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Classification,biosynthesis,and biological functions of triterpene esters in plants

plant Communications 2024年第4期5卷 67-93页

作者： Jia Liu Xue Yin Chengxi Kou Ramesha Thimmappa Xin Hua Zheyong Xue key laboratory of Saline-alkali Vegetation Ecology Restoration(Northeast Forestry University) Ministry of EducationHarbin 150040China heilongjiang key laboratory of plant bioactive substance biosynthesis and utilization Northeast Forestry UniversityHarbin 150040China Amity Institute of Genome Engineering Amity UniversityNoidaUP India 201313India State key laboratory for Quality Ensurance and Sustainable Use of Dao-di Herbs Beijing 100700P.R.China

Triterpene esters comprise a class of secondary metabolites that are synthesized by decorating triterpene skeletons with a series of oxidation,glycosylation,and acylation *** triterpene esters with important bioactivities have been isolated and identified,including those with applications in the pesticide,pharmaceutical,and cosmetic *** also play essential roles in plant defense against pests,dis-eases,physical damage(as part of the cuticle),and regulation of root ***,there has been no recent summary of the biosynthetic pathways and biological functions of plant triterpene ***,we classify triterpene esters intofive categories based on their skeletons andfind that C-3 oxidation may have a significant effect on triterpenoid *** acid and aromatic moieties are common li-gands present in triterpene *** further analyze triterpene ester synthesis-related acyltransferases(TEsACTs)in the triterpene biosynthetic *** an evolutionary classification of BAHD acyltrans-ferases(BAHD-ATs)and serine carboxypeptidase-like acyltransferases(SCPL-ATs)in Arabidopsis thaliana and Oryza sativa,we classify 18 TEsACTs with identified functions from 11 *** the triterpene-skel-eton-related TEsACTs belong to BAHD-AT clades IIIa and I,and the only identified TEsACT from the SCPL-AT family belongs to the CP-I *** comprehensive review of the biosynthetic pathways and bioactivities of triterpene esters provides a foundation for further study of their bioactivities and applica-tions in industry,agricultural production,and human health.

关键词： triterpene esters acyltransferases classification biosynthesis biological functions

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Stereochemical determination of tetrahydropyran-substituted xanthones from fungus Chaetomium murorum

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Chinese Chemical Letters 2015年第12期26卷 1507-1510页

作者： Meng-Hua Wang Li Li Tao Jiang Xue-Wei Wang Bin-Da Sun Bo Song Qiu-Bo Zhang Hong-Mei Jia Gang Ding Zhong-Mei Zou key laboratory of bioactive substances and Resources utilization of Chinese Herbal Medicine Ministry of EducationInstitute of Medicinal Plant Development Chinese Academy of Medical Sciences State key laboratory of bioactive substance and Function of Natural Medicines Institute of Materia Medica Chinese Academy of Medical Sciences State key laboratory of Mycology Institute of Microbiology Chinese Academy of Sciences

Chaetoxanthone D（1）, a new tetrahydropyran-substituted xanthone originated from polyketide pathway, together with the four known natural products chaetoxanthone C（2）, alternariol methyl ether（3）, alternariol（4） and 2,5-dimethyl-7-hydroxychromone（5） was isolated from a strain of Chaetomium murorum. The structures of these compounds were elucidated based on extensive spectroscopic analyses. The absolute configurations of 1 and 2 were determined by using quantum chemical electronic circular dichroism（ECD） calculations.

关键词： substituted elucidated spectroscopic absolute fungus originated pyran circular aromatic planar

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Efficient heterologous biosynthesis of verazine,a metabolic precursor of the anti-cancer drug cyclopamine,in Nicotiana benthamiana

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plant Communications 2024年第6期5卷 1-4页

作者： Chengxi Kou Jingling Liu Xue Yin Di He Jia Liu Xin Hua Rui Ma Wei Sun Zheyong Xue Pengda Ma College of Life Sciences Northwest A&F UniversityYangling 712100China key laboratory of Saline-alkali Vegetation Ecology Restoration(Northeast Forestry University) Ministry of EducationHarbin 150040China heilongjiang key laboratory of plant bioactive substance biosynthesis and utilization Northeast Forestry UniversityHarbin 150040China Jilin Provincial key laboratory of Agricultural Biotechnology Jilin Academy of Agricultural SciencesChangchun 130033China key laboratory of Beijing for Identification and Safety Evaluation of Chinese Medicine Institute of Chinese Materia MedicaChina Academy of Chinese Medical SciencesBeijing 100700China

Dear Editor,Among the large number of Veratrum steroid alkaloids(Zhang et al.,2020),cyclopamine has been shown to have various inhibitory mechanisms against cancer,including inhibition of the hedgehog signaling pathway,improvement of tumor tissue microenvironment,inhibition of cell respiration,promotion of cell apoptosis,and reversal of tumor drug resistance(Liu et al.,2023).The biosynthetic pathway of verazine,a possible metabolic precursor of cyclopamine,has been discovered in Veratrum californicum(Augustin et al.,2015).However,the content of Veratrum steroid alkaloids in plants is very low(Supplemental Figure 2),so reliance on direct extraction from plants for commercial production is not feasible.A more effective strategy is to synthesize rare plant secondary metabolites using synthetic biology technology(Liu et al.,2022).

关键词： cyclopamine cancer

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HPLC Fingerprint Combined with Chemometrics and Network Pharmacology for Q-Markers Prediction Analysis of Saposhnikovia divaricata

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Journal of Analysis and Testing 2024年第1期8卷 83-94页

作者： Renguo Zhang Xinjian Liu Tong Wang Jie Yu Mengyuan Wang Jianmin Sun Xueling Yu Na Niu Ligang Chen College of Chemistry Chemical Engineering and Resource UtilizationKey Laboratory of Forest Plant EcologyNortheast Forestry UniversityHarbin 150040China

Saposhnikovia divaricata(SD)has high medicinal and edible value,but relatively little research has been done on its qual-ity markers(Q-markers).To further clarify the Q-markers of SD with their corresponding pharmacodynamic *** this experiment,14 batches of SD were identified and screened for Q-marker candidate components using a combination of HPLC fingerprint with similarity analysis,principal component analysis,hierarchical cluster analysis,and partial least squares discriminant ***,network pharmacology was used to predict Q-markers and core *** results showed that 5-O-methylvisammioside,cimifugin,and prim-O-glucosylcimifugin could be used as Q-markers of SD;while,MAPK1,MAPK3,PIK3CA,JUN,and MAPK8 were the core targets of SD for drug *** further evaluate the bind-ing efficiency of Q-markers,molecular docking of the main active ingredients of SD to the core targets was *** results showed that the compounds bind well to their targets,and binding energies were all less than-5 kcal/*** Q-markers obtained from the screening were closely related to the core target genes,which could achieve therapeutic effects by modulating the relevant signaling *** study offers a reference for the establishment of a set of quality control evaluation system for SD potential Q-markers prediction analysis,and lays the foundation for elucidating the mechanism of actionunderlying itspharmacodynamic substance.

关键词： Saposhnikovia divaricata Q-markers Fingerprint Chemometrics Network pharmacology Molecular docking

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Fingerprinting Analysis of Saposhnikovia divaricata using ~1H Nuclear Magnetic Resonance Spectroscopy and High Performance Liquid Chromatography

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Journal of Integrative plant Biology 2010年第9期52卷 782-792页

作者： Yue-Yang Xin An-Jun Deng Guan-Hua Du Jin-Lan Zhang Hai-Lin Qin key laboratory of bioactive substances and Resources utilization of Chinese Herbal Medicine Ministry of Education & Institute of Materia Medica Chinese Academy of Medical Sciences and Peking Union Medical College Beijing 100050 China

The 1H nuclear magnetic resonance （1H NMR） fingerprints of fractionated non-polar and polar extracts （control substance for plant drug [CSPD] A and B） from the roots of 12 specimens of Saposhnikovia divaricata （Turcz.） Schischk were achieved with Fourier Transform （FT）-NMR spectrometer and assigned by comparison to each other and to the 1H NMR spectra of the isolated individual compounds. These fingerprints were found to be uniform in terms of the specificity for the implication of all 12 specimens being systematically of the same origin. The uniformity was further affirmed by high performance liquid chromatography （HPLC）, which also revealed exactly identical specificity for the identified S. divaricata species with the 1H NMR appearances of corresponding CSPD on the part of the composition of characteristic constituents when comparing to corresponding individual compounds. This investigation unambiguously shows that the specific signals from the chemotaxonomically significant compounds of chromones and coumarins in S. divaricata are exhibited distinctively in the composite features of both 1H NMR fingerprints and HPLC profiles. The 1H NMR and HPLC profiles established can successfully be used as reference for the authentication of the origin of S. divaricata species as well as for chemotaxonomic studies.

关键词： FINGERPRINTS NUCLEAR magnetic resonance spectroscopy HIGH performance liquid chromatography COUMARINS CHEMOTAXONOMY

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In vitro and in vivo antioxidative and hepatoprotective activity of aqueous extract of Cortex Dictamni

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World Journal of Gastroenterology 2017年第16期23卷 2912-2927页

作者： Lin Li Yun-Feng Zhou Yan-Lin Li Li-Li Wang Hiderori Arai Yang Xu Institute of Medicinal plant Development Chinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100193China key laboratory of bioactive substances and Resources utilization of Chinese Herbal Medicine Ministry of EducationBeijing 100193China Department of Human Health Sciences Kyoto University Graduate School of MedicineKyoto 606-8507Japan

AIM To investigate the antioxidant and hepatoprotective effects of Cortex Dictamni aqueous extract(CDAE) in carbon tetrachloride(CCl4)-induced liver damage in *** The in vitro antioxidant effect of CDAE was investigated using α,α-diphenyl-β-picrylhydrazyl(DPPH), 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)(ABTS), β-carotene bleaching, reducing power, and thiobarbituric acid reactive substance assays. A linoleic acid system, including ferric thiocyanate(FTC) and thiobarbituric acid(TBA) assays, was used to evaluate the inhibition of lipid peroxidation. The in vivo hepatoprotective and antioxidant effects of CDAEagainst CCl4-induced liver damage were evaluated in Sprague-Dawley rats. Silymarin was used as a positive control. Liver damage was assessed by determining hepatic histopathology and liver marker enzymes in serum. Enzyme and non-enzyme antioxidant levels and lipid peroxide content were measured in the liver. Cytochrome P450 2E1(CYP2E1) protein expression was measured via immunohistochemical staining. Nuclear factor E2-related factor(Nrf2), heme oxygenase-1(HO-1), NAD(P)H quinine oxidoreductase 1(NQO1), and γ-glutamylcysteine synthetase catalytic subunit(γ-GCSc) protein expression was measured by Western *** Our results showed that CDAE exhibited a strong antioxidant activity in vitro. CDAE scavenged DPPH and ABTS radicals in a dose-dependent manner. CDAE inhibited lipid peroxidation with a lipid peroxide inhibition rate of 40.6% ± 5.2%. In the FTC and TBA assays, CDAE significantly inhibited lipid peroxidation(P < 0.01). In vivo histopathological studies indicated that CCl4-induced liver injury was alleviated following CDAE treatment in rats of both sexes. CDAE(160 and 320 mg/kg) significantly prevented CCl4-induced elevations of alkaline phosphatase, glutamate pyruvate transaminase, aspartate aminotransferase, and total bilirubin levels in rats of both sexes(P < 0.05, 0.01, or 0.001). Moreover, CDAE restored the decreased activities

关键词： Cortex Dictamni Antioxidant activity Hepatoprotective Carbon tetrachloride Nrf2

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Self-adjuvant Astragalus polysaccharide-based nanovaccines for enhanced tumor immunotherapy:a novel delivery system candidate for tumor vaccines

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Science China(Life Sciences) 2024年第4期67卷 680-697页

作者： Nan Li Yun Zhang Miaomiao Han Tian Liu Jinjia Wu Yingxia Xiong Yikai Fan Fan Ye Bing Jin Yinghua Zhang Guibo Sun Xiaobo Sun Zhengqi Dong State key laboratory for Quality Ensurance and Sustainable Use of Dao-di Herbs Chinese Academy of Medical Sciences&Peking Union Medical College(CAMS)Institute of Medicinal Plant Development(IMPLAD)Beijing 100193China key laboratory of bioactive substances and Resources utilization of Chinese Herbal Medicine from Ministry of Education Beijing Key Laboratory of Innovative Drug Discovery of Traditional Chinese Medicine(Natural Medicine)and Translational MedicineKey Laboratory of New Drug Discovery Based on Classic Chinese Medicine Prescription from Chinese Academy of Medical SciencesCAMSIMPLADBeijing 100193China Department of Pharmaceutics School of Pharmaceutical SciencesHeilongjiang University of Chinese MedicineHarbin 150036China Jilin Academy of Chinese Medicine Sciences Changchun 130012China Joint Research Center for Chinese Medicinal Herbs IMPLADABRC&ACCLBeijing 100193China

The study of tumor nanovaccines(NVs)has gained interest because they specifically recognize and eliminate tumor ***,the poor recognition and internalization by dendritic cells(DCs)and insufficient immunogenicity restricted the vaccine ***,we extracted two molecular-weight Astragalus polysaccharides(APS,12.19 k D;APSHMw,135.67 k D)from Radix Astragali and made them self-assemble with OVA257–264directly forming OVA/APS integrated nanocomplexes through the microfluidic *** nanocomplexes were wrapped with a sheddable calcium phosphate layer to improve *** in the formed nanocomplexes served as drug carriers and immune adjuvants for potent tumor *** optimal APS-NVs were approximately 160 nm with uniform size distribution and could remain stable in physiological saline *** FITC-OVA in APS-NVs could be effectively taken up by DCs,and APS-NVs could stimulate the maturation of DCs,improving the antigen cross-presentation efficiency in *** possible mechanism was that APS can induce DC activation via multiple receptors such as dectin-1 and Toll-like receptors 2 and *** accumulation of APS-NVs both in draining and distal lymph nodes were observed following *** APS-NVs could easily access the lymph ***,APS-NVs could markedly promote antigen delivery efficiency to DCs and activate cytotoxic T *** addition,APS-NVs achieve a better antitumor effect in established B16-OVA melanoma tumors compared with the OVA+Alum treatment *** antitumor mechanism correlated with the increase in cytotoxic T cells in the tumor ***,the poor tumor inhibitory effect of APS-NVs on the nude mouse model of melanoma also confirmed the participation of antitumor adaptive immune response induced by ***,this study developed a promising APS-based tumor NV that is an efficient tumor immunotherapy without systemic side effects.

关键词： Astragalus polysaccharides nanovaccines OVA immunotherapy self-adjuvant

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OsWRKY78 regulates panicle exsertion via gibberellin signaling pathway in rice

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Journal of Integrative plant Biology 2024年第4期66卷 771-786页

作者： Enyang Mei Mingliang He Min Xu Jiaqi Tang Jiali Liu Yingxiang Liu Zhipeng Hong Xiufeng Li Zhenyu Wang Qingjie Guan Xiaojie Tian Qingyun Bu State key laboratory of Black Soils Conservation and utilization Key Laboratory of Soybean Molecular Design BreedingNortheast Institute of Geography and AgroecologyChinese Academy of SciencesHarbin 150081China University of Chinese Academy of Sciences Beijing 100049China key laboratory of Saline-alkali Vegetation Ecology Restoration Northeast Forestry UniversityMinistry of EducationHarbin 150040China College of Life Science Northeast Forestry UniversityHarbin 150040China

Panicle exsertion is one of the crucial agronomic traits in rice(Oryza sativa).Shortening of panicle exsertion often leads to panicle enclosure and severely reduces seed ***(GA)plays important roles in regulating panicle ***,the underlying mechanism and the relative regulatory network remain ***,we characterized the oswrky78 mutant showing severe panicle enclosure,and found that the defect of oswrky78 is caused by decreased bioactive GA *** analysis demonstrates that OsWRKY78 can directly activate GA biosynthesis and indirectly suppress GA ***,we found OsWRKY78 can interact with and be phosphorylated by mitogen-activated protein kinase(MAPK)kinase OsMAPK6,and this phosphorylation can enhance OsWRKY78 stability and is necessary for its biological *** together,these results not only reveal the critical function of OsWRKY78,but also reveal its mechanism via mediating crosstalk between MAPK and the GA signaling pathway in regulating panicle exsertion.

关键词： gibberellin MAPK cascades OsWRKY78 panicle exsertion rice

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Crc1,6RhaT is involved in the synthesis of hesperidin of the main bioactive substance in the Citrus reticulata ‘Chachi' fruit

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Horticultural plant Journal 2024年第6期10卷 1321-1335页

作者： Na Shang Panpan Tong Peng Ye Jianmu Su Mei Bai Hong Wu State key laboratory for Conservation and utilization of Subtropical Agro-bioresources Guangdong Laboratory for Lingnan Modern AgricultureCollege of Life SciencesSouth China Agricultural UniversityGuangzhouGuangdong 510642China Guangdong Technology Research Center for Traditional Chinese Veterinary Medicine and Natural Medicine South China Agricultural UniversityGuangzhouGuangdong 510642China

Hesperidin is a dihydroflavonoids, accounting for more than 50% of the total flavonoids in Citri Reticulatae Pericarpium(CRP) of traditional Chinese medicine. It is an effective antioxidant and free radical scavenger that has anti-inflammatory, antiviral and hypoglycemic *** latest studies reported that hesperidin has a potential for novel coronavirus resistance. However, little is known about the synthesis regulation and accumulation site of hesperidin in plants. In this study, hesperidin synthase gene Crc1,6RhaT was cloned, and the protein can be completely transformed flavanone-7-O-glucoside into hesperidin in vitro and in vivo. Studies on biological characteristics of ovary walls and exocarps showed that the relative expression levels of the Crc1,6RhaT gene and protein decreased gradually with the development of citrus fruits, and the relative content of hesperidin firstly increased, then sequentially decreased. In situ hybridization results further revealed that Crc1,6RhaT transcription was mainly concentrated in the secretory cavity cells, which are revealed to be the site of flavonoid *** localization results showed that the Crc1,6RhaT was mainly located in the endoplasmic reticulum, nucleus and vacuole of secretory cells. We inferred that the Crc1,6RhaT was synthesized in the endoplasmic reticulum, then was transported into the vacuoles through enlarged vesicles at the end of the endoplasmic reticulum. Our results not only revealed that Crc1,6RhaT may be involved in the synthesis of hesperidin of the main bioactive substance in the medicinal plant Citrus reticulata ‘Chachi' fruit, but also provided novel insights into the main subcellular sites of hesperidin biosynthesis in vacuoles.

关键词： Citri Reticulatae Pericarpium Citrus Hesperidin Flavonoids Crc1 6RhaT Secretory cavity

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plant-derived squalene supplementation improves growth performance and alleviates acute oxidative stress-induced growth retardation and intestinal damage in piglets

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Animal Nutrition 2023年第4期15卷 386-398页

作者： Junquan Tian Qian Jiang Xuetai Bao Fan Yang Yuying Li Haihui Sun Kang Yao Yulong Yin National Engineering laboratory for Pollution Control and Waste utilization in Livestock and Poultry Production Key Laboratory of Agro-ecological Processes in Subtropical RegionLaboratory of Animal Nutritional Physiology and Metabolic ProcessInstitute of Subtropical AgricultureChinese Academy of SciencesChangsha410125China University of Chinese Academy of Sciences Beijing100008China College of Animal Science and Technology Hunan Agricultural UniversityChangsha410000China Institute of Bast Fiber Crops Chinese Academy of Agricultural SciencesChangsha410205China Yichun Dahaigui Life Science Co. LtdYichun336000China

Piglets are particularly susceptible to oxidative stress,which causes inferior growth performance and intestinal ***(SQ),a natural bioactive substance enriched in shark liver oil,shows excellent antioxidant properties and can currently be obtained at a low cost from deodorizer distillate during the production of plant *** study aimed to evaluate the effects of plant-derived SQ supplementation on the growth performance of piglets and explore the beneficial roles of SQ against oxidative stress and intestinal injury in diquat-challenged *** piglets were randomly divided into five groups and fed a basal diet supplemented with SQ at 0,500,1000,or 2000 mg/kg for 5 *** oxidative stress was induced in the piglets with diquat(10 mg/kg BW)at the fourth week of the experiment,followed by a 7-d recovery *** showed that before the diquat challenge,SQ supplementation significantly improved growth performance(average daily gain and feed conversion ratio)and serum antioxidant status,and after the diquat challenge,SQ supplementation significantly mitigated diquat-induced growth arrest,intestinal villous atrophy,intestinal epithelial cell apoptosis,intestinal hyperpermeability,and deficiency of intestinal epithelial tight junction proteins(zonula occludens-1,occludin,and claudin-3).Under oxidative stress induced by diquat,SQ supplementation consistently improved the antioxidant status of the small intestine,liver,and *** vitro,SQ was shown to alleviate hydrogen peroxide(H2O2)-induced increase of the levels of intracellular reactive oxygen species and apoptosis of porcine intestinal epithelial *** together,SQ supplementation improves growth performance and effectively alleviates acute oxidative stress-induced growth retardation and intestinal injury via improving antioxidant capacity in *** findings may provide an efficient strategy for alleviating oxidative stress-induced inferior growth performance and intestinal da

关键词： Squalene Growth performance Oxidative stress Intestinal injury Antioxidant Piglet

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