Hyperforatone A(1),the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol,possessed an unusual bicyclo[5.4.0]undecane skeleton bearing a 5/7/6/5 ring system,and two known biosynthetically related precurs...Hyperforatone A(1),the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol,possessed an unusual bicyclo[5.4.0]undecane skeleton bearing a 5/7/6/5 ring system,and two known biosynthetically related precursors(2 and 3)were isolated from Hypericum perforatum(St.John's wort).The structure and absolute configuration were unambiguously confirmed by a combination of comprehensive spectroscopic data,computational methods including residual dipolar couplings(RDCs),and X-ray crystallography.Density functional theory(DFT)calculations revealed that the cationic cyclization reaction was key to proposed formation mechanism for hyperforatone A.Furthermore,in vitro and in vivo experiments demonstrated that compound 1 was a potential anti-neuroinfiammatory agent.展开更多
Monosescinol A(1),the first example of sesquiterpene–polycyclic polyprenylated acylphloroglucinol(PPAP)adduct,which represented a new subclass of PPAP-type natural products,along with two new congeners with normal sp...Monosescinol A(1),the first example of sesquiterpene–polycyclic polyprenylated acylphloroglucinol(PPAP)adduct,which represented a new subclass of PPAP-type natural products,along with two new congeners with normal spiro 6/6/5 tricyclic architecture,were isolated from Hypericum longistylum.Monosescinol A possessed an unprecedented 6/5/5/6/6 pentacyclic carbon skeleton that might be assembled from the 6/6/5 carbon skeleton,via the splitting decomposition of C-3/C-14,and the attack from the C-3 in the PPAP core to C-28 in sesquiterpene section.In addition,we have firstly confirmed that 24R configuration was existed in sec–Bu containing PPAPs by single crystal diffraction data analysis of monosescinol B(2),that might provide an enlightenment in the configurational determination of sec–Bu containing PPAPs.Significantly,further pharmacological research has found that compound 1 exhibited remarkable pharmacological effects against acute myeloid leukemia(AML)cell lines,with direct inhibition of mitochondrial complex V and an increase in mitochondrial membrane potential,and led to an induction of oxidative stress,endogenous inflammation,and apoptosis of AML cells.展开更多
Hyperforin is a representative polycyclic polyprenylated acylphloroglucinols(PPAPs)that exerts a variety of pharmacological activities.The complete biosynthesis pathway of hyperforin has not been elucidated due to its...Hyperforin is a representative polycyclic polyprenylated acylphloroglucinols(PPAPs)that exerts a variety of pharmacological activities.The complete biosynthesis pathway of hyperforin has not been elucidated due to its complex structure and unclear genetic background of its source plants.This mini-review focuses on the bioactivity and biosynthesis of hyperforin.These analyses can provide useful insights into the biosynthesis investigations of hyperforin and other PPAPs with complex structures.展开更多
Twenty-one benzoylated phloroglucinol derivatives bearing homoadamantyl frameworks were isolated from the aerial parts of Hypericum sampsonii,including two new ones named hyperisampsins N and O（1 and 2）.The structur...Twenty-one benzoylated phloroglucinol derivatives bearing homoadamantyl frameworks were isolated from the aerial parts of Hypericum sampsonii,including two new ones named hyperisampsins N and O（1 and 2）.The structures of 1 and 2 were elucidated by extensive NMR and mass spectrometric analyses.Their absolute configurations were further determined by using TDDFT ECD calculations.Compounds 2,7,and 8 were evaluated for their cytotoxic activities against five human cancer cell lines,of which,2 and 8 exhibited significant cytotoxic activities toward HL-60 cell and moderate activities against others cell lines.展开更多
介绍了证明汽车零部件工厂自身制造能力和满足顾客产品要求的有效的五大质量工具之一的生产件批准过程PPAP(Production Part Approval Process)质量工具的适用范围、提交等级及过程要求等,为企业实施TS16949汽车质量管理体系提供了参考...介绍了证明汽车零部件工厂自身制造能力和满足顾客产品要求的有效的五大质量工具之一的生产件批准过程PPAP(Production Part Approval Process)质量工具的适用范围、提交等级及过程要求等,为企业实施TS16949汽车质量管理体系提供了参考。事实证明世界汽车行业供应链中采用TS16949汽车质量管理体系标准确实行之有效。展开更多
Spirohypatone A(1),a spirocyclic PPAP(polycyclic polyprenylated acylphloroglucinol) bearing an unprecedented hexahydro-1’H-spiro[cyclohexane-1,2’-pentalene]-2,4,6-trione core and a new homologue(spirohypatone B,2) w...Spirohypatone A(1),a spirocyclic PPAP(polycyclic polyprenylated acylphloroglucinol) bearing an unprecedented hexahydro-1’H-spiro[cyclohexane-1,2’-pentalene]-2,4,6-trione core and a new homologue(spirohypatone B,2) were isolated from Hypericum patulum together with two known biosynthetic precursors.Compound 1 represents the first spirocyclic PPAP possessing a 5/5/6 carbon ring system,biogenetically derived from the intermediate 3(attack from C-3 to C-12),which was differed from normal spirocyclic PPAPs(attack from C-3 to C-11).In addition,through extensive spectroscopic analysis,an interconversion mechanism of keto-enol of 1 was postulated and confirmed by its methylated reaction.The structures and absolute configurations of 1 and 2 were determined by comprehensive spectroscopic and chemical derivatized methods and X-ray crystallography.Compounds 1,2,and 4 were tested to exhibit cytotoxic activities against several cancer cell lines.展开更多
基金financially supported by the National Natural Science Foundation of China(Nos.22077102,32201249)the Science and Technology Program of Gansu Province(No.22YF7GA046)。
文摘Hyperforatone A(1),the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol,possessed an unusual bicyclo[5.4.0]undecane skeleton bearing a 5/7/6/5 ring system,and two known biosynthetically related precursors(2 and 3)were isolated from Hypericum perforatum(St.John's wort).The structure and absolute configuration were unambiguously confirmed by a combination of comprehensive spectroscopic data,computational methods including residual dipolar couplings(RDCs),and X-ray crystallography.Density functional theory(DFT)calculations revealed that the cationic cyclization reaction was key to proposed formation mechanism for hyperforatone A.Furthermore,in vitro and in vivo experiments demonstrated that compound 1 was a potential anti-neuroinfiammatory agent.
基金supported financially by the National Natural Science Foundation for Distinguished Young Scholars(No.81725021)the National Natural Science Foundation of China(Nos.82003633 and 82104043)the National Natural Science Foundation of Hubei Province(No.2023AFB791)。
文摘Monosescinol A(1),the first example of sesquiterpene–polycyclic polyprenylated acylphloroglucinol(PPAP)adduct,which represented a new subclass of PPAP-type natural products,along with two new congeners with normal spiro 6/6/5 tricyclic architecture,were isolated from Hypericum longistylum.Monosescinol A possessed an unprecedented 6/5/5/6/6 pentacyclic carbon skeleton that might be assembled from the 6/6/5 carbon skeleton,via the splitting decomposition of C-3/C-14,and the attack from the C-3 in the PPAP core to C-28 in sesquiterpene section.In addition,we have firstly confirmed that 24R configuration was existed in sec–Bu containing PPAPs by single crystal diffraction data analysis of monosescinol B(2),that might provide an enlightenment in the configurational determination of sec–Bu containing PPAPs.Significantly,further pharmacological research has found that compound 1 exhibited remarkable pharmacological effects against acute myeloid leukemia(AML)cell lines,with direct inhibition of mitochondrial complex V and an increase in mitochondrial membrane potential,and led to an induction of oxidative stress,endogenous inflammation,and apoptosis of AML cells.
基金supported by the National Natural Science Foundation of China(No.82073970)the National Key Research and Development Program of China(No.2020YFA0908000).
文摘Hyperforin is a representative polycyclic polyprenylated acylphloroglucinols(PPAPs)that exerts a variety of pharmacological activities.The complete biosynthesis pathway of hyperforin has not been elucidated due to its complex structure and unclear genetic background of its source plants.This mini-review focuses on the bioactivity and biosynthesis of hyperforin.These analyses can provide useful insights into the biosynthesis investigations of hyperforin and other PPAPs with complex structures.
基金financially supported by the Program for New Century Excellent Talents in University,State Education Ministry of China(No.NCET-2008-0224)National Science and Technology Project of China(No.2011ZX09102-004)+2 种基金the National Natural Science Foundation of China(Nos.31370372,81573316,81641129 and 21502057)the Fundamental Research Fund for the Central Universities(No.2016YXMS149)the China Postdoctoral Science Foundation(No.2015M572154)
文摘Twenty-one benzoylated phloroglucinol derivatives bearing homoadamantyl frameworks were isolated from the aerial parts of Hypericum sampsonii,including two new ones named hyperisampsins N and O（1 and 2）.The structures of 1 and 2 were elucidated by extensive NMR and mass spectrometric analyses.Their absolute configurations were further determined by using TDDFT ECD calculations.Compounds 2,7,and 8 were evaluated for their cytotoxic activities against five human cancer cell lines,of which,2 and 8 exhibited significant cytotoxic activities toward HL-60 cell and moderate activities against others cell lines.
文摘介绍了证明汽车零部件工厂自身制造能力和满足顾客产品要求的有效的五大质量工具之一的生产件批准过程PPAP(Production Part Approval Process)质量工具的适用范围、提交等级及过程要求等,为企业实施TS16949汽车质量管理体系提供了参考。事实证明世界汽车行业供应链中采用TS16949汽车质量管理体系标准确实行之有效。
基金financially supported by the NSFC-Joint Foundation of Yunnan Province(No.U1902213)the Second Tibetan Plateau Scientific Expedition and Research(STEP)Program(No.2019QZKK0502020303)+1 种基金Southeast Asia Biodiversity Research Institute,CAS(No.2017CASSEABRIQG003)the Natural Sciences Foundation of Yunnan Province(No.2019FA003)。
文摘Spirohypatone A(1),a spirocyclic PPAP(polycyclic polyprenylated acylphloroglucinol) bearing an unprecedented hexahydro-1’H-spiro[cyclohexane-1,2’-pentalene]-2,4,6-trione core and a new homologue(spirohypatone B,2) were isolated from Hypericum patulum together with two known biosynthetic precursors.Compound 1 represents the first spirocyclic PPAP possessing a 5/5/6 carbon ring system,biogenetically derived from the intermediate 3(attack from C-3 to C-12),which was differed from normal spirocyclic PPAPs(attack from C-3 to C-11).In addition,through extensive spectroscopic analysis,an interconversion mechanism of keto-enol of 1 was postulated and confirmed by its methylated reaction.The structures and absolute configurations of 1 and 2 were determined by comprehensive spectroscopic and chemical derivatized methods and X-ray crystallography.Compounds 1,2,and 4 were tested to exhibit cytotoxic activities against several cancer cell lines.
