Eudesmanolides and diterpenes from Wedelia trilobata and an ent-kaurenic acid derivative from Aspilia parvifolia

The reinvestigation of the aerial parts of Wedelia trilobata afforded, in addition to known compounds, six new eudesmanolides, two ent-kaurenic acid derivatives as well as a degraded one. A corresponding hydroxy compound was present in Gnaphalium undulatum. From Aspilia parvifolia new ent-kaurenic acid epoxides were isolated. The structures were elucidated by spectroscopic methods. The chemotaxonomic situation is discussed briefly.     

Eudesmanolides and kaurene derivatives from Wedelia hookeriana

From the aerial parts of Wedelia hookeriana eight new eudesmanolides, all derivatives of ivangustin, and a new ent-kaurenic acid derivative togethe     

Diterpenoids from Wedelia prostrata and Their Derivatives and Cytotoxic Activities

One new ent‐kaurane diterpenoid, 11β,16α‐dihydroxy‐ent‐kauran‐19‐oic acid ( 1 ), together with eight known analogues 2 – 9 were isolated from the aerial parts of Wedelia prostrata. One of the acidic diterpenoids, kaurenoic acid ( 3 ), was converted to seven derivatives, 10 – 16 . All compounds were evaluated for their cytotoxic activity in vitro against human leukemia (K562), liver (HepG‐2), and stomach (SGC‐7901) cancer cell lines. Only four kaurenoic acid derivatives, 13 – 16 , with 15‐keto and substitutions at C(19) position, exhibited notable cytotoxic activities on these tumor cell lines with IC₅₀ value ranging from 0.05 to 3.71 μm . Compounds 10 – 12 , with oxime on C(15) showed moderate inhibitory effects and compounds 1 – 9 showed no cytotoxicities on them. Structure–activity relationships were also discussed based on the experimental data obtained. The known derivative, 15‐oxokaurenoic acid 4‐piperdin‐1‐ylbutyl ester ( 17 ), induced typical apoptotic cell death in colon SW480 cells upon evaluation of the apoptosis‐inducing activity by flow‐cytometric analysis.     

南美蟛蜞菊毛状根诱导及其离体培养

为了探讨利用南美蟛蜞菊毛状根来改良其观赏性状和生产次生物质,研究了南美蟛蜞菊Wedelia trilobata(L.)A.S.Hitche毛状根的诱导及其离体培养过程中培养基N源、碳源、磷和钙的消耗变化。结果表明,发根农杆菌Agrobacterium rhizogenes ATCC15834感染南美蟛蜞菊幼嫩叶片外植体7d后从其叶片切口中脉处产生毛状根。毛状根能在无外源激素的培养基上自主生长。PCR扩增结果显示发根农杆菌Ri质粒的rol B和rol C基因已在南美蟛蜞菊毛状根基因组中插入、整合并得到表达。毛状根液体培养0~7d内处于生长迟滞期、7~21d为快速生长期、21d后进入生长平台期。在毛状根液体培养过程中培养基的蔗糖、硝态氮、PO43?、Ca2+被逐渐吸收和消耗,培养至7d时,蔗糖被消耗近50%;硝态氮含量只剩下起始硝态氮含量的5.8%;至35d时,蔗糖和硝态氮含量分别约为其起始浓度的3.39%和1.82%。与Ca2+浓度变化不同的是,培养基的无机磷被快速消耗,培养至7d时其浓度约为其起始浓度的1.76%;但培养至35d时培养基中仍残存有占起始浓度约61.3%的Ca2+。该结果为今后利用南美蟛蜞菊毛状根来改良其观赏性状和设计合适的培养基来规模培养生产其次生物质提供了可能性。     

New Cytotoxic Bibenzyl and Other Constituents from Bauhinia ungulata L. (Fabaceae)

A new bibenzyl, 2′‐hydroxy‐3,5‐dimethoxy‐4‐methylbibenzyl ( 1 ) and four known compounds identified as 2′‐hydroxy‐3,5‐dimethoxybibenzyl ( 2 ), liquiritigenin ( 3 ), guibourtinidol ( 4 ) and fisetinidol ( 5 ) were isolated from the roots of Bauhinia ungulata L. Phytochemical investigations of the stems of B. ungulata led to the isolation of the known compounds identified as liquiritigenin ( 3 ), guibourtinidol ( 4 ), fisetinidol ( 5 ), taraxerol ( 6 ), betulinic acid ( 7 ), taraxerone ( 8 ), glutinol ( 9 ), a mixture of sitosterol ( 10 ) and stigmasterol ( 11 ), pacharin ( 12 ), naringenin ( 13 ) and eriodictyol ( 14 ). The structures of these compounds were elucidated on the basis of their spectral data (IR, MS, 1D‐ and 2D‐NMR). The cytotoxicity of the bibenzyl 1 has been evaluated against four human cancer cell lines, showing the IC₅₀ values of 4.3 and 6.5 μg ml^?1 against pro‐myelocytic leukemia (HL‐60) and cervical adenocarcinoma (HEP‐2) cell lines, respectively. This article also registers for the first time the ¹³C‐NMR data of the known bibenzyl 2 .     

Phosphate-solubilizing bacteria improve the phytoremediation efficiency of Wedelia trilobata for Cu-contaminated soil

In a controlled experiment, we assessed the effect of phosphate-solubilizing bacterium (PSB) on the soil metal (Cu²⁺) phytoremediation by Wedelia trilobata and examined the effect of the interaction of Cu contamination and PSB on the growth of W. trilobata. We also explored the effect of the interaction of Cu contamination and PSB on the soil microflora. The results showed that the removal efficiency of Cu from soil by W. trilobata increased with an increase in the concentration of PSB, and the translocation factors of Cu (i.e., leaf:root and stem:root) were both significantly upregulated by PSB. The PSB significantly promoted the growth of W. trilobata; however, the effect of the Cu–PSB interaction on the leaf net photosynthetic rate (Pn) of W. trilobata was not significant, whereas copper contamination had a significant negative influence on the soil microflora, PSB had a significant positive influence on the soil microflora. Thus, PSB improved the phytoremediation efficiency of W. trilobata in Cu-contaminated soil because of the positive influence on the soil microflora, improving soil quality, which then increased the growth of W. trilobata in Cu-contaminated soil. The vigorous growth of W. trlobata led to higher of Cu absorption and translocation from soil as the ultimate result.     

Chemical Constituents of Plants from the Genus Psychotria

Psychotria is a genus of ca. 1500 species in the family Rubiaceae. Up to now, 41 species of the Psychotria genus have been chemically investigated, and 159 compounds, including alkaloids of indole, quinoline and benzoquinolizidine type, terpenoids, steroids, phenolics and aliphatic compounds have been isolated. These compounds show potent bioactivities, such as antimicrobial, antiviral, and antiparasitic activities.     

Chemical Constituents from the Flowers of Wild Gardenia jasminoides J.Ellis

Four new iridoids, 2′‐O‐(E)‐coumaroylshanzhiside ( 1 ), 6′‐O‐(E)‐coumaroylshanzhiside ( 2 ), 8α‐butylgardenoside B ( 3 ), 6α‐methoxygenipin ( 4 ), and one new phenylpropanoid glucoside, 5‐(3‐hydroxypropyl)‐2‐methoxyphenyl β‐d ‐glucopyranoside ( 5 ), together with sixteen known compounds, were isolated from the edible flowers of wild Gardenia jasminoides J.Ellis . Their chemical structures were characterized by extensive spectroscopic techniques, including 1D‐ and 2D‐NMR, HR‐ESI‐MS, and CD experiments. The absolute configurations of the new isolates’ sugar moiety were assigned by HPLC analysis of the acid hydrolysates. Furthermore, the antioxidant activities of those isolates were preliminarily evaluated by DPPH scavenging experiment. And comparison of ¹H‐NMR spectra for the EtOH extract of G. jasminoides J.Ellis , gardenoside B and geniposide revealed that the flowers of this plant have a considerable content of gardenoside B instead of geniposide in the fruits, indicating different activities and applications in people's daily life.     

Metabolomics approach to investigate phytotoxic effects of Wedelia trilobata leaves,litter and soil

Although release and accumulation of plant metabolites from plant into soil can influence allelopathy, little information is known about metabolite changes that occur in leaf, litter and soil. In this study, seed germination bioassay tests and metabolomics analysis were performed to investigate the phytotoxic effects and metabolic variations (measured as buckets) in the ethanolic extracts of leaf, leaf litter and soil of Wedelia trilobata. Increasing the ethanolic extracts concentration of all extracts significantly inhibited Lactuca sativa germination rate (GR), shoot height (SH) and root length (RL). Soil exerted the strongest inhibition but contained the lowest number of buckets relative to those of leaf and leaf litter extracts. An overlap overview on the metabolome revealed a poor bucket overlap and redundancy among the leaf, leaf litter and soil extracts. Canonical correspondence analysis concluded that the SH of L. sativa was more sensitive to leaf litter extract and the leaf extract exerted a strong influence on the GR and RL of L. sativa. Multivariate analysis suggested that the metabolome of the leaf, leaf litter and soil differ substantially. Finally, putative identification using MS/MS data demonstrated various plant metabolites with phytotoxic effects that can contribute to the allelopathy of W. trilobata.     

A New Iridoid Dimer and Other Constituents from the Traditional Kurdish Plant Pterocephalus nestorianus Nábělek

Accompanied by other rare compounds, a new iridoid dimer, named kurdnestorianoside ( 1 ), showing an unprecedented secologanol configuration, has been isolated for the first time from the Kurdish medicinal plant Pterocephalus nestorianus, which is used in Kurdistan for treating oral diseases and inflammation. The structure of 1 was established from 1D‐ and 2D‐NMR spectroscopic data. Kaempferol 3‐O‐[3,6‐di‐O‐(E)‐p‐coumaroyl]‐β‐d ‐glucopyranoside ( 7 ) showed a remarkable antiproliferative activity against several human tumor cell lines.     

Cytotoxic Triterpenoids from Roots of Actinidia chinensis

Phytochmical investigation of roots of Actinidia chinensisPlanch . led to the isolation triterpenoids 1 – 16 , including a new compound 2α,3α,23,24‐tetrahydroxyursa‐12,20(30)‐dien‐28‐oic acid ( 1 ). Their structures were identified on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR, HR‐ESI mass spectrometry, and by comparison with the literatures. The cytotoxicities of triterpenoids 1 – 16 against a panel of cultured human cancer cell lines (HepG2, A549, MCF‐7, SK‐OV‐3, and HeLa) were evaluated. The new compound 1 exhibited moderate antitumor activities with IC₅₀ values of 19.62 ± 0.81, 18.86 ± 1.56, 45.94 ± 3.62, 62.41 ± 2.29, and 28.74 ± 1.07 μm , respectively. The experiment data might be available to explain the use of roots of A. chinensis to treat various cancers in traditional Chinese medicine.     

干旱和复水对入侵植物三裂叶蟛蜞菊叶片叶绿素荧光特性的影响

选取入侵植物三裂叶蟛蜞菊(Wedelia trilobata)及其本地近缘种蟛蜞菊(W. chinensis)为实验材料,比较干旱和复水后二者叶片的叶绿素荧光特性和抗氧化酶活性等生理指标的变化规律,探讨入侵种三裂叶蟛蜞菊对干旱的响应和生态适应性.结果发现,在自然干旱处理过程中,入侵种三裂叶蟛蜞菊与本地种蟛蜞菊相比土壤含水量下降较快,对它们叶片气孔形态的比较发现,干旱胁迫11d后三裂叶蟛蜞菊叶片气孔开度明显大于蟛蜞菊,这可能是导致其失水较快的原因之一.干旱胁迫11d后三裂叶蟛蜞菊的PSⅡ最大光能转化效率(Fv/Fm)降低了43.8%,而蟛蜞菊只降低了3.7%;同时,与蟛蜞菊相比,三裂叶蟛蜞菊的PSⅡ实际光化学量子产量(Yield)、表观光合电子传递速率(ETR)和光化学猝灭系数(qP)也表现出较大幅度的降低,说明三裂叶蟛蜞菊对干旱胁迫较敏感;但复水后,三裂叶蟛蜞菊能够较快地恢复到正常水平,且与本地种不存在显著差异.这主要是由于入侵种在遭受干旱胁迫时提高了对其过量激发能的热耗散能力以及超氧化物歧化酶(SOD)和抗坏血酸还原酶(APX)的活性,保护光合机构少受不可逆的损伤,使其在干旱胁迫解除后光合功能得以迅速恢复.研究结果初步表明三裂叶蟛蜞菊容易受到水分条件的限制,它向干旱地区扩散的可能性较小.     

Two New Chromone Glycosides from the Roots of Saposhnikovia divaricata

Five chromone glycosides were isolated from the water‐soluble portions of 70% EtOH extract of the roots of Saposhnikovia divaricata, including two new chromone glycosides 1 and 2 . The structures of the chromone glycosides were identified as (3′S)‐3′‐O‐β‐d ‐apiofuranosyl‐(1 → 6)‐β‐d ‐glucopyranosylhamaudol ( 1 ), (2′S)‐4′‐O‐β‐d ‐apiofuranosyl‐(1 → 6)‐β‐d ‐glucopyranosylvisamminol ( 2 ), 3′‐O‐glucopyranosylhamaudol ( 3 ), 4′‐O‐β‐d ‐glucopyranosylvisamminol ( 4 ), and 4′‐O‐β‐d ‐glucopyranosyl‐5‐O‐methylvisamminol ( 5 ) on the basis of extensive spectroscopic methods, and the absolute configurations of the new compounds were elucidated by the electronic circular dichroism (ECD) calculation and acid hydrolysis. The cytotoxic activities of the glycosides 1 – 5 against three human cancer cell lines (PC‐3, SK‐OV‐3, and H460) were evaluated. The result showed that compounds 1 – 5 had weak cytotoxic activities against the human cancer cell lines with IC₅₀ values in the range of 48.54 ± 0.80 – 94.25 ± 1.45 μm .     

Superbanone,A New 2‐Aryl‐3‐benzofuranone and Other Bioactive Constituents from the Tube Roots of Butea superba

Phytochemical investigation from the tube roots of Butea superba, led to the isolation and identification of a new 2‐aryl‐3‐benzofuranone named superbanone ( 1 ), one benzoin, 2‐hydroxy‐1‐(2‐hydroxy‐4‐methoxyphenyl)‐2‐(4‐methoxyphenyl)ethanone ( 2 ), eight pterocarpans ( 3  –  10 ), and eleven isoflavonoids ( 11  –  21 ). Compound 2 was identified for the first time as a natural product. The structure of the isolated compounds was elucidated using spectroscopic methods, mainly 1D‐ and 2D‐NMR. The isolated compounds and their derivatives were evaluated for α‐glucosidase inhibitory and antimalarial activities. Compounds 3 , 7 , 8 , and 11 showed promising α‐glucosidase inhibitory activity (IC₅₀ = 13.71 ± 0.54, 23.54 ± 0.75, 28.83 ± 1.02, and 12.35 ± 0.36 μm , respectively). Compounds 3 and 11 were twofold less active than the standard drug acarbose (IC₅₀ = 6.54 ± 0.04 μm ). None of the tested compounds was found to be active against Plasmodium falciparum strain 94. On the basis of biological activity results, structure–activity relationships are discussed.     

外来植物南美蟛蜞菊、裂叶牵牛和五爪金龙的光合特性

对南美蟛蜞菊、裂叶牵牛和五爪金龙的光合生理特性进行研究 ,结果表明 :(1) 3种植物都具有较强的 CO2 固定能力 ,南美蟛蜞菊的净光合速率峰值达 2 2 .1μm ol/ (m2 · s) ,高于裂叶牵牛 (17.2 μmol/ (m2 · s) )和五爪金龙 (18.6 μmol/ (m2 · s) ) ;(2 ) 3种植物光合速率、蒸腾速率的日进程曲线呈“双峰”型 ,气孔导度变化规律与蒸腾速率相似 ,在中午前后均出现一定程度的下降 ;(3)暗呼吸速率曲线呈单峰型 ,在中午时出现高峰 ,暗呼吸速率大小次序为 :五爪金龙 >裂叶牵牛 >南美蟛蜞菊。(4 )南美蟛蜞菊的光饱和点为 15 31μm ol/ (m2· s) ,光补偿点为 2 0 .0 μmol/ (m2· s) ,而裂叶牵牛的光饱和点 114 6 μmol/ (m2· s) ,光补偿点39.3μmol/ (m2· s) ;五爪金龙的光饱和点 12 6 1μmol/ (m2· s) ,光补偿点 4 4 .1μm ol/ (m2· s) ,3种植物都表现为喜阳植物的特性 ,且对弱光条件的适应力也较强 ,其中尤以南美蟛蜞菊的有效光合辐射范围最广 ,光量子利用效率较高 ,具有很强忍耐强光及适应阴生环境的能力。该项研究有助于解释南美蟛蜞菊生长迅速、生产力高、竞争性强的生物学特点     

Salvisertin A,a New Hexacyclic Triterpenoid,and Other Bioactive Terpenes from Salvia deserta Root

Using various chromatographic methods, a new hexacyclic triterpenoid, 2β,3β,24β‐trihydroxy‐12,13‐cyclotaraxer‐l4‐en‐28oic acid ( 1 ), together with ten known compounds, 2α,3α,23‐trihydroxyurs‐12,20(30)‐dien‐28oic acid ( 2 ), 6,7‐dehydroroyleanone ( 3 ), horminone ( 4 ), 7‐O‐methylhorminone ( 5 ), sugiol ( 6 ), demethylcryptojaponol ( 7 ), 14‐deoxycoleon U ( 8 ), 5,6‐didehydro‐7‐hydroxy‐taxodone ( 9 ), ferruginol ( 10 ), and dichroanone ( 11 ), were isolated from the roots of Salvia deserta. Their structures were identified on the basis of spectroscopic analysis and comparison with the reported data. The individual compounds ( 1 , 3  –  8 ) were screened for cytotoxic activity, using the sulforhodamine B bioassay (SRB) method. As the results, Compounds 3 , 5 , and 8 showed cytotoxic potency against A549, MDA‐MB‐231, KB, KB‐VIN, and MCF7 cell lines with IC₅₀ values ranging from 6.5 to 10.2 μm .     

Chemical Constituents of Plants from the Genus Ixora

Ixora is a genus of ca. 400 species in the family Rubiaceae. Since the 1940s, eighty‐one compounds including phenolics, peptides, terpenoids, and sterols have been isolated from six species of the genus Ixora. Pharmacological studies have shown that these compounds and extracts from the Ixora genus have extensive activities, such as antitumor, chemoprotective, and antioxidant activities. In this review, we summarize the phytochemical progress and list the compounds isolated from the genus Ixora. The biological activities of this genus are also covered.     

Four New Diterpenoid Alkaloids from the Roots of Aconitum carmichaelii

Aconitum carmichaelii Debeaux is a widely used traditional Chinese medicine and an important source of clinical drugs, of which the parent and lateral roots are known as ‘Chuanwu’ and ‘Fuzi’, respectively. Four new C₁₉‐diterpenoid alkaloids, carmichasines A – D ( 1 – 4 ), were isolated from the roots of Aconitum carmichaelii, together with twelve known compounds ( 5 – 16 ). Their structures were elucidated via spectroscopic analyses, including HR‐ESI‐MS, IR, and NMR. Carmichasine A ( 1 ) is the first natural C₁₉‐diterpenoid alkaloid possessing a cyano group. Most of the diterpenoid alkaloids isolated were C₁₉‐category, which might provide further clues for understanding the chemotaxonomic significance of this plant. The cytotoxicity of the new compounds was also investigated against several human cancer cell lines, including MCF‐7, HCT116, A549, and 786‐0, and none of them showed considerable cytotoxic activity.     

Detection and Toxicity Evaluation of Pyrrolizidine Alkaloids in Medicinal Plants Gynura bicolor and Gynura divaricata Collected from Different Chinese Locations

Two edible plants in Southeast Asia, Gynura bicolor and G . divaricata , are not only known to be nutritive but also useful as medicinal herbs. Previous phytochemical investigation of Gynura species showed the presence of hepatotoxic pyrrolizidine alkaloids (PA s), indicating the toxic risk of using these two plants. The present study was designed to analyze the distribution of PA components and tried to evaluate the preliminary toxicity of these two Gynura species. Eight samples of G . bicolor and G . divaricata from five different Chinese locations were collected and their specific PA s were qualitatively characterized by applying an UPLC /MS /MS spectrometry method. Using a pre‐column derivatization HPLC method, the total retronecine ester‐type PA s in their alkaloids extracts were quantitatively estimated as well. Finally, their genotoxicity was investigated with an effective high‐throughput screening method referred to as Vitotox ? test and their potential cytotoxicity was tested on HepG2 cells. It was found that different types of PA s were widely present in Gynura species collected from south of China. Among them, no significant genotoxic effects were detected with serial concentrations through the present in vitro assay. However, the cytotoxicity assay of Gynura plants collected from Jiangsu displayed weak activity at the concentration of 100 mg/ml. It is important to note that this research validates in part the indication that the use of Gynura species requires caution.     

外源钙对镉胁迫下南美蟛蜞菊毛状根生长、抗氧化酶活性和镉吸收的缓解效应

为了探讨外源钙对重金属镉(Cd)缓解南美蟛蜞菊Wedelia trilobata毛状根毒害的生理机理,采用溶液培养法研究了重金属Cd单独及其与Ca组合对南美蟛蜞菊毛状根生长、抗氧化酶超氧化物岐化酶(SOD)和过氧化物酶(POD)活性及对Cd2+吸收的影响。结果表明,Cd≤50μmol/L时促进毛状根生长;高于100μmol/LCd则抑制其生长,使其侧根短小,根尖变褐或变黑。与对照相比,不同浓度Cd培养的毛状根POD活性、SOD活性和MDA含量都比对照明显提高,但高于100μmol/L Cd培养的毛状根可溶性蛋白含量均比对照降低。与仅添加200μmol/L或300μmol/L Cd的毛状根相比,Cd和10~30 mmol/L Ca组合培养可促进毛状根生长,使其主、侧根变粗;提高其可溶性蛋白含量;降低其MDA含量、POD活性及SOD活性。原子吸收分光光度法测定结果表明,南美蟛蜞菊毛状根能吸收和吸附重金属Cd2+,当Cd2+浓度为100μmol/L时毛状根对Cd2+的吸收量最大,而Cd2+浓度为300μmol/L时毛状根对Cd2+的吸附量最大。外源加入10~30 mmol/L Ca2+可显著减少毛状根对Cd2+的吸收和吸附,并可调节其抗氧化酶活性,降低其膜脂过氧化水平而解除重金属镉对毛状根生长的抑制或毒害。