Terpenoids from Laurencia luzonensis

Luzodiol (4), a diterpene possessing a new carbon skeleton, and five new sesquiterpenes (5-9) of the snyderane class have been isolated from the red alga Laurencia luzonensis and their structures determined by spectroscopic analysis. The relative stereochemistry of the known luzonensol (3) was assigned by its conversion to palisadin B (10).     

Terpenoids and norlignans from Metasequoia glyptostroboides

Four new terpenoids, metaseglyptorin A (1), metasequoic acid C (2), 12α-hydroxy-8,15-isopimaradien-18-oic acid (3), and (-)-acora-2,4(14),8-trien-15-oic acid (4), and three new norlignans, metasequirins D-F (5-7), were isolated from Metasequoia glyptostroboides, together with 15 known compounds. Structures of the new compounds were determined by analysis of their spectroscopic data, and the absolute configuration of 7 was established by the modified Mosher method. All of the compounds were evaluated for cytotoxicity against five human tumor cell lines.     

大白杜鹃中萜类化学成分研究

目的:研究大白杜鹃Rhododendron decorum.枝叶的次级代谢产物。方法:利用硅胶、MCI、ODS、Sephadex LH-20、半制备HPLC等分离手段,对大白杜鹃的乙醇提取物进行分离纯化,对其理化性质、波谱数据进行分析并鉴定结构。结果:从大白杜鹃的95%乙醇提取物中分离鉴定了8个化合物,其中包括6个二萜类化合物,2个降倍半萜类化合物,分别是grayanotoxin I(1),grayanotoxin X(2),grayanotoxin VIII(3),rhododecorumin VII(4),leucothol A(5),grayanotoxin XXI (6),(+)-Dehydrovomifoliol (7),5α,6α-Epoxy-3β-hydroxy-megastigm-7-en-9-one(8)。结论:除了化合物4,其余化合物均为首次从大白杜鹃枝叶中分离得到。     

山柰根茎中一对磺酸化的双苯庚烷差向异构体(英文)

目的:为了从传统中药山柰中寻找新的活性化学成分。方法:应用D101大孔树脂,MCI,SephadexLH-20和制备液相等色谱方法对山柰根茎的乙醇提取物中水溶性部分进行分离纯化。结果:两个新的C-1磺酸化双苯庚烷差向异构体从山柰根茎中分离得到,分别命名为山柰磺酸A(1)和山柰磺酸B(2),并通过波谱学方法鉴定化合物的结构。两个化合物的绝对构型是通过比较电子激发圆二色谱(ECD)以及化学计算结合Mo2(OAc)4诱导圆二色谱(ICD)的方法确定。结论:化合物1和2为新化合物,并且首次对这两个化合物的绝对构型进行了确定。     

Antiulcer principle from Zingiber montanum

Ethnopharmacological relevance

Rhizome of Zingiber montanum has been extensively used as a folk medicine to ameliorate peptic ulcer at northern part of Bangladesh.

Aim of the study

To identify the antiulcer principle of the MeOH extract of the rhizome of Zingiber montanum by an ex vivo bioassay guided chromatographic separation and purification, and structure elucidation of the purified compound by spectroscopic methods.

Materials and methods

Dried powder of Zingiber montanum rhizomes was extracted with MeOH. The antiulcer activity of the crude extract and its chromatographic fractions were evaluated by the inhibition of 1 N HCl induced gastric lesions in Swiss albino mice. The pure compound was purified from the active fraction by crystallization with hexanes. Structure of the pure compound was elucidated by spectroscopic methods. The antiulcer activity of the pure compound was evaluated by the inhibition of 1 N HCl, 95% ethanol and indomethacin induced gastric lesions in mice.

Results

The MeOH extract of Zingiber montanum showed 61.97% and 83.10% inhibition of the 1 N HCl induced gastric lesions at doses of 200 mg/kg and 400 mg/kg, respectively, in mice. Chromatographic separation on silica gel of the extract was yielded seven fractions and the fraction 2 was found to have most potent antiulcer activity in mice. This fraction showed 77.46% inhibition of the 1 N HCl induced gastric lesions at a dose of 40 mg/kg in mice. Crystallization of the fraction yielded 1 (zerumbone, 180 mg). It showed statistically 45.77% and 92.25% inhibition of 1 N HCl induced gastric lesions in mice at doses of 20 mg/kg and 40 mg/kg, respectively. It also showed 29.07% and 45.35% inhibition of 95% ethanol induced gastric mucosal damage, and 64.76% and 72.38% inhibition of indomethacin induced gastric lesions in mice at doses of 20 mg/kg and 40 mg/kg, respectively.

Conclusion

Zerumbone (1) showed potent cytoprotective effect against necrotizing agent (HCl) and non-steroidal anti-inflammatory drug (indomethacin) induced gastric ulceration. It also exhibited moderate cytoprotective effect against noxious agent (EtOH) induced gastric lesions. It can be considered as a promising new antiulcer natural drug lead.     

缬草中的两个新的萜类化合物

目的：对缬草（Valeriana officinalis L.）的化学成分进行研究。方法：采用多种色谱层析技术进行分离并采用现代波谱技术解析各化合物的结构。结果：得到缬草新萜醇（4β,10α,15-三羟基香木兰烷）（1）和缬草单酯A（kanokoside A的苷元）（2）2个新化合物,另有8个已知化合物分别为鳞盖红菇醇（3）、山山山（4）、松脂醇（5）、缬草烯山（6）、β-谷甾醇（7）、kanokosideA（8）、青刺尖木脂醇苷（9）和8-羟基松脂醇苷（10）。结论：化合物1～4均为首次从该植物中分离得到;其中缬草新萜醇、缬草单酯A为2个新的天然产物。     

Terpenoids from Chloranthus serratus and their anti-inflammatory activities

Seven new terpenoids, including two sesquiterpene dimers (1, 2), two norditerpenoids (3, 4), and three sesquiterpenes (5-7), along with six known sesquiterpene dimers and four known sesquiterpenes were isolated from the whole plant of Chloranthus serratus. Their structures and relative configurations were elucidated on the basis of spectroscopic data analysis. The absolute configuration of 1 was determined by the CD exciton chirality method. These isolates were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells. Compound 2 and two known compounds, shizukaols B and D, showed significant anti-inflammatory activities, with IC(50) values of 0.22, 0.15, and 7.22 μM, respectively.     

巨柏茎叶的萜类成分（英文）

目的：对巨柏（Cupressus gigantea）茎叶的化学成分进行研究。方法：采用硅胶和 Sephadex LH-20 柱色谱的方法分离和纯化化合物, 通过 NMR, MS 及理化性质鉴定化合物结构。结果：从巨柏茎叶分离得到 15 个 labdane-type二萜, 其中一个为新化合物, 分别为：15-methoxy-18-hydroxylabda-8（17）,13-diene （1）, 13-epitoruolsol （2）, labd-8（17）,14-dien-13-ol （3）, 13-epi-cupressic acid （4）, cis-communic acid （5）, trans-communic acid （6）, labd-15-aceoxy-8（17）,13E-dien （7）, labd-8（17）,13E-dien-15-ol （8）, isocupressic acid （9）, acetylisocupressic acid （10）, isoabienol （11）, 13-oxo-14,15-dinor-labd-8（17）-en-19-oic acid （12）, pimarenic acid （13）, sandaracopimaric acid （14）, and pimarol （15） 此外还有两个已知倍半萜 ent-oplopanone （16） 和 （＋）-T-Cadinol （17）。结论：化合物（1）为新的倍半萜, 所有化合物均为首次从该植物中分得。     

大叶山楝枝叶中的萜类成分

目的:大叶山楝Aphanamixis grandifolia为楝科山楝属植物,具有舒筋活络、通痹及祛风除湿等功效,该文旨在研究大叶山楝枝叶中的萜类成分,揭示其发挥药效的物质基础。方法:取大叶山楝干燥枝叶22 kg,采用90%乙醇加热回流提取3次,减压回收溶剂成浸膏。浸膏加适量的水混匀后,依次用石油醚、乙酸乙酯进行萃取。石油醚和乙酸乙酯层萃取物分别经大孔树脂柱色谱,硅胶柱色谱,LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20)柱色谱和ODS柱色谱进行分离纯化,并通过质谱、核磁共振技术(1H和13C-NMR)和相关文献数据等对所得化合物进行结构鉴定。结果:从大叶山楝枝叶中分离并鉴定了12个萜类化合物,分别为16α-hydroxy-oxo-24-methyllanosta-7,9(11),24(31)-triene-21-oic acid(1),23(E)-cycloart-en-25-ethoxy-3-ol(2),23(Z)-9,19-cycloart-ene-3β,25-diol(3),23(E)-cycloart-23-en-3β,25-diol(4),labda-8,13-(E)-dien-15-ol(5),labda-7,13-(E)-dien-15-ol(6),vulgarol(7),(S,E)-6-[6-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl)-2-methylhepta-1,6-dien-1-yl]-4-methyl-5,6-dihydro-2H-pyran-one(8),nemoralisin(9),nemoralisin C(10),1S,4R,5S,6R,7S,10S-1(5),6(7)-diepoxy-4-guaiol(11),1S,4S,5S,10R-4,10-guaianediol(12)。结论:分离得到的化合物类型涉及三萜,二萜和倍半萜,其中8个化合物(1～3,5～8,12)为首次从该种植物中分离得到,也是首次从该属中分离得到。     

A new dimeric diarylheptanoid from the rhizomes of Alpinia officinarum简

AIM： To study the chemical constituents of the rhizomes ofAlpinia officinarum Hance. METHOD： Compounds were isolated by repeated column chromatography, and their structures were elucidated on the basis of spectral analysis. The cytotoxic activities of these compounds were evaluated with the T98G and B 16F10 cell lines by the MTT assay. RESULTS： A dimeric diarylheptanoid, named alpinin B （1）, along with three known diarylheptanoids were obtained, and their structures were identified as alpinin B （1）, 1, 7-diphenyl-3,5-heptanedione （2）, （4E）-1, 7-diphenylhept-4-en-3-one （3） and （4E）-7- （4-hydroxyphenyl）- 1-phenylhept-4-en-3-one （4）. CONCLUSION： Compound 1 is a new dimeric diarylheptanoid. The biosynthetic pathway of 1 was speculated to originate from a Michael reaction between compounds 2 and 3. Compound 3 showed cytotoxicity against the human glioblastoma T98G cell line with IC50 of 27 μmol·L-1.     

狼毒大戟根中的萜类成分研究

目的:研究狼毒大戟Euphorbia fischeriana根中的萜类成分。方法:利用硅胶、MCI、ODS、Sephadex LH-20柱色谱及半制备高效液相色谱法(HPLC)等分离手段对狼毒大戟根中的萜类成分进行分离纯化,根据理化性质、波谱学数据分析鉴定化合物结构。结果:从狼毒大戟根的80%丙酮提取物中分离鉴定了7个萜类化合物,包括5个二萜类化合物和2个三萜类化合物,分别鉴定为7-羰基脱氢松香酸(1)、trogopteroid F(2)、陶塔二酚(3)、18-羟基弥罗松酚(4)、19-羟基弥罗松酚(5)、环木波罗-22-烯-3β,25-二醇(6)和羽扇豆醇(7)。结论:除了化合物6和7,其余化合物均为首次从狼毒大戟中分离得到。     

三叶荚蒾中萜类化学成分的研究

采用硅胶、反向硅胶、Sephadex LH-20及MCI柱色谱等多种色谱技术和方法对三叶荚蒾Viburnum ternatum进行化学成分研究,运用现代波谱学方法并结合文献对分离得到的化合物进行结构鉴定。从该植物枝叶70%丙酮水提取液的醋酸乙酯萃取部分中分离并鉴定了12个化合物,包括4个环烯醚萜类成分ternatumin A(1),2,9-dioxatricyclo[4.3.1.03,7]decanes(2),7,10,2'-triacetylsuspensolide F(3)和7,10,2',3'-tetra-acetylsuspensolide F(4),5个环烯醚萜苷类成分viburtinoside IV(5),viburtinoside II(6),viburtinoside B(7),luzonoside A(8)和luzonoside B(9)以及3个三萜类成分2α,3β,24-trihydroxy-12-ursen-28-oic acid(10),6-hydroxy-20(29)-lupen-3-one(11)和pomalic acid(12)。其中,化合物1为新化合物,化合物2为新天然产物,化合物3~12为首次从该植物中分离得到。     

Terpenoids from the medicinal plant Maytenus ilicifolia

Four new terpenoids (1-4) were isolated from the root bark of Maytenus ilicifolia. Their structures were determined by spectroscopic studies, and complete 1H and 13C NMR assignments were achieved by 2D NMR spectroscopy. We also report an efficient method for the separation of quinonemethide triterpenes based on centrifugal partition chromatography.     

Terpenoids from the stems of Cipadessa baccifera

In our systematical investigation on Chinese Meliaceae plants, the stems of Cipadessa baccifera collected in Yunnan province were studied. Two new tetranortriterpenoids, cipadessalide ( 1) and rubralin D ( 2), one new pregnane, 3beta,4beta-dihydroxy-2beta-acetoxypregnan-16-one ( 3), and two new sesquiterpenoids, bacciferins A ( 4) and B ( 5), along with 10 known compounds were isolated. Their structures were elucidated by 1D and 2D NMR spectra and other spectroscopic studies, as well as chemical conversion.     

Terpenoids from the roots and rhizomes of Nardostachys chinensis

A new diterpene, 10-isopropyl-2,2,6-trimethyl-2,3,4,5-tetrahydronaphtha[1,8-bc]oxocine-5,11-diol (1), and a new monoterpene, 6-hydroxy-7-(hydroxymethyl)-4-methylenehexahydrocyclopenta[c]pyran-1(3H)-one, together with four known sesquiterpenes, delta1(10)-aristolene-9beta-ol, debilon, nardosinone, and kanshone A, were isolated from the roots of Nardostachys chinensis. The structures of the new compounds were established on the basis of their spectroscopic data, and the structure of 1 was confirmed by X-ray crystallographic analysis.     

珊瑚菌总萜提取工艺研究

目的研究水浴提取珊瑚菌总萜的最佳工艺。方法以总萜含量为指标,利用单因素和正交实验设计考察水浴提取工艺的最佳组合。结果最佳工艺为以80%乙醇为提取剂,在液料比25∶1(ml∶g),70℃下提取60 min,总萜含量为1.45%。结论在以上最佳条件下,珊瑚菌总萜提取率高;该方法重复性好,稳定性高,加样回收率在95.1%～104.0%范围内,结果可信,操作简单,方法可行。     

Terpenoids from the aerial parts of Parasenecio deltophylla

Five new modified eremophilane-type sesquiterpenes (1-5), including three norsesquiterpenes (1-3), and one new monoterpene (6) were isolated from the aerial parts of Parasenecio deltophylla. Their structures were established on the basis of HRMS and NMR methods. The cytotoxicity of compounds 1-4 and 6 against selected cancer cell lines, including human promyelocytic leukemia (HL-60) and human hepatoma (Hep-G2), was evaluated. Antioxidant activities of these compounds were assessed by ABTS and DPPH methods.     

勐醒芒毛苣苔三萜类化学成分研究

目的：研究勐醒芒毛苣苔Aeschynanthus mengxinensis叶醋酸乙酯部分的化学成分。方法：采用各种色谱法分离，运用多种波谱技术鉴定结构。结果：从勐醒芒毛苣苔的醋酸乙酯部位分离鉴定了4个化合物：2α，3β，19β-trihydroxy-olean-12-ene-23，28-dioic acid(1)，2α，3β，21β-trihydroxyolean-12-ene-28-oic acid(2)，2α，3β，23-trihydroxyurs-12-ene-28-oic acid(3)和豆甾-5(6)，22(23)-二烯-3β-醇(4)。结论：运用HMBC和HMQC，首次对化合物1碳谱和氢谱数据进行全归属，化合物1～4均为首次从该科植物中得到。     

New diarylheptanoids and diarylheptanoid glucosides from the rhizomes of Tacca chantrieri and their cytotoxic activity

Two new diarylheptanoids (1, 2) and seven new diarylheptanoid glucosides (3-9) were isolated from the rhizomes of Tacca chantrieri. Their structures were determined by spectroscopic analysis, including 2D NMR data, and the results of hydrolytic cleavage. The absolute configurations of the 3,5-dihydroxyheptane moieties of the new diarylheptanoids were determined to be 3R and 5R by the application of the CD exciton chirality method to the corresponding 3,5-bis-p-bromobenzoyl derivatives. The cytotoxic activities of the isolated compounds and some derivatives against HL-60 human promyelocytic leukemia cells, HSC-2 human oral squamous carcinoma cells, and normal human gingival fibroblasts (HGF) are reported.