Harzianic acids and oxazolidinone from the endophytic fungus Ilyonectria sp. and their cytotoxicity activity.

Four undescribed compounds including three harzianic acids (1, 3 and 4) and one oxazolidinone (2), along with three known ones (5-7) were isolated from the solid fermented product of endophytic fungus Ilyonectria sp., their structures were elucidated as 1-amino-harzianic acid (1), ilyonectria-oxazolidinone (2),10'-nor- isoharzianic acid (3), isohomoharzianic acid (4), harzianic acid (5), isoharzianic acid (6), homoharzianic acid (7) by means of detailed chemical evidences and spectroscopic data analysis. All the compounds were evaluated for cytotoxicity against SMMC-7721 human cancer cell lines by MTS assay. Among the seven tested compounds, 1-amino-harzianic acid (1) demonstrated well cytotoxic activity against SMMC-7721 with IC50 value of 26.84 µM. The results of molecular docking indicated that compound exhibited moderate anti-tumor activity may through binding to apoptosis related proteins.

Three new pyrrole alkaloids from the endophytic fungus Albifimbria viridis.

Three new pyrrole alkaloids albifipyrrols A-C (1-3), were isolated from the endophytic fungus Albifimbria viridis collected from the Chinese medicinal plant. Their structures were elucidated by extensive NMR and HRESIMS spectrometric analyses. All compounds were evaluated for immunosuppressive activity. Fortunately, compound 2 exhibits certain inhibition specifically against the LPS-induced proliferation of B lymphocyte cells with IC50 value 16.16 µM.

Structure and cytotoxicity of trichothecenes produced by the potato-associated fungus Trichothecium crotocinigenum.

Seven previously undescribed trichothecenes, named trichothecrotocins M-S (1-7), along with five known compounds, were isolated from rice cultures of the potato-associated fungus Trichothecium crotocinigenum. Their structures and absolute configurations were determined through spectroscopic methods, single-crystal X-ray diffraction, and quantum chemistry calculations on ECD. Compound 1 possesses a rare 6,11-epoxy moiety in the trichothecene family. Compound 6 exhibited strong cytotoxic activity against MCF-7 cancer cell lines with an IC50 value of 2.34 ± 0.45 µM. It promoted apoptosis induction in MCF-7 cells. Moreover, cell cycle analysis showed cell cycle arrest caused by compound 6 at the G2/M phase which resulted to cell proliferation inhibition and pro-apoptotic activity. Further quantitative real-time PCR (qRT-PCR) analysis confirmed that the G2/M arrest was accompanied by upregulation of p21 and down regulation of cyclins B1 in 6-treated MCF-7 cells.

Identification and Bioactivities of Secondary Metabolites Derived from Endophytic Fungi Isolated from Ethnomedicinal Plants of Tujia in Hubei Province: A Review.

Tujia is a national minority, inhabiting in the mountainous Wuling area in China. Since 1978, Tujia medicine has been studied, summarized and developed, leading to numerous achievements by Chinese researchers, such as the publishing of approximately 30 monographs of Tujia medicine. These publications are focused on summarizing and improving the theory of Tujia medicine and developing clinical therapies from this system of medicine. The shortage of natural medicinal plants used in Tujia medicine has created the need to discover new resources to replace them and protect endangered natural plant species. Endophytic fungi are one of the conservation options, are considered a source of new bioactive natural products, and are a renewable and inexhaustible source of new drugs and agrochemicals. This review summarizes 260 compounds from endophytic fungi that have been previously isolated from the medicinal plants of Tujia. These compounds include steroids, terpenoids, meroterpenoids, polyketides, alkaloids, peptides, aliphatic compounds, aromatic compounds, and heterocyclic compounds.

Characterization of the complete chloroplast genome of a well-known Chinese medicinal herb, Scrophularia ningpoensis.

Scrophularia ningpoensis has been used as a famous traditional medicinal herb in Asian countries to treat jaundice, dysentery, and the pain of rheumatism. In this paper, the complete chloroplast (cp) genome sequence of S. ningpoensis was reported and characterized. The cp genome is 153,175 bp in length, composed of a pair of 25,490 bp inverted repeat (IR) regions separated by a large single copy (LSC) region of 84,257 bp and a small single copy (SSC) region of 17,938 bp. There were 130 predicted genes (85 protein-coding genes, 37 tRNA genes, and 8 rRNA genes) in the genome, and the overall GC content of the genome is 38%. Phylogenetic analysis based on the cp genome data showed that S. ningpoensis was sister to S. buergeriana.

Trichothecrotocins D-L, Antifungal Agents from a Potato-Associated Trichothecium crotocinigenum.

Seven new merosesquiterpenoids, trichothecrotocins D-J (1-7), two new trichothecene sesquiterpenoids, trichothecrotocins K (12) and L (13), and six known compounds (8-11, 14, and 15), were isolated from a potato-associated fungus, Trichothecium crotocinigenum. Compounds 5 and 6 were racemates which were further separated as pure enantiomers. Structures together with absolute configurations were established by extensive spectroscopic analysis, as well as quantum chemistry calculations on ECD and optical rotations. Compounds 1-4 are rare meroterpenoids featuring a seco-phenyl group, while 1 and 2 possessed a novel 6-6/5 fused ring system. Compounds 1-4, 8, 11, and 12 showed antifungal activity against four plant pathogens with MIC values of 8-128 µg/mL. It is suggested that the meroterpenoids produced by T. crotocinigenum may play an important role in the antifungal property of the fungus, thereby protecting the host plant, i.e., potato.

Depsidones and diaryl ethers from potato endophytic fungus Boeremia exigua.

Three depsidones boremexins A-C (1-3), two diaryl ethers boremexins D (4) and E (5), together with four known compounds were obtained from cultures of potato endophytic fungus Boeremia exigua. Their structures with absolute configurations were established by extensive spectroscopic methods and electronic circular dichroism (ECD) calculations. Compounds 1-4, 6, and 9 displayed anti-inflammatory properties on nitric oxide production in LPS-induced RAW264.7 macrophages with an IC50 range of 19.4-34.4 µM. Compounds 2 and 5 exhibited cytotoxicities to human breast cancer cell line (MCF-7) with IC50 values of 33.1 and 4.0 µM, respectively.

Dietary Ginkgo biloba leaf extract alters immune-related gene expression and disease resistance to Aeromonas hydrophila in common carp Cyprinus carpio.

Ginkgo biloba leaf is widely used in traditional medicine in China. The present study aimed to illustrate the effects of dietary Ginkgo biloba leaf extract (GBLE) on growth performance and immune responses in common carp infected by Aeromonas hydrophila. Six different diets either not treated (control) or treated with 0.5, 1, 2, 5 and 10 g/kg of GBLE were designed to feed the fishes for 8 weeks. The results indicated that, compared to the control groups, 10 g/kg dietary GBLE significantly increased body growth and feed utilization. In GBLE dietary groups, red blood cell levels, white blood cells, hematocrit, hemoglobin, total protein, albumin and globulin were significantly increased relative to the control groups. Dietary supplementation with 5 g/kg GBLE increased the phagocytic ratio, and phagocytic indexes increased in the 2, 5 and 10 g/kg groups relative to the control groups. Moreover, 2, 5 and 10 g/kg GBLE diets increased O2- production compared to the control groups. Additionally, GBLE diets stimulated lysozyme activity (in 10 g/kg group) and inhibited bactericidal activity (in 0.5, 2, 5 and 10 g/kg group). Quantitative real-time PCR showed that IL1ß, IL8, TNF-α, IL10, TGFß, and inducible enzyme genes were prone to decrease while SAA, hepcidin and GPX1 were increased due to the GBLE diet in the intestine. In the head-kidney, the GBLE treatment decreased IL1ß, IL8, TNF-α, IL10, TGFß, INOS and arginase gene expressions, whereas SOD upregulation was found in the GBLE condition. The mRNA expressions of IL1ß, IL8, TNF-α, IL10 and INOS were decreased, but SAA, hepcidin, GPX1 and SOD mRNA levels were increased in the spleen in the GBLE diet compared to the control. Additionally, diet supplemented with GBLE improved the survival rate infected with A. hydrophila. Our observations suggest that GBLE effectively enhanced growth performance, modulated immune-related gene expression. It improved survival rate of common carp after A. hydrophila infection and the optimum concentration we recommend is 10 g/kg of GBLE.

Cytotoxic 19,20-epoxycytochalasans from endophytic fungus Xylaria cf. curta.

Nine new 19,20-epoxycytochalasans (1-9) were isolated from the rice fermentation extracts of endophytic fungus Xylaria cf. curta, along with four known compounds 19,20-epoxycytochalasin C (10), 18-desoxy-19,20-epoxycytochalasin C (11), 19,20-epoxycytochalasin D (12) and 5,6-dihydro-7-oxo-19,20-epoxycytochalasin C (13). Their structures and absolute configurations were determined by 1D and 2D NMR, HRESIMS, X-ray diffraction and ECD calculation. The cytotoxicity of obtained compounds (1-13) was evaluated against human cancer cell lines HL-60, A549, SMMC-7721, MCF-7, and SW480. Remarkably, compound 10 showed significant specific cytotoxicity against HL-60 cell lines with IC50 value of 1.11 µM.

Characterization of the complete chloroplast genome of Paederia scandens (Rubiaceae): a Chinese folk medicinal plant.

Paederia scandens has been used as a traditional medicine in Asian countries to treat jaundice, dysentery, and the pain of rheumatism. The complete chloroplast (cp) genome sequence of P. scandens was reported and characterized in this study. The cp genome is 153,626 bp in length, composed of a pair of 26,513 bp inverted repeat (IR) regions separated by a large single-copy (LSC) region of 83,712 bp and a small single-copy (SSC) region of 16,888 bp. There were 131 predicted genes (86 protein-coding genes, 37 tRNA genes, and 8 rRNA genes) in the genome, and the overall GC content of the genome is 37.7%. Phylogenetic analysis based on the cp genome data showed that P. scandens was sister to the clade formed by Galium mollugo and G. aparine.

The complete plastid genome of Iris domestica: a traditional Chinese medicine.

Iris domestica has been used as Chinese traditional medicine to treat inflammation and throat disorders for many centuries. In this study, the complete plastid genome of I. domestica was first reported and characterized. The complete plastid genome is a typical quadripartite circular molecule of 153,729 bp in length, including a large single copy (LSC) region of 83,136 bp and a small single copy (SSC) region of 18,165 bp separated by two inverted repeat (IR) regions of 26,214 bp. A total of 132 genes including 86 protein-coding genes, 38 tRNA genes, and eight rRNA genes were identified. The phylogenetic analysis revealed that I. domestica was closer to I. gatesii.

The complete chloroplast genome sequence of a traditional Chinese medicine: Achyranthes bidentata (Amaranthaceae).

Achyranthes bidentata (Amarathaceae) has been commonly used as a traditional Chinese medicine in the treatment of osteoporosis and bone nonunion. Here, the complete chloroplast genome of A. bidentata was assembled and characterized. The cp genome is 151,451 bp in length, composed of a pair of 25,150 bp inverted repeat (IR) regions separated by a large single-copy (LSC) region of 83,899 bp and a small single-copy (SSC) region of 17,252 bp. The whole cp genome of A. bidentata contains 130 genes(85 protein-coding genes, 37 tRNAs and eight rRNAs) and the overall GC content is 36.5%. Phylogenetic analysis based on the cp genome data showed that A. bidentata was close to Cyathula capitata.

Anti-bacterial chromones from cultures of the endophytic fungus Bipolaris eleusines.

One previously undescribed chromone (S)-5-hydroxyl-2-(1-hydroxyethyl)-7-methylchromone (1) and one known analogue (2), as well as four known sativene-type sesquiterpenoids bipolenins A‒C (3‒5), were isolated from cultures of the endophytic fungus Bipolaris eleusines. Their structure were elucidated by extensive spectroscopic methods and the data comparison with those reported in the literature. Compounds 1 and 2 showed weak inhibitory activities against Staphylococcus aureus subsp. aureus with the inhibition rates of 56.3 ± 0.48 and 32 ± 1.27%, respectively, at the concentration of 128 µg/mL.

Piperidine alkaloids and xanthone from the roots of Caulophyllum robustum Maxim.

Two undescribed piperidine racemates, (±)-caulophines A and B (1 and 2), a new N-containing xanthone derivative (3), together with six known piperidines, were isolated from the roots of Caulophyllum robustum Maxim. Their structures were determined by extensive spectroscopic techniques. Compounds 3 and 7 exhibited weak cytotoxicities against human palace cancer hela cell line with inhibitory rates of 32.2% and 39.7%, respectively, at the concentration of 40 µM.

Two new megastigmanes from Chinese traditional medicinal plant Sedum sarmentosum.

To discover new bioactive compounds from nature plants, a primary screening of traditional Chinese medicines had been taken. The screening results showed that a EtOAc extract of Sedum sarmentosum displayed a certain degree of cytotoxic activity and bioassay-directed isolation of EtOAc extract gave two new megastigmanes, (6S,9R)-2-hydroxy-4-(2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-butyric acid (1) and (6S,9R)-2-hydroxy-4-(2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-butyric acid methyl ester (2) together with seven known flavonoids. The chemical structures of 1 and 2 were elucidated on the basis of detailed 1D, 2D NMR and MS data. When tested against HepG2 and Hep3B hepatocellular carcinoma cell lines, compounds 1-9 showed weak anti-HCC activity. In addition, in vitro antioxidant activities of 1-9 were evaluated by ABTS radical cation-scavenging assay. 1 and 2 exhibited weak activity with per micromoles equivalent to 0.039 and 0.042 µM of Trolox, respectively. The flavonoid component, quercetin (9) showed the highest antioxidant activities with per micromoles equivalent 0.67 µM of Trolox.

Four new C18-diterpenoid alkaloids with analgesic activity from Aconitum weixiense.

Four new C18-diterpenoid alkaloids, weisaconitines A-D (1-4), were isolated from Aconitum weixiense. Based on extensive UV, IR, MS, 1D and 2D NMR analyses, their structures were elucidated as 8-O-ethyldolaconine (1), 4-demethylgenicunine B (2), 14-oxoaconosine (3), and 8-O-ethylaconosine (4). The analgesic activity of compound 4 was studied with CH3COOH-induced writhing model in mice. Compound 4 showed writhing inhibitions of 24% (50 mg/kg), 26% (100 mg/kg) and 34% (200 mg/kg), respectively, as compared to the reference drug aspirin (63%) at a dose of 200 mg/kg.

Two new C19-diterpenoid alkaloids from Aconitum transsectum.

Two new C(19)-diterpenoid alkaloids, named aconitramines D (1) and E (2), were isolated from the roots of Aconitum transsectum. Based on comprehensive spectroscopic analyses including IR, ESI-MS, HR-ESI-MS, and 1D and 2D NMR, their structures were elucidated as 18-demethoxyltransconitine A (1) and 8-O-anisoyl-14-hydroxylacoforesticine (2).