Ozoroalide, a new macrolide from Ozoroa insignis

From the roots of Ozoroa insignis a new orsellinic acid named ozoroalide (1) and anacardic acid methyl ester (2) were isolated and identified on the basis of spectroscopic methods.     

Antituberculosis activity of natural and semisynthetic azorellane and mulinane diterpenoids

The antituberculosis activity of 14 natural azorellane and mulinane diterpenoids isolated from Azorella compacta, Azorella madreporica, Mulinum crassifolium, and Laretia acaulis, together with eight semisynthetic derivatives, was evaluated against two Mycobacterium tuberculosis strains. The natural azorellanes azorellanol (3) and 17-acetoxy-13-α-hydroxyazorellane (6), and the semisynthetic mulinanes 13-hydroxy-mulin-11-en-20-oic-acid methyl ester (13) and mulinenic acid methyl ester (23), showed the strongest activity, with MIC values of 12.5 μg/mL against both strains. The methylated derivatives 13-hydroxy-mulin-11-en-20-oic-acid methyl ester (13), mulin-11,13-dien-20-oic acid methyl ester (15) and mulinenic acid methyl ester (23) proved to be more active than the parent compounds.     

基于GC-MS流苏树种子挥发性成分分析

为研究流苏树种子的成分,探讨不同溶剂提取流苏树种子成分的差异。本研究分别采用石油醚、二氯甲烷和丙酮提取流苏树种子成分,以GC-MS联用技术对其化学成分进行分析。结果显示:石油醚提取物含有10种烷烃类、16种酯类和1种酰胺类化合物,占色谱总流出峰面积的91.36%,其中十六烷酸甲酯(10.83%)、反式-13-十八碳烯酸甲酯(60.67%)和6-十八碳烯酸甲酯(11.29%)含量较高;二氯甲烷提取物含有10种烷烃类、4种酯类、2种酸类和3种烯烃类化合物,占色谱总流出峰面积的80.85%,其中1,2-二甲基环戊烷(8.21%)、十六烷酸(14.51%)、(Z,Z)-9,12-十八碳二烯酸(35.93%)等化合物含量较高;丙酮提取物含有10种烷烃类、11种酯类和2种烯烃类化合物,占色谱总流出峰面积的98.23%,其中十六烷酸甲酯(14.07%)、(Z,Z)-9,12-十八碳二烯酸甲酯(44.65%)、(E)-9-十八碳烯酸甲酯(12.27%)和十八酸甲酯(15.62%)含量较高。石油醚和丙酮提取酯类的效果优于二氯甲烷,在提取酸类和烷烃类化合物时,二氯甲烷效果更佳。不同的溶剂提取流苏树种子成分的组成和含量存在一定的差异。     

A new dihydrodibenzodioxinone from Hypericum x ‘Hidcote’

One new compound, 4-hydroxy-4a,7-dimethoxy-4,4a-dihydrodibenzo-p-dioxin-2(3H)-one (1), was isolated from the aerial parts of the hybrid Hypericum x ‘Hidcote’, together with 8 known compounds: caryophyllene-4,5-epoxide, quercetin, quercitrin, quercetin-3-O-β-D-galactopyranoside, epicatechin, betulinic acid methyl ester, β-sitosterol and β-sitosterol glucoside. The structure of the new compound, as well as its absolute configuration, was established by means of spectroscopic data analyses, including 2D NMR spectroscopy and X-ray structural analysis.     

Three new triterpenoid saponins from root of Gardenia jasminoides Ellis

Three new compounds (Gardeniside A–C), 11α,12α-epoxy-3β-[(O-β-D-glucuronopyranoside-6′-O-methly ester)oxy]olean-28,13-olide (1), siaresinolic acid 3-O-β-D-glucuronopyranoside-6′-O-methly ester (2), and 3-O-β-D- glucuronopyranoside-6′-O-methly ester-siaresinolic acid-28-O-β-D- glucopyranoside (3), with seven known compounds oleanolic acid 3-O-β-D- glucuronopyranoside-6′-O-methly ester (4), oleanolic acid 3-O-β-D- glucuropyranoside (5), hederagenin 3-O-β-D- glucuronopyranoside-6′-O- methly ester (6), chikusetsusaponin IVa methyl ester (7), chikusetsusaponin (8), chikusetsusaponin IVa butyl ester (9), siaresinolic acid 28-o-β-d-glucopyranosyl ester (10) were isolated from the root of Gardenia jasminoides Ellis. Six compounds (1, 4–7, and 9) showed cytotoxic activities against HeLa, A549, MCF-7 and A354-S2 cell lines.     

3,5-Dicaffeoylquinic acid isolated from Artemisia argyi and its ester derivatives exert anti-Leucyl-tRNA synthetase of Giardia lamblia (GlLeuRS) and potential anti-giardial effects

An aqueous ethanol extract of Artemisia argyi inhibited the aminoacylation activity of LeuRS from Giardia lamblia (GlLeuRS). The bioassay-guided fractionation of the extract led to the isolation of 3,5-dicaffeoylquinic acid (1), with an IC(50) of 5.82μg/mL. The ester derivatives of 1 were also found to possess strong anti-GlLeuRS effects, with IC(50) values of 1.79, 5.51 and 2.56μg/mL respectively. Anti-giardial assay showed that the derivatives, especially 3,5-dicaffeoylquinic acid propyl ester (4) (IC(50)=4.62μg/mL), were effective at killing G. lamblia.     

Acyl quinic acid derivatives from the stems of Erycibe obtusifolia

Eleven new acyl quinic acid derivatives, 4-O-caffeoyl-3-O-syringoylquinic acid methyl ester (1), 4-O-caffeoyl-3-O-vanilloylquinic acid (2), 4-O-caffeoyl-3-O-vanilloylquinic acid methyl ester (3), 5-O-caffeoyl-3-O-vanilloylquinic acid (4), 5-O-caffeoyl-3-O-vanilloylquinic acid methyl ester (5), 5-O-caffeoyl-3-O-sinapoylquinic acid (6), 5-O-caffeoyl-4-O-vanilloylquinic acid (7), 4-O-(7‴S, 8‴R)-glycosmisoyl-5-O-caffeoylquinic acid methyl ester (8), 4-O-(7‴S, 8‴R)-glycosmisoyl-5-O-caffeoylquinic acid (9), 3-O-(7‴S, 8‴R)-glycosmisoyl-4-O-caffeoylquinic acid (10), and 3-O-(7‴S, 8‴R)-glycosmisoyl-4-O-caffeoylquinic acid methyl ester (11), have been isolated from the stems of Erycibe obtusifolia together with eight known compounds (12–19). Their structures were elucidated on the basis of spectroscopic data analysis (UV, IR, HRESIMS, CD, and 1D and 2D NMR) and chemical evidence. In in vitro assay, compounds 7 and 16–18 exhibited significant neuroprotective effects against rotenone induced PC12 cell damage at 10 μM.     

Endothelium-independent relaxation of aorta rings by two stilbenoids from the orchids Scaphyglottis livida

Gigantol (1) and 3,7-dihydroxy-2,4-dimethoxyphenanthrene (2) from the orchid Scaphyglottis livida induced a significant concentration-dependent relaxation of the contractions evoked by noradrenaline (NA) in endothelium-intact and denuded rat aorta rings. Incubation with N(G)-nitro-L-arginine methyl ester (L-NAME, 1x10(-5) M) or methylene blue (MB, 1x10(-7) M) significantly reduced the relaxation induced by the stilbenoids 1 and 2. The results suggested that two or more mechanisms are involved in the vasorelaxant effects of both compounds.     

脱氢枞酸基ATRP引发剂的合成与表征

以脱氢枞酸为原料,通过酰氯化得到脱氢枞酸酰氯(DA-Cl)后与乙二醇(EG)反应合成脱氢枞酸羟乙酯(DA-EH),然后再与2-溴代异丁酰溴(2-BiBr)进行酯化反应,合成了脱氢枞酸基原子转移自由基聚合(ATRP)引发剂——脱氢枞酸(2-溴代异丁酸乙基)酯(DA-2-iBBrEH)。通过单因素试验考察了不同条件对合成DA-EH和DA-2-iBBrEH的影响规律。结果表明,DA-EH合成的优化条件为:催化剂为4-二甲氨基吡啶(DMAP),n(DA-Cl)∶n(EG)∶n(DMAP)为1∶5∶5,反应时间5h,反应温度50℃;DA-2-iBBrEH合成的适宜条件为:催化剂为DMAP,n(DA-EH)∶n(2-BiBr)∶n(DMAP)为1∶2∶2。利用傅里叶红外光谱(FT-IR)、核磁共振氢谱(1HNMR)和核磁共振碳谱(13CNMR)对两者的结构进行了确证。以DA-2-iBBrEH为引发剂,采用ATRP法制备了聚甲基丙烯酸甲酯均聚物(PMMA)。GPC测试结果表明,DA-2-iBBrEH具有良好的ATRP反应引发活性,所制备的PMMA的数均相对分子质量(Mn)为8500,相对分子质量分布(PDI)为1.3。     

山东主栽光皮木瓜品种香气成分的研究

光皮木瓜(Chaenomeles sinensis (Thouin) Koehe)系蔷薇科(Rosaceae)木瓜属(Chaenomeles Lindl.)植物,主要分布于陕西、甘肃、山东、江苏、安徽、浙江、云南等地[1].木瓜集观赏、食用、药用于一体,是不可多得的经济和药用树种;其果实成熟后呈暗黄或金黄色,气味芳香,且内含有多种活性物质,具有抗肿瘤、保肝、抑菌、强心、利尿、抗衰老等功效,是医药工业的重要原料[2].     

Ganoderic acid Df,a new triterpenoid with aldose reductase inhibitory activity from the fruiting body of Ganoderma lucidum

Ganoderic acid Df, a new lanostane-type triterpenoid, was isolated from the fruiting body of Ganoderma lucidum. Its structure was characterized as 7β, 11β-dihydroxy-3, 15, 23-trioxo-5α-lanosta-8-en-26-oic acid by 1D- and 2D-NMR spectra. This compound exhibited potent human aldose reductase inhibitory activity, with an IC₅₀ of 22.8 μM in vitro. A carboxyl group of this compound's side chain is essential for eliciting inhibitory activity because its methyl ester is much less active.     

New antioxidant and antiglycation active triterpenoid saponins from the root bark of Aralia taibaiensis

Four new oleanane type triterpenoid saponins (1-4) and a known saponin (5) were isolated from the root bark of Aralia taibaiensis Z.Z. Wang et H.C. Zheng. The structures of the four new compounds were elucidated as 3-O-{β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucurono-pyranosyl}-olean-11,13(18)-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (1), 3-O-{β-d-gluco-pyranosyl-(1 → 3)-[α-l-arabinofuranosyl-(1 → 4)]-β-d-glucuronopyranosyl}-olean-11,13(18)-diene-28-oic acid 28-O-β-D-glucopyranosyl ester (2), 3-O-{β-d-glucopyranosyl-(1 → 2)-[α-l-arabinofuranosyl-(1 → 4)]-β-d-glucuronopyranosyl}-oleanolic acid 28-O-β-D-glucopyranosyl ester (3) and 3-O-{β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucuronopyranosyl}-oleanolic acid 28-O-β-d-glucopyranosyl ester (4), on the basis of extensive spectral analysis and chemical evidence. Compounds 1-5 exhibited moderate effects on antioxidant and antiglycation activities, which correlated with treatment of diabetes mellitus.     

A new triterpene glycoside from Centella erecta

A new (2α,3β)-23-sulphonyl-2,3-dihydroxyurs-12-en-28-oic acid O-α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1) together with eighteen known compounds were isolated from Centella erecta (L.f.) Fern. Their structures were elucidated mainly by NMR and HRESIMS, as well as on comparison with the reported data.     

Antihypertensive effect of an aqueous extract of the calyx of Hibiscus sabdariffa

The present study was designed to investigate the efficacy of an aqueous calyx extract of Hibiscus sabdariffa (HS) in two forms of experimental hypertension: salt-induced and L-NAME (N(omega)-L-arginine methyl ester)-induced and in normotensive controls. The blood pressure and heart rate fell dose-dependently in both the hypertensive and normotensive rats after intravenous injection of 1-125 mg/kg of HS, suggesting that HS possesses anti-hypertensive, hypotensive and negative chronotropic effects. The fall in mean arterial pressure was significantly pronounced in the hypertensive rats (salt-induced: 94.4+/-8.6 mm Hg; L-NAME-induced: 136.5+/-10.3 mm Hg) than in the normotensive controls (50.2+/-5.1 mm Hg; P<0.05).     

Cytotoxic triterpene saponins from the leaves of Aralia elata

Phytochemical investigation of the leaves of Aralia elata has led to the isolation of four new compounds, 3-O-β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl oleanolic acid (1), 3-O-[β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl (1→3)]-[β-D-glucopyranosyl (1→2)]-β-d-glucopyranosyl hederagenin 28-O-β-D-glucopyranoside (2), 3-O-{[β-D-glucopyranosyl (1→2)]-[β-d-glucopyranosyl (1→3)-β-d-glucopyranosyl (1→3)]-β-D-glucopyranosyl} oleanolic acid 28-O-β-D-glucopyranosyl ester (3) and 3-O-[β-D-glucopyranosyl (1→2)]-[β-D-glucopyranosyl (1→3)]-β-d-glucopyranosyl caulophyllogenin (4) and two known compounds, 3-O-[β-D-glucopyranosyl (1→3)-α-l-arabinopyranosyl]-echinocystic acid (5) and 3-O-α-L-arabinopyranosyl echinocystic acid (6). The structural determination was accomplished with spectroscopic analysis, in particular (13)C-NMR, 2D-NMR and HR-ESI-MS techniques. Compounds 1-6 were tested for their inhibition of the growth of HL60, A549 and DU145 cancer cells. Compound 1 showed significant cytotoxic activity against HL60 and A549 cancer cells with IC(50) values of 6.99μM and 7.93μM respectively. In addition, compounds 5 and 6 showed significant cytotoxic activity against HL60 cancer cells with IC(50) values of 5.75μM and 7.51μM, respectively.     

Ent-trachyloban-19-oic acid isolated from Iostephane heterophylla as a promising antibacterial agent against Streptococcus mutans biofilms

From the roots of Iostephane heterophylla, six known compounds, namely, ent-trachyloban-19-oic acid (1), the mixture of ent-kaur-16-en-19-oic acid (2) and ent-beyer-15-en-19-oic acid (3), xanthorrhizol (4), 16α-hydroxy-ent-kaurane (5) and 16α-hydroxy-ent-kaur-11-en-19-oic acid (6) were isolated using a bioassay-guided fractionation method. The known compounds (1-6) were identified by comparison of their spectroscopic data with reported values in the literature. In an attempt to increase the resultant antimicrobial activity of 1 and 4, a series of reactions was performed on ent-trachyloban-19-oic acid (1) and xanthorrhizol (4), to obtain derivatives 1a, 1b, and 4a-4d. All the isolated compounds (1-6) and the derivatives 1a, 1b, and 4a-4d were evaluated for their antimicrobial activity against two oral pathogens, Streptococcus mutans and Porphyromonas gingivalis associated with caries and periodontal disease, respectively. Compounds 1, 1b, 2+3, 4 and 4d inhibited the growth of S. mutans with concentrations ranging from 4.1 μg/mL to 70.5 μg/mL. No significant activity was found on P. gingivalis except for 4 with an MIC of 6.8 μg/mL. The ability of 1, 1b, 2+3, 4 and 4d to inhibit biofilm formation by S. mutans was evaluated. It was found that 1, 1b, 4 and 4d interfered with the establishment of S. mutans biofilms, inhibiting their development at 32.5, 125.0, 14.1 and 24.4 μg/mL, respectively.     

A cytotoxic triterpenoid saponin from under-ground parts of Gypsophila pilulifera Boiss.& Heldr

A cytotoxic triterpenoid saponin was isolated from the under-ground parts of Gypsophila pilulifera Boiss.& Heldr. (Caryophyllaceae) naturally grow in the southwestern region of the Turkey. The structures of saponin was elucidated as 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→4]-α-l-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester on the basis of extensive spectral analysis and chemical evidence. The separated triterpenoid saponin was isolated from Gypsophila pilulifera for the first time. The saponin compound displayed significant cytotoxicity against A549 cell line with IC(50) values >16μM.     

New megastigmane sesquiterpene and indole alkaloid glucosides from the aerial parts of Bupleurum chinense DC

A new megastigmane sesquiterpene glucoside named chaihuxinoside A (1), and a new indole diglucoside named chaihuxinoside B (9) were isolated from the aerial parts of Bupleurum chinense DC. along with eight known compounds. Structures of two new compounds were elucidated by a combination of chemical and spectroscopic methods. Chaihuxinosides A and B were characterized as 11-hydroxyl-4-en-3,9-dioxo- megastigmane-11-O-beta-D-glucopyranoside (1), and 3-carboxy-indole-10-O-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl ester (9), respectively.     

Chemical constituents of the Vietnamese liverwort Porella densifolia

From the ether extract of Porella densifolia, the first liverwort collected and chemically investigated in Vietnam, a kaurane diterpenoid, ent-kauren-15-one (1) and two sesquiterpene norpinguisone (2) and norpinguisone methyl ester (3) have been purified. Their structures were elucidated by spectroscopic analysis. In addition, an X-ray crystal structure of norpinguisone was obtained, allowing to determine its stereochemistry. Furthermore, the inhibitory activity of nitric oxide (NO) production in RAW 264.7 cells stimulated by lipopolysaccharide (LPS) of compounds 1–3 was examined with their IC₅₀ values of 69.4, 45.5 and 1.68 μM, respectively.