A new angular furanocoumarin, 2′ acetylangelicin (8), along with oroselone (1), columbianadin (3), bergapten (4), O acetyl columbianetin (5), cniforin A (6), edultin (7) and β sitosterol (2), was isolated fro...A new angular furanocoumarin, 2′ acetylangelicin (8), along with oroselone (1), columbianadin (3), bergapten (4), O acetyl columbianetin (5), cniforin A (6), edultin (7) and β sitosterol (2), was isolated from the fruit of Cnidium monnieri. The structures were elucidated by spectral methods. Compound 1 was isolated from this plant for the first time.展开更多
Furanocoumarins (FCs) are a group of related plant defense metabolites occurring in several plant families, including some species in the genus citrus, such as grapefruit and pummelo. FCs function as toxins against pa...Furanocoumarins (FCs) are a group of related plant defense metabolites occurring in several plant families, including some species in the genus citrus, such as grapefruit and pummelo. FCs function as toxins against pathogens, insects and other plant pests and some are toxic to humans at high levels. Although the levels of FCs in grapefruits are non-toxic to humans, they inhibit the intestinal enzyme CYP3A, thus preventing degradation of medicines, such as statins, and causing dangerous overdose effects. This overdosing can cause devastating side effects, ranging from stomach bleeding to kidney problems, muscle aches and irregular heartbeats. In the present study, we utilize LC/MS to characterize the levels of FCs pathway intermediates and end products in twelve citrus cultivars, including mandarin (Citrus reticulata), orange [Citrus sinensis (L.) Osbeck], Pummelo [Citrus maxima (Burm.) Merr.], grapefruit (Citrus paradisi Macf.), and two newly selected grapefruit like varieties [(Citrus reticulate) X [Citrus maxima (Burm.) Merr]. The orange and mandarin varieties do not contain FCs or FCs precursor compounds suggesting that this biosynthetic pathway is absent or inactive in mandarins and oranges and therefore a good genetic source for null alleles to FCs biosynthesis. We report the selection and characterization of two new low FCs and seedless grapefruit-like varieties, “Aliza” and “Coocki”, developed by a cross between pummelo and mandarin. Fruits of these varieties resemble grapefruit and contain high levels of the flavanone naringin, typical of grapefruit, but contain only trace amounts of FCs (based on LCMS analysis). Based on the variability of FCs content and inheritance in citrus species, the results suggest that future development of new low-FCs grapefruit varieties is an achievable objective.展开更多
A new dimeric psoralen-type furanocoumarin, notopterol-（18-O-20＇）-notopol （1）, was isolated from Notopterygium incisum for the first time and its structure was elucidated by spectroscopic methods.
Oxypeucedanin hydrate monoacetate (Mol. Formula = C18H18O7) micro-crystals were obtained by acetylation of oxy-peucedanin hydrate, a furanocoumarin, isolated from the roots of Prangos pabularia. The composition relate...Oxypeucedanin hydrate monoacetate (Mol. Formula = C18H18O7) micro-crystals were obtained by acetylation of oxy-peucedanin hydrate, a furanocoumarin, isolated from the roots of Prangos pabularia. The composition related structural, thermal and optical properties were investigated. All the crystals were found to have triclinic structure. From thermal studies of these crystals, stability, melting point and other relevant informations were obtained. Their blue emission, less absorption in entire visible range and band gap predicts these crystals as good candidate for modern optoelectronic devices.展开更多
Isopimpinellin(C13H10O5),alternative name 5,8-dimethoxypsoralen,is one of the furocoumarin compounds.This traditional Chinese medicine extract has attracted a great deal of attention in recent years due to its pharmac...Isopimpinellin(C13H10O5),alternative name 5,8-dimethoxypsoralen,is one of the furocoumarin compounds.This traditional Chinese medicine extract has attracted a great deal of attention in recent years due to its pharmacological properties,especially its antifungal effect.The main purpose of this study was to study the molecular structure and chemical reactivity of isopimpinellin using the density functional theory method.To understand and interpret the reactivity of isopimpinellin,various chemical reactivity descriptors such as chemical potential(μ),electronegativity(χ),chemical hardness(η)and electrophilicity(ω)and local reactivity index condensed Fukui function(fi(r))have been calculated with five hybrid functionals PBE1PBE,MPW1PW91,B3LYP,X3LYP and B3PW91.These chemical reactivity descriptors indicate that the isopimpinellin molecule has a good antioxidant activity,which could be one of the reasons for its action as an effective antifungal drug.The condensed Fukui functions of isopimpinellin molecule provide a complete scheme of chemical reactivity of one molecule.展开更多
Coumarins,derived from the phenylpropanoid pathway,represent one of the primary metabolites found in angiosperms.The alignment of the tetrahydropyran(THP)and tetrahydrofuran(THF)rings with the lactone structure result...Coumarins,derived from the phenylpropanoid pathway,represent one of the primary metabolites found in angiosperms.The alignment of the tetrahydropyran(THP)and tetrahydrofuran(THF)rings with the lactone structure results in the formation of at least four types of complex coumarins.However,the mechanisms underlying the structural diversity of coumarin remain poorly understood.Here,we report the chromosome-level genome assembly of Notopterygium incisum,spanning 1.64 Gb,with a contig N50 value of 22.7 Mb and 60,021 annotated protein-coding genes.Additionally,we identified the key enzymes responsible for shaping the structural diversity of coumarins,including two p-coumaroyl CoA 2′-hydroxylases crucial for simple coumarins basic skeleton architecture,two UbiA prenyltransferases responsible for angular or linear coumarins biosynthesis,and five CYP736 cyclases involved in THP and THF ring formation.Notably,two bifunctional enzymes capable of catalyzing both demethylsuberosin and osthenol were identified for the first time.Evolutionary analysis implies that tandem and ectopic duplications of the CYP736 subfamily,specifically arising in the Apiaceae,contributed to the structural diversity of coumarins in N.incisum.Conclusively,this study proposes a parallel evolution scenario for the complex coumarin biosynthetic pathway among different angiosperms and provides essential synthetic biology elements for the heterologous industrial production of coumarins.展开更多
Furanocoumarins in citrus fruit can cause adverse drug interactions;however,there are few reports on furanocoumarins and drug interactions in common edible citrus cultivars except grapefruit.An ultra-performance liqui...Furanocoumarins in citrus fruit can cause adverse drug interactions;however,there are few reports on furanocoumarins and drug interactions in common edible citrus cultivars except grapefruit.An ultra-performance liquid chromatography(UPLC)-based method for ten furanocoumarins in citrus fruit was established,and the effects on cytochrome P450 activity were investigated.Furanocoumarins were more abundant(2-43 times)in the peel than in the pulp.The pulp of Xiyou,Hongyou,and Navel orange exhibited P450 inhibition,with 50% maximal inhibitory concentration(ICso)values of 0.63,0.67,and 1.02 mg/mL,respectively.The peel of all the varieties except Huyou and Satsuma exhibited P450 inhibition.Xiyou,Baiyou,Huangjinyou,Hongyou,Ponkan,and Navel orange had IC_(50)values of 0.33,0.76,0.38,0.35,0.43,and 0.37 mg/mL,respectively.These findings indicate that,except for Xiyou,Hongyou,and Navel orange,the consumption of the pulp of popular Chinese varieties of citrus fruit has a low risk of drug interactions,and the use of citrus products including peel may carry a significant risk of adverse drug interactions.展开更多
文摘A new angular furanocoumarin, 2′ acetylangelicin (8), along with oroselone (1), columbianadin (3), bergapten (4), O acetyl columbianetin (5), cniforin A (6), edultin (7) and β sitosterol (2), was isolated from the fruit of Cnidium monnieri. The structures were elucidated by spectral methods. Compound 1 was isolated from this plant for the first time.
文摘Furanocoumarins (FCs) are a group of related plant defense metabolites occurring in several plant families, including some species in the genus citrus, such as grapefruit and pummelo. FCs function as toxins against pathogens, insects and other plant pests and some are toxic to humans at high levels. Although the levels of FCs in grapefruits are non-toxic to humans, they inhibit the intestinal enzyme CYP3A, thus preventing degradation of medicines, such as statins, and causing dangerous overdose effects. This overdosing can cause devastating side effects, ranging from stomach bleeding to kidney problems, muscle aches and irregular heartbeats. In the present study, we utilize LC/MS to characterize the levels of FCs pathway intermediates and end products in twelve citrus cultivars, including mandarin (Citrus reticulata), orange [Citrus sinensis (L.) Osbeck], Pummelo [Citrus maxima (Burm.) Merr.], grapefruit (Citrus paradisi Macf.), and two newly selected grapefruit like varieties [(Citrus reticulate) X [Citrus maxima (Burm.) Merr]. The orange and mandarin varieties do not contain FCs or FCs precursor compounds suggesting that this biosynthetic pathway is absent or inactive in mandarins and oranges and therefore a good genetic source for null alleles to FCs biosynthesis. We report the selection and characterization of two new low FCs and seedless grapefruit-like varieties, “Aliza” and “Coocki”, developed by a cross between pummelo and mandarin. Fruits of these varieties resemble grapefruit and contain high levels of the flavanone naringin, typical of grapefruit, but contain only trace amounts of FCs (based on LCMS analysis). Based on the variability of FCs content and inheritance in citrus species, the results suggest that future development of new low-FCs grapefruit varieties is an achievable objective.
基金in part,by NSFC grants(No.90713040,30640068),MOST(No.2003CB716601),NCET grant(No.NCET-06-0422)STCSM grants(No.06DZ19002,06PJ14033,07DZ22006).The authors are grateful to Dr.Jiang-Nan Peng and Prof.Mark T.Hamann(Department of Pharmacognosy,The University of Mississippi),Prof.Jian-Ming Yue(Shanghai Institute of Materia Medica),and Prof.Zheng Zhao(Shanghai Key Laboratory of Brain Functional Genomics)for their assistance of the measurement of MS spectral data.The authors wish to thank Prof.Jian-Wei Chen(Nanjing University of Traditional Chinese Medicine)for the plant identification.
文摘A new dimeric psoralen-type furanocoumarin, notopterol-（18-O-20＇）-notopol （1）, was isolated from Notopterygium incisum for the first time and its structure was elucidated by spectroscopic methods.
文摘Oxypeucedanin hydrate monoacetate (Mol. Formula = C18H18O7) micro-crystals were obtained by acetylation of oxy-peucedanin hydrate, a furanocoumarin, isolated from the roots of Prangos pabularia. The composition related structural, thermal and optical properties were investigated. All the crystals were found to have triclinic structure. From thermal studies of these crystals, stability, melting point and other relevant informations were obtained. Their blue emission, less absorption in entire visible range and band gap predicts these crystals as good candidate for modern optoelectronic devices.
文摘Isopimpinellin(C13H10O5),alternative name 5,8-dimethoxypsoralen,is one of the furocoumarin compounds.This traditional Chinese medicine extract has attracted a great deal of attention in recent years due to its pharmacological properties,especially its antifungal effect.The main purpose of this study was to study the molecular structure and chemical reactivity of isopimpinellin using the density functional theory method.To understand and interpret the reactivity of isopimpinellin,various chemical reactivity descriptors such as chemical potential(μ),electronegativity(χ),chemical hardness(η)and electrophilicity(ω)and local reactivity index condensed Fukui function(fi(r))have been calculated with five hybrid functionals PBE1PBE,MPW1PW91,B3LYP,X3LYP and B3PW91.These chemical reactivity descriptors indicate that the isopimpinellin molecule has a good antioxidant activity,which could be one of the reasons for its action as an effective antifungal drug.The condensed Fukui functions of isopimpinellin molecule provide a complete scheme of chemical reactivity of one molecule.
基金supported by the Western Light Project of the Chinese Academy of Sciences and the Young Qihuang Scholars Project of the National Administration of Traditional Chinese Medicine.This research was also funded by the open foundation of Shaanxi University of Chinese Medicine state key laboratory of R&D of Characteristic Qin Medicine Resources(SUCM-QM202202,China)the fund of Traditional Chinese Medicine Institute of Anhui Dabie Mountain(TCMADM-2023-18,China)+2 种基金“Double FirstClass”University Project of China Pharmaceutical University(CPU2022QZ27,China)supported by the key project at the central government level:the ability establishment of sustainable use for valuable Chinese medicine resources(2060302,China)the open research fund of Yunnan characteristic plant extraction laboratory(YKKF2023002,China)。
文摘Coumarins,derived from the phenylpropanoid pathway,represent one of the primary metabolites found in angiosperms.The alignment of the tetrahydropyran(THP)and tetrahydrofuran(THF)rings with the lactone structure results in the formation of at least four types of complex coumarins.However,the mechanisms underlying the structural diversity of coumarin remain poorly understood.Here,we report the chromosome-level genome assembly of Notopterygium incisum,spanning 1.64 Gb,with a contig N50 value of 22.7 Mb and 60,021 annotated protein-coding genes.Additionally,we identified the key enzymes responsible for shaping the structural diversity of coumarins,including two p-coumaroyl CoA 2′-hydroxylases crucial for simple coumarins basic skeleton architecture,two UbiA prenyltransferases responsible for angular or linear coumarins biosynthesis,and five CYP736 cyclases involved in THP and THF ring formation.Notably,two bifunctional enzymes capable of catalyzing both demethylsuberosin and osthenol were identified for the first time.Evolutionary analysis implies that tandem and ectopic duplications of the CYP736 subfamily,specifically arising in the Apiaceae,contributed to the structural diversity of coumarins in N.incisum.Conclusively,this study proposes a parallel evolution scenario for the complex coumarin biosynthetic pathway among different angiosperms and provides essential synthetic biology elements for the heterologous industrial production of coumarins.
基金supported by the corporate-funded project(KYY-HX-20230378)the National Natural Science Foundation of China(No.31771982).
文摘Furanocoumarins in citrus fruit can cause adverse drug interactions;however,there are few reports on furanocoumarins and drug interactions in common edible citrus cultivars except grapefruit.An ultra-performance liquid chromatography(UPLC)-based method for ten furanocoumarins in citrus fruit was established,and the effects on cytochrome P450 activity were investigated.Furanocoumarins were more abundant(2-43 times)in the peel than in the pulp.The pulp of Xiyou,Hongyou,and Navel orange exhibited P450 inhibition,with 50% maximal inhibitory concentration(ICso)values of 0.63,0.67,and 1.02 mg/mL,respectively.The peel of all the varieties except Huyou and Satsuma exhibited P450 inhibition.Xiyou,Baiyou,Huangjinyou,Hongyou,Ponkan,and Navel orange had IC_(50)values of 0.33,0.76,0.38,0.35,0.43,and 0.37 mg/mL,respectively.These findings indicate that,except for Xiyou,Hongyou,and Navel orange,the consumption of the pulp of popular Chinese varieties of citrus fruit has a low risk of drug interactions,and the use of citrus products including peel may carry a significant risk of adverse drug interactions.
