Two new diarylheptanoids from the pericarps of Juglans regia L.

Two new cyclic diarylheptanoids juglanin A （1） and juglanin B （2） were isolated from the pericarps of Juglans regia L. Their structures were elucidated by various spectroscopic methods including 2D NMR techniques （COSY, HMQC, HMBC, NOESY） and HR-ESIMS.

Synthetic Studies on Diarylheptanoids──Syntheses of 1,7-Bis(4-Hydroxyphenyl)-1,4,6-Heptatriene-3-One and Acetogenin G

The two new diarylheptanoids, 1,7-bis(4-hydroxyphenyl)-1,4,6 (l) and aecrogenin G (2) were Synthesized starting from 4-hydroxybenzaldehyde (3) and acetone

α-Glucosidase inhibitive diarylheptanoids from Ottelia acuminata var.acuminata,a traditional vegetable of Bai Nationality in Yunnan

Diabetes is an urgent health issue characterized by ethnic and regional variations,and is inseparable from the differ-ent dietary habits.It is worthy to note that the incidence of diabetes in Bai nationality has been reported to be much lower than Han in China.As a daily vegetable of Bai,the phytochemical and antidiabetic study of Ottelia acuminata var.acuminata had not been carried out.In this study,41 metabolites with diverse diarylheptanoid(six new ones,Otteacumienes A-F),flavone,sesquiterpenoid,coumarin,lignan,polyacetylene,and alkaloid skeletons were charac-terized from O.acuminata var.acuminata.Among them,the racemic nature of 3 was characterized by chiral resolution and calculated ECD methods.The biological study revealed diarylheptanoids showed significantα-glucosidase inhibi-tory activities with 5 as the most effective one(60-fold stronger than acarbose).Molecular docking studies indicated that these structures have different binding cavities with acarbose.This study demonstrated that O.acuminata var.acuminata might correlated with the low incidence diabetes of Bai and the diarylheptanoids may have potential therapeutic value for diabetes mellitus.

Two New Diarylheptanoids from the Rhizomes of Zingiber officinale

Two new diaryheptanoids, (5S)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3- heptanone (1) and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane (2) were isolated from the rhizomes of Zingiber officinale. Their structures were elucidated by spectral methods.

Bioactive Diarylheptanoids from Alpinia coriandriodora

Eight new diarylheptanoids,coriandralpinins A-H(1-8),were isolated from the rhizomes of Alpinia coriandriodora,an edible plant of the ginger family.Their structures,including the absolute configurations,were established by extensive spectroscopic analysis and ECD calculations.Compounds 1-8 have a 1,5-O-bridged diarylheptanoid structure featuring polyoxygenated aryl units.When evaluated for intracellular antioxidant activity using t-BHP stressed RAW264.7 mac-rophages,all these compounds scavenged reactive oxygen species(ROS)in a concentration-dependent manner.Compounds 3 and 5 also showed inhibitory activity against NO release in LPS-induced RAW 264.7 cells.Six known flavonols,7,4′-di-O-methylkaempferol,7-O-methylquercetin,7,4′-di-O-methylquercetin,7,3′,4′-tri-O-methylquercetin,kaempferol 3-O-β-d-(6-O-α-l-rhamnopyranosyl)glucopyranoside,and 3-O-β-d-glucopyranuronosylquercetin were also isolated and characterized from the rhizomes.

Four new diarylheptanoids and two new terpenoids from the fruits of Alpinia oxyphylla and their anti-inflammatory activities

Four previously unreported diarylheptanoids(1a/1b-2a/2b),one undescribed sesquiterpenoid(8),one new diterpenoid(12),and twelve known analogs were isolated from the fruits of Alpinia oxyphylla.The structural elucidation of these compounds was achieved through a comprehensive analysis of spectroscopic data,single-crystal X-ray diffraction,electronic circular dichroism(ECD),and modified Mosher's method.Enantiomeric mixtures(1a/1b,2a/2b,3a/3b,4a/4b,and 5a/5b)were separated on a chiral column using acetonitrile-water mixtures as eluents.Among them,compounds 3a/3b and 4a/4b were isolated as optically pure enantiomers in the initial chiral separation.Furthermore,most of the isolates were evaluated for their inhibitory effects against the production of nitric oxide(NO)and interleukin-6(IL-6)in lipopolysaccharide(LPS)-induced RAW264.7 macrophages.Interestingly,2 and 4 showed significant inhibitory activities against NO production with IC50 values of 33.65 and 9.88μmol·L^(-1)(hydrocortisone:IC_(50)34.26μmol·L^(-1)),respectively.Additionally,they also partially reduced the secretion of IL-6.

Diarylheptanoids from the root bark of Juglans cathayensis

A new diarylheptanoid glucoside,（8R,9R）-17-methoxy-2-oxatricyclo[13.2.2.1^（3.7）]icosa-l（17）,3（20）,4,6, 15,18-hexaene-4,9,10-triol-9-O-β-D-glucopyranoside（1）,namely jugcathayenoside,together with two known diarylheptanoids,（＋）-galeon（2） and 4-hydroxy-17-methoxy-2-oxatricyclo[13.2.2.1^（3,7） ]icosa-1（17）,3（20）,4,6,15,18-hexaene-9-one（3）,were isolated from the root bark of Juglans cathayensis. Their structures were elucidated on the basis of extensive spectroscopic data analysis.

Antioxidant and Cytotoxic Diarylheptanoids Isolated from Zingiber officinale Rhizomes

One new diarylheptanoid, namely （4E,6E）-7-（3,4-dihydroxy-5-methoxyphenyl）-1-（4-hydroxy-3-methoxyphenyl）- hepta-4,6-dien-3-one （1）, was isolated from the rhizomes of Zingiber officinale, along with ten known ones, tetra- hydrocurcumin （2）, curcumin （3）, 5-hydroxy-1,7-bis（4-hydroxy-3-methoxyphenyl）heptan-3-one （4）, gingerenone A （5）, 7-（3,4-dihydroxyphenyl）-5-hydroxy-1-（4-hydroxy-3-methoxyphenyl）heptan-3-one （6）, （E）-1,7-bis（4-hydroxy- 3-methoxyphenyl）hept-1-ene-3,5-dione （7）, （E）-7-（4-hydroxy-3-methoxyphenyl）-1-（4-hydroxyphenyl）-hept-l-ene- 3,5-dione （8）, shogasulfonic acid A （9）, 1,5-epoxy-3-hydroxy-1-（3,4-dihydroxy-5-methoxyphenyl）-7-（4-hydroxy-3- methoxyphenyl）heptane （10）, and （3S, SS）-3,5-diacetoxy-1,7-bis（3,4-dihydroxyphenyl）heptane （11）. Their structures were elucidated on the basis of spectral evidence and comparisons with literature data. The free radical scavenging activity of 1--11 was evaluated by the 1,l-diphenyl-2-picrylhydrazyl （DPPH） assay. Most of the isolated com- pounds were found to be better antioxidants than the positive control ascorbic acid. These compounds were also evaluated for their cytotoxicity against HeLa and MNK-45 cells using the MTT assay. Our results suggest that com- pounds 3 and 5-8 inhibited HeLa cells, and 3, 5, 7 and 8 inhibited MNK-45 cells. It was found that compound 5 was markedly cytotoxic against HeLa and MNK-45 cell lines with ICs0 values of 6.4 and 7.8 μmol/L, respectively.

Two new cyclic diarylheptanoids from the stems of Ostryopsis nobilis

Two new cyclic diarylheptanoids named ostryopsitrienol（1） and ostryopsitriol（2）,together with six known compounds,were isolated from the stems of endemic medicinal plant of Ostryopsis nobilis （Betulaceae）.The structures of the new compounds were elucidated by means of HRMS,~1D NMR,~2D NMR and X-ray crystallography analysis.

A New Antioxidant Cyclic Diarylheptanoid from the Rhizomes of Zingiber officinale

The bioassay was directed to the fractionation of the methanol extract of the rhizomes of Zingiber officinale Roscoe leading to the isolation of a new antioxidant cyclic diarylheptanoid. The structure of the new compound was established as 1, 5-epoxy-3-hydroxy-1-(3,4-dihydroxy-5-methoxy-phenyl)-7-(3,4-dihydroxyphenyl) heptane (1) on the basis of MS, 1D and 2D-NMR experiments.

Diarylheptanoid-myricanone isolated from ethanolic extract of Myrica cerifera shows anticancer effects on HeLa and PC3 cell lines:signalling pathway and drug-DNA interaction

OBJECTIVE： To test if myricanone （02H2405）, a cyclic diarylheptanoid, has anticancer effects on two different cancer cell lines HeLa and PC3. The present study was conducted with a note on the drug-DNA interaction and apoptotic signalling pathway. METHODS： Several studies like cytotoxicity, nuclear damage, annexin-V-fluorescein isothiocyanate （FITC）/propidium iodide （PI）-Iabelled apoptotic assay and cell cycle arrest, immunoblot and reverse transcriptase-polymerase chain reaction （RT-PCR） were used following standard protocols. Circular dichroism （CD） spectroscopy was also done to evaluate whether myricanone effectively interacted with DNA to bring about conformational changes that could strongly inhibit the cancer cell proliferation. RESULTS： Myricanone showed a greater cytotoxic effect on PC3 cells than on HeLa cells. Myricanone promoted G0/G arrest in HeLa cells and S phase arrest in PC3 cells. Nuclear condensation and annexin V-FITC/PI studies revealed that myricanone promoted apoptotic cell death. CD spectroscopic data indicated that myricanone had an interaction with calf thymus DNA that changed DNA structural conformation. RT-PCR and immunoblot studies revealed that myricanone activated the apoptotic signalling cascades through down-regulation of transcription factors like nuclear factor-KB （NF-KB） （p65）, and signal transducers and activators of transcription 3 （STAT3）; cell cycle regulators like cyclin D1, and survivin and other signal proteins like Bcl-2 and up-regulation of Bax, caspase-9 and caspase-3. CONCLUSION： Myricanone induced apoptosis in both types of cancer cells by triggering caspase activation, and suppression of cell proliferation by down-regulation of NF-KB and STAT3 signalling cascades, which makes it a suitable candidate for possible use in the formulation of therapeutic alent for combatin cancer.

Synthesis of Gingerenone C and 5-Hydroxy-1-(4′-hydroxy-3-methoxyphenyl)-7-(4′′-hydroxyphenyl)-3-heptanone

The two diarylheptanoids (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4- hydroxyphenyl)-3-heptanone 2 were synthesized from vanillin 3 and 4-hydroxybenzaldehyde 9.

A new diarylheptanoid from the bark of Myrica rubra

A new diarylheptanoid, 3,5-dimethoxy1-17-hydroxyl-4, 11, 19-triketo-[7,0]meta-cyclophane, named as rubanone 1, was isolated from the bark of Myrica rubra along with four known compounds 2-5. Their structures were elucidated by various spectroscopic methods including 2D-NMR techniques or comparison with authentic samples.

A novel diarylheptanoid bearing flavonol moiety from the rhizomes of Alpinia officinarum Hance

A novel diarylheptanoid bearing flavonol moiety,named officinin A(1),along with two known compounds galangin and kaempferide were isolated from the rhizomes of Alpina officinarum Hance.The structure elucidation was accomplished by HRESI -MS,1D and 2D NMR methods.

Two new compounds from Zingiber officinale

A new cyclic diarylheptanoid, 1,5-epoxy-3-hydroxy-1-（3-methoxy-4,5-dihydroxyphenyl）-7-（4-hydroxyphenyl）-heptane （1）, as well as a new monoterpene, 10-O-β-n-glucopyranosyl-hydroxy cineole （2） were isolated from the rhizomes of Zingiber officinale. The structures of compounds 1 and 2 were established based on their spectral data. In addition, the antioxidant activities of these compounds were also measured.

Chemical constituents from the aerial parts of Musella lasiocarpa

Phytochemical investigation of the aerial parts of the monotypic plant,Musella lasiocarpa,led to the isolation of four rare bicyclic diarylheptanoids,musellarins B-E(2-5),two new phenylphenalenones,2-methoxy-9-(3′,4′-dihydroxyphenyl)-1H-phenalen-1-one(9),2-methoxy-9-(3′-methoxy-4′-hydroxyphenyl)-1H-phenalen-1-one(10),a new acenaphtylene derivative,trans-(1S,2S)-3-(4′-methoxyphenyl)-acenaphthene-1,2-diol(13),and two new sucrose esters,1,2′,3′,4′,6′-O-pentaacetyl-3-O-trans-p-coumaroylsucrose(16),1,2′,3′,4′,6′-O-pentaacetyl-3-O-cis-p-coumaroylsucrose(17),together with nine known compounds.In addition,(4E,6E)-1-(3′,4′-dihydroxyphenyl)-7-(4′′-hydroxyphenyl)-hepta-4,6-dien-3-one(15)was isolated for the first time from a natural source.The structures of new compounds were elucidated by analysis of their spectroscopic data.Compounds 2,6,8-10,12,and 14 were cytotoxic toward several of the human tumor cell lines(HL-60,SMMC-7721,A-549,MCF-7,and SW480).Of these,the new compound 9 was the most potent one,with IC50 values of 5.8,10.3,6.3,3.3,and 2.3μM,respectively.

Pterocarine, a New Diarylheptanoid from Pterocarya tonkinesis, its Cell Cycle Inhibition at G_0/G_1 Phase and Induction of Apoptosis in HCT-15 and K562 Cells

Pterocarine (1), a new diarylheptanoidal compound, was isolated from Pterocaryatonkinesis (Franch.) Dode. together with a known diarylheptanoid, myricatomentogenin (2), througha bioassay-guided fractionation procedure. The structure of 1 was elucidated as (+)-3', 4''-epoxy-1-(4'-hydroxyphenyl)-7-(3''-hydroxyphenyl)-heptane-3-one by the spectroscopic methods.Pterocarine (1) inhibited the proliferation of tsFT210, HCT-15 and K562 cells with the inhibitionrates of 20.2±2.4, 23.8±2.4 and 50.5±1.2% at 100 μg/mL, respectively. Flow cytometric analysisindicated that 1 could inhibit the cell cycle of tsFT210, HCT-15 and K562 cells at the G0/G1 phaseand could also induce apoptosis in HCT-15 (19%) and K562 (11%) cells.

New Diarylheptanoid from the Barks of Alnus japonica Steudel

A new diarylheptanoid glycoside, 1,7-bis-（3,4-dihydroxyphenyl）-5-hydroxyheptane- 3-O-β-D-xylopyranoside （1）, together with nine known diarylheptanoids （2-10） were isolated from the fresh bark of Alnus japonica which is a species of the genus Alnus species, growing throughout Korea.

Molecular basis of the anti-inflammatory potential of a diarylheptanoid in murine macrophage RAW 264.7 cells

Natural products play a significant role in human health in relation to the prevention and treatment of inflammatory disorders. In this study, we examined the molecular basis of the anti-inflammatory potential of a diarylheptonoid (DAH) isolated from Alpinia officinarum hexane extract (AOHE) with special emphasis on their ability to modulate the nuclear factor-κB (NF-кB) signaling involved in the inflammatory response. Measurement of Nitrite by Griess reaction which revealed the effect of DAH in RAW 264.7 macrophages showed an inhibition in the nitric oxide production through the suppression of inducible nitric oxide synthase (iNOS) gene level expression. NF-кB reporter gene assay suggests inhibition of NF-кB transcriptional activity, thus inhibiting LPS-induced phosphorylation and degradation of IкBα and a downregulation of NF-кB protein expression confirms the immunomodulatory effect of DAH. Furthermore, downregulation in the gene level expression of NF-кB signaling markers such as IL-1β, TNF-α and COX-2 suggests the anti-inflammatory potential of DAH via inhibition of NF-кB activation.

Identification and characterization of major constituents in Juglans mandshurica using ultra performance liquid chromatography coupled with time-of-flight mass spectrometry(UPLC-ESI-Q-TOF/MS)

The present study was designed to identify and characterize the major constituents in Juglans mandshurica Maxim. A simple, efficient and sensitive ultra performance liquid chromatography coupled with time-of-flight mass spectrometry(UPLC-ESIQ-TOF/MS) method was established and validated under positive and negative ion modes. The separation was performed on a Waters ACQUITY UPLC BEH C18 column(2.1 mm × 100 mm, 1.7 μm) by gradient elution with a mobile phase(Phase A: 0.1% aqueous formic acid solution, Phase B: 0.1% formic acid acetonitrile solution). A total of 165 compounds were rapidly selected by Targeted and Non-Targeted Peak Finding approaches, and then tentatively identified by comparing with reference substances or inferred through mass spectrometry fragment ion analysis and literature data. These compounds included 68 naphthalenequinones, 20 diarylheptanoids, 29 flavonoids, 20 triterpenes, and 28 phenolic acids. In conclusion, the present study provided an effective approach to identifying components in complex matrices of herbal medicines such as Juglans mandshurica Maxim.