Mufolinin A(1),a ring A-seco rearranged limonoid with an unprecedented ethyl at C-10 and novel 6/6/6/5 fused-ring skeleton,together with three new potential precursors(ring A-seco limonoids,2–4)were isolated from Mun...Mufolinin A(1),a ring A-seco rearranged limonoid with an unprecedented ethyl at C-10 and novel 6/6/6/5 fused-ring skeleton,together with three new potential precursors(ring A-seco limonoids,2–4)were isolated from Munronia unifoliolata.Their structures and absolute configurations were confirmed by nuclear magnetic resonance(NMR),high resolution electrospray ionization mass spectroscopy(HRESIMS),X-ray crystallography,electronic circular dichroism(ECD)calculations and NMR calculations with DP4+analyses.The unprecedented ethyl group of 1 was hypothesized to be derived from methyl migration and ring reduction rearrangement of ring A-seco limonoid 4.Compounds 2 and 4 showed significant multidrug resistance(MDR)reversal activities in MCF-7/DOX cells with reversal fold(RF)values of 13.1 and 8.0,respectively.展开更多
Guided by MS/MS molecular networks strategy,chlospicenes A and B(1 and 2),the first example of cyclopropane moiety cracked lindenane sesquiterpene Michael addition dimers,along with their biogenetic analogues(3 and 4)...Guided by MS/MS molecular networks strategy,chlospicenes A and B(1 and 2),the first example of cyclopropane moiety cracked lindenane sesquiterpene Michael addition dimers,along with their biogenetic analogues(3 and 4),were targetedly discovered from the roots of Chloranthus henryi.Their structures including absolute configurations were characterized by NMR,ECD and X-ray diffraction analysis.The plausible biogenic pathway speculation indicated that cyclopropylcarbinyl rearrangement may dominate the key crack of cyclopropane moiety.In addition,compounds 1 and 2 showed significant anti-nonalcoholic steatohepatitis(NASH)activity in free fatty acid(FFA)-induced HepG2 cells by decreasing intracellular lipid accumulation.展开更多
Twenty-two new limonoids,mufolinoids A—V(1—22),including six rings A,B-seco limonoids(1—6),twelve ring A-seco limonoids(7—18),four ring-intact limonoids(19—22),together with thirteen known compounds(23—35)were i...Twenty-two new limonoids,mufolinoids A—V(1—22),including six rings A,B-seco limonoids(1—6),twelve ring A-seco limonoids(7—18),four ring-intact limonoids(19—22),together with thirteen known compounds(23—35)were isolated from Munronia unifoliolata.Their structures including absolute configurations were elucidated by combination of NMR,HR-MS,single-crystal X-ray diffraction and calculations of ECD and NMR technologies.Compounds 24,25,33,34 could be significantly reversed the multidrug resistance of MCF-7/doxorubicin(DOX)cells,and the reversal fold(RF)was much higher than that of positive drug Verapamil.Compounds 24,28,and 29 exhibited significant anti-inflammatory activity with the IC50 values in the range of 17.7—39.4μmol/L.Furthermore,compound 29 could markedly inhibit the release of IL-1βby inhibiting the initiation and assembly of NLRP3 inflammasome,which demonstrates the great potential of limonoids as an anti-inflammatory agent.展开更多
Elodexanthones A—J (1—10), two pairs of rearranged isoprenylated xanthone enantiomers with an unprecedent 6/6/5/6 tetracyclic core (1—2) along with seven new isoprenylated xanthones (3—9) and a pair of phenylpropa...Elodexanthones A—J (1—10), two pairs of rearranged isoprenylated xanthone enantiomers with an unprecedent 6/6/5/6 tetracyclic core (1—2) along with seven new isoprenylated xanthones (3—9) and a pair of phenylpropanoid xanthones (10), were purified and enantio-separated from the whole plant of Hypericum elodeoides. Their structures including absolute configurations were characterized by the comprehensive analysis of NMR, HRESIMS, NMR calculations, and ECD calculations. Through Bayer-Villiger oxidation, Claisen condensation and electrophilic addition, the rearranged skeletons of elodexanthones A—B (1—2) were generated from isoprenylated xanthone precursors. The bioactivities evaluation exhibited that compounds 3, 5, 8—10 showed anti-inflammatory activity with the IC_(50) values in the range of 9.53—34.39 μmol/L, and compounds 3—7, and 9 showed notable α-glucosidase inhibitory activity (IC_(50): 6.02—257.11 μmol/L).展开更多
基金supported by the National Natural Science Foundation of China(No.31470416)the 111 Project from Ministry of Education of China and the State Administration of Foreign Export Affairs of China(No.B18056).ll supported in part by SciGrid,Chinese Academy of Sciences。
文摘Mufolinin A(1),a ring A-seco rearranged limonoid with an unprecedented ethyl at C-10 and novel 6/6/6/5 fused-ring skeleton,together with three new potential precursors(ring A-seco limonoids,2–4)were isolated from Munronia unifoliolata.Their structures and absolute configurations were confirmed by nuclear magnetic resonance(NMR),high resolution electrospray ionization mass spectroscopy(HRESIMS),X-ray crystallography,electronic circular dichroism(ECD)calculations and NMR calculations with DP4+analyses.The unprecedented ethyl group of 1 was hypothesized to be derived from methyl migration and ring reduction rearrangement of ring A-seco limonoid 4.Compounds 2 and 4 showed significant multidrug resistance(MDR)reversal activities in MCF-7/DOX cells with reversal fold(RF)values of 13.1 and 8.0,respectively.
基金supports from the National Natural Science Foundation of China(No.32070389)the“Double First-Class”University Project(No.CPU2018GY08)。
文摘Guided by MS/MS molecular networks strategy,chlospicenes A and B(1 and 2),the first example of cyclopropane moiety cracked lindenane sesquiterpene Michael addition dimers,along with their biogenetic analogues(3 and 4),were targetedly discovered from the roots of Chloranthus henryi.Their structures including absolute configurations were characterized by NMR,ECD and X-ray diffraction analysis.The plausible biogenic pathway speculation indicated that cyclopropylcarbinyl rearrangement may dominate the key crack of cyclopropane moiety.In addition,compounds 1 and 2 showed significant anti-nonalcoholic steatohepatitis(NASH)activity in free fatty acid(FFA)-induced HepG2 cells by decreasing intracellular lipid accumulation.
基金sponsored by the National Natural Science Foundation of China(31470416)the 111 Project from Ministry of Education of Chinathe State Administration of Foreign Export Affairs of China(B18056).
文摘Twenty-two new limonoids,mufolinoids A—V(1—22),including six rings A,B-seco limonoids(1—6),twelve ring A-seco limonoids(7—18),four ring-intact limonoids(19—22),together with thirteen known compounds(23—35)were isolated from Munronia unifoliolata.Their structures including absolute configurations were elucidated by combination of NMR,HR-MS,single-crystal X-ray diffraction and calculations of ECD and NMR technologies.Compounds 24,25,33,34 could be significantly reversed the multidrug resistance of MCF-7/doxorubicin(DOX)cells,and the reversal fold(RF)was much higher than that of positive drug Verapamil.Compounds 24,28,and 29 exhibited significant anti-inflammatory activity with the IC50 values in the range of 17.7—39.4μmol/L.Furthermore,compound 29 could markedly inhibit the release of IL-1βby inhibiting the initiation and assembly of NLRP3 inflammasome,which demonstrates the great potential of limonoids as an anti-inflammatory agent.
基金supported by the National Natural Science Foundation of China(32170406)the“Double First-Class”University project(CPU2018GY08).
文摘Elodexanthones A—J (1—10), two pairs of rearranged isoprenylated xanthone enantiomers with an unprecedent 6/6/5/6 tetracyclic core (1—2) along with seven new isoprenylated xanthones (3—9) and a pair of phenylpropanoid xanthones (10), were purified and enantio-separated from the whole plant of Hypericum elodeoides. Their structures including absolute configurations were characterized by the comprehensive analysis of NMR, HRESIMS, NMR calculations, and ECD calculations. Through Bayer-Villiger oxidation, Claisen condensation and electrophilic addition, the rearranged skeletons of elodexanthones A—B (1—2) were generated from isoprenylated xanthone precursors. The bioactivities evaluation exhibited that compounds 3, 5, 8—10 showed anti-inflammatory activity with the IC_(50) values in the range of 9.53—34.39 μmol/L, and compounds 3—7, and 9 showed notable α-glucosidase inhibitory activity (IC_(50): 6.02—257.11 μmol/L).
