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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

白桦皮化学成分与药理作用的研究进展

白桦皮为桦木科植物白桦(Betula platyphylla)的干燥树皮,含有多种化学成分,包括三萜类、芳基丁烷及二芳基庚烷类、黄酮类、木脂素类、甾体类等。三萜类和芳基丁烷及二芳基庚烷类为白桦皮的主要成分。三萜类包括羽扇豆烷型、乌苏烷型、齐墩果烷型和达玛烷型,其含量会随着季节的变化而呈现出显著差异。白桦皮具有广泛的药理作用,包括祛痰止咳、保肝、抗肿瘤、抗氧化等。国内外对白桦皮的报道聚焦于研究白桦皮的三萜类、芳基丁烷及二芳基庚烷类化学成分及药理作用,为了更好地开发和利用白桦皮资源,有必要进一步挖掘其他化学成分的功效,同时深入研究三萜类、芳基丁烷及二芳基庚烷类化合物药理作用、作用机制及构效关系等。

山姜属二苯基庚烷类化合物及其生物活性研究进展

山姜属(Alpinia)为姜科中药的主要药用植物来源,该属包含高良姜、益智、草豆蔻等多种传统中药。目前,研究者从山姜属的药用植物中发现数量众多且结构新颖的二苯基庚烷类化合物,该类型化合物是山姜属植物的代表性成分类型之一,其具有广泛的药理活性,包括抗氧化、抗肿瘤、抗炎、降血糖、抗病毒等。本文对山姜属中二苯基庚烷类化合物的结构和生物活性进行了总结,以化合物类型对结构进行分类,归纳讨论了无环直链二苯基庚烷、环氧二苯基庚烷、二苯基庚烷二聚体、二苯基庚烷-单萜聚合体和二苯基庚烷-黄酮聚合体的结构特征和他们的主要药理作用,以期为该属植物的开发利用提供参考。

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.

中药益智化学成分的研究

目的 :研究中药益智AlpiniaoxyphyllaMiq .的化学成分。 方法 :利用各种色谱技术进行分离纯化 ,根据化合物的理化性质和光谱数据进行结构鉴定 ;用GC MS联机技术鉴定挥发油的化学成分。结果 :从益智分得 10种化合物 ,其中 2个二芳基庚酮 :yakuchinoneA ( 1)、益智醇 (oxyphyllacinol 2 ) ,3个eremophilane烷碳架的倍半萜valencene ( 3 )、nootkanone ( 4 )、nootkanol ( 5 ) ,两个黄酮 :杨芽黄酮 (tectochrysin 6)、白杨素 (chrysin 7) ,以及 β 谷甾醇( 8)、胡萝卜苷 ( 9)和脂肪酸 ( 10 )。用GC MS鉴定了挥发油中 64个化学成分 ,其中含量较高的有 :p cymene( 4 4 87% ) ,valencene ( 9 13 % ) ,linalool ( 4 3 9% ) ,myrtenal ( 3 90 % ) ,β pinene ( 3 87% ) ,α pinene ( 2 93 % ) ,furopelargone ( 2 62 % ) ,terpinen 4 ol( 2 5 6% )等。 结论 :益智醇 ( 2 )为新二芳基庚醇 ,其化学结构为 1 ( 4′ hyroxy 3′ methoxy phenyl) 7 phenyl 3 heptanol,3 ,6和

天然线性二芳基庚烷类化合物

本文对目前已发现的天然线性二芳基庚烷类化合物在植物中的分布及其结构特征、生源合成途径和药理学研究进展作一简要的综述。

干姜中的二芳基庚烷类化合物及其在四逆汤煎煮过程中的立体选择性反应

采用高效液相色谱多级质谱联用鉴定了干姜水煎剂的18个二芳基庚烷类化合物。发现此类化合物的电喷雾质谱碰撞诱导裂解反应的特征主要表现在吡喃环的次级逆Diels Alder反应裂解或C1和C5OH发生次级麦氏重排裂解,这两种裂解反应对归属芳环的取代非常重要。比较了复方四逆汤配伍对二芳基庚烷类化合物的影响,从色谱保留行为、质谱数据等推测化合物2-(3,4-二羟基-5-甲氧基苯基)-6-(3,4-二羟基苯乙基)-2氢-吡喃-4-醇(Ⅲ-1)的一组差向异构体,2-(3,4-二羟基-5-甲氧基苯基)-6-(4-羟基苯乙基)-2氢-吡喃-4-醇(Ⅲ-2)的一组差向异构体以及2-(3,4-二羟基-5-甲氧基苯基)-6-(4-二羟基-3-甲氧基苯乙基)-2氢-吡喃-4-醇(Ⅲ-3)的2组差向异构体在复方煎煮过程中发生显著的立体选择性反应,由外消旋体变成单一旋光异构体。吡喃环4-位的乙酰化可能是减少这种反应的关键因素。

天然二芳基庚烷类化合物的化学修饰及生理活性研究

中药高良姜（Ａｌｐｉｎｉａ ｏｆｆｉｃｉｎａｒｕｍ Ｈａｎｃｅ）主要有效成分二芳基庚烷类化合物１，７－二苯基－５－醇－３－庚酮、１－苯基－７－（３＇苯基－７（３＇－甲氧基－４＇－羟基）苯基５－醇－３－庚酮，经化学还原和乙酰化修饰后得到新的系列二芳基庚烷衍生物１，７－二苯基－５－乙酰氧基－３－庚酮．１－苯基－３－庚酮．１－苯基－７（３＇甲氧基－４＇－乙酰氧基）苯基－５－乙酰氧基－３－庚酮、１．７二苯基－３，５－庚二醇、１－苯基－７－（３＇－甲氧基－４＇－羟基）苯基－３，５－庚二醇、１．７－二苯基－３．５－二乙酰氧基庚烷、１－苯基－７－（３’甲氧基－４’－乙酰氧基）苯基－３，５－二乙酰氧基庚烷，并研究了它们的生理活性。

天然产物中环状二芳基庚烷类化合物的研究进展

环状二芳基庚烷类化合物是一类广泛分布于核桃属、桤木属、杨梅属、嘉榄属等植物中的天然产物化学成分。大量的研究表明该类化合物具有抗炎、清除自由基、抗氧化、抗肿瘤、调节免疫功能等多种药理作用。综述了天然产物中环状二芳基庚烷类化合物的化学结构、光谱学鉴定特征、植物分布、生源合成途径和药理活性研究进展,为该类化合物研究、开发和应用提供一定参考。