A New Isoprenylated flavonol from the Leaves of Broussonetia kazinoki

A new isoprenylated flavonol, named broussonol A (1) was isolated from the leaves of Broussonetia kazinoki Sieb. The structure of broussonol A was characterized by chemical and spectral methods.

Isoprenylated flavonoids and clerodane diterpenoids from Dodonaea viscosa

Phytochemical investigation of the aerial parts of Dodonaea viscosa led to the isolation of six new compounds including four isoprenylated flavonoids,dodovisones A-D(1-4),and two clerodane diterpenoids,dodovislactones A and B(5 and 6).Their structures were established by extensive spectroscopic analysis.

Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata

Three new C-methylated and isoprenylated chalcone derivatives,dentichalcones A–C(1–3),together with six known compounds(4–9),were isolated from the twigs and leaves of Macaranga denticulata.Their structures were elucidated by spectroscopic analysis,including 1D,2D NMR,and MS data.The known compounds,(2E)-1-(5,7-dihydroxy-2,2,6-trimethyl-2H-benzopyran-8-yl)-3-(4-methoxyphenyl)-2-propen-1-one(4),(2E)-1-(5,7-dihydroxy-2,2-dimethyl-2H-benzopyran-8-yl)-3-phenyl-2-propen-1-one(5),laxichalcone(6),macarangin(7),bonanniol A(8),and bonannione A(9),showed inhibitory activities against protein tyrosine phosphatase 1B(PTP1B)in vitro.Graphical Abstract Three new C-methylated and isoprenylated chalcone derivatives,dentichalcones A–C(1–3),together with six known compounds,were isolated from the twigs and leaves of Macaranga denticulata.Some compounds showed inhibitory activities against PTP1B in vitro.

Dearomatized Isoprenylated Acylphloroglucinol Derivatives with Potential Antitumor Activities from Hypericum henryi

A series of dearomatized isoprenylated acylphloroglucinols derivatives,hyperhenols A-E(1-5),as well as seven known analogues(6-12),were characterized from Hypericum henryi.Their structures were determined by combination of NMR,ECD spectroscopy,and X-ray difraction analysis.Compounds 1 and 6-8 were tested to exhibit potential antitumor properties,of which 6 and 7 inhibited cell growth through inducing apoptosis and cell cycle arrest.In addition,these compounds could induce autophagy and PINK1/Parkin-mediated mitophagy in cancer cell lines,as well as suppress lung cancer A549 cells metastasis in vitro.

Diverse Polyphenols from Hypericum faberi

Six new polyphenols with diferent isoprenylated xanthones,isoprenylated acylphloroglucinols,and chromone architectures,hyperfaberols A-F(1-6),were isolated from the whole plants of Hypericum faberi along with seven other related known compounds.In which hyperfaberols A/B(1/2)and 12-13 were isoprenylated xanthones,hyperfaberols C-E(3-5)and 8-11 were seven isoprenylated acylphloroglucinol derivatives,while 6-7 were two chromones.Their structures were elucidated by comprehensive analysis of their spectroscopic data as well as detailed comparison with the literature data.Compounds 1 and 11 showed cytotoxities against the human esophageal cancer cell line(ECA-109)and the pancreatic tumor cell line(PANC-1)in vitro,respectively.

Isoprenylated Flavonoids as Cav3.1 Low Voltage-Gated Ca^(2+)Channel Inhibitors from Salvia digitaloides

Saldigones A-C(1,3,4),three new isoprenylated flavonoids with diverse flavanone,pterocarpan,and isoflavanone architec-tures,were characterized from the roots of Salvia digitaloides,together with a known isoprenylated flavanone(2).Notably,it’s the first report of isoprenylated flavonoids from Salvia species.The structures of these isolates were elucidated by extensive spectroscopic analysis.All of the compounds were evaluated for their activities on Cav3.1 low voltage-gated Ca^(2+)channel(LVGCC),of which 2 strongly and dose-dependently inhibited Cav3.1 peak current.

Plant geranylgeranyl diphosphate synthases: every (gene) family has a story

Plant isoprenoids(also known as terpenes or terpenoids)are a wide family of primary and secondary metabolites with multiple functions.In particular,most photosynthesis-related isoprenoids(including carotenoids and chlorophylls)as well as diterpenes and polyterpenes derive from geranylgeranyl diphosphate(GGPP)produced by GGPP synthase(GGPPS)enzymes in several cell compartments.Plant genomes typically harbor multiple copies of differentially expressed genes encoding GGPPS-like pro-teins.While sequence comparisons allow to identify potential GGPPS candidates,experimental evidence is required to ascertain their enzymatic activity and biologi cal function.Actually,functional analyses of the full set of potential GGPPS paralogs are only available for a handful of plant species.Here we review our current knowledge on the GGPPS families of the model plant Arabidopsis thaliana and the crop species rice(0ryza sativa),pepper(Capsicum annuum)and tomato(Solanum lycopersicum).The results indicate that a major determinant of the biological role of particular GGPPS paralogs is the expression profile of the corresponding genes even though specific interactions with other proteins(including GGPP-consuming enzymes)might also contribute to subfunctionalization.In some species,however,a single GGPPS isoforms appears to be responsible for the production of most if not all GGPP required for cell functions.Deciphering the mechanisms regulating GGPPS activity in particular cell compartments,tissues,organs and plant species will be very useful for future metabolic engineering approaches aimed to manipulate the accumulation of particular GGPP-derived products of interest without negatively impacting the levels of other isoprenoids required to sustain essential cell functions.

Elodexanthones A—J, Isoprenylated Xanthone Derivatives with Diverse Skeletons and Bioactivities from Hypericum elodeoides

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).

Two New Isoprenylated Stilbenes from Artocarpus chama

Two new stllbenes with two Isoprenoid groups, namely artostllbenes A （compound 1） and B （compound 2）, were Isolated from the stems of Arfocarpus chama Buch.-Ham. by repeated column chromatography. The＆ structures were elucldated as （E）-4-[2-（7-meth-xy-2-2-d-methy-6-（3-methy-but-2-eny-）-2H-1-benz-pyran-5-y-）v-ny-]benzene-1- 2-dlol （compound 1） and （Z）-4-[2-（7-meth-xy-2-2-dimethy--6-（3-methy-but-2-eny-）-2H-1-benz-pyran-5-y-）v-ny-]ben- zene-l,2-dlol （compound 2） by spectroscopic methods, mainly by 1D-, 2D-NMR and MS spectra. Compounds 1 and 2 are two cls- and trans-lsomers and compound 2 is the flrst cis-stllbene isolated from Moraceous plants.