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Comparative organelle genomics in daphniphyllaceae reveal phylogenetic position and organelle structure evolution

BMC GENOMICS 2025年第1期26卷 1-16页

作者： Zhang, Rongxiang Liu, Yin Liu, Shuwen Zhao, Yuemei Xiang, Niyan Gao, Xiaoman Yuan, Tao Guizhou Educ Univ Sch Biol Sci Guiyang 550018 Peoples R China Wuhan Univ Coll Life Sci State Key Lab Hybrid Rice Lab Plant Systemat & Evolutionary Biol Wuhan 430072 Peoples R China Tibet Univ Sch Ecol & Environm Lhasa 850000 Peoples R China Hubei Univ Sch Resources & Environm Sci Wuhan 430062 Peoples R China

The family daphniphyllaceae has a single genus, and no relevant comparative phylogenetic study has been reported on it. To explore the phylogenetic relationships and organelle evolution mechanisms of daphniphyllaceae species, we sequenced and assembled the chloroplast and mitochondrial genomes of Daphniphyllum macropodum. We also conducted comparative analyses of organelles in daphniphyllaceae species in terms of genome structure, phylogenetic relationships, divergence times, RNA editing events, and evolutionary rates, etc. Results indicated differences in the evolutionary patterns of the plastome and mitogenome in D. macropodum. The plastome had a more conserved structure but a faster nucleotide substitution rate, and the mitogenome showed a more complex structure while the mitotic genome shows a more complex structure but a slower nucleotide substitution rate. We identified several unidirectional protein-coding gene transfer events from the plastome to the mitogenome based on homology analysis, but no transfer events occurred from the mitogenome to the plastome. Multiple TE fragments existed in organelle genomes, and two organelles showed different preferences for nuclear TE insertion types. The estimation of divergence time indicated that the differentiation of daphniphyllaceae and Altingiaceae at around 29.86 Mya might be due to the dramatic uplift of Tibetan Plateau during the Oligocene. About 75% of codon changes in organelles were found to be hydrophilic to hydrophobic amino acids. The RNA editing in protein-coding transcripts is the result of amino acid changes to increase their hydrophobicity and conservation in alleles, which may contribute to the formation of functional 3D structures in proteins. This study would enrich genomic resources and provide valuable insights into the structural dynamics and molecular biology of daphniphyllaceae species.

关键词： daphniphyllaceae Organelle genomes Structure dynamic Phylogenetic relationships Divergence time

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Daphniphyllum peltatum, a new species of daphniphyllaceae from limestone areas in southwestern Guangxi, China

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TAIWANIA 2020年第2期65卷 232-236页

作者： Meng, Tao Nong, Dong-Xin Yuan, Quan Liu, Yan Guangxi Zhuang Autonomous Reg & Chinese Acad Sci Guangxi Inst Bot Guangxi Key Lab Funct Phytochem Res & Utilizat Guilin 541006 Guangxi Peoples R China Guangxi Bot Garden Med Plants Nanning 530023 Guangxi Peoples R China Guangxi Normal Univ Coll Life Sci Guilin 541004 Guangxi Peoples R China

Daphniphyllum peltatum Yan Liu & T. Meng, a new species of daphniphyllaceae from southwestern Guangxi, China, is described and illustrated. The new species is mainly similar to D. calycinum Benth. in the shape of leaf blade, lunate anthers, elliptic drupes and the length of infructescence, but it can be easily distinguished by blue green branchlets, peltate leaves, obviously raised midvein and lateral veins on both surfaces. We also provide a key to all species of Daphniphyllum in China, and a table to distinguish the new species from D. calycinum.

关键词： China daphniphyllaceae Daphniphyllum peltatum limestone flora new taxa southwestern Guangxi taxonomy

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Daphnicalycinones A and B, Daphniphyllum alkaloids from the roots of Daphniphyllum calycinum with anti-inflammatory activity

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PHYTOCHEMISTRY LETTERS 2025年 67卷

作者： Guo, Jiaqi Li, Wenlong Ma, Runchao Han, Lizhu Ying, Jiani Meng, Xiongyu Li, Huaqiang Shi, Qi Qin, Luping Zhejiang Chinese Med Univ Sch Pharmaceut Sci Baichuan St 260 Hangzhou 311402 Peoples R China Shaanxi Univ Chinese Med Coll Pharm Xianyang 712046 Peoples R China Zhejiang Chinese Med Univ Acad Chinese Med Sci Med Res Ctr Binwen Rd 548 Hangzhou 310053 Peoples R China

Two undescribed Daphniphyllum alkaloids, daphnicalycinones A and B (1 and 2), together with three known analogues, daphnezomine D (3), calycindaphine H (4) and calycindaphine A (5) were isolated from the roots of Daphniphyllum calycinum. Their planar structures and stereo-structures were determined by extensively spectral analyses, including HRESIMS, NMR, DP4 + computational method and single-crystal X-ray crystallography. The anti-inflammatory activities of compounds 1-5 were tested on LPS-induced RAW 264.7 cells, and the results showed that 2 and 5 exhibited potent inhibitory effects with the IC50 values of 1.53 +/- 0.35 mu M and 10.13 +/- 0.72 mu M, respectively.

关键词： daphniphyllaceae Daphniphyllum calycinum Daphniphyllum alkaloids Anti-inflammatory activity

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Chemical constituents from the stems of Daphniphyllum angustifolium Hutch. and their chemotaxonomic significance

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Biochemical Systematics and Ecology 2025年 122卷

作者： Huang, Xiao-Juan Zhang, Heng-Gang Li, Xiao-Hong Wei, Yu-Bin Mohamed, Khalid-Hassan Yin, Chang-Qin Yu, Hao-Fei Ding, Cai-Feng Zhang, Lan-Chun School of Pharmaceutical Sciences Department of Yunnan Key Laboratory for Natural Products Yunnan College of Modern Biomedical Industry and Department of Zoology Kunming Medical University Kunming 650500 China College of Humanities and Management Yunnan University of Traditional Chinese Medicine Kunming 650500 China First Affiliated Hospital Kunming Medical University Kunming 650032 China

The phytochemical investigation of the stems of Daphniphyllum angustifolium resulted in the isolation of sixteen known compounds (1–16). This collection included six phenolic compounds (1–6), one sterol (7), one triterpene (8), and eight lignans (9–16). Among them, fifteen compounds (1–6, 8–16) were identified for the first time within the daphniphyllaceae family. The isolated compounds underwent in vitro testing for antibacterial activity against three bacterial strains, including Bacillus subtilis, Staphylococcus aureus, and Escherichia coli. Compound 15 exhibited significant antimicrobial activity against these bacteria. The chemotaxonomic significance of the isolated compounds from the *** is discussed in detail. © 2025 Elsevier Ltd

关键词： Antimicrobial activity Chemotaxonomy daphniphyllaceae Daphniphyllum angustifolium Lignan

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Daphniphyllum Alkaloids: Recent Findings on Chemistry and Pharmacology

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PLANTA MEDICA 2013年第17期79卷 1589-1598页

作者： Wu, Haifeng Zhang, Xiaopo Ding, Lisheng Chen, Shilin Yang, Junshan Xu, Xudong Chinese Acad Med Sci Inst Med Plant Dev Beijing 100193 Peoples R China Peking Union Med Coll Beijing 100193 Peoples R China Chinese Acad Sci Chengdu Inst Biol Chengdu Peoples R China China Acad Chinese Med Sci Inst Chinese Mat Med Beijing Peoples R China

The unique polycyclic fused ring systems of Daphniphyllum alkaloids, along with their extensive bioactivities, make this family of alkaloids especially attractive targets for total synthesis and biogenetic studies. Successive discoveries of new alkaloids with unprecedented skeletons have made a great contribution to structural diversities of alkaloids elaborated by plants of the genus Daphniphyllum. By the end of 2008, more than 200 alkaloids belonging to 14 different skeletal types have been isolated from different parts of plants of thirteen Daphniphyllum species. These alkaloids show cytotoxic, antioxidant, vasorelaxant, and antiplatelet activating factor effects. The plausible biosynthetic pathways for Daphniphyllum alkaloids have been proposed and biomimetic total syntheses of some alkaloids completed. To provide an update of the previous reviews published in 2009, new structures, synthesis, and bioactivity of Daphniphyllum alkaloids reported in recent years are presented in this article. In the meantime, an additional 54 novel alkaloids have been isolated and identified. Among them, some possess unprecedented frameworks. Several inspired organic syntheses were completed.

关键词： Daphniphyllum daphniphyllaceae alkaloids synthesis biological activity

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Daphmacrimines A-K, Daphniphyllum alkaloids from Daphniphyllum macropodum Miq

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PHYTOCHEMISTRY 2024年 223卷 114106页

作者： Xu, Li -Li Niu, Zhen -Peng Chen, Duo-Zhi Zhang, Yu Zhao, Qian Liang, Hong Li, Sheng Li, Jin-Liang Ding, Xiao Yang, Chong-Lin Hao, Xiao-Jiang Yunnan Univ Ctr Life Sci Sch Life Sci Kunming 650091 Peoples R China Chinese Acad Sci Kunming Inst Bot State Key Lab Phytochemistry & Plant Resources Wes Kunming 650201 Peoples R China Chinese Acad Sci Kunming Inst Bot Yunnan Key Lab Nat Med Chem Kunming 650201 Peoples R China Univ Chinese Acad Sci Beijing 100049 Peoples R China Chinese Acad Med Sci Res Unit Chem Biol Nat Antivirus Prod Beijing 100730 Peoples R China Chinese Acad Sci Xinjiang Tech Inst Phys & Chem Urumqi 830011 Peoples R China Yunnan Characterist Plant Extract Lab Kunming 650106 Peoples R China

Daphmacrimines A - K ( 1 - 11 ) were isolated from the leaves and stems of Daphniphyllum macropodum Miq. Their structures and stereochemistries were determined by extensive techniques, including HRESIMS, NMR, ECD, IR, and single-crystal X-ray crystallography. Daphmacrimines A - D ( 1 - 4 ) are unprecedented Daphniphyllum alkaloids with a 2-oxazolidinone ring. Daphmacrimine I ( 9 ) contains a nitrile group, which is relatively rare in naturally occurring alkaloids. The abilities of daphmacrimines A - D and daphmacrimines G - K to enhance lysosomal biogenesis were evaluated through LysoTracker Red staining. Daphmacrimine K ( 11 ) can induce lysosomal biogenesis and promote autophagic flux.

关键词： Daphniphyllum macropodum miq. daphniphyllaceae Daphniphyllum alkaloids Structural elucidation Lysosomal biogenesis

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SEGREGATE FAMILIES FROM THE EUPHORBIACEAE

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BOTANICAL JOURNAL OF THE LINNEAN SOCIETY 1987年第1-2期94卷 47-66页

作者： RADCLIFFESMITH, A Herbarium Royal Botanic Gardens Kew Richmond Surrey

Several families have been segregated from the Euphorbiaceae. Some of these are of long-standing, and are now generally accepted. Others are more recent, and somewhat controversial. Five such have recently been recogn... 详细信息

关键词： Aextoxicaceae Androstachydaceae Androstachys Antidesma Aristogeitonia Bischqfia Bischofiaceae Buxaceae Celaenodendron daphniphyllaceae Didymelaccae Hyaenanche Hymenocardia Hymenocardiaceae Mischodon Oldfieldia Paivaeusa Paivaeusinae Palo Prieto Pandaceae Pera Peraceae Picrodendraceae Picrodendron Piraiera Preta Piranhea Piranheira Simmondsia Stilaginaceae Uapaca Uapacaceae

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Hybridaphniphyllines A and B, Daphniphyllum alkaloid and iridoid hybrids suggestive of Diels-Alder cycloaddition in Daphniphyllum longeracemosum

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PHYTOCHEMISTRY 2013年 95卷 428-435页

作者： Wang, Fei Mao, Mei-Fen Wei, Guo-Zhu Gao, Yuan Ren, Fu-Cai Liu, Ji-Kai Chinese Acad Sci State Key Lab Phytochem & Plant Resources West Ch Kunming Inst Bot Kunming 650201 Peoples R China BioBioPha Co Ltd Kunming 650201 Peoples R China

Two Daphniphyllum alkaloid and iridoid hybrids with the hitherto unknown decacyclic fused skeletons, hybridaphniphyllines A and B, along with one diamino Daphniphyllum alkaloid, daphnicyclidin I, were isolated from dried stems and leaves of Daphniphyllum longeracemosum. Their structures were elucidated on the basis of extensive spectroscopic analysis, and the absolute configuration of daphnicyclidin I was deduced by the CD exciton chirality method. A biogenetic pathway for 1 and 2 involving natural Diels-Alder cycloaddition is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

关键词： Daphniphyllum longeracemosum daphniphyllaceae C-22 nor-Daphniphyllum alkaloid Alkaloid and iridoid hybrid Hybridaphniphylline Diels-Alder cycloaddition

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Daphmacromines K-O, alkaloids from Daphniphyllum macropodum

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FITOTERAPIA 2013年第1期89卷 205-209页

作者： Cao, Ming-Ming Wang, Lei Zhang, Yu He, Hong-Ping Gu, Yu-Cheng Zhang, Qiang Li, Yan Yuan, Chun-Mao Li, Shun-Lin Di, Ying-Tong Hao, Xiao-Jiang Chinese Acad Sci Kunming Inst Bot State Key Lab Phytochem & Plant Resources West Ch Kunming 650201 Yunnan Peoples R China Univ Chinese Acad Sci Beijing 100049 Peoples R China Syngenta Jealotts Hill Int Res Ctr Bracknell RG42 6EY Berks England Northwest A&F Univ Yangling 712100 Shaanxi Peoples R China

Five new yuzurimine-type Daphniphyllum alkaloids, daphmacromines K-O (1-5), were isolated from the leaves and stems of Daphniphyllum macropodum. Their structures were elucidated by extensive spectroscopic techniques, including 2D NMR spectroscopy and mass spectrometry. Daphmacromine O (5) showed moderate cytotoxic activity against brine shrimp. Crown Copyright (C) 2013 Published by Elsevier B.V. All rights reserved.

关键词： daphniphyllaceae Daphniphyllum macropodum Cytotoxic activity Daphmacromines K-O

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Himalsamines A and B, two new amino sugar isomers from the leaves of Daphniphyllum himalaense subsp. macropodum

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PHYTOCHEMISTRY LETTERS 2022年第0期48卷 19-22页

作者： Cheng, Ju-Chien Yeh, Yung-Ju Huang, Hui-Chi Hwang, Syh-Yuan Chao, Chih-Hua China Med Univ Dept Med Lab Sci & Biotechnol Taichung 40402 Taiwan China Med Univ Dept Chinese Pharmaceut Sci & Chinese Med Resourc Taichung 40402 Taiwan Council Agr Endem Species Res Inst Nantou 552203 Taiwan China Med Univ Sch Pharm Taichung 406040 Taiwan China Med Univ Hosp Chinese Med Res & Dev Ctr Taichung 40447 Taiwan

A phytochemical investigation performed on the leaves of Daphniphyllum himalaense has led to the characterization of two new amino sugars (1 and 2) and six known daphniphyllum alkaloids. The structures of new compounds were determined based on the interpretation of spectroscopic data. Some of the alkaloids were found to possess moderate to weak activity against the hepatitis C virus infection.

关键词： daphniphyllaceae Daphniphyllum himalaense Amino sugar Tagatose Anti-HCV activity Alkaloid

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