Two new triterpenoids from the resin of Boswellia carterii

Two new triterpenoids, 3-oxotirucalla-7,9(11),24-trien-21-oic acid (1) and 18Hα,3β,20β-ursanediol (2), along with 15 known triterpenes, α-amyrin, α-boswellic acid, β-boswellic acid, acetyl α-boswellic acid, acetyl β-boswellic acid, 9,11-dehydro-β-boswellic acid, 9,11-dehydro-α-boswellic acid, acetyl 11α-methoxy-β-boswellic acid, 11-keto-β-boswellic acid, acetyl 11-keto-β-boswellic acid, acetyl α-elemolic acid, 3β-hydroxytirucalla-8,24-dien-21-oic acid, elemonic acid, 3α-hydroxytirucalla-7,24-dien-21-oic acid, and 3α-hydroxytirucall-24-en-21-oic acid, were isolated from the resin of Boswellia carterii Birdw.     

Studies on triterpenoid corticomimetics (III)

From olibanum, acetylboswellic acid (I) and boswellic acid (II) were isolated as mixed crystals of α-and β-forms in the ratio of 1 to 2 and 1 to 4, respectively. And acetyl-11-keto-β-boswellic acid (III) and 11-keto-β-boswellic acid (IV) were also isolated and their α-forms were not found in olibanum by GC/selected ion monitoring MS technique. Contents of four compounds were determined.     

HPLC法测定乳香药材中11-羰基-β-乙酰乳香酸的含量

目的测定乳香药材中11-羰基-β-乙酰乳香酸的含量,建立有效方法。方法采用HPLC法,二极管阵列检测器;Empower色谱工作站;用十八烷基硅烷键合硅胶为填充剂;C18柱(250×4.6mm,5μm);以乙腈-水-冰乙酸(79∶21∶0.1)为流动相;检测波长为249nm。结果11-羰基-β-乙酰乳香酸在12μg.mL-1~495μg.mL-1(r=0.9999)范围内线性关系良好,平均回收率为100.12%,RSD为1.51%(n=6)。结论所测11-羰基-β-乙酰乳香酸含量符合标准,本法可作为11-羰基-β-乙酰乳香酸的质量控制方法。     

土槿皮的化学成分研究(英文)

对松科Pinaceae植物金钱松Pseudolarix kaempferi Gord的干燥根皮—土槿皮的化学成分进行了研究。应用硅胶,Sephadex LH-20,MCI柱色谱以及高效液相色谱等技术进行分离纯化,利用化合物的理化常数和波谱数据鉴定其结构。分离并鉴定了26个化合物,分别为:土槿丁酸(1),土槿甲酸(2),土槿乙酸(3),土槿丙酸(4),3β-乙酰氧基-齐墩果烷-11,13(18)二烯(5),3β-乙酰氧基-齐墩果烷-9(11),12二烯(6),3β-羟基-齐墩果烷-11,13(18)二烯(7),3β-羟基-齐墩果烷-9(11),12二烯(8),Celangulatin C(9),Celangulatin E(10),17β-通关藤苷元B(11),11α-O-(2-甲基丁酰基)-12β-O-乙酰基通关藤苷元B(12),11α-O-(2-甲基丁酰基)-12β-O-巴豆酰基(顺芷酰基)通关藤苷元B(13),β-谷甾醇酯(14),伞形花内酯(15),5,7-二羟基香豆素(16),花椒毒素(17),异虎耳草素(18),芒柄花黄素(19),毛蕊异黄酮(20),Cnidimol B(21),胸腺嘧啶(22),3-呋喃甲酸(23),2-呋喃甲酸(24),香草酸(25),原儿茶酸(26)。其中化合物5–24为首次从该植物中分离得到;并首次归属化合物1的1H和13CNMR谱数据。     

西黄丸中11-羰基-β-乙酰乳香酸的鉴别及含量测定

目的：建立西黄丸中11-羰基-β-乙酰乳香酸的定性定量检验方法.方法：采用薄层色谱法和高效液相色谱法建立西黄丸中乳香类成分11-羰基-β-乙酰乳香酸的方法.结果：运用建立的薄层色谱法检测12个生产厂家提供的17批西黄丸,均含有11-羰基-β-乙酰乳香酸,但含量差别大,运用高效液相色谱法对其进行含量测定,其中11-羰基-β-乙酰乳香酸含量最低为0.27％,最高为1.05％.结论：建立薄层色谱法和高效液相色谱法可用于西黄丸中11-羰基-β-乙酰乳香酸的定性定量检验,可作为西黄丸现行法定检验标准中乳香显微鉴别的有益补充.     

Boswellia serrata, a potential antiinflammatory agent: an overview

The resin of Boswellia species has been used as incense in religious and cultural ceremonies and in medicines since time immemorial. Boswellia serrata (Salai/Salai guggul), is a moderate to large sized branching tree of family Burseraceae (Genus Boswellia), grows in dry mountainous regions of India, Northern Africa and Middle East. Oleo gum-resin is tapped from the incision made on the trunk of the tree and is then stored in specially made bamboo basket for removal of oil content and getting the resin solidified. After processing, the gum-resin is then graded according to its flavour, colour, shape and size. In India, the States of Andhra Pradesh, Gujarat, Madhya Pradesh, Jharkhand and Chhattisgarh are the main source of Boswellia serrata. Regionally, it is also known by different names. The oleo gum-resins contain 30-60% resin, 5-10% essential oils, which are soluble in the organic solvents, and the rest is made up of polysaccharides. Gum-resin extracts of Boswellia serrata have been traditionally used in folk medicine for centuries to treat various chronic inflammatory diseases. The resinous part of Boswellia serrata possesses monoterpenes, diterpenes, triterpenes, tetracyclic triterpenic acids and four major pentacyclic triterpenic acids i.e. β-boswellic acid, acetyl-β-boswellic acid, 11-keto-β-boswellic acid and acetyl-11-keto-β-boswellic acid, responsible for inhibition of pro-inflammatory enzymes. Out of these four boswellic acids, acetyl-11-keto-β-boswellic acid is the most potent inhibitor of 5-lipoxygenase, an enzyme responsible for inflammation.     

Cytotoxic triterpenoids and steroids from the bark of Melia azedarach

Two new triterpenoids (1, 2) and two new steroids (3, 4) along with twelve related known compounds (5-16) were isolated from the bark of Melia azedarach. The new structures were elucidated by means of spectroscopic methods and molecular modeling studies and found to be 21,24-cycloeupha-7-ene-3 β,16 β,21 α,25-tetrol (1), 3 β-acetoxy-12 β-hydroxy-eupha-7,24-dien-21,16 β-olide (2), 29-hydroperoxy-stigmasta-7,24(28) E-dien-3 β-ol (3), and 24 ξ-hydroperoxy-24-vinyl-lathosterol (4). All isolated compounds were tested for their cytotoxic activity against three human cancer cell lines (A549, H460, HGC27) using the CellTiter Glo? luminescent cell viability assay. Among them, compounds 2- 4, 24 ξ-hydroperoxy-24-vinyl-cholesterol (6), kulinone (7), meliastatin 3 ( 8), 3-oxo-olean-12-en-28-oic acid (10), and (22 E,24 S)-5 α,8 α-epidioxy-24-methyl-cholesta-6,22-dien-3 β-ol (12) were found to have cytotoxic effects, with IC?? values of 5.6-21.2?μg/mL.     

Preparation of Novel Analogues of the Nonredox-Type Non-Competitive Leukotriene Biosynthesis Inhibitor AKBA

AKBA (acetyl-11-keto-β-boswellic acid, 1 ) and KBA (11-keto-β-BA, 2 ) from Boswellia serrata Roxb. and Boswellia carterii Birdw. are direct, nonredox-type inhibitors of 5-lipoxygenase, the key enzyme for leukotriene biosynthesis (IC₅₀ = 1.5 and 3μM in intact neutrophils, respectively). In order to study the impact of the carboxyl function for enzyme inhibition, we synthesized novel analogues of boswellic acids. The C-4 alcohol derivative of KBA ( 4 ) still exerted 5-lipoxygenase inhibitory activity (IC₅₀ = 4.5 μM), whereas ( 8 ), the C-4 alcohol analogue of β-boswellic acid ( 7 ), the methyl ester analogue of KBA ( 5 ), and acetyl-11-keto-amyrin ( 9 ) possessed no inhibitory potential in concentrations up to 50 μM. These findings reveal that a hydrophilic group at C4 in combination with an 11-keto-function is essential for 5-lipoxygenase inhibition by boswellic acids.     

腰痛宁胶囊中11-羰基-β-乙酰乳香酸的含量测定方法研究

目的建立腰痛宁胶囊中11-羰基-β-乙酰乳香酸的含量测定方法。方法采用高效液相色谱法测定腰痛宁胶囊中11-羰基-β-乙酰乳香酸的含量,色谱柱为Agilent SB-C 18(4.6×150mm,5μm),流动相为乙腈-0.1%甲酸(82∶18),检测波长为251nm,流速为1.0mL·min^-1,进样体积为10μL。结果11-羰基-β-乙酰乳香酸的线性范围:1.014~50.72μg·mL^-1(r=1),平均加样回收率为100.59%,RSD为0.88%(n=9)。结论所建立的方法准确、灵敏、简便,稳定性和重现性良好,专属性强,可较好地控制腰痛宁胶囊的质量。     

New terpenes from Salvia palaestina Benth. and Salvia syriaca L. growing wild in Jordan

The novel seco-ursane-type triterpenoid 3β,11α-dihydroxy-17,22-seco-17(28), 12-ursadien-22-oic acid (1) was isolated for the first time from a natural source from two Salvia species growing wild in Jordan, Salvia palaestina Benth. and Salvia syrica L. In addition to compound 1, S. syriaca afforded a new sesquiterpene named syriacine (2). S. palaestina also afforded 15 other known compounds, 6 of which are isolated for the first time from the plant, and these include velutin, hyptadienic acid, cirsilineol, 2α,3β-dihydroxyurs-12-en-28-oic acid, 2α,3α-dihydroxy-24-nor-4(23),12-oleanan-28-oic acid, and 2α,3β,24-trihydroxyurs-12-en-28-oic acid. S. syriaca also afforded 16 other known compounds, 7 of which are isolated for the first time from the plant. These are 1α,3α-dihydroxyolean-9(11),12-diene, maslinic acid, 2α,3β,24-trihydroxyolean-12-en-28-oic acid, 11-oxo-oleanolic acid, 11-oxo-ursolic acid, poriferast-5-en-3,7-diol, and pectolinangenin.     

Discovery of cyclooxygenase inhibitors from medicinal plants used to treat inflammation

Eleven authenticated botanicals used in the traditional Chinese medicine Huo-Luo-Xiao-Ling Dan were screened for ligands to cyclooxygenase (COX) using pulsed ultrafiltration liquid chromatography–mass spectrometry, and a mass spectrometry-based enzyme assay was used to determine the concentration of each of 17 ligands that inhibited COX-1 or COX-2 by 50% (IC₅₀). Acetyl-11-keto-β-boswellic acid, β-boswellic acid, acetyl-α-boswellic acid, acetyl-β-boswellic acid, and betulinic acid were COX-1 selective inhibitors with IC₅₀ values of approximately 10 μM. Senkyunolide O and cryptotanshinone were COX-2 selective inhibitors with IC₅₀ values of 5 μM and 22 μM, respectively. Roburic acid and phenethyl-trans-ferulate inhibited COX-1 and COX-2 equally. COX inhibition and the IC₅₀ values of most of these natural product ligands have not been reported previously.     

Poriacosones A and B: two new lanostane triterpenoids from Poria cocos

Two new lanostane triterpenoids, poriacosones A (8) and B (9), together with eight known compounds were isolated from the sclerotia of Poria cocos (Schw.) Wolf (Polyporaceae), and identified by spectroscopic analysis, including IR, UV, CD, ESI-TOF-MS, HR-SIMS, 1D-, and 2D-NMR spectra. The structures of the new compounds were established as 3alpha,16alpha-dihydroxy-24-oxolanost-7,9(11)-dien-21-oic acid (8) and 3beta,16alpha-dihydroxy-24-oxolanost-7,9(11)-dien-21-oic acid (9).     

Poriacosones A and B: two new lanostane triterpenoids from Poria cocos

Two new lanostane triterpenoids, poriacosones A (8) and B (9), together with eight known compounds were isolated from the sclerotia of Poria cocos (Schw.) Wolf (Polyporaceae), and identified by spectroscopic analysis, including IR, UV, CD, ESI-TOF-MS, HR-SIMS, 1D-, and 2D-NMR spectra. The structures of the new compounds were established as 3alpha,16alpha-dihydroxy-24-oxolanost-7,9(11)-dien-21-oic acid (8) and 3beta,16alpha-dihydroxy-24-oxolanost-7,9(11)-dien-21-oic acid (9).     

Constituents of Cupuliferae,XVII: Triterpene Saponins and Falvonoids from Quercus laurifolia Michx.

In addition to fourteen known glycosides from leaves of Quercus laurifolia Michx., a new acylated triterpene soponin has been isolated and identified as 3-O-galloyl-28-β-D -glucopyranosyl diester of the 2α,3β,19α,23-tetrahydroxyurs-12-ene-28-oic acid ( 1 ). The structure of the previously described α-D -glucopyranosyl ester of the 2α,3β,19α,23-tetrahydroxyurs-12-ene-28-oic acid was revised to β-D -glucopyranosyl ester of the 2α,3β,19α,23-tetrahydroxyurs-12-ene-28-oic acid ( 2 ).     

云南甘草中新三萜成分的研究

自云南甘草(Clycyrrhiza yunnanensis)根中分离出10个化合物,经化学方法和光谱解析,鉴定9个为五环三萜类化合物:3β,21α,24-三羟基-齐墩果-12-烯-29-羧酸(Ⅰ)、3β,21α-二羟基-齐墩果-12-烯(Ⅱ)、3β,21α,24-三羟基-齐墩果-12-烯(Ⅲ)、桦木酸(Ⅳ)、23-羟基桦木酸(Ⅴ)、齐墩果酸(Ⅵ)、3β-羟基-16-氧-11,13(18)-二烯-3O-羧酸(Ⅶ)、24-羟基甘草内酯(Ⅷ)和21α-乙酰氧基木栓烷-3-酮(Ⅸ);另一个为β-胡萝卜甙(Ⅹ)。其中Ⅰ和Ⅱ为新化合物,分别命名为云南甘草皂甙元B1和B2。其余7个是已知物,但Ⅴ和Ⅸ首次得自甘草属植物,Ⅳ,Ⅵ和Ⅷ首次自云南甘草中分离得到。     

LC-MS/MS as a tool for identification of bioactive compounds in marine sponge Spongosorites halichondriodes (Dendy 1905)

The sensitivity, specificity and selectivity of liquid chromatography/mass spectrometry tandem mass spectrometry (LC-MS/MS) make it an essential tool for the characterization and identification of low molecular compounds such as fatty acids, sterols, cholastane derivatives, nucleosides etc. In the current work, the marine sponge Spongosorites halichondriodes (order Halichondrida, Family Halichondriidae); a particularly rich source of cytotoxic compounds is studied for the initial characterization of bioactive compounds. The composition of ethyl acetate and butanol extracts were subjected to LC-MS and LC-MS/MS. Many novel sterol derivatives compounds which were not reported in any marine sponge mainly belonged to the group of C₂₅-C₂₈ saturated and unsaturated esters like 3β, 4β, 7α, 12α-tetrahydroxy-5β-cholan-24-oic acid methyl ester, 7 α, 12 β-dihydroxy-5 β-cholan24-oic acid methyl ester, novel isocoumarin citrinolactone A, a triterpenoid glycyrrhetinic acid as well as other unknown compounds in this species such as nucleoside inosine was identified. Other compound investigated was 3β, 6β, 7α-trihydroxy-5β-cholan-24-oic acid methyl ester. All the sterol ester derivatives are reported here for the first time in marine sponge belonging to family Halichondriidae. However, the literature report supports the occurrence of 3β-hydroxy sterols which is considered as a biomarker for this family.     

藤山柳根茎中的三萜成分

目的　研究我国特有的单种属药用植物藤山柳[Clematoclethrascandens (Franch .)Maxim .]根茎的甲醇提取物正丁醇萃取部分的化学成分。方法　将甲醇提取物分散于水中,经石油醚和乙酸乙酯萃取后,再用正丁醇进行萃取,对正丁醇萃取物进行柱色谱分离纯化,用波谱方法鉴定化合物结构。结果　分离鉴定了5个三萜化合物:2α,3β,24-三羟基乌苏-12 ,18-二烯-28-酸-28-O-β-D-吡喃葡糖酯(I) ,niga-ichigoside F₁ (II) ,asiaticacid (III) ,2α,3α,24-三羟基乌苏-12-烯-28-酸(IV) ,2α,3α,19α,24-四羟基乌苏-12-烯-28-酸(V)。结论　以上三萜化合物均为首次从该属植物中获得,其中I是一个新三萜皂苷     

黄腊果叶中化学成分的分离与鉴定(Ⅰ)

目的研究黄腊果(Stauntonia brachyanthera Hand.-Mazz.)叶中的化学成分。方法采用反复硅胶柱色谱法、Sephadex LH-20柱色谱法、制备薄层色谱法和重结晶等方法进行分离纯化,通过理化性质与波谱分析方法鉴定化合物的结构。结果从黄腊果叶体积分数70%乙醇溶液提取物中分离鉴定6个化合物,分别为3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-D-glucopyrano-side(1)、牡荆素(vitexin,2)、山奈酚(kaempferol,3)、apigenin-7-O-β-D-neospheroside(4)、3,23-di-hydroxy-akebonic acid(5)、3-O-β-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid(6)。结论化合物1～4为首次从野木瓜属植物中分离得到,化合物5为首次从黄腊果中分离得到。     

黄腊果果皮化学成分的分离与鉴定

目的研究黄腊果果皮的化学成分。方法采用反复硅胶柱色谱法、Sephadex LH-20柱色谱法、重结晶和HPLC等方法进行分离纯化,并通过NMR技术鉴定其化学结构。结果从黄腊果中分离得到8个化合物,分别鉴定为:3-羟基-2-甲基-4-吡喃酮(3-hydroxy-2-methyl-4-pyrone,1)、芥子醛(sinapaldehyde,2)、2-甲基-4-吡喃酮-3-O-β-D-吡喃葡萄糖苷(2-methyl-4-pyrone-3-O-β-D-glucopyr-anoside,3)、3,5-二甲氧基-4-羟基苯甲酸-7-O-β-D-葡萄糖苷(3,5-dimethoxyl-4-hydroxybenzoic acid-7-O-β-D-glucopyranoside,4)、胡萝卜苷(daucosterol,5)、β-谷甾醇(sitosterol,6)、3-O-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-30-降甲基齐墩果-12,20(29)-二烯-28-羧酸(3-O-α-Lrhamnopyrano-syl-(1→2)-α-L-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid,7)、3-O-β-D-吡喃葡萄糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-30-降甲基齐墩果-12,20(29)-二烯-28-羧酸(3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-D-glucopyranosyl-(1→3)-α-L-arabi-nopyranosyl-30-norolean-12,20(29)-dien-28-oic acid,8)。结论化合物1-4为首次从木通科植物中分离得到,化合物6-8为首次从黄腊果中分离得到。     

Cytotoxic triterpenoids from Berberis koreana

A bioassay-guided fractionation and chemical investigation of the trunk of Berberis koreana led to the isolation and identification of three new triterpenoids, 2 α,3 α,19 α-trihydroxy-urs-12-en-24-formyl-28-oic acid (1), 2 α,3 β,21 α-trihydroxy-urs-12-en-28-oic acid ( 2), and 3 β-acetyloxy-1-oxo-olean-12-en-28-oic acid (3), along with seven known triterpenoids (4-10). The structures of these new compounds were determined through spectral analysis, including extensive 2D-NMR data. The new compounds 1-3 showed significant cytotoxicity against the A549, SK-OV-3, SK-MEL-2, and HCT-15 human tumor cell lines with IC(50) values ranging from 7.17 to 48.73?μM.