Tirucallane Triterpenoids from the Stems of Brucea mollis

Three new tirucallane triterpenoids, brumollisols A–C ( 1 – 3 , resp.), together with five known analogues, (23R,24S)‐23,24,25‐trihydroxytirucall‐7‐ene‐3,6‐dione ( 4 ), piscidinol A ( 5 ), 24‐epipiscidinol A ( 6 ), 21α‐methylmelianodiol ( 7 ), and 21β‐methylmelianodiol ( 8 ), were isolated from an EtOH extract of the stems of Brucea mollis. Their structures were elucidated by means of spectroscopic methods including 1D‐ and 2D‐NMR techniques and mass spectrometry. In the in vitro assays, compound 6 exhibited significant cytotoxic activity against A549 and BGC‐823 cancer cells with IC₅₀ values of 1.16 and 3.01 μM , respectively. At a concentration of 10 μM , compounds 1 – 5, 7 , and 8 were found to inhibit NO production in mouse peritoneal macrophages with inhibitory ratios ranging from 39.8±7.7 to 68.2±4.5%.     

Diterpenes from Dysoxylum lukii Merr

Six new diterpenes and two known compounds were isolated from the stems of Dysoxylum lukii Merr and characterized on the basis of spectral data. Dysokusone F(1), 2-Oxoneoclerod-3, 13Z-dien-15-ol (2), 3α-(4-Hydroxy-3,5-dimethoxy-benzoyloxyl)-clerod-14-ene-4β,13-diol (3), 3α-(4-Hydroxybenzoyloxyl)-clerod-14-ene-4β,13-diol (4), and 3α-(4-Hydroxy-3-methoxybenzoyloxyl)-clerod-14-ene-4β,13-diol (5) exhibited inhibitory effects against PTP-1B with IC₅₀ values of 51.62±6.55, 56.74±7.96, 17.04±3.43, 28.96±4.59, and 19.70±2.57 μM, respectively.     

Sesquiterpenoids and diarylheptanoids from Nidus vespae and their inhibitory effects on nitric oxide production

Two coriamyrtin-type sesquiterpenes, fengfangin A (1) and tutin (2), and six diarylheptanoids, namely alnusone (3), centrolobol (4), muricarpone B (5), 1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptan-3-one (6), (3S)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptan-3-ol (7), and (3S)-1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)heptan-3-ol (8), were isolated from the 95% EtOH extract of nidus vespae, the nest of Polistes species. Their structures were identified by spectroscopic methods. Compounds 1 and 8 are new products. The absolute configuration of 1 was determined by single-crystal X-ray diffraction analysis using Flack parameter. The biological tests showed that compounds 5, 6, and 8 could inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells with IC(50) values in the range of 13-17 μM, whereas the sesquiterpenes were inactive in this assay (>25 μM). In addition, the ecological significance of the presence of neurotoxic sesquiterpene lactones in nidus vespae is briefly discussed.     

裂褶菌化学成分研究

经硅胶反复柱层析,从裂褶菌子实体的醇提物中首次分离得到8个化合物,利用波谱方法及理化性质鉴定为5,α8α-过氧麦角甾-6,22E-二烯-3β-醇(1)、麦角甾-7,22-二烯-3β醇(2)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(3)、烟酸(4)、苯甲酸(5)、D-阿拉伯糖醇(6)、甘露醇(7)、海藻糖(8)。     

New Isopropyl Chromone and Flavanone Glucoside Compounds from the Leaves of Syzygium cerasiforme (Blume) Merr. & L.M.Perry and Their Inhibition of Nitric Oxide Production

A new isopropyl chromone ( 1 ) and a new flavanone glucoside ( 2 ) together with eleven known compounds ( 3–13 ) were isolated from the leaves of Syzygium cerasiforme (Blume) Merr. & L.M.Perry. Their structures were elucidated as 5,7-dihydroxy-2-isopropyl-6,8-dimethyl-4H-chromen-4-one ( 1 ), 5,7-dihydroxyflavanone 7-O-β-D-(6′′-O-galloylglucopyranoside) ( 2 ), strobopinin ( 3 ), demethoxymatteucinol ( 4 ), pinocembrin-7-O-β-D-glucopyranoside ( 5 ), (2S)-hydroxynaringenin-7-O-β-D-glucopyranoside ( 6 ), afzelin ( 7 ), quercetin ( 8 ), kaplanin ( 9 ), endoperoxide G3 ( 10 ), grasshopper ( 11 ), vomifoliol ( 12 ), litseagermacrane ( 13 ) by the analysis of HR-ESI-MS, NMR, and CD spectral data. Compounds 1 , 2 , 5 , 6 and 10 inhibited NO production on LPS-activated RAW264.7 cells with IC₅₀ values of 12.28±1.15, 8.52±1.62, 7.68±0.87, 9.67±0.57, and 6.69±0.34 μM, respectively, while the IC₅₀ values of the other compounds ranging from 33.38±0.78 to 86.51±2.98 μM, compared to that of the positive control, N^G-monomethyl-L-arginine acetate (L-NMMA) with an IC₅₀ value of 32.50±1.00 μM.     

BACE1 (Beta‐Secretase) Inhibitory Phenolic Acids and a Novel Sesquiterpenoid from Homalomena occulta

Four phenolic acids, namely 2‐[(Z)‐heptadec‐11‐enyl]‐6‐hydroxybenzoic acid ( 1 ), 2‐[(6Z,9Z,12Z)‐heptadeca‐6,9,12‐trienyl]‐6‐hydroxybenzoic acid ( 2 ), 2‐[(9Z,12Z)‐heptadeca‐9,12‐dienyl]‐6‐hydroxybenzoic acid ( 3 ), and 2‐hydroxy‐6‐(12‐phenyldodecyl)benzoic acid ( 4 ), and one sesquiterpene, asperpenoid ( 5 ), were isolated from the 95% EtOH extract of the roots of Homalomena occulta, among which 1, 2 , and 5 represent new compounds. Further, the phenolic acids 1 – 4 exhibited BACE1 (β‐secretase) inhibitory activity with IC₅₀ values of 6.23±0.94, 6.28±0.63, 7.93±0.38, and 7.65±0.62 μM , respectively.     

Δ5-3β,7β-二羟基甾醇及其C-7差向异构体波谱特征及胆碱酯酶的抑制活性

本文对Δ5-3β,7β-二羟基甾醇(1~3)和Δ5-3β,7α-二羟基甾醇(4~6)的一些核磁共振波谱特征进行了比较。活性测试表明化合物1~6对乙酰胆碱酯酶(AChE)无明显的抑制活性,对丁酰胆碱酯酶(BuChE)则有较强的抑制活性,其中24-亚甲基胆甾-5-烯-3β,7α-二醇(6)的IC50值为9.5μM。通过活性数据比较我们发现7α-羟基甾醇对丁酰胆碱酯酶的抑制活性明显比相应的7β-羟基甾醇高。我们通过计算7位羟基和四环平面之间的二面角角度来尝试解释这些活性差别。     

Six New Constituents from the Fruit of Hypericum patulum and Their Anti-Inflammatory Activity

Four new xanthone glucosides, 3-hydroxy-2-methoxyxanthone-4-O-β-D-glucopyranoside ( 1 ), 4,8-dihydroxy-2-methoxyxanthone-3-O-β-D-glucopyranoside ( 2 ), 2-methoxyxanthone-5-O-β-D-glucopyranoside ( 3 ), 4-hydroxy-2-methoxyxanthone-3-O-β-D-glucopyranoside ( 4 ), a new phenolic acid, 4,4′-dihydroxy-3,3′-imino-di-benzoic acid monomethyl ester ( 5 ), and a new isoquinoline, methyl 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate ( 6 ) were isolated from the fruit of Hypericum patulum. The structural elucidation of the isolated compounds was primarily based on HR-ESI-MS, UV, IR, 1D and 2D NMR. All compounds were evaluated for their inhibitory effect against LPS-induced NO production in RAW 264.7 cells. Compound 2 , 3 exhibited moderate inhibitory activity against NO production.     

黑柄炭角菌的化学成分

从黑柄炭角菌(Xylaria nigripe)子实体中分离得到10个化合物,通过波谱分析等方法分别鉴定为(22E,24R)-麦角甾-5,7,22-三烯-3β-醇(1)、5α,8α-过氧-(22E,24R)-麦角甾-6,22-二烯-3β-醇(2)、脑苷酯B(3)、脑苷酯D(4)、stearic acid(5)、甘油的亚油酸三酯(trilinolein,6)、α-kojibiose(7)、D-阿洛糖醇(8)、L-氨基丙酸(9)和尿囊素(10)。所有化合物均为首次从该子实体中分离得到。     

云南红豆杉内生真菌Talarom yces sp.T1BF的化学成分研究

采用色谱技术从云南红豆杉内生真菌Talaromyces sp.T1BF的PDA平板发酵物中分离得到4个化合物.经波谱数据分析及与文献对照,分别鉴定为5α,6α-环氧-24( R)-甲基胆甾-7,22-二烯-3β-醇(1)、醌茜素(2)、苔色酸(3)和间甲基苯酚(4).化合物1为首次从该属真菌中分离获得.     

Inhibitory constituents of Nardostachys chinensis on nitric oxide production in RAW 264.7 macrophages

The activity-guided fractionation of the MeOH extract of the rhizomes and roots of Nardostachys chinensis led to the isolation of two new sesquiterpenoids, narchinol B (8) and narchinol C (9), along with 10 known compounds, ursolic acid (1), nardosinone (2), pinoresinol (3), desoxo-narchinol A (4), kanshone B (5), epoxyconiferyl alcohol (6), debilon (7), 4α,5-dimethyl-1,3-dioxo-1,2,3,4,4α,5,6,7-octahydronaphthalene (10), p-coumaric acid (11), and isoferulic acid (12). Their structures were determined using spectroscopic techniques, which included 1D- and 2D-NMR. Among the isolates, compounds 2, 4, 5, 8 and 9 showed inhibitory activity against LPS-induced NO production with IC(50) values of 4.6-21.6 μM.     

Triterpenes from Douglas fir sapwood

The saponified ether-soluble extractives of Douglas fir sapwood contained (24R)- 4α,14α,24-trimethyl-9β,19-cyclo-5α-cholestan-3β-ol(24R-cyclocucalanol),a new natural product; 4α,14α-dimethyl-9β,19-cyclo-24-methylene-5α-cholestan-3β- ol (cycloeucalenol); and (24R)-4α,24-dimethyl-5α-cholest-7-en-3β-ol (24R- methyllophenol); this is the first time they have been reported from Douglas fir.     

根霉3078的代谢产物的研究

从根霉3078菌丝体的甲醇提取物中分离得到9个化合物,通过波谱分析,鉴定为5α,8α-表二氧-(20S,22E,24R)-麦角甾-6,22-二烯-3β-醇(1)、甘油醇-1-单油酸酯(2)、4-羟基苯乙酮(3)、4-羟基苯乙酸(4)、(20S,22E,24R)-麦角甾-7,22-二烯-3β,5α,6β三醇(5)、(S)-3-羟基-3-苯基丙酸(6)、胸腺嘧啶(7)、尿嘧啶(8)和腺苷(9)。     

Chemical constituents of Polygala tenuifolia roots and their inhibitory activity on lipopolysaccharide-induced nitric oxide production in BV2 microglia

A methanolic extract of the roots of Polygala tenuifolia (Polygalaceae) significantly attenuated nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated BV2 microglia cells. Five xanthones, 1-hydroxy-7-methoxyxanthone (1), 3,6-dihydroxy-1,2,7-trimethoxyxanthone (2), 1,3,6-trihydroxy-2,7-dimethoxyxanthone (3), 1,7-dihydroxy-2,3-dimethoxyxanthone (4) and 1,7-dihydroxy-3-methoxyxanthone (5), and five phenylpropanoids, 4-hydroxy-3-methoxypropiophenone (6), methyl 4-hydroxy-3-methoxycinnamic acid (7), 3,4,5-trimethoxycinnamic acid (8), 4-methoxycinnamic acid (9) and β-d-(3-O-sinapoyl) fructofuranosyl-α-d-(6-O-sinapoyl)glucopyranoside (10), were isolated from CHCl(3) fraction using bioactivity-guided fractionation. Among these compounds, compounds 1, 2, 4, 5 and 7 showed significant inhibitory effects on LPS-induced NO production in BV2 microglia cells at the concentration ranging from 10.0 to 100.0 μM.     

Four New Polyhydroxy Cyclohexanes from the Stems of Fissistigma tientangense

Four undescribed polyhydroxy cyclohexanes, fissoxhydrylenes A–D ( 1–4 ), together with two known biogenetically related polyhydroxy cyclohexanes ( 5 and 6 ) were isolated from the stems of Fissistigma tientangense Tsiang et P. T. Li. Their structures were elucidated by detailed analysis of NMR, HR-ESI-MS, IR, UV and Optical rotations data. The absolute configuration of 1 was confirmed by X-ray crystallographic. The absolute configurations of 2–4 were confirmed by chemical reaction and optical rotations. Compound 4 represent the first example of a no substituent polyhydroxy cyclohexanes from natural products. All isolated compounds were evaluated for their anti-inflammatory activities against the lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells in vitro. Compounds 3 and 4 showed inhibitory activities with the IC₅₀ values of 16.63±0.06 μM and 14.38±0.08 μM, respectively.     

三种毒菌的化学成分研究

本文对三种毒菌的化学成分进行了研究。从光盖伞(Psilocybe spp)分离鉴定了4个化合物,经波谱分析鉴定为:(22E,24R)-麦角甾-7,22-二烯-3β-十八烷酸酯(1)、β-胡萝卜苷(2)、(22E,24R)-5α,6α-环氧麦角甾-8,22-二烯-3β,7α-二醇(3)、色氨酸(4);从假褐云斑鹅膏(Amanita pseudoporphyria)分离鉴定了4个化合物:(22E,24R)-3β-羟基-5α,8α-过氧化麦角甾-6,22-二烯(5)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(6)、1-O-β-D-吡喃葡萄糖基-(2S,3R,4E,8E,2′R)-2-N-(2′-羟基棕榈酰)-9-甲基-4,8-脱氢鞘氨醇(7)、1-O-β-D-吡喃葡萄糖基-(2S,3R,4E,8E,2′R)-2-N-(2′-羟基十八烷酰)-9-甲基-4,8-脱氢鞘氨醇(8);大青褶伞(Chlorophyllum molybdites)发酵菌丝体分离鉴定了4个化合物:5、6、(22E,24R)-5α,6α-环氧麦角甾-8(14),22-二烯-3β,7α-二醇(9)、(22E,24R)-麦角甾-7,22-二烯-3β-醇(10)。除化合物9外其它化合物均为首次从以上相应毒菌中分离得到。     

南海疏枝刺柳珊瑚中甾醇类化合物的研究

本文对采自海南三亚海域的疏枝刺柳珊瑚(Echinogorgia pseudossapo)化学成分进行研究,分离到11个甾醇类化合物。经波谱数据分析,分别鉴定为cholest-5-en-3β-ol(1),24-methylene-cholest-4-ene-3β,6β-diol(2),24-norcholesta-22-en-3β-ol(3),acanthovagasteroid A(4),calicoferol E(5),calicoferol F(6),6-hydroxy-cholest-4-ene-3-one(7),echinoflorasterol(8),echissaposterol(9),24-methylcholest-5-en-3β,7α-diol(10)和24-methylcholest-5,22(E)-dien-3β,7α-diol(11)。除化合物8外,其余化合物均首次从该种海洋动物中分离得到。     

蓝柄丽齿菌的化学成分

从担子菌亚门蓝柄丽齿菌(Calodon suaveolens)中首次分离得到8个化合物,通过波谱学技术并借助必要的化学方法最终确定结构,它们是：(22E,24R)-麦角甾-7,22-二烯-3β-醇(1),(22E,24R)-5α,8α-过氧麦角甾-6,22-二烯．3β-醇(2),(22E,24R)-麦角甾．5,7,22-三烯-3β-醇(3),(22E,24R)-3β-羟基麦角甾-5,22-二烯-7-酮(4),对羟基苯甲酸(5),尿嘧啶(6),polyozellin(7),(4E,BE）-2-N-(2’-羟基棕榈酰)-1-O-β-D-吡喃葡萄糖基-9-甲基-4,8-sphingadienine(8)。     

陆地革菌的化学成分研究

从陆地革菌(Thelephora terrestris)子实体中分离得到9个已知化合物,经波谱学分析鉴定为:(22E,24R)-麦角甾-7,22-二烯-3β -醇 (1),(22E, 24R)-麦角甾-7, 22-二烯-3β ,5α,6β -三醇 (2),(22E,24R)-麦角甾-4,6,8(14),22-四烯-3-酮 (3),24-亚甲基羊毛甾-8-烯-3β -醇 (4),熊果酸 (5),木栓酮 (6),cerebroside B (7),(2S,3S,4R,2'R)-2-(2'-羟基二十二碳酰氨基)-十八碳烷-1,3,4-三醇 (8),(2S,3S,4R,2'R)-2-(2'-羟基二十三碳酰氨基)-十八碳烷-1,3,4-三醇 (9)。     

Isocucurbic Acid Derivatives and Soluble Epoxide Hydroxylase Inhibitors from the Flowers of Chrysanthemum indicum L.

Soluble epoxide hydrolase (sEH) inhibitory activity guided fractionation and isolation of two new isocucurbic acid derivatives ( 1 and 2 ) and nine known compounds ( 3 – 11 ) from the flowers of Chrysanthemum indicum L. Their structures were elucidated on the basis of spectroscopic data interpretation and comparison with those reported in previous studies. Luteolin ( 3 ), acacetin-7-O-β-D-glucopyranoside ( 6 ), and methyl 3,4-di-O-caffeoylquinate ( 10 ) displayed sEH inhibitory activities with IC₅₀ values ranging from 13.7±3.6 to 20.8±0.4 μM. Enzyme kinetic analysis revealed that 3 , 6 , and 10 were non-competitive inhibitors with K_i values of 14.8±0.5, 31.2±0.8, and 3.9±0.2 μM, respectively. Additionally, molecular docking studies indicated compound 10 had the ability to form six hydrogen bonds at sEH active site, resulting binding energy as low as −9.58 Kcal/mol.