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Acta Pharmaceutica Sinica B 2023年第8期13卷 3414-3424页

作者： Kailong Ji Wei Liu Weihang Yin Xiangrong Kong Honghong Xu Zeng-Wei Lai Jing-Ya Li Jian-Min Yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China School of Chinese Materia Medica Nanjing University of Chinese MedicineNanjing 210023China

A new class of potent liver injury protective compounds,phychetins A-D(1-4)featuring an unique 6/6/5/6/5 pentacyclic framework,were isolated and structurally characterized from a Chinese medicinal plant Phyllanthus franchetianus.Compounds 2-4 are three pairs of enantiomers that were initially obtained in a racemic manner,and were further separated by chiral HPLC preparation.Compounds 1-4 were proposed to be originated biosynthetically from a coexisting lignan via an intramolecular Friedel-Crafts reaction as the key step.A bioinspired total synthesis strategy was thus designated,and allowed the effective syntheses of compounds 2-4 in high yields.Some of compounds exhibited significant anti-inflammatory activities in vitro via suppressing the production of pro-inflammatory cytokine IL-1β.Notably,compound 4,the most active enantiomeric pair in vitro,displayed prominent potent protecting activity against liver injury at a low dose of 3 mg/kg in mice,which could serve as a promising lead for the development of acute liver injury therapeutic agent.

关键词： Phychetins Phyllanthusfranchetianus structural elucidation Total synthesis Liver injury protection Anti-inflammation

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structural elucidation and HPLC Analysis of Six Flavone Glycosides from Artemisiafrigida Willd.

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Chemical Research in Chinese Universities 2013年第3期29卷 439-444页

作者： WANG Qing-hu AO Wu-li-ji DAI Na-yin-tai College of Traditional Mongolian Medicine lnner Mongolia University for Nationalities Tongliao 028000 P. R. China

An investigation of the EtOAc-soluble fraction from the aerial parts ofArtemisiafrigida Willd.（A. frigida） led to the isolation of three new flavonoid glycosides together with three known compounds. Their structures were elucidated by spectral experiments. At the same time, high-performance liquid chromatographic（HPLC） method was used for the simultaneous determination of the six flavonoid glycosides from the aerial parts ofA. frigida. The separation by gradient elution was performed on a Hypersil ODS-2 column（250 mm×4.6 mm, 5 μm） at 30℃ with acetonitrile and water as the mobile phase, and monitored by absorbance at 276 nm. The parameters of linearity, precision, accuracy and specificity of the method were evaluated. The recovery of the method is 96.50%--98.01%, and linearity（r〉0.9992） was obtained for all the flavonoid glycosides. A high degree of specificity as well as repeatability and reproducibility（relative standard deviation values less than 2.0%） were also achieved. This assay was applied to the determination of six flavonoid glycosides in ten samples. The results indicate that the developed assay method was rapid, accurate, reliable and could be readily utilized as a quantitative analysis method for A. frigida.

关键词： structural elucidation High-performance liquid chromatography simultaneous determination Flavonoid glycoside Artemisia frigida

New pimarane diterpenoids with antibacterial activity from fungus Arthrinium sp.ZS03

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Chinese Journal of Natural Medicines 2024年第4期22卷 356-364页

作者： ZHAO Songfeng JING Ziwei Department of Pharmacy the First Affiliated Hospital of Zhengzhou UniversityZhengzhou 450052China

A comprehensive chemical study of the endophytic fungus Arthrinium sp. ZS03, associated with Acorus tatarinowii Schott, yielded eleven pimarane diterpenoids (compounds 1–11), including seven novel compounds designated arthrinoids A–G (1–7). The determination of their structures and absolute configurations was achieved through extensive spectroscopic techniques, quantum chemical calculations of electronic circular dichroism (ECD), and single-crystal X-ray diffraction analysis. Furthermore, 7 demonstrated inhibitory activity against Klebsiella pneumoniae, comparable to the reference antibiotic amikacin, with a minimum inhibitory concentration (MIC) of 8 μg·mL^(−1).

关键词： Arthrinium sp.ZS03 Pimarane diterpenoids structural elucidation Antibacterial activity

Dcalycinumines A-E,Alkaloids with Cytotoxic Activities of Nasopharyngeal Carcinoma Cells from Daphniphyllum calycinum

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Chinese Journal of Chemistry 2024年第1期42卷 35-42页

作者： Qing Tang Xiao-Yong Dai Qiang Lin Zhi-Peng Ling Yi-Kun Hao Tian-Xi Zhu Ji-Hui Zhang Yi-Bo Hou Yao-Lan Li Lai-Qiang Huang Jing-Hao Wang Guo-Cai Wang Yu-Bo Zhang Guangdong Clinical Translational Centerfor Targeted Drug Department of PharmacologySchoolof MedicineJinan University GuangzhouGuangdong 510632China Institute of Traditional Chinese Medicine&Natural Products Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs ResearchCollegeof PharmacyJinan UniversityGuangzhouGuangdong511443China Institute of Biopharmaceutical and Health Engineering Shenzhen Key Laboratory of Gene and Antibody TherapyState Key Laboratory of Chemical OncogenomicsShenzhen International Graduate SchoolTsinghua UniversityShenzhenGuangdong 518055China The Guangzhou Key Laboratoryof Basic and Translational Research on Chronic Disease Department of PharmacyThe First Affiliated HospitalJinan UniversityGuangzhouGuangdong 510630China

Fivenovel Daphniphyllum alkaloids,named dcalycinumines A-E(1-4,6),andeight previously described Daphniphyllum alkaloids(5,7-13)were isolated from Daphniphyllum calycinum.Compound 1 is the first Daphniphyllum alkaloid possessing a highly rearranged 6/6/6/7/5/6 hexacyclic architecture with a unique 3-methyl-1-azabicyclo[4,4,0]decane ring system.Compound 2 represents a rare diamino Daphniphyllum alkaloid with an unprecedented 6/5/5/6/6/5 carbon skeleton featuring a unique 1-aza-6-azaspiro[4,5]decane unit,whereas 3 also represents a rare diamino Daphniphyllum alkaloid as a possible precursor of 2.Compound 4 is the second example of c-22-nor yuzurimine-type alkaloids.Their structures and absolute configurations were elucidated by HRESIMS,NMR spectroscopic analyses,EcD calculations,and single-crystal X-ray diffraction.Moreover,compound 1 showed remarkable antitumor activities,which could inhibit the proliferation,migration and invasion of nasopharyngeal carcinoma cells,and promoted nasopharyngeal carcinoma cells apoptosis.

关键词： Daphniphyllum calycinum Natural products Daphniphyllum alkaloid structural elucidation Biological activity Apoptosis Nasopharyngealcarcinoma

Contribution to structural elucidation: Behaviours of Substructures Partially Defined from 2D NMR

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Chinese Journal of Chemistry 2003年第10期21卷 1268-1274页

作者： EPOUHE Celine 范波涛袁身刚 PANAYE A. DOUCET J.P. ITODYS Université Paris 7 Denis Diderot Shanghai Institute of Organic Chemistry

structural elucidation (automatic determination of the structure of amolecule from its spectra) is frequently hampered by combinatorial explosion when trying to assemblethe identified substructures. We devised a new method which can avoid this pitfall by a systematicexamination of allowed ^(13)C chemical shifts ranges for all substructures chemically possible andcombined with a progressive pruning thanks to neighbouring relationships appearing from 2D NMR. Thismethod is explained by a detailed example.

关键词： structural elucidation ^(13)C NMR 2D NMR partially defined substructure

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REPORT ON structural elucidation OF SEX PHEROMONE COMPONENTS OF A TEA PEST (Ectropis obliqua PROUT)

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Progress in Natural Science:Materials International 1991年第6期 566-569页

作者：么恩云李正名罗志强尚稚珍殷坤山洪北边 Hangzhou 310024 Nankai University PRC Tea Institute The Key Laboratory of Elemento-Organic Chemistry Elemento-Organic Chemistry Institute Tianjin 300071

A tea Geometridae insect(Ectropis obliqua Prout)is an important pest which causes seri-ous damage to tea plants in southern provinces in China.Application of some chemicalpesticides causes environmental pollution and undesired residue effect.Certain new non-pollution measures are urgently needed for tea pest control.In 1978—1982,Du et al.car-ried out a research project on the elucidation of Ectropis obliqua and identified a multi-components,yet the chemical structures were not mentioned.Ectropis obliqua belongs toGeometridae insects and a few of their sex pheromones have been reported in the early1980s.Till today,no report on the exact structures of sex pheromones of Ectropis

关键词： Ectropis obliqua sex pheromones structural elucidation GC-MS analysis

Meroterpenoids Possessing Diverse Rearranged Skeletons with Anti-inflammatory Activity from the Mangrove-Derived Fungus Penicillium sp. HLLG-122

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Chinese Journal of Chemistry 2023年第19期41卷 2507-2517页

作者： Yu-Yue Qin Wan-Shan Li Xuan Zhang Zhang-Xin Yu Xiao-Bao Li Han-Yi Chen Yan-Ru Lv Chang-Ri Han Guang-Ying Chen Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education and Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province College of Chemistry and Chemical EngineeringHainan Normal UniversityHaikouHainan571158 China Key Laboratory of Medicinal and Edible Plants Resources of Hainan Province Hainan Vocational University of Science and TechnologyHaikouHainan571126 China

Fifteen new meroterpenoids, littoreanoids A—O (1—15), including three rearranged skeleton meroterpenoids (1—3), were isolated from the mangrove-derived fungus Penicillium sp. HLLG-122. Compound 1 was a novel berkeleyacetal-derived meroterpenoid featuring an unusual spirocyclic 2-oxaspiro[5.5]undeca-4,7-dien-3-one moiety. Compound 2 possessed an unusual 6/6/6/6/6 pentacyclic system with a novel 1-hydroxy-7,7-dimethyl-2-oxabicyclo[2.2.2]octan-5-yl acetate moiety. Compound 3 was an unusual 6/7/6/5/6/5/4 polycyclic systems containing a β-lactone ring. The structures and absolute configurations of new compounds were elucidated by HRESIMS, NMR spectroscopy, single crystal X-ray diffraction analysis, and electronic circular dichroism calculations. The plausible biosynthetic pathways of 1—3 were also proposed. Compounds 6 and 11 exhibited anti-inflammatory effects with IC_(50) values of 30.41 and 19.02 μmol/L, respectively. The bioactive compound 11 was selected for the investigation of preliminary mechanism using molecular docking and Western blotting experiments. Compound 11 could suppress the levels of TNF-α and IL-6, and down-regulate the protein expression of iNOS and COX-2 in RAW 264.7 cells.

关键词： Penicillium sp Terpenoids structural elucidation Anti-inflammatory activities Conformation analysis Natural products

Cephalotane-Type Norditerpenoids from Cephalotaxus fortunei var.alpina

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Chinese Journal of Chemistry 2022年第10期40卷 1177-1184页

作者： Zhan-Peng Ge Bin Zhou Flavia M.Zimbres Maria B.Cassera Jin-Xin Zhao Jian-Min Yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences555 Zuchongzhi RoadShanghai 201203China Department of Biochemistry and Molecular Biology Center for Tropical and Emerging Global Diseases(CTEGD)University of GeorgiaAthensGeorgia30602UnitedStates

A chemical investigation of the 95%EtoH extract of the seeds of Cephalotaxus fortunei var.alpina led to the isolation of nine new cephalotane-type norditerpenoids,ceforalides A-I(1-9),and two known analogues(10 and 11).Compounds 1-8 belong to a rare class of A-ring-contracted cephalotane-type norditerpenoids,of which compound 8 incorporates a unique tetrasubstituted 2,5-cyclohexadienone A-ring.Compound 9 is a rare 13,14-seco-17-nor-cephalotane-type diterpenoid.Their structures were determined based on NMR,HRESIMS,ECD,and X-ray diffraction analysis.Biological tests revealed compounds 10 and 11 displayed moderate antimalarial activity.

关键词： Cephalotaxus fortunei var.alpine Natural products structural elucidation Cephalotane norditerpenoids I Antimalarial activity

Rearranged Dichapetalin-Type Triterpenoids with Cytotoxic Activity from Dichapetalum gelonioides

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Chinese Journal of Chemistry 2022年第21期40卷 2531-2538页

作者： Xin-Hua Gao Xi-Yuan Wang Jun-Su Zhou Yan Zhang Hong-Chun Liu Bin Zhou Jian-Min Yue State Key Laboratory of Drug Research Shanghai lnstitute of Materia MedicaChinese Academy of SciencesShanghai 201203China Research Units of Discovery of New Drug Lead Molecules Chinese Academy of Medical SciencesShanghai 201203china Shandong Laboratory of Yantai Drug Discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantaiShandong 264117China

Dichagelinoids A—C(1—3),three unusual dichapetalin-type triterpenoids,together with two biogenetically related derivatives dichagelinoids D and E(4 and 5)were isolated and characterized by solid data from Dichapetalum gelonioides.Compounds 1—3 possess a common rearranged C ring and different C6—C2 modified motifs at the A rings.Biological evaluation revealed that compounds 1—3 showed distinct cytotoxic activity against the tested human cancer cell lines.

关键词： Dichapetalum gelonioides Natural products Dichapetalin-type triterpenoids structural elucidation Cytotoxic activity

Alkaloid constituents from the fruits of Flueggea virosa

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Chinese Journal of Natural Medicines 2020年第5期18卷 385-392页

作者： XIE Qiu-Jie ZHANG Wei-Yan WU Zhen-Long XU Ming-Tao HE Qi-Fang HUANG Xiao-Jun CHE Chun-Tao WANG Ying YE Wen-Cai Institute of Traditional Chinese Medicine&Natural Products College of PharmacyJinan UniversityGuangzhou 510632China Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM&New Drugs Research Jinan University Guangzhou 510632China Department of Pharmaceutical Sciences College of PharmacyUniversity of Illinois at ChicagoChicago 60612United States

Three new indole alkaloids, flueindolines A–C(1–3), along with nine known alkaloids(4–12), were isolated from the fruits of Flueggea virosa(Roxb. ex Willd.) Voigt. Compounds 1 and 2 are two new fused tricyclic indole alkaloids possessing an unusual pyrido[1, 2-a]indole framework, and 3 presents a rare spiro(pyrrolizidinyl-oxindole) backbone. Their structures with absolute configurations were elucidated by means of comprehensive spectroscopic analysis, chemical calculation, as well as X-ray crystallography. Chiral resolution and absolute configuration determination of the known compounds 4, 10, and 11 were reported for the first time. The hypothetical biogenetical pathways of 1–3 were herein also proposed.

关键词： Flueggea virosa Indole alkaloids structural elucidation Biogenetical pathway

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