Anti-oxidative action of ent-kaurene diterpenoids

Nine ent-kaurene diterpenoids, leukamenin E, glaucocalyxin A, wangzaozi A, epinodisinol, epinodosin, rabdosin B, rabdosinate, lasiokaurin and oridonin, were separated from Isodon racemosa (Hemsl) Hara and Isodon japonica (Burm.f) Hara var. galaucocalyx (maxin). The protection against DNA damage induced by hydrogen peroxide in human peripheral blood mononuclear cells (PBMCs) and inhibition of lipid peroxidation in rat liver microsome were studied with comet assay and thiobarbituric acid reactive substances determination. All nine diterpenoids showed concentration-dependent protection in DNA damage in human PBMCs induced by 50 μM H₂O₂. The effects were similar and weaker than quercetin. The inhibitions of lipid peroxidation were obviously difference. Rabdosin B and oridonin were the strongest inhibitors, followed by lasiokaurin and wangzaozin A. Rabdosinate was the weakest and others were medium. The structure-activity relationship is discussed.     

Simultaneous determination of glaucocalyxin A and glaucocalyxin B in rat plasma by LC‐MS/MS and its application to a pharmacokinetic study after oral administration of Rabdosia japonica extract

A specific and sensitive liquid chromatography tandem mass spectrometry (LC‐MS/MS) method was developed and validated for the analysis of glaucocalyxin A and glaucocalyxin B in rat plasma using praeruptorin A as an internal standard. Separation was performed on a Hypurity C₁₈ column (2.1 × 50 mm, 5 μm) with isocratic elution using 0.2% formic acid in water–acetonitrile (20:80, v/v). Mass spectrometric detection was conducted using selected reaction monitoring via an electrospray ionization source. Both analytes exhibited good linearity within their concentration ranges (r² > 0.9932). The lower limit of quantitation of glaucocalyxin A and glaucocalyxin B was 1.10 ng/mL. Intra‐ and inter‐day precision exhibited an RSD within 14.5%, and the accuracy (RE) ranged from –12.1 to 15.0% at the lower limit of quantitation and three quality control levels. The developed assay was successfully applied to a pharmacokinetic study of glaucocalyxin A and glaucocalyxin B in rats after oral administration of Rabdosia japonica extract.     

Studies on the structure of xindongnins A and B

Two new diterpenoids, xindongnins A (1) and B (2) with an ent-kaurene skeleton were isolated from the leaves of Rabdosia rubescens (Hemsl.) Hara collected in Xinyang of Henan, and their structures were deduced from spectral and chemical evidence.     

Two New ent—Kaurane Diterpenoids from Isodon japonica

Two new ent-kauranoids,named maoyecrystals A (1) and B(2),were isolated from the EtOAc extract of the dried leaves of Isodon japonica (Burman f.) Hara collected in Tongbai mountains ,Henan Province,Their structures were determined on the basis of spectral data,especially by 2D NMR.     

中草药溪黄草低极性组份的研究

１前言溪黄草（Ｒａｂｄｏｓｉａ．ｓｅｒｒａ（Ｍａｘｉｍ．）Ｈａｒａ）属于唇形科香茶菜属植物，是一种多年生草本植物。据中华大辞典记载，其具有清热祛湿，凉血散瘀之功效，对急性肝炎，肠炎，痢疾等有较好效果。但是该植物化学组成的研究目前在国外尚未有报道，国内研究报道有４篇卜’１。共分出８个化合物：ＲａｂｄｏｓｅｒｒｉｎＡ，ＲａｂｄｏｓｅｒｒｉｎＢ，ＢｘｃｌｓａｎｌｎＡ，Ｋａｍｅｂａｋａｕｎｎ，Ｚａ一羟基乌索酸，乌索酸，卜谷自醇及一ｐ谷尚醇一Ｄ一葡萄糖贰。该植物的石油醚提取层的化学组分未见报道。我们利用高…     

Terpenoids and related compounds from plants of the family Compositae (Asteraceae)

This review will summarize the authors' studies on the structures of terpenoids and related compounds from plants of the family Compositae (Asteraceae). Eighty three new compounds have been obtained and characterized from seven species of the plants, namely, Erigeron annuus (L.) Pers., Erigeron philadelphicus L., Erigeron sumatrensis Retz, Ligularia dentata Hara, Ligularia stenocephala Matsum. et Koidz., Petasites japonicus Maxim. and Tussilago farfara L.     

细胞毒活性化合物Glaucocalyxin A的晶体结构和DFT研究

采用单晶x射线衍射技术对化合物的晶体结构进行了研究．研究结果表明,Glaucocalyxin A分子含3个六元环和1个五元环,其中六元环均为椅式构象,五元环为扭曲信封式构象．Glaucocalyxin A晶体结构属正交晶系．采用密度函数理论和Hartree—Fock方法对该化合物晶体的键长、键角和两面角进行计算,并与X衍射测定值进行比较,结果表明理论值与实验值符合相当好．应用规范不变原子轨道,分别在不同水平上,计算了GlaucocalyxinA的^1 H和^13 C NMR化学位移,并对理论计算值的误差进行了统计分析,结果表明计算值与实验值的符合是令人满意的．通过对该分了的三维分子表面静电位的研究,提出了该分子抗癌活性的可能部位．     

Total Synthesis of (−)‐Glaucocalyxin A

A practically useful method for the formation of the highly oxygenated bicyclo[3.2.1]octane ring system through Mn(OAc)₃‐mediated radical cyclization of alkynyl ketones was developed, which opens up a new avenue for the total synthesis of a number of highly oxidized diterpenoids. Application of this method enabled the first total synthesis of (?)‐glaucocalyxin A. Other salient features of the synthesis include a highly enantioselective conjugate addition/acylation cascade reaction, a Yamamoto aldol reaction, and an intramolecular Diels–Alder reaction to assemble the A/B ring system.     

A new phenylethanoid glycoside from Rabdosia lophanthoides （Buch.-Ham.ex D.Don） Hara.

A new phenylethanoid glycoside,3-hydroxy-4-methoxy-β-phenylethoxy-O-α-L-rhamnopyranosyl-(1→3)-2-O-acetyl-O-β-D-glucopyranoside, named lophanthoside A,was isolated from Rabdosia lophanthoides(Buch.-Ham.ex D.Don) Hara.Its structure was determined by spectroscopic evidences.     

Abietane Quinones from Rabdosia serra

Rabdosiu Serra (M4-YId Hara is a chinese traditional medicine for the treatment ofhepatitis. enteritis. acute cholecystitis and dysentery'. The present communicationdescribes the first isolation of three abietane quinone diterpenoids from the herb (Figure1 ). The new abietane quinone, 16-acetoxy-7Q-ethoxyroyleanone I was elucidated. Inaddition. two known abietane quinones, horminone 2, 16-acetoxy-7-0-acetylhorminone 3and 6-sitosterol. stigmasterol. ursolic acid. palmitic acid were identifie…     

Studies on the constituents of Gardenia species. III. New iridoid glycosides from the leaves of Gardenia jasminoides cv. fortuneana Hara

Two new iridoid glycosides, 7 beta,8 beta-epoxy-8 alpha-dihydrogeniposide (1) and 8-epiapodantheroside (2), were isolated, together with six known (3-8) and three artifact (9-11) iridoids, from the leaves of Gardenia jasminoides cv. fortuneana Hara. Their structures were established based on chemical and spectral data.     

Levels, trends and risk assessment of arsenic pollution in Yangzonghai Lake, Yunnan Province, China

The arsenic contamination accident in Yangzonghai Lake, Yunnan has been of wide concern. In order to investigate the arsenic distribution and concentration trends after the accident, samples including lake water, sediments, soil, aquatic organisms and crops were collected in November 2008, as well as in February, May and September 2009. The average arsenic concentrations (arithmetic average) in lake water in the four sampling events were 176.9, 147.3, 159.3, and 161.1 μg/L, while those in the sediments were 32.87, 62.41, 62.99, and 46.96 μg/g, respectively. The highest content of total arsenic in soil in the vicinity of Yangzonghai was 23.33 μg/g, which was below the limits of the relevant national standard. The total arsenic levels in most aquatic plants were in the range of 100–200 μg/g, with Vallisneria natans (Lour.) Hara having the highest concentration of ～300 μg/g. The arsenic levels of fish and shrimps were in the range of 1.52–11.4 μg/g (dry weight).     

Analysis of the main conjugated linoleic acid (CLA) precursors (C18:2 n-6 and C18:3 n-3) in Brachiaria ruzizienses by capillary zone electrophoresis

An alternative method for extraction optimization of C18:2 n-6 and C18:3 n-3, the main precursors for the synthesis of conjugated linoleic acid (CLA), in Brachiaria ruzizienses forages was proposed. Three methods of lipid extraction were tested: 1. Hara & Radin, 2. Micro Folch and 3. Bligh & Dyer. The preliminary test showed the Hara & Radin method as the most promising procedure. Then, a 3³ Box Behnken design with triplicate in the central point was applied in Hara & Radin method in order to optimize the extraction procedure. The optimization extraction was monitored by quantification of C18:2 n-6 and C18:3 n-3 through capillary zone electrophoresis (CZE). The results obtained by CZE were compared to gas chromatography (AOCS official method) in real samples using the paired t-test. No significant difference between methods was found within a 95% confidence interval (p-value= 0.937). The alternative CZE method for Brachiaria ruzizienses forages analysis has some advantages in comparison with official GC method such as, short analysis time (10 min), no derivatization step for sample preparation, absence of specific separation columns, lower analytical cost and high throughput.      

A phenolic glycoside from Fagopyrum dibotrys (D.Don) Hara

A new phenolic constituent along with five known compounds were isolated from Fagopyrum dibotrys(D.Don)Hara.The new compound was characterized as 1,3-dimethoxy-2-O-β-xylo-pyranosyl-5-O-β-glucopyranosyl-benzene,by spectroscopic analysis and enzymatic hydrolysis.     

Isolation of a new natural kingiside aglucone derivative and other anti-inflammatory constituents from Syringa reticulata

Abstract

A new secoiridoid, (1R,5S,8S,9R)-1-methyl-kingiside aglucone (1), along with nine known compounds (2–10), were isolated from the ethanol extract of the stem bark of Syringa reticulata (Bl.) Hara. The structure of compound 1 was elucidated using HR-ESI-MS, 1D and 2D NMR spectroscopy. Compounds 1–10 were evaluated for their inhibitory activity against NO, TNF-α and IL-6 production. Compounds 1, 3, 5 and 7–10 significantly inhibited the levels of NO, TNF-α and IL-6 in LPS-induced RAW264.7 cells from concentrations of 3 to 30?μM.     

Studies on constituents of Isodon japonicus hara : The structures and absolute stereochemistry of isodonal,trichodonin and epinodosin

Seven diterpenoids have been isolated from Isodon japonicus Hara. Isodonal, trichodonin and epinodosin are formulated by chemical and spectroscopic evidence as the structures 2, 4 and 5 Antimicrobial activity has been tested.     

Solvent selection in liquid-solid chromatography of steroids

Summary Based on the previously observed proportionality between the retention constant of some mono-and polyfunctional steroids and the retention constant of the steroid hydroxyl group in pure solvent, a relatively simple procedure is described for the calculation of equi-eluotropic binary solvent systems in liquid-solid chromatography of steroids. This method is compared with the proposals of Snyder and Hara.     

Study of Chemical Compositions and Anticancer Effects of Paris polyphylla var. Chinensis Leaves

Paris polyphylla var. chinensis (Franch.) Hara is a perennial herb belonging to the Trilliaceae family. Ultraperformance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC/Q–TOF MS) was used to detect the composition of different fractions of Paris polyphylla var. chinensis leaves. Meanwhile, the extracts of different fractions were evaluated for their cytotoxic activities against four selected human cancer cell lines and one human normal epithelial cell line based on the MTT assay method. Multivariate statistical analysis was performed to screen differential compounds and to analyze the distributions between different fractions. Finally, more than 60 compounds were obtained and identified from the different fractions of Paris polyphylla var. chinensis leaves, and the chloroform and n−butanol extracts showed significant cytotoxic effects on these four cancer cells. Several compounds were preliminarily identified from different fractions, including 36 steroidal saponins, 11 flavonoids, 10 ceramides, 8 lipids, 6 organic acids, and 8 other compounds. Various compounds were screened out as different chemical components of different fractions, which were considered as a potential substance basis for the cytotoxicity of Paris polyphylla var. chinensis leaves.     

大萼香茶菜中的新二萜化合物

报道从大萼香茶菜叶的乙醇提取物中分离得到一种新的二萜类化合物, 并命名为大萼香茶菜癸素(1). 其药理活性实验结果证明, 该化合物对体外培养的Hela细胞有较强的抑制作用.     

Isolation and Crystal Structure of Horminone

1　INTRODUCTIONhorminoneRabdsia serra( Maxim) hara,a tradi-tional Chinese medicine for the treatmentofhepatitis,enteritis,acute cholecystitis anddysentery,is a perennial herb distributedmainly in central and southeastern parts ofChina〔1〕.In previous reports,four diter-penoids,Rabdoserrin A,Rabdoserrin B,Excisanin A and Kamebakaurin which be-long to ent- kaurene diterpenoids have beenisolated from this source〔2 ,3〕.Horminonewhich has the structure of abietane quinonewas once isolate…