracts of seed from Camellia Oleifera > positive control drug > aqueous extracts of seed from Camellia Japonica. CONCLUSION: Plants of Camellia genus have different degree anti-osteoporosis effect, which can offer significant theory basis for progressive investigation and exploitation of them.

Isolation and identification of two new compounds from marine-derived fungus Acremonium fusidioides RZ01.

Two new compounds, (22E)-25-carboxy-8ß,14ß-epoxy-4α,5α-dihydroxyergosta-2,22-dien-7-one (1) and fusidione (3), along with two known compounds, 5α,8α-epidioxy ergosta-6,22-diene-3ß-ol (2) and microperfuranone (4), were isolated from the fermentation products of the marine-sourced fungus Acremonium fusidioides RZ01. The structures of compounds 1 and 3 were elucidated by extensive spectroscopic methods, especially 2D NMR, and their absolute configurations were suggested on the basis of the circular dichroism spectral analysis and the NOESY data. Both new compounds showed inhibitory activity against HL-60 cells with IC50 values being16.6 and 44.9 µmol·L-1, respectively.

Three new secolignan glycosides from Urtica fissa E. Pritz.

Three new secolignan glycosides {3,4-trans-4-[bis(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-ß-glucopyranoside (1), {3,4-trans-4-[(3-methoxy-4-hydroxyphenyl)(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-ß-glucopyranoside (2) and {3,4-cis-4-[(3-methoxy-4-hydroxyphenyl)(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-ß-glucopyranoside (3) were isolated from the roots of Urtica fissa E. Pritz. Their structures were identified by spectral methods including 1D NMR, 2D NMR and HR-EI-MS.