Aromatic acid derivatives from the lateral roots of Aconitum carmichaelii

Seven new aromatic acid derivatives (1–7), together with five known analogs, were isolated from the lateral roots of Aconitum carmichaelii. Structures of the new compounds were determined by spectroscopic and chemical methods as 4-methyl ( ? )-(R)-hydroxyeucomate (1), 4-butyl ( ? )-(R)-hydroxyeucomate (2), 4-butyl-1-methyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (3), 1-butyl-4-methyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (4), dimethyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (5), dimethyl (+)-(R)-2-O-(4′-hydroxybenzoyl)malate (6), and methyl ( ± )-3-(4′-hydroxy-3′-methoxyphenyl)-3-sulfopropionate (7), respectively. Compounds 1 and 2 are 2-benzylmalates (eucomate derivatives), 3–6 belong to 2-O-benzoylmalates, and 7 is a rare phenylpropionate containing a sulfonic acid group. The absolute configurations of eucomate derivatives were confirmed by X-ray crystallographic analysis of 4-methyl eucomate (11).     

Ceramides and cerebrosides from the marine bryozoan Bugula neritina inhabiting South China Sea

From the marine bryozoan Bugula neritina inhabiting South China Sea, a new ceramide named (2S,3R,4E)-2-(14′-methyl-pentadecanoylamino)-4-octadecene-l,3-diol (1) and a new cerebroside named 1-O-(β-d-glucopyranosyl)-(2S,3R,4E)-2-(heptadecanoylamino)-4-octadecene-l,3-diol (6), together with one known ceramide (2) and three known cerebrosides (3, 4, and 5), were isolated. Their structures were deduced by extensive spectral analysis and chemical evidences. Compound 1 is branched with a methyl [–CH(CH₃)₂] in the fatty acid moiety, which is a rare structural feature among ceramides. Compound 6 is a new cerebroside with 17 carbons in the fatty acid moiety, while 5 is a new natural product which was isolated from a natural origin for the first time.     

Minor dammarane saponins from the hongshen extract of Shenmai injection

A new dammarane-type triterpenoid saponin, (20R)-ginsenoside ST₂ (1), along with five known saponins was isolated from the hongshen extract of Shenmai injection. The structure of 1 was elucidated to be (20R)-dammar-23(E)-ene-3β,6α,12β,20,25-pentol 6-O-β-d-glucopyranoside by means of spectroscopic methods.     

白芍中的一种新的单萜苷

目的研究中药白芍的化学成分。方法用现代色谱分离方法进行化学成分分离,并通过理化性质和各种色谱学分析鉴定化合物的结构。结果从中药白芍中分离得到一种苷元与葡萄糖2位相连成苷的单萜苷类化合物白芍苷R₁。 结论白芍苷R₁是一新化合物。     

Pharmacokinetic properties of albiflorin and paeoniflorin after oral administration of pure compound,Radix Paeoniae alba extract and Danggui-Shaoyao-San extract to rats

This study compared the pharmacokinetics of albiflorin (ALB) and paeoniflorin (PAE), respectively, after oral administration of ALB, PAE, Radix Paeoniae alba (RPA) extract, and Danggui-Shaoyao-San (DSS) extract to rats on separate occasions. Analytes were detected simultaneously with liquid chromatography-tandem mass spectrometry. Noncompartmental pharmacokinetic parameters were calculated. After oral administration of RPA and DSS extract to rats, ALB reached maximum concentrations of 4637 ± 2774 ng/ml (0.40 ± 0.14 h) and 226 ± 122 ng/ml (0.35 ± 0.14 h) and PAE reached maximum concentrations of 2132 ± 560 ng/ml (0.40 ± 0.14 h) and 143 ± 65 ng/ml (0.45 ± 0.11 h), respectively. Compared to the AUC_0 ? t value (1122 ± 351 and 722 ± 158 ng h/ml for ALB and PAE, respectively) after administration of monomers, larger AUC_0 ? t value of ALB (4755 ± 2560 ng h/ml) and PAE (2259 ± 910 ng h/ml) after administration of RPA extract and smaller AUC_0 ? t value of ALB (411 ± 118 ng h/ml) and PAE (242 ± 126 ng h/ml) after administration of DSS extract were obtained. The C _max, AUC, and K _el of ALB and PAE were remarkably increased (P < 0.05, 0.01 or 0.005) during oral administration of RPA extract in comparison to that of DSS extract.     

Note: A new compound from Rhododendren anthopogonosides maxim

A new compound, (2R)-4-phenyl-2-O-[β-d-xylopyranosyl(1→6)-β-d-glucopyranosyl]butane (1), has been isolated from the aerial parts of Rhododendren anthopogonoides, together with two known compounds, fraxin (2), and lyoniside (3). Their structures were determined by means of physico-chemical evidence and spectral analyses, including UV, IR, HR-FABMS, ¹H and ¹³C NMR, and 2D NMR data.     

A new triterpenoid from <Emphasis Type="Italic">Panax ginseng</Emphasis> exhibits cytotoxicity through p53 and the caspase signaling pathway in the HepG2 cell line

A new triterpenoid, 20(R),22(ξ),24(S)-dammar-25(26)-ene-3β,6α,12β,20,22,24-hexanol (1), and three known triterpenoids, β-D-glucopyranoside,(3β,12β)-12,20-dihydroxydammar-24-en-3-yl,6-acetate (2), 20(R)-ginsenoside Rg₃ (3), and 20(R)-ginsenoside Rh₂ (4), were isolated from the leaves of Panax ginseng. Their structures were determined by chemical analysis and spectral methods (IR, 1D and 2D NMR, HR-ESI-MS). Compounds 1–4 were exhibited various degrees of cytotoxicity in the human hepatoma cell line, HepG2. Compound 1 had the highest cytotoxic potency, with an IC₅₀ value of 20.1 μM, by stimulating p53-mediated cell cycle arrest at the G1 to S phase transition, leading to apoptosis via activation of the caspase signaling pathway.     

Two pairs of phenylpropanoid enantiomers from the leaves of Eucommia ulmoides

Abstract

Two pairs of phenylpropanoid enantiomers, (+)-(7S,8S)-alatusol D (1a), (?)-(7R,8R)-alatusol D (1b), (?)-(7S,8R)-alatusol D (2a) and (+)-(7R,8S)-alatusol D (2b) were isolated from the leaves of Eucommia ulmoides Oliver. Among them, 1a and 2b were firstly obtained by chiral enantiomeric resolution. Their structures were elucidated based on extensive spectroscopic analysis and the induced CD (ICD) spectrum caused by adding Mo₂(AcO)₄ in DMSO. All compounds were tested on Hep G2 tumor cell lines. However, none of the compounds showed potential cytotoxic activity against Hep G2 in vitro.     

A new chromone and a new aliphatic ester isolated from Daldinia eschscholtzii

Abstract

A new chromone and a new aliphatic ester were isolated from the EtOAc extract of myceliums of Daldinia eschscholtzii. Their structures were elucidated as (R)-5-hydroxy-8-methoxy-2-methylchroman-4-one (1) and (E)-6-(non-3-en-1-yl) -2H-pyran-2-one (2) by interpretation of the spectroscopic evidence.     

Two novel dammarane-type compounds from the leaves and stems of Panax quinquefolium L.

Two new dammarane-type compounds were isolated from the leaves and stems of Panax quinquefolium L. The new compounds were named as pseudo-ginsenoside RT₆ (1) and pseudoginsengenin R₁ (2). The structures of the new compounds were elucidated by the combined analysis of NMR and HR-ESI-MS as (20S,24R)-6-O-β-d-glucopyranosyl-dammar-3-one-20,24-epoxy-6α,12β,25-triol (1) and (20S,24R)-dammar-3-one-20,24-epoxy-6α,12β,25-triol (2).     

Two novel flavanes from the leaves of Morus alba L.

Two new flavanes, (2R,4S)-2′,4′-dihydroxy-2H-furan-(3″,4″:8,7)-flavan-4-ol (1) and (2S)-2′,4′-dihydroxy-7-methoxyl-8-butyricflavane (2), together with four known flavonoids, were isolated from the leaves of Morus alba L. Their structures were determined on the basis of spectroscopic analysis.     

A bisamide and four diketopiperazines from a marine-derived Streptomyces sp.

A new bisamide N ₁-acetyl-N ₇-phenylacetyl cadaverine (1) and a series of diketopiperazines including a new diketopiperazine cyclo(2-hydroxy-Pro-R-Leu) (2), together with a new natural product cyclo(4-hydroxy-S-Pro-S-Trp) (3) and two known leucine-based diketopiperazines cyclo(4-hydroxy-R-Pro-S-Leu) (4) and cyclo (S-Pro-R-Leu) (5), were isolated from ethyl acetate extract of a fermentation broth of a marine-derived Streptomyces sp. Their structures were elucidated by the interpretation of spectroscopic analysis. The antitumor activities of compounds 1–3 against HL-60 cell lines were tested by MTT assay.     

经典名方芍药甘草汤解痉功效的关键质量属性研究

目的 基于血清药物化学、网络药理学和体外实验验证，阐明芍药甘草汤(Shaoyao-Gancao decoction，SGD)治疗痉挛性疾病的关键质量属性。方法 采用UHPLC-Q-Exactive Orbitrap MS技术对SGD体内入血移行成分进行分析鉴定；利用Cytoscape构建“入血成分-解痉靶点-通路”网络图，筛选SGD解痉核心功效成分；通过离体肠平滑肌实验对核心成分进行验证，明确SGD解痉功效的关键质量属性。结果 据高分辨质谱提供的精确分子量和碎片离子信息，结合对照品比对和相关文献报道，共鉴定出17个SGD入血原型成分，分别为氧化芍药苷、芍药内酯苷、芍药苷、异甘草苷、甘草苷、甘草酸、苯甲酰芍药苷、甘草查尔酮B、芒柄花苷、异甘草素、甘草素、甘草查尔酮A、甘草查尔酮C、光甘草定、甘草次酸、没食子酸。网络药理学预测SGD中光甘草定、甘草素、芍药内酯苷、芍药苷和苯甲酰芍药苷度值较高，可能通过GRIN2A、VCP、ABCB1、CYP2C9、CYP3A4、CHRNB2、SNCA等靶点，作用于药物代谢-细胞色素P450、神经活性配体-受体相互作用、cAMP、钙信号通路等发挥解痉作用。生物活性测定结果表明，芍药苷、甘草素、芍药内酯苷、光甘草定和苯甲酰芍药苷均可降低乙酰胆碱(acetylcholine，Ach)引起的离体肠平滑肌收缩张力，是SGD解痉功效的关键质量属性，其中芍药苷和甘草素解痉效果较强，与Ach模型组比较，差异具有统计学意义(P<0.05或P<0.01)。结论 本实验构建经典名方芍药甘草汤关键质量属性筛选方法，明确SGD解痉功效的关键质量属性，为SGD的精准质量控制及其产品二次开发提供实验依据。     

Three new flavanoids from artificially induced dragon’s blood of Dracaena cambodiana

Three new flavanoids, (2R)-7,4′-dihydroxy-8-methylflavan (1), (2R)-7,4′-dihydroxy-6-methylflavan (2), and (3R)-7,3′,4′-trihydroxyhomoisoflavan (3), together with seven known compounds (4–10), were isolated from artificially induced dragon’s blood of Dracaena cambodiana, and their structures were determined based on HR-ESI-MS and extensive spectroscopic techniques (UV, IR, 1D-, and 2D-NMR). Compound 2 exhibited weak cytotoxicity against BEL-7402 cells line with the IC₅₀ value of 39.2 μM. In addition, compound 3 showed significant acetylcholinesterase (AChE) inhibitory activity.     

Triterpenoids from the roots ofRubus parvifolius

From the roots ofRubus parvifolius L., four triterpenoidal sapogenins, ursolic acid1, 2α-hydroxyursolic acid2, euscapic acid3, 2α, 3β, 19α-trihydroxyurs-12-en-23,28-dioic acid4 and one triterpenoidal glycoside, suavissimoside R₁ 5, were isolated. The structures were elucidated by spectroscopic methods and chemical transformations. Compound4 was first isolated as free form.     

Two new dammarane-type triterpene saponins from red American ginseng

Two new dammarane-type triterpene saponins were isolated from the red American ginseng. The new saponins were named as pseudoginsenoside G₁ (1) and pseudoginsenoside G₂ (2). Their structures were elucidated by the combined analysis of NMR and mass spectrometry as 3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl]-dammar-12-one-20S,24R-epoxy-3β,25-diol (pseudoginsenoside G₁) (1) and 3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl]-dammar-12-one-20S,24S-epoxy-3β,25-diol (pseudoginsenoside G₂) (2).     

白芍单萜苷成分与生物合成相关基因的时空表达特性及其相关性研究

目的 揭示白芍不同发育时期不同组织部位中单萜苷含量及其生物合成基因的表达差异和两者之间的相关性。方法 通过HPLC测定白芍叶、花、果、根及根中不同部位(韧皮部、木质部、须根和根皮)在不同发育时期氧化芍药苷、白芍内酯苷、芍药苷和苯甲酰芍药苷含量。采用RT-PCR对筛选出来的8个白芍单萜苷生物合成相关基因进行相对含量测定。应用R语言分析4种单萜苷含量与各生物合成相关基因表达量的相关性。结果 芍药苷和苯甲酰芍药苷主要分布于根中,而氧化芍药苷和白芍内酯苷主要分布于花中。氧化芍药苷、芍药苷和苯甲酰芍药苷主要分布于木质部中,白芍内酯苷主要在韧皮部和须根。4种单萜苷成分在根中花期和果期含量均较低,在黄枯期中最高,展叶期次之。单萜苷含量与其关键酶基因表达量相关性分析结果表明,HMGR2和IDI基因与芍药苷、苯甲酰芍药苷和氧化芍药苷含量呈高度正相关。结论 白芍单萜苷及其生物合成相关基因存在时空特异表达模式,甲羟戉酸途径是白芍中生物合成萜类骨架的主要途径。     

Isolation of megastigmane sesquiterpenes from the silkworm (<Emphasis Type="Italic">Bombyx mori</Emphasis> L.) droppings and their promotion activity on HO-1 and SIRT1

The silkworm (Bombyx mori L.) droppings were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned in succession with EtOAc, n-BuOH, and H₂O. From the EtOAc fraction, five megastigmane sesquiterpenes were isolated through repeated silica gel and ODS column chromatography. According to the results of spectroscopic data, such as NMR, MS, and IR, the chemical structures of the isolated compounds were determined as (3S,5R,8R)-3,5-dihydroxymegastigma-6,7-dien-9-one (1), (S)-dehydrovomifoliol (2), (6R,7E,9R) -9-hydroxy-4,7-megastigmadien-3-one (3), (3S,5R,6S,7E)-3,5,6-trihydroxy-7-megastigmen-9-one (4), (6R,9R)-9-hydroxy-4-megastigmen-3-one (5). Compounds 2 through 5 were isolated for the first time from silkworm droppings. GC/MS analysis indicated silkworm powder contained compound 3, and mulberry leaves contained compound 4. Compounds 1 and 5 increased the expression of heme oxygenase-1 and SIRT1 in HepG2 and HEK239 cells, respectively. Heme oxygenase-1 is considered to be an antioxidant enzyme that catabolizes heme to carbon monoxide, free iron and biliverdin, while SIRT1 is the mammalian homologue of the yeast silent information regulator (Sir)-2, which are involved in the suppression of inflammatory mediators or factors that may be used to improve atopy-related symptoms.     

Indoloquinazoline alkaloids from Euodia rutaecarpa and their cytotoxic activities

Nine indoloquinazoline alkaloids (1–9) were isolated from the dried and nearly ripe fruits of Euodia rutaecarpa (Juss.) Benth. (Euodiae Fructus), along with limonin and β-sitosterol. Their structures were elucidated on the basis of their spectroscopic data. Among them, compounds 1 and 2 were new compounds and characterized as (7R,8S)-7-hydroxy-8-methoxy-rutaecarpine and (7R,8S)-7-hydroxy-8-ethoxy-rutaecarpine, respectively, and 1-hydroxy-rutaecarpine (3) and (7R,8S)-7,8-dihydroxy-rutaecarpine (4) were isolated from Euodiae Fructus for the first time. The nine indoloquinazoline alkaloids were evaluated for their cytotoxic activities against human promyelocytic leukemia HL-60 cells and human gastric carcinoma N-87 cells.