Two new diterpenes from the seeds of Caesalpinia minax Hance

Molecules with diterpene skeletons often possess valuable medicinal properties. Two new diterpenes 1α,6α,7β-triacetoxy-5α-hydroxy-14β-ethyl-O-vouacapane (1) and 2α-acetoxy-14,15-cyclopimara-7β,16-diol (2) were isolated from the seeds of Caesalpinia minax Hance. Their structures were established on the basis of extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D, and 2D NMR (HSQC, HMBC, NOESY) methods. The stereochemical structure of 1 was confirmed via the circular dichroism spectrum and calculated ECD experiment. The inhibitory activity of nitric oxide production of RAW264.7 macrophages stimulated by lipopolysaccharide of compounds 1 and 2 was evaluated, and compound 1 was found to show significant inhibitory effect.     

喙荚云实种子中的新二萜

目的研究喙荚云实的化学成分。方法采用多种色谱方法分离纯化,依据理化性质、波谱数据分析进行结构鉴定。结果从喙荚云实的体积分数为95%的乙醇回流提取物中分离鉴定了1个二萜类化合物。结论此二萜类化合物为新化合物。     

A new cassane diterpenoid from the seeds of Caesalpinia decapetala

Phytochemical investigation on the seeds of Caesalpinia decapetala led to the isolation of a new cassane diterpenoid with an unusual O bridge between C-19 and C-20, named phanginin Q (1), together with three known cassane diterpenoids, caesaljapin (2), caesaldekarin A (3), and caesaldekarin B (4). The structure of the new compound was elucidated by spectroscopic methods, including ¹H NMR, ¹³C NMR, HSQC, ¹H ? ¹H COSY, HMBC, NOESY, and HR-ESI-MS.     

Two new cassane-type diterpenes from the seeds of Caesalpinia crista

Two new cassane-type diterpenes, phangininoxys D and E (1 and 2), together with five known compounds were isolated from the seeds of Caesalpinia crista Linn. The structures of these compounds were elucidated by means of various spectroscopic analyses. All the isolated compounds were evaluated for cytotoxicity activities against HeLa, HT-29 and KB cell lines, and compound 7 showed moderate selective activities against KB cell line with an IC₅₀ value of 17.1 μM.     

苦石莲化学成分的分离与鉴定（IV）

目的对苦石莲中的化学成分做进一步研究。方法采用硅胶柱色谱、凝胶柱色谱和重结晶等多种方法分离纯化,根据理化性质及波谱学数据进行结构鉴定。结果分离得到9个化合物,分别鉴定为全反式-5-脱氧戊糖酸-γ-内酯(all-trans-5-deoxy-pentonic acid-γ-lactone,1)、腺苷(adeno-sine,2)、胡萝卜苷-6’-O-硬脂酸酯(daucosterol-6’-O-stearate,3)、7-acetoxybonducellpin C(4)、caesal-pinin K(5)、norcaesalpinin E(6)、neocaesalpin A(7)、neocaesalpin L(8)、neocaesalpin M(9)。结论化合物1、2为首次从云实属植物中分离得到,化合物3～5、7为首次从喙荚云实植物中分离得到。     

Two new diterpenes,neocaesalpin MR and minaxin C,from Caesalpinia minax

Two new cassane-type diterpenes, neocaesalpin MR (1) and minaxin C (2), were isolated from Caesalpinia minax HANCE. The structures of these compounds were elucidated by means of spectroscopic analysis. Among these isolated compounds, neocaesalpin MR showed mild activities toward HeLa and colon cancer (HCT-8) human cancer cell lines.     

喙荚云实的化学成分

目的喙荚云实的化学成分研究。方法采用多种色谱方法分离纯化,依据理化性质、波谱数据分析进行结构鉴定。结果从喙荚云实的体积分数为95%的乙醇溶液提取物中分离纯化得到7个化合物,分别鉴定为-βamyrin(1)、Caffeine(2)、Caesalmin C(3)、Caesalmin D(4)、Caesalpin F(5)、β-谷甾醇(-βsitosterol,6)、胡萝卜苷(Daucosterol,7)。结论化合物1,2为首次从该属植物中分离得到的化合物,化合物6,7为首次从该植物中分离得到的化合物。     

苦石莲对CCl4所致小鼠急性肝损伤保护作用研究

目的：研究苦石莲对四氯化碳（CCl4）所致小鼠急性肝损伤的保护作用。方法：用苦石莲预防性给药若干天后,用CCl4所致肝损伤模型为研究对象,检测小鼠血清ALT、AST及肝脏系数等指标。结果：苦石莲能抑制小鼠急性肝损伤血清ALT、AST的含量和肝脏系数的升高（P〈0．01,P〈0．05）。结论：苦石莲对CCl4所致小鼠急性肝损伤具有一定保护作用。     

南蛇勒蛋白对黑色素瘤细胞的抑制及分化作用

目的从南蛇勒中分离纯化具有抑制黑色素瘤作用的蛋白质———南蛇勒蛋白 (CMP) ,并对黑色素瘤细胞KI735M2增殖的抑制及细胞的分化进行研究。方法采用盐析、凝胶色谱的方法对CMP进行分离纯化 ,溴化四唑蓝法检测CMP对黑色素瘤细胞KI735M2增殖的抑制作用的量效和时效关系 ,形态学观察法检测细胞的分化。结果CMP相对分子质量为 1980 0 ,2 2 .0 μg/mlCMP抑制黑色素瘤细胞增殖 6 0 % (P <0 .0 5 ) ,使细胞增殖第 5天处于停顿 ,抑制率为 96 % (P <0 .0 5 ) ,不同浓度的CMP使黑色素瘤细胞形成具有分化特征的树突状结构。结论CMP对黑色素瘤细胞KI735M2的增殖具有抑制作用。     

Irritant potential of some constituents from the seeds of Caesalpinia bonducella (L.) Fleming

The irritant potential of four triterpenoids, isolated for the first time from the seeds of Caesalpinia bonducella, identified as f -amyrin [12-ursen-3 g -ol], g -amyrin [12-oleanex-3 g -ol], lupeol [lup-20(29)-en-3 g -ol] and lupeol acetate [lup-20(29)-en-3 g -yl acetate] was investigated by open mouse ear assay, evaluating their ID₅₀ (irritant dose in 50% animals) after acute effects and by irritant units (IU) after chronic effects. f -Amyrin, lupeol acetate and g -amyrin were the most potent and persistent irritant compounds with red weals of 1.5-2.1 cm diameter areas of the animal skin and with lowest ID₅₀ =0.078, 0.186 and 0.190 mg/10 w l after 1.5, 2.10 and 3.5 h, respectively. Their reactions lasted for 24 h with IU=2.5; 0.312 and 1.25 mg/10 w l, respectively. Lupeol was the least irritant and least persistent compound with ID₅₀ =0.603 mg/10 w l after 4.5 h. Its reaction subsided before 24 h.     

A new homoisoflavan from Caesalpinia sappan

A new homoisoflavan, 7,3′,4′-trihydroxy-3-benzyl-2H-chromene (1), was isolated from the dried heartwood of Caesalpinia sappan L., together with seven known phenolic compounds. The structure of the new compound (1) was determined on the basis of spectroscopic analysis.     

Antitubercular cassane furanoditerpenoids from the roots of Caesalpinia pulcherrima

Activity-guided fractionation of a root extract of Caesalpinia pulcherrima led to the isolation of two cassane-furanoditerpenoids, 6 beta-benzoyl-7 beta-hydroxyvouacapen-5 alpha-ol (1) and 6 beta-cinnamoyl-7beta-hydroxyvouacapen-5 alpha-ol (2). Compound 2 showed strong antitubercular activity with a minimum inhibitory concentration (MIC) of 6.25 microg/mL, whereas the benzoyl analogue (1) was less active (MIC 25 microg/mL). Both compounds expressed moderate cytotoxic activity towards KB (human oral carcinonoid cancer), BC (human breast cancer) and NCl-H187 (small cell lung cancer) cell lines.     

In vivo immunomodulatory activities of the aqueous extract of bonduc nut Caesalpinia bonducella seeds

This study evaluated the in vivo immunomodulatory activities of the aqueous extract of Caesalpinia bonducella Fleming (Caesalpiniaceae) seeds. C. bonducella is a plant widely used in the traditional medicinal systems of India. In the present investigation, the aqueous extract of C. bonducella seeds was tested for its effect on cell mediated and humoral components of the immune system in rats. Administration of C. bonducella seed extract produced an increase of 93.03?±?4 mean hemagglutinating antibody (HA) titer and a change of 0.56?±?0.058?mm in delayed type hypersensitivity (DTH) as compared to control at a dose of 400?mg/kg body weight. Thus, the results of this study indicate that C. bonducella extract could be a promising immunostimulatory agent.     

Two new daphnane diterpenes from the roots of Stelleropsis tianschanica

Abstract

Two new daphnane diterpenes named tianchaterpenes A and B were isolated from the roots of Stelleropsis tianschanica. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses and HRESIMS. Compounds 1 and 2 were evaluated for their cytotoxic activities against HeLa and HCT-8 cell lines. The results showed that all compounds displayed weak cytotoxicities to the HeLa cells and were inactive to the HCT-8 cells.     

Chemical constituents from the the twigs and leaves of Caesalpinia enneaphylla

Fifteen compounds were isolated from the twigs and leaves of Caesalpiniaenneaphylla. Their structures were identified to be: (E)-3-(4-hydroxybenzylidene)- 5,7-dihydroxychroman-4-one (1), 8-methoxybonducellin (2), (E)-3-(3,4- dihydroxybenzylidene)-5,7-hydroxychroman-4-one (3), 2′,4′-dihydroxychalcone (4), oxyfadichalcone B (5), 7-hydroxyflavonone (6), pinocembrin (7), kaempferol (8), quercitrin (9), kaempferol 3-O-α-L-rhamnopyranoside (10), quercetin 3-O-α-D-arabinoside (11), trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]-cyclohexa-4,6-diene (12), 3-hydroxybenzyl benzoate (13), 2-acetoxybenzyl benzoate (14), and glutinol (15). All the compounds were isolated from C. enneaphylla for the first time.     

New cytotoxic clerodane diterpenes from the leaves of Premna tomentosa

Bio-activity directed investigation of hexane extract from the leaves of Premna tomentosa led to the isolation of three new clerodane diterpenes (1–3) along with four known compounds (4–7). The structures of new compounds were established using IR, MS, 1D, and 2D NMR techniques. The in vitro cytotoxicity of the crude hexane extract and the isolated compounds were evaluated against seven human cancer cell lines and results indicated that compounds 2 and 4 depicted significant cytotoxicity against hepatocellular carcinoma cell line.     

Cassane-type Diterpenes from the Seeds of Caesalpinia minax with Their Antineoplastic Activity

Five new cassane-type diterpenes, neocaesalpin AA (1), neocaesalpin AB (2), neocaesalpin AC (3), neocaesalpin AD (4) and neocaesalpin AE (5), were isolated from Caesalpinia minax together with three known compounds, 12α-methoxyl,5α,14β-dihydroxy-1α,6α,7β-triacetoxycass-13(15)-en-16,12-olide (6), spirocaesalmin (7) and magnicaesalpin (8). Their structures were elucidated based on 1D and 2D NMR, MS and CD analyses. Compounds 1-6 were tested against Hela, HCT-8, HepG-2, MCF-7 and A549 cancer cells and showed moderate cytotoxicity with IC50 values from 18.4 to 83.9 μM.     

Phenolic compounds from the twigs and leaves of Tara (Caesalpinia spinosa)

Two new homoisoflavans, 4′-hydroxy-7-methoxy-3-benzyl-2H-chromene (1) and 3,4-cis-di-O-3-hydroxy-7-methoxy-3-(4-hydroxybenzyl)-4-ethoxychroman (2), one new coumarin, 7-methoxy-3-(4-hydroxybenzyl)coumarin (4), together with seven known phenolic compounds, bonducellin (3), anemarcoumarin A (5), (+)-syringaresinol (6), curuilignan D (7), scopoletin (8), and p-hydroxybenzaldehyde (9), were isolated from Tara (Caesalpinia spinosa Kuntze). The structures of the new compounds were characterized from their 1D and 2D NMR spectral data. All the compounds were isolated from this plant for the first time.     

Labdane diterpenes from the seeds of Platycladus orientalis

Two new labdane diterpenes, 14(R),15-dihydroxy-8(17),12(E)-labdadien-19-oic acid (1) and 16-methyl–12,15-epoxy-8(17),13-labdadien-19-oic acid (2), together with four known compounds, were isolated from the seeds of Platycladus orientalis. Their structures were established by spectroscopic methods. The stereochemistry of compound 1 was defined by X-ray crystallographic analysis.     

Labdane diterpenes from the seeds of Platycladus orientalis

Two new labdane diterpenes, 14(R),15-dihydroxy-8(17),12(E)-labdadien-19-oic acid (1) and 16-methyl-12,15-epoxy-8(17),13-labdadien-19-oic acid (2), together with four known compounds, were isolated from the seeds of Platycladus orientalis. Their structures were established by spectroscopic methods. The stereochemistry of compound 1 was defined by X-ray crystallographic analysis.