Search

The aim of this work is to explore the effects of herbal medicine on secondary metabolites of microorganisms during fermentation. Clonostachys rogersoniana was found to metabolize only small amounts of polyketide glycosides rogerson B and C on fresh potatoes, but after replacing the medium to the medicinal plant Rubus delavayi Franch., the type and content of the metabolized polyketones showed significant changes. The sugars and glycosides in R. delavayi are probably responsible for the changes in secondary metabolites. Six polyketide glycosides including a new metabolite, rogerson F, and two potential antitumor compounds, TMC-151C and TMC-151D, were isolated from the extract of R. delavayi fermented by C. rogersoniana. In addition, 13C labeling experiments were used to trace the biosynthesis process of these compounds. TMC-151C and TMC-151D showed significant cytotoxic activity against PANC-1, K562 and HCT116 cancer cells but had no obvious cytotoxic activity against BEAS-2B human normal lung epithelial cells. The yields of TMC-151C and TMC-151D reached 14.37 ± 1.52 g/kg and 1.98 ± 0.43 g/kg, respectively, after fermentation at 28 °C for 30 days. This is the first study to confirm that herbal medicine can induce microbes to metabolize active compounds. And the technology of fermenting medicinal materials can bring more economic value to medicinal plants. [Display omitted] • Secondary metabolites of microorganisms can be affected by herbal medicine. • TMC-151 s were enriched by fermentation of R. delavayi with C. rogersoniana. • The yields of TMC-151C and TMC-151D reached 14.37 ± 1.52 and 1.98 ± 0.43 g/kg. • Biosynthetic pathways of TMC-151 s were predicted by 13C labeling experiments. [ABSTRACT FROM AUTHOR]

A series of new Lycopodium alkaloids, namely 1- epi -malycorin A ( 1 ), 1- epi -17 S -hydroxymalycorin A ( 2 ), 6 α -hydroxyphlegmariurine A ( 3 ), 2 S ,4 R -dihydroxyfawcettimine ( 4 ), and 16-hydroxylycodine ( 5 ), together with 24 known ones, have been isolated from the club moss Phlegmariurus henryi . The structures of the new compounds were determined by extensive spectroscopic analysis, including 1D and 2D NMR, as well as X-ray crystallographic analysis. Among them, the absolute configurations of 1 , 2 , and 4 and the structure of 3 were confirmed on the basis of the single-crystal X-ray diffraction analysis. 1- Epi -17 S -hydroxymalycorin A ( 2 ) was a unique C 19 N-type Lycopodium alkaloid consisting of a serratinine skeleton with 1,2-propanediol unit. 2 S ,4 R -dihydroxyfawcettimine ( 4 ) was a 2,4-dihydroxy derivative of fawcettimine. 16-Hydroxylycodine ( 5 ) was the oxidative product of lycodine with an unusual hydroxymethyl group at C-15. All new compounds were evaluated for in vitro acetylcholinesterase (AChE) inhibitory activity and cytotoxicity against four human cancer cell lines. [ABSTRACT FROM AUTHOR]

Ten new neo -clerodane derivatives ( 1 – 10 ) and 10 known diterpenoids were identified from the aerial parts of Salvia leucantha . The structures of 1 – 10 were established by 1D and 2D NMR spectroscopic data analysis. The absolute configurations of 1 , 3 , 6 , and 7 were determined by X-ray diffraction data. Compound 16 exhibited cytotoxicity against HCT116, BT474, and HepG2 cancer cell lines and was identified as a heat shock protein 90 inhibitor. Compounds 8 , 15 , and 16 exhibited moderate acetyl cholinesterase inhibitory activity. [ABSTRACT FROM AUTHOR]

Six new cassane diterpenoids ( 1–6 ) and 15 known compounds were isolated and identified from the seeds of Caesalpinia sappan . The structures of the new compounds were determined based on the spectroscopic methods, including 1D and 2D NMR techniques. Compound 1 is a rare cassane diterpenoid featuring a nitrogen containing bridge between C-19 and C-20. Compounds 1 and 2 exhibited moderate cytotoxicity against HCT116, AGS, and HepG2 cell lines with IC 50 values ranging from 6.36 to 27.86 μM. [ABSTRACT FROM AUTHOR]

Abstract: Cheliensisin A is a natural styryl-lactone isolated from Goniothalamus cheliensis Hu in considerably large quantity with putative anticancer activities. However, its poor water solubility and chemical instability have precluded cheliensisin A as a potential drug candidate. To explore the strategy to overcome these problems, 21 novel derivatives of cheliensisin A with different substitutions at C-7 and C-8 positions were designed and synthesized. Inhibition of proliferation against five tumors cell lines indicates that eight new derivatives with embedment of oxazole or oxazoline exhibit improved cytotoxicity on SK-BR-3 and PANC-1, and compounds 2d and 2g show 5–8 folds higher potency than cisplatin. HPLC investigation of representative compounds indicates that oxazole and oxazoline analogs exhibit much improved chemical stability than their natural parent. [Copyright &y& Elsevier]

Abstract: Aim: To study the chemical constituents of the aerial parts of Isodon adennolmus collected in the Shangrila region of Yunnan Province, China. Method: Compounds 1–10 were separated and purified by silica gel and C18 reversed phase silica gel column chromatography. The structures were elucidated by extensive spectroscopic methods (IR, UV, MS and NMR), and the absolute configuration of 1 was determined by single crystal X-ray diffraction analysis. Compounds 2–5 and 10 were evaluated for their in vitro cytotoxicity against human tumor cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW-480. Results: One ent-abietane, two abietane, and seven ent-kaurane diterpenoids were isolated and identified. Conclusion: Compounds 1–3 are new diterpenoids. Compounds 2–4 and 10 showed moderate inhibitory effects on several of the five tumor cell lines. [Copyright &y& Elsevier]

Abstract: Six new (rubiyunnanins C–H, 1–6) and five known (7–11) cyclic hexapeptides were isolated from the roots of Rubia yunnanensis (Franch.) Diels. The structures and stereochemistry of 1–6 were established by extensive spectroscopic analyses and chemical methods. All compounds (1–11) not only exhibited cytotoxic activities against a panel of eleven cancer cell lines with IC50 values ranging from 0.001 to 56.24μM, but also exerted inhibitory activities against nitric oxide (NO) production in LPS and IFN-γ-induced RAW 264.7 murine macrophages with IC50 values ranging from 0.05 to 12.68μM. Furthermore, this is the first time it is being reported that compounds 2 and 7–10 significantly inhibited TNF-α-induced NF-κB activation in HEK-293-NF-κB luciferase stable cells with IC50 values of 35.07, 0.03, 1.69, 12.64 and 1.18μM, respectively. [ABSTRACT FROM AUTHOR]

Abstract: Phytochemical investigation on the roots of Cimicifuga heracleifolia afforded nine new 9,19-cycloartane triterpenes (1–9), along with seven known constituents (10–16). The new structures were elucidated by spectroscopic and chemical methods. Biological evaluation of the compounds against human HL-60, SMMC-7721, A549, MCF-7, and SW-480 cell lines indicated that eight cimigenol-type compounds (1–3, 5, 10–12, 14) showed different levels of cytotoxic activities, with IC50 values ranging from 0.83 to 23.94 μM. In addition, their structural and bioactive features enriched the structure–activity relationships we proposed before. [Copyright &y& Elsevier]

Abstract: A new 4α-methyl sterol, cimisterol A (1), together with five known compounds (2–6), were isolated from the aerial parts of Cimicifuga foetida L. The new compound''s structure was determined with the help of extensive 1D and 2D NMR spectroscopy. Compound 1 exhibited broad-spectrum and potent cytotoxic activities against human HL-60, Jurkat, K562, U937, HepG-2, and SGC-7091 cell lines, with IC50 values of 7.23, 2.89, 6.88, 3.38, 4.21, and 4.89μM, respectively. Compound 3 showed moderate to weak activities to all cell lines, except for SGC-7091, having IC50 values ranging from 13.37 to 17.72μM. This is the first time a cytotoxic 4α-methyl sterol constituent was discovered from Cimicifuga spp. [Copyright &y& Elsevier]

The ethanol extract of the aerial parts of Alstonia yunnanensis Diels afforded five new monoterpenoid indole alkaloids, alstiyunnanenines A–E ( 1 – 5 ), along with one known compound, alstoniascholarine I ( 6 ). The structures of the isolated compounds were established based on 1D and 2D ( 1 H- 1 H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. The isolated compounds were tested in vitro for cytotoxic potential using eight tumor cell lines. As a result, alkaloids 4 – 6 exhibited cytotoxicities against all tested tumor cell lines, especially against osteosarcoma cell lines (SOSP-9607, MG-63, Saos-2, M663) with IC 50 values < 6 μM. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the flowers of Inula japonica led to isolation of nine sesquiterpenoids, inujaponins A-I, as well as eighteen known ones. These sesquiterpenoids belong to six skeletal-types, including eudesmane, 1,10-seco-eudesmane, germacrane, guaiane, 4,5-seco-guaiane, and pseudoguaiane sesquiterpenoids. Their structures were established by extensive spectroscopic analysis. The absolute configurations of inujaponin A, eupatolide, and deacetylovatifolin were determined by Cu-Kα X-ray crystallographic analysis. Most of the isolated compounds exhibited potent cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cancer cell lines, with IC 50 values ranging from 1.57 to 22.58 μ M. Some selected compounds also possessed significant inhibitory activity against LPS-induced NO production in RAW264.7 macrophages with IC 50 values ranging from 1.42 to 8.99 μ M. [ABSTRACT FROM AUTHOR]

Seven new vibsane-type diterpenes, vibsanols C–H ( 1 – 6 ) and vibsanin X ( 7 ), together with seven analogues, were isolated from the leaves and twigs of Viburnum odoratissimum . The structures of the new compounds were elucidated by extensive spectroscopic methods. All the new compounds were detected for their cytotoxicity. Compound 1 showed significant cytotoxicity against all the tested cell lines (HL-60, SMMC-7721, A-594, MCF-7, and SW-480), with IC 50 values of 3.35, 4.41, 5.18, 11.30, and 3.70 μM, respectively. Compounds 4 and 5 also displayed significant cytotoxicity against hepatocellular carcinoma SMMC-7721 cell line, with IC 50 values of 3.69 and 3.52 μM, respectively. [ABSTRACT FROM AUTHOR]

Abstract: Fourteen new lanostane triterpene acids (1–14), and five known analogues (15–19) were isolated from the stems of Kadsura polysperma. Compound 1, with a rearranged tetracyclic skeleton, is an important biogenic precursor of longipedlactone skeleton. Compounds 2–6 are members of 18(13→12)-abeo-lanostane triterpene acids. The structures of new compounds were elucidated by spectroscopic evidence. Selected compounds were evaluated for their in vitro cytotoxicity against human tumor HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines. [Copyright &y& Elsevier]

Abstract: Two novel cyclic hexapeptides, named rubiyunnanins A (1) and B (2), were isolated from the roots of Rubia yunnanensis (Franch.) Diels. Their structures were elucidated extensively by spectroscopic analysis and theoretical computation. Possible biosynthetic pathways for RAs, 1, and 2 were proposed. Compound 2 showed moderate cytotoxicities against 11 cancer cell lines and inhibited nitric oxide (NO) production in LPS and IFN-γ-induced RAW 264.7 murine macrophages. [ABSTRACT FROM AUTHOR]