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.     

Two new triterpenoids from the fungus Perenniporia maackiae

Two new triterpenoids, 3β-(2-methoxy-oxalyloxy)-24-methylene-lanost-8-en-21-oic acid (1) and 3β-(2-methoxy-oxalyloxy)-15α-hydroxy-24-methylene-lanost-8-en-21-oic acid (2), were isolated from cultures of the fungus Perenniporia maackiae, together with two previously known triterpenoids (3 and 4). Their structures were determined by spectroscopic methods, including 1D and 2D NMR, and MS analyses. All compounds were evaluated for their cytotoxic activities on five tumor cell lines.     

New sterol esters from the flowers of Punica granatum Linn.

Two new β-sitosterol esters have been isolated from the flowers of Punica granatum Linn. (Punicaceae) along with the known compounds n-tricosane (3), n-heptacosanyl n-hexanoate (4), olean-5,12-dien-3β-ol-28-oic acid (5), and olean-12-en-3β-ol-28-oic acid (6). The structures of the new phytosterols have been elucidated as stigmast-5-en-3β-ol-3β-dodecanoate (β-sitosterol laurate, 1) and stigmast-5-en-3β-ol-3β-tetradecanoate (β-sitosterol myristate, 2) on the basis of spectral data and chemical analyses.     

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     

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。     

Microbial transformation of the anti-diabetic agent corosolic acid by Cunninghamella echinulata

The pentacyclic triterpenoid corosolic acid was metabolized by Cunninghamella echinulata CGMCC 3.2000 to its C-24 aldehyde group metabolite and five other hydroxylated metabolites: madasiatic acid (2), 2α, 3β, 7β-trihydroxyurs-12-en-28-oic acid (3), 2α, 3β, 15α-trihydroxyurs-12-en-28-oic acid (4), 2α, 3β, 6β, 7β-tetrahydroxyurs-12-en-28-oic acid (5), 2α, 3β, 7β, 15α-tetrahydroxyurs-12-en-28-oic acid (6), and 2α, 3β,7β-trihydroxy-24-al-urs-12-en-28-oic acid (7); compounds 3, 5, and 7 were new compounds. The α-glucosidase inhibitory effects of the metabolites were also evaluated.     

A new isopimarane-type diterpene and a new natural atisane-type diterpene from Excoecaria agallocha

From the woods of Excoecaria agallocha, a new isopimarane-type diterpene, 3α,11β-dihydroxy-ent-isopimara-8(14),15-dien-2-one (1) and a new natural atisane-type diterpene, 16β-hydroxy-ent-atisan-3-one (2) were isolated together with three known compounds, ribenone (3), ent-labda-8(17),13E-diene-3β,15-diol (4), and ent-3β-hydroxybeyer-15-ene-2,12-dione (5). Their structures were determined by spectral data and x-ray crystallography evidence.     

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.     

Triterpenes from Astilbe chinensis

Six new triterpenes, 3β,6β-dihydroxyurs-12-en-27-oic acid (1), 3β,6β,24-trihydroxyurs-12-en-27-oic acid (2), 3β,6β,7α-trihydroxyurs-12-en-27-oic acid (3), 3β-acetoxy-6β-hydroxyurs-12-en-27-oic acid (4), 3β,6β,24-trihydroxyolean-12-en-27-oic acid (5), and 3β,6β,7α-trihydroxyolean-12-en-27-oic acid (6), were isolated from the rhizomes of Astilbe chinensis. Their structures were elucidated on the basis of 1D- and 2D-NMR analyses and HR-MS experiments. The isolated compounds exhibited significant cytotoxic activities against the SK-N-SH and HL-60 cell lines.     

Triterpenoids from Peganum nigellastrum

Two triterpenoids were isolated from the roots of Peganum nigellastrum Bunge. Their structures were elucidated as 3α-acetoxy-27-trans-caffeoyloxyolean-12-en-28-oic acid methyl ester (1) and 3-oxotirucalla-7, 24-dien-21-oic acid (2) on the basis of spectroscopic evidence. 1 is a new triterpene ester and 2 is a known compound isolated for the first time from genus Peganum.     

锁阳中三萜及甾体成分的研究

From the whole parasitic plant of Cynomorium songaricum Rupr. three ursane type triterpenes, three steroidal compounds, palmitic acid and sucrose were isolated. The triterpenes were identified as acetyl ursolic acid (2), ursolic acid (3) and a new compound, ursa-12-ene-28-oic acid, 3β-propanedioic acid monoester (1). The steroidal compounds were identified as β-sitosterol palmitate (4), β-sitosterol (5) and β-sitosterol glucoside (daucosterol, 6). Compounds 2 and 5 were found in this genus for the first time.     

Two new triterpenoids from Callicarpa kwangtungensis

Two new triterpenoids, 2α,3β,16α,19α,23-pentahydroxyolean-12-en-28-oic acid (1) and 2α,3α,11α,21α,23-pentahydroxyurs-12-en-28-oic acid (2), were isolated from the aerial parts of Callicarpa kwangtungensis. Their structures were elucidated by 1D and 2D analyses, as well as MS and IR spectra.     

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 ).     

Saikosaponin v-1 from Roots of Bupleurum Chinense DC

Abstract

Three triterpenoidal saponins, saikosaponin v-1(1), 6″-O-acetyl-saikosaponin b ₂ (2) and 6″-O-acetyl-saikosaponin d(3) were isolated from the roots of the title plant and the structures were identified on the basis of spectral analysis. Saikosaponin v-1 is a new compound, which was identified as 3β,16α,23,28-tetrahydroxy-olean-11,13(18)-dien-30-oic acid–3-O-β-D-glucopyranosyl-(1 → 3)- β-D-fucopyranosyl-30-O-xylitol ester.     

Two new triterpenoids from the resin of Styrax tonkinensis

Two new triterpenoids, 3β,6β-dihydroxy-12-oxo-13Hα-olean-28,19β-olide (1) and 3-oxo-olean-11,13(18)-dien-28,19β-olide (2) were isolated from the resin of Styrax tonkinensis (Pier.) Craib. The structures of both triterpenoids were determined by physicochemical and spectroscopic methods. Compound 1 is the second triterpene found with cis-fused C/D ring from the resin, which is rarely observed in oleanane-type triterpenes.     

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.     

New compounds with antimicrobial activities from Elaeodendron buchananii stem bark

The plant species Elaeodendron buchananii Loes is widely used in folklore medicine to manage microbial infections in Kenya. Previous studies on the plant fruits and root bark revealed the presence of steroids and terpenoids. The present phytochemical analysis of the plant stem bark has led to the isolation of four new triterpenes characterized as methyl 3β-acetoxy-11α, 19α, 28-trihydroxyurs-12-en-23-oic acid (1), 3β, 11α, 19α-trihydroxyurs-12-en-23, 28-dioic acid (2), 3β-acetoxy-19α, 23, 28-trihydroxyurs-12-ene (3) and 3-oxo-19α, 28-dihydroxyurs-12-en-24-oic acid (4), together with ten known ones (5–14), whose structures were elucidated using spectroscopic techniques. The isolate canophyllol (8) showed promising antibacterial activity against N. meningitides with MIC value of 31.25 μg/ml.     

Two new triterpenoid saponins from Ilex cornuta

Two new triterpenoid saponins (1 and 2) were isolated from the stems of Ilex cornuta, along with two known triterpenoids (3 and 4). The structures of compounds 1 and 2 were determined as ursane-12,19-diene-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (1), 3α,23α-dihydroxy-olean-9(11),12-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (2), on the basis of hydrolysis and spectral evidence, including 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) analyses. Protective effects of compounds 1–4 were tested against H₂O₂-induced H9c2 cardiomyocyte injury, and the data showed that all these compounds had no cell-protective effect.     

甘草中新三萜皂甙元的分离和结构鉴定

自乌拉尔甘草(Glycyrrhiza uralensis Fisch.)根茎中提取皂甙。经盐酸甲醇水解,柱层分离,得到七个皂甙元。本文报道新三萜皂甙元乌拉内酯(uralenolide)及18α-羟基甘草次酸甲酯的结构鉴定。后者为首次得自乌拉尔甘草。