Yuemao Shen

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Organization: Xiamen University
Department: Key Laboratory of the Ministry of Education for Cell Biology and Tumor Cell Engineering, School of Life Sciences
Title:
Co-reporter:Yi-xin Ou, Yao-yao Li, Xiao-ming Qian, Yue-mao Shen
Phytochemistry 2012 Volume 78() pp:190-196
Publication Date(Web):June 2012
DOI:10.1016/j.phytochem.2012.03.002
Thirteen diterpenoids, named radianspenes A–M (1–13), including three lactams radianspenes J (10), K (11) and L (12) and one dimer radianspene M (13), were isolated from fermentation products of the higher fungal strain Coprinus radians M65. All these compounds possessing guanacastane skeleton were evaluated for antitumor activity using MDA-MB-435 cell line. Radianspene C exhibited inhibitory activity with IC50 of 0.91 μM.Graphical abstractThirteen diterpenoids, named radianspenes A–M (1–13), including three lactams, radianspenes J (10), K (11) and L (12) and one dimer radianspene M (13), were isolated from Coprinus radians M65.Highlights► Radianspenes A–M with guanacastane skeleton were isolated from Coprinus radians M65. ► Radianspene M represents a dimeric diterpenoid besides ent-kaurane dimer. ► The structure of radianspene M was confirmed by X-ray diffraction analysis. ► Radianspene C shows cytotoxicity to MDA-MB-435 with IC50 of 0.91 μM.
Co-reporter:Ting Lin;Xiao Lin;Chun-Hua Lu ;Yue-Mao Shen
Helvetica Chimica Acta 2011 Volume 94( Issue 2) pp:301-305
Publication Date(Web):
DOI:10.1002/hlca.201000220

Abstract

From the fermentation extract of Xylarialean sp. A45, an endophytic fungus of Annona squamosa L., three new triterpenes, namely xylariacins A–C (13, resp.) were obtained. Their structures were determined by spectroscopic analyses, including 1D- and 2D-NMR experiments and HR-ESI-Q-TOF mass spectrometry. The in vitro cytotoxic activities of compounds 13 were tested against human tumor cell line HepG2, and these compounds showed modest cytotoxic activity.

Co-reporter:Jifeng Wang, Baobing Zhao, Wei Zhang, Xuan Wu, Ruoyu Wang, Yaojian Huang, Dong Chen, Kum Park, Bart C. Weimer, Yuemao Shen
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 23) pp:7054-7058
Publication Date(Web):1 December 2010
DOI:10.1016/j.bmcl.2010.09.105
Mycoepoxydiene (MED) is a polyketide isolated from a marine fungus associated with mangrove forests. It contains an oxygen-bridged cyclooctadiene core and an α,β-unsaturated δ-lactone moiety. MED induced the reorganization of cytoskeleton in actively growing HeLa cells by promoting formation of actin stress fiber and inhibiting polymerization of tubulin. MED could induce cell cycle arrest at G2/M in HeLa cells. MED-associated apoptosis was characterized by the formation of fragmented nuclei, PARP cleavage, cytochrome c release, activation of caspase-3, and an increased proportion of sub-G1 cells. Additionally, MED activated MAPK pathways. Interestingly, the time of JNK, p38, and Bcl-2 activation did not correlate with the release of cytochrome c. This study is the first report demonstrating the action mechanism of MED against tumor cell growth. These results provide the potential of MED as a novel low toxic antitumor agent.Mycoepoxydiene (MED) is a polyketide isolated from a marine fungus associated with mangrove forests. MED induced the reorganization of cytoskeleton in HeLa cells by promoting formation of actin stress fiber and inhibiting polymerization of tubulin. MED could induce cell cycle arrest at G2/M in HeLa cells. MED-associated apoptosis was characterized by the formation of fragmented nuclei, PARP cleavage, cytochrome c release, activation of caspase-3, and an increased proportion of sub-G1 cells. Additionally, MED activated MAPK pathways. It showed encouraging biological activities.
Co-reporter:Zhi-Yu Hu;Yao-Yao Li;Chun-Hua Lu;Ting Lin;Ping Hu ;Yue-Mao Shen
Helvetica Chimica Acta 2010 Volume 93( Issue 5) pp:925-933
Publication Date(Web):
DOI:10.1002/hlca.200900323

Abstract

Seven novel polyketides, namely, 1-(xylarenone A)xylariate A (1), xylarioic acid B (2), xylariolide A (3), xylariolide B (4), xylariolide C (5), methyl xylariate C (6), and xylariolide D (7), together with the known one taiwapyrone (8), were isolated from the endophytic fungal strain Xylaria sp. NCY2 of Torreya jackiiChun. Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments, and on the basis of HR-Q-TOF mass spectrometry. Antitumor and antibacterial assays of compounds 18 were carried out, which show moderate activities.

Co-reporter:Yao-Yao Li;Zhi-Yu Hu;Chun-Hua Lu ;Yue-Mao Shen
Helvetica Chimica Acta 2010 Volume 93( Issue 4) pp:796-802
Publication Date(Web):
DOI:10.1002/hlca.200900296

Abstract

One new diterpenoid, xylarenolide (1), and three new sesquiterpenoids, xylaranol A (2), xylaranol B (3), and xylaranic acid (4), were obtained from the fungal strain Xylaria sp. 101, which was isolated from the fruiting body of Xylaria sp. collected in Gaoligong Mountain, Yunnan Province. Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments, and by HR-Q-TOF mass spectrometry. Their antimicrobial activities were evaluated.

Co-reporter:Yao-Yao Li ;Yue-Mao Shen
Helvetica Chimica Acta 2010 Volume 93( Issue 11) pp:2151-2157
Publication Date(Web):
DOI:10.1002/hlca.200900470

Abstract

Four novel diterpenoids, namely (4β)-4,4-O-dihydrocrinipellin A (1), (4β,8α)-4,4-O,8,8-O-tetrahydrocrinipellin B (2), crinipellin C (3), and crinipellin D (4), along with three known ones, (3β,4β)-3,3-C,4,4-O-tetrahydrocrinipellin A (5), (4β)-4,4-O-dihydrocrinipellin B (6), and phlebiakauranol alcohol, were isolated from the fungal strain Crinipellis sp. 113. Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments, and by HR-Q-TOF mass spectrometry. Antitumor and antibacterial assays with the novel compounds 14 were carried out, showing moderate activities against HeLa cells and no effects on the growth of tested bacteria or yeast.

Co-reporter:Mingzi Wang;Shaosong Liu;Yaoyao Li;Ren Xu;Chunhua Lu
Current Microbiology 2010 Volume 61( Issue 4) pp:254-260
Publication Date(Web):2010 October
DOI:10.1007/s00284-010-9604-7
Tubercularia sp. TF5 is an endophytic fungal strain isolated from the medicinal plant Taxus mairei. Previously, taxol has been detected in the fermentation products of this strain. However, it lost the capability of producing taxol after long-term laboratory culture. Herein, we tried to reactivate the production of taxol by protoplast mutations and genome shuffling. The protoplasts of Tub. sp. TF5 were prepared from its mycelia, and mutated by UV and NTG. The mutant strains regenerated from the mutated protoplasts were selected and classified into four groups on the basis of their phenotypes, the profile of their metabolites analyzed by TLC, MS, and bioassay data. Then, genome shuffling was subsequently carried out with eight mutant strains, with two representatives from each protoplast mutant group, and genome shuffling mutant strains were obtained and screened using the same screening procedure. Although taxol has not been detected in any mutant, two important mutants, M-741 and G-444 were selected for metabolites isolation and determination due to their phenotypes, and differences in TLC analysis result from TF5 and other mutants. Three new sesquiterpenoids, namely tuberculariols A–C (1–3), and a known dihydroisocoumarin (4) were obtained from M-741. Eighteen novel compounds were isolated from G-444, including five new sesquiterpenoids (5-9), two new dihydroisocoumarins (10, 11), one new tetralone (12), together with 10 known compounds (13–20, 1, and 2). The compounds isolated from the M-741 and G-444 were different in structure types and substitutions from those of TF5 (15, 21–29). The results showed, for the first time, that protoplast mutations and genome shuffling are efficient approaches to mining natural products from endophytic fungi. Understanding the mechanisms of unlocking the biosynthesis of new metabolites will facilitate the manipulation of the secondary metabolism in fungi.
Co-reporter:Jian Li, Chunhua Lu and Yuemao Shen
The Journal of Antibiotics 2010 63(10) pp:595-599
Publication Date(Web):September 8, 2010
DOI:10.1038/ja.2010.95
Five new 16-membered macrolides (1–5), belonging to the bafilomycin subfamily, were isolated from the fermentation broth of Streptomyces sp. CS, a commensal microbe of Maytenus hookeri. Their structures including relative configurations were elucidated based on NMR data and analysis of single crystal X-ray diffraction data. The cytotoxicities of compounds 1–5 on the MDA-MB-435 cell line were analyzed by the MTT method and the IC50 values were found to be 4.2, 4.5, 5.5, 3.8 and 11.4 μM, respectively.
Co-reporter:Lin Zhao;Peng-fei Li;Chun-hua Lu;Shu-guang Li
Journal of Microbiology 2010 Volume 48( Issue 4) pp:438-444
Publication Date(Web):2010 August
DOI:10.1007/s12275-010-0048-3
3-O-α-D-ribofuranosyl epothilone A (epothiloneoside A) is a major component of glycosylated epothilones in Sorangium cellulosum strain So0157-2. The production and glycosylation ratios of epothiloneoside A in both solid and liquid culture conditions with various pH values and carbon sources were studied. The results showed that glycosylation occurs whenever epothilones are produced, regardless of changes in pH values, production time curves, and different carbon sources. We suggest that glycosylation is a stable process, paralleling the biosynthesis of epothilones in the So0157-2 strain.
Co-reporter:Ting Lin;Xiang Lin;Chunhua Lu;Zhiyu Hu;Wenyu Huang;Yaojian Huang
European Journal of Organic Chemistry 2009 Volume 2009( Issue 18) pp:2975-2982
Publication Date(Web):
DOI:10.1002/ejoc.200801021

Abstract

Eleven new metabolites, including nine lovastatin analogues [oblongolides N–V (12 and 511), which were defined as naphthalene-type fungal polyketides], one linear furanopolyketide (13) and a monoterpene named dihydroxysabinane (14), together with four known compounds including oblongolides B (3) and C (4), one linear furanopolyketide (12) and the sesterterpene terpestacin (15), were isolated from the endophytic fungal strain Phomopsis sp. XZ-26 of Camptotheca acuminate. Their structures were elucidated by spectroscopic analyses including HR-ESI-MS, 1H and 13C NMR, 2D NMR (HMQC, HMBC, 1H-1H COSY and NOESY), and X-ray single-crystal analysis. The antimicrobial activities of 15, 8, 10 and 1315 were evaluated, but none showed a substantial effect. Additionally, a hypothetical biosynthetic pathway for oblongolides was proposed.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Co-reporter:Xin Wu;Chun-Hua Lu ;Yue-Mao Shen
Helvetica Chimica Acta 2009 Volume 92( Issue 12) pp:2783-2789
Publication Date(Web):
DOI:10.1002/hlca.200900168

Abstract

Five diterpenoids, including three new ent-trachylobane diterpenoids, i.e., (3α)-3-hydroxy-ent-trachylobane-17,19-dioic acid 19-methyl ester (1), ent-trachylobane-17,19-dioic acid 19-methyl ester (2), ent-trachylobane-17,19-dioic acid (3), and two known atisane-type ones, i.e., (16α)-16,17-dihydroxy-ent-atisan-19-oic acid methyl ester (4), and 17-hydroxy-ent-atisan-19-oic acid methyl ester (5), were isolated from the co-culture extract of the calli of Trewia nudiflora and its endophytic fungus Fusarium sp. WXE. Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments, and HR-Q-TOF mass spectrometry. The antitumor and antibacterial properties of the new compounds were evaluated.

Co-reporter:Lin Yuan;Pei-Ji Zhao;Juan Ma;Chun-Hua Lu;Yue-Mao Shen
Helvetica Chimica Acta 2009 Volume 92( Issue 6) pp:1118-1125
Publication Date(Web):
DOI:10.1002/hlca.200800424
Co-reporter:Ren Xu;Ming-Zi Wang;Chun-Hua Lu;Zhong-Hui Zheng ;Yue-Mao Shen
Helvetica Chimica Acta 2009 Volume 92( Issue 8) pp:1514-1519
Publication Date(Web):
DOI:10.1002/hlca.200800451

Abstract

Three new sesquiterpenes, tuberculariols A–C (13, resp.), were isolated from the mutant strain M-741 of Tubercularia sp. TF5, an endophytic fungus of Taxus mairei. Their structures were elucidated by spectroscopic analyses including 1D- and 2D-NMR experiments, and HR-Q-TOF-MS. Antitumor and antibacterial properties of these compounds were evaluated.

Co-reporter:Lin Yuan;Xiang Lin;Pei-Ji Zhao;Juan Ma;Yao-Jian Huang;Yue-Mao Shen
Helvetica Chimica Acta 2009 Volume 92( Issue 6) pp:1184-1190
Publication Date(Web):
DOI:10.1002/hlca.200800416
Co-reporter:Na Zhu;Peiji Zhao
Current Microbiology 2009 Volume 58( Issue 1) pp:
Publication Date(Web):2009 January
DOI:10.1007/s00284-008-9284-8
To verify the hypothesis on the involvement of commensal actinomycetes in the biosynthesis of plant maytansinoids that belong to the ansamycin family, selective isolation and targeted screenings were conducted. In total, 164 endophytic actinomycetes isolates were obtained from the roots, twigs, seeds, callus, and germ-free seedlings of “maytansinoids-producing” Trewia nudiflora Linn. by selective isolation methods. Crude extracts of the isolates were screened by antifungal bioassay against Penicillium avellaneum UC-4376, thin-layer chromatography, and liquid chromatography–mass spectrometry detection according to the bioactivity as well as structural characteristics of maytansinoids. Respectively, 25.0%, 64.8%, and 26.7% of the extracts were positive in corresponding screenings. Ten isolates showed positive results in all three different screenings. To confirm on a genetic level, 28 representative isolates from 20 morphological groups were screened by polymerase chain reaction with 3-amino-5-hydroxybenzoic acid synthase gene and carbamoyltransferase gene primers, both of which were involved in the biosynthesis of ansamycins. According to the results of the targeted screenings, two isolates Streptomyces sp. 5B and Streptomyces sp. M27m3 might have the potential of producing ansamycins, which further enhanced the hypothesis that endophyte(s) might be involved in the biosynthesis of plant maytansinoids.
Co-reporter:Peiji Zhao, Linquan Bai, Juan Ma, Ying Zeng, Lei Li, Yirong Zhang, Chunhua Lu, Huanqin Dai, Zhaoxian Wu, Yaoyao Li, Xuan Wu, Gang Chen, Xiaojiang Hao, Yuemao Shen, Zixin Deng, Heinz G. Floss
Chemistry & Biology 2008 Volume 15(Issue 8) pp:863-874
Publication Date(Web):25 August 2008
DOI:10.1016/j.chembiol.2008.06.007
Ansamitocins are potent antitumor maytansinoids produced by Actinosynnema pretiosum. Their biosynthesis involves the initial assembly of a macrolactam polyketide, followed by a series of postpolyketide synthase (PKS) modifications. Three ansamitocin glycosides were isolated from A. pretiosum and fully characterized structurally as novel ansamitocin derivatives, carrying a β-D-glucosyl group attached to the macrolactam amide nitrogen in place of the N-methyl group. By gene inactivation and complementation, asm25 was identified as the N-glycosyltransferase gene responsible for the macrolactam amide N-glycosylation of ansamitocins. Soluble, enzymatically active Asm25 protein was obtained from asm25-expressing E. coli by solubilization from inclusion bodies. Its optimal reaction conditions, including temperature, pH, metal ion requirement, and Km/Kcat, were determined. Asm25 also showed broad substrate specificity toward other ansamycins and synthetic indolin-2-ones. To the best of our knowledge, this represents the first in vitro characterization of a purified antibiotic N-glycosyltransferase.
Co-reporter:Zhi-Yu Hu;Yao-Yao Li;Yao-Jian Huang;Wen-Jin Su;Yue-Mao Shen
Helvetica Chimica Acta 2008 Volume 91( Issue 1) pp:46-52
Publication Date(Web):
DOI:10.1002/hlca.200890011

Abstract

Three new sesquiterpenoids, xylarenones A (1) and B (2), and xylarenic acid (3), were obtained from the endophytic fungal strain Xylaria sp. NCY2, which was isolated from Torreya jackiiChun. Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments, and by HR-Q-TOF mass spectrometry. The antitumor and antibacterial properties of the new compounds were evaluated.

Co-reporter:Jian Li;Chun-Hua Lu ;Yue-Mao Shen
Helvetica Chimica Acta 2008 Volume 91( Issue 4) pp:741-745
Publication Date(Web):
DOI:10.1002/hlca.200890075

Abstract

From the endophytic strain Streptomyces sp. CS of Maytenus hookeri, five novel type III polyketides, compounds 15, were isolated. Their structures were elucidated by spectroscopic analyses including 1D- and 2D-NMR experiments, and by HR-ESI-MS.

Co-reporter:Lin Yuan;Pei-Ji Zhao;Juan Ma;Guo-Hong Li;Yue-Mao Shen
Helvetica Chimica Acta 2008 Volume 91( Issue 8) pp:1588-1594
Publication Date(Web):
DOI:10.1002/hlca.200890172

Abstract

Five new mixed terpenoids, tricycloalternarenes (TCAs) A–E (15), together with two known compounds, TCA 1b (6) and TCA 2b (7), were isolated from the solid-state-cultured endophytic fungus Alternaria alternata of Maytenus hookeri. Their structures were identified by extensive spectroscopic (especially 2D-NMR) experiments. Compound 7 showed weak activity against human tumor cell lines by MTT assay.

Co-reporter:Yong-Biao Zheng;Chun-Hua Lu;Zhong-Hui Zheng;Xin-Jian Lin;Wen-Jin Su;Yue-Mao Shen
Helvetica Chimica Acta 2008 Volume 91( Issue 11) pp:2174-2180
Publication Date(Web):
DOI:10.1002/hlca.200890235

Abstract

Three new sesquiterpenes, pyxidatol A–C (13, resp.), were obtained from the fermentation culture of Clavaria pyxidata, together with two known ones, tsugicoline E (4) and omphadiol (5). Their structures were elucidated through spectroscopic analyses, including 1D- and 2D-NMR experiments, HR-ESI-Q-TOF mass spectrometry, chemical correlation, and X-ray single-crystal diffraction.

Co-reporter:Xiping Du, Chunhua Lu, Yaoyao Li, Zhonghui Zheng, Wenjin Su and Yuemao Shen
The Journal of Antibiotics 2008 61(4) pp:250-253
Publication Date(Web):2008-04-01
DOI:10.1038/ja.2008.37
Two new 10-membered macrolides, named Phomolides A (1) and B (2), and one new derivative of benzofuran (3) were isolated from the culture of Phomopsis sp. hzla01-1, and their structures were elucidated based on spectroscopic analyses, particularly 2D NMR experiments. Compounds 1, 2 and 3 showed significant antimicrobial activities against Escherichia coli CMCC44103, Candida albicans AS2.538, Saccharomyces cerevisiae ATCC9763 with MICs 5~10 μg/ml. The most significant, compound 3 showed strong activity against Bacillus subtilis CMCC63501 with the MIC value 1.25 μg/ml. None of the three compounds showed significant cytotoxicity against the HeLa cell line at 10 μg/ml.
Co-reporter:Chunhua Lu and Yuemao Shen
The Journal of Antibiotics 2007 60(10) pp:649-653
Publication Date(Web):2007-10-01
DOI:10.1038/ja.2007.84
One novel ansamycin, namely naphthomycin K, together with two known naphthomycins A and E, were isolated from the commensal strain Streptomyces sp. CS of the medicinal plant Maytenus hookeri. Their structures were elucidated by the analysis of NMR and MS data. Naphthomycin K showed evident cytotoxicity against P388 and A-549 cell lines, but no inhibitory activities against Staphylococcus aureus and Mycobacterium tuberculosis.
Mitogen-activated protein kinase p38
c-Jun N-terminal kinase
Gelatinase B
BENZO[B][1,4]BENZODIOXEPIN-6-ONE
(+)-mycoepoxydiene