Two new triterpenoid saponins from Rhaponticum uniflorum

Two new triterpenoid saponins were isolated from the roots of Rhaponticum uniflorum.Their structures were elucidated as 3-O-[β-D-glucopyranosyl] -ilexolic acid-28-O-[β-D-glucopyranosyl]ester 1 and 3-O-[β-D-glucopyranosyl]-urs-12,19(29)-dien-oic acid-28-O-[β-D-glucopyranosyl]ester 2 mainly by 1D,2D NMR techniques and chemical methods.     

祁州漏芦中蜕皮甾酮类化学成分的研究

从祁州漏芦的根中分离得到7个蜕皮甾酮化合物,采用近代光谱方法鉴定其为ajugasteroneC-2,3;20,22-diacetonide(1);25-deoxy-9(11)-dehydro-20-hydroxyecdysone-20,22-monoacetonide(2);ajugasteroneC-20,22-monoacetonide(3);ajugasteroneC(4);rhapontisteroneC(5);ecdysterone(6);11α-hydrox-yecdysteroneecdysterone(7).其中化合物1和2是在自然界中首次分离到的新化合物,化合物3是首次在祁州漏芦中分离得到的.     

A New Ecdysteroid from Rhaponticum uniflorum

The root of Rhaponticum uniflorum (L.) DC. was used in China as a chinese traditional medicine for the treatment of fever and intoxications1. Since the 1980s this plant have been studied and some phytoecdysteroids and other compounds were isolated2-4. We report here the isolation and structural elucidation of a new ecdysteroid 2, 3, 20, 22-diacetonide ajugasterone (1), as well as the isolation of three known ecdysteroids, ecdysterone (2), ajugasterone C (3), ajugasterone C-20, 22-monoacetoni…     

New Pentacyclic Triterpenoids from Centella asiatica

Three new pentacyclic triterpenoids, named centellasaponins G, H, and F ( 1 – 3 , resp.), together with four known compounds, 4 – 7 , were isolated from the whole plants of Centella asiatica. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D‐ and 2D‐NMR and HR‐MS experiments, and by comparison with literature data.     

Three New Thiophene Acetylenes from Rhaponticum uniflorum (L.) DC.

Three new thiophene‐acetylenes, 7‐chloroarctinone‐b ( 1 ), rhapontiynethiophenes A ( 2 ) and B ( 3 ), along with arctinone‐b ( 4 ) were isolated from the MeOH extract of the roots of Rhaponticum uniflorum (L.) DC. The structures of the new compounds were elucidated by detailed spectroscopic data analysis and by comparison with known compounds.     

Three New Pentacyclic Triterpenoids from Centella asiatica

Three new pentacyclic triterpenoids, named centellasaponin I ( 1 ), centellasaponin J ( 2 ), and centellasaponin E ( 3 ), together with three known compounds, were isolated from the whole plants of Centella asiatica. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D‐ and 2D‐NMR and HR‐MS experiments, and by comparison with literature data.     

Triterpenoids from Cedrela sinensis

Twenty-three new triterpenoids (1-23), all having an apotirucallane skeleton, were isolated from the seeds, leaves, and stems of Cedrela sinensis (Meliaceae). Their structures were determined by 2D NMR experiments, X-ray crystallographic analysis, and chemical methods. These triterpenoids showed a moderate cytotoxic activity against P-388 murine leukemia cells (IC₅₀ 0.26-9.9 μg/mL).     

Two New Lanostane-type Triterpenoids from Mulgedium tataricum

Mulgedium tataricum L. has long been used for treatment of appendicitis, erysipelas andextravasated blood1. From the methanol extract of the whole plants, two newtriterpenoids 1 and 2 were isolated. In this paper, we report the structural elucidation ofth…     

南中国海星骨海绵Stelletta sp.中的三萜化合物

最近,我们又从采自广西涠洲岛海域的星骨海绵Stelletta sp.中分离得到3个黄色三萜色素1,2和3(见下式).通过IR,UV,MS和1D NMR,2D NMR等方法测定了它们的结构,并对化合物1的所有C和H进行了指认.同时,通过X射线单晶衍射分析测定了化合物1的立体化学结构.初步的药理实验表明,这3个化合物对P388肿瘤细胞均有很强的抑制活性,ED₅₀值依次为0.01,0.5和1.0μg/mL,提示Stelletta属海绵中的这类三萜具有很好的药用开发前景.     

Bioactive compounds and antioxidant activity of Rhaponticum acaule (L.) DC

Abstract

Rhaponticum acaule (L.) DC. is a medicinal plant commonly used for the treatment of some illnesses such as gastrointestinal infections. In this work, we report the composition of different parts of this plant on phenolic compounds, their quantification, and antioxidant activity. The obtained results reported that methanolic extracts of the three parts studied revealed high phenolic contents. For flavonoid contents, the highest contents were reported in organic extracts of leaf part. In addition, results obtained from the study of the antioxidant activity showed that methanolic extract of root presented the highest activity, in DPPH^? scavenging ability test with an IC₅₀ of 0.31?±?0.04?mg/mL and in FRAP test with an EC₅₀ of 1.06?±?0.02?mg/mL. The RP-HPLC-PDA analysis revealed the presence of five phenolic acids (sinapic, caffeic, chlorogenic, ferulic and syringic acids), one flavanone (naringenin), one flavonol (rutin) and vanillin.     

Two New Disulfated Triterpenoids from Zygophyllum fabago

From the aerial parts of Zygophyllum fabago, two new monosodium salts of sulfated derivatives of ursolic acid, along with two known quinovic acid glycosides were isolated. The structures of the new compounds were determined as (3β,4α)‐3,23,30‐trihydroxyurs‐20‐en‐28‐al 3,23‐di(sulfate) sodium salt (1 : 1) ( 1 ) and of (3β,4α)‐3,23,28‐trihydroxyurs‐20‐en‐30‐yl β‐D ‐glucopyranoside 3,23‐di(sulfate) sodium salt (1 : 1) ( 2 ) with the molecular formula C₃₀H₄₇NaO₁₀S₂ and C₃₆H₅₉NaO₁₅S₂, respectively. The structures of the known compounds were 3‐O‐(2‐O‐sulfo‐β‐D ‐quinovopyranosyl)quinovic acid 28‐β‐D ‐glucopyranosyl ester ( 3 ) and 3‐O‐(β‐D ‐glucopyranosyl)quinovic acid 28‐β‐D ‐glucopyranosyl ester ( 4 ) (quinovic acid=(3β)‐3‐hydroxyurs‐12‐ene‐27,28‐dioic acid). The structures of all these compounds were determined by using 1D‐ and 2D‐NMR spectroscopic techniques.     

Two New Triterpenoids from Saussurea petrovii

Saussurea petrovii Lipsch (Compositae) is a perennial herb mainly distributed in Gansu and Inner Mongolia provinces of China. Its whole herb has been used as a folk remedy for the treatment of rheumatism and bleeding1. In order to find active principles, the chemical constituents of Saussurea petrovii were studied and two new triterpenoids 1 and 2 were isolated from the acetone extract of the rhizome. In this paper, we report the structural elucidation of the compound 1 and 2. Compound 1 wa…     

石墨炉原子吸收光谱法测定中药漏芦中微量铅

中药漏芦具有抑制动脉粥样硬化、抗脂质过氧化、减弱血小板聚集和提高免疫力等作用[1]。测定中药中微量元素的含量,对于探讨中药药理、提高药效和降低毒副作用有重要的意义[2,3]。铅是一种毒性元素,它在人体中具有累积性,通过肠胃道吸收,严重损害神经系统、造血系统和消化系统,从而导致肌体免疫力降低。本文选用磷酸氢二铵为基体改进剂,采用石墨炉原子吸收光谱法,对漏芦中Pb的含量进行了测定,考察了影响测定结果的主要因素。样品分析结果表明,本法简便、快速、灵敏、准确。1　实验部分1 1　仪器及工作条件180 80型原子吸收分光光度计、…     

Anticandida Agents from a Tanzanian Plant Albizia anthelmintica

Candidiasis is one of the most frequent opportunistic infections in individuals with severe immunosupression and further development of resistance against the available antifungal drugs has created an alarming situation. This requires intensive drug discovery to develop new, more effective, affordable and accessible antifungal agents possessing novel modes of action. Albizia anthelmintica, which is ethno medically used to treat vaginal candidiasis in the Morogoro and coastal regions of Tanzania, on activity guided fractionation and subsequent purification resulted in the isolation and characterization of an isomer of methyl cyclitol ( 1 ) and six echinocystic acid saponins ( 2 – 7 ). Saponins 6 and 7 are new and being reported for the first time from nature. Among all the isolated compounds, 3‐O‐[α‐L‐arabinopyranosyl (1→2)][α‐L‐arabinopyranosyl (1→6)]‐2‐acetamido‐2‐deoxy‐β‐D‐glucopyranosyl echinocystic acid ( 4 ), 3‐O‐[α‐L‐arabinopyranosyl (1→2)] [α‐L‐arabinopyranosyl (1→6)]‐2‐amino‐2‐deoxy‐β‐D‐glucopyranosyl echinocystic acid ( 6 ) and 3‐O‐[β‐D‐glucopyranosyl (1→3)] [α‐L‐arabinopyranosyl (1→2)] [α‐L‐arabinopyranosyl (1→6)]‐2‐amino‐2‐deoxy‐β‐D‐glucopyranosyl echinocystic acid ( 7 ) and their combinations were active against the various strains of C. albicans with MICs ranging from 12.5 to 125 μg/ml.     

Three New Triterpenoid Saponins from the Seeds of Aesculus chinensis

Inpreviouspaperswehavereportedtheisolationandidentificationofescinsla,fo,IVa.IVbandIVel2.Nowwedescribethestructureelucidationofthreemorenewtriterpenoidsaponins.namedescinsIVc(l),IVd(2)andIVf(3).CompoundIwasisolatedaswhiteamorphouspowder.HR-SI-MSrevealedthecompositionofC,,H,,O,,bymolecularionpeakatm/z1129.5438.Comparedwiththe:3CandiHNMRspectraofescinla,compoundIisalsoaglycosideofprotoaescigeninacylatedbythetigloylandtheacetylgroup.Thesignificantdifferencesbetweenthemwerethechemicals…     

Oleanane Saponins from Rhizome of Anemone raddeana

Two new oleanolic acid‐type triterpenoid saponins, raddeanosides R₂₂ and R₂₃ ( 1 and 2 , resp.), together with four known saponins were isolated from the rhizome of Anemone raddeana Regel. The structures of the new compounds were elucidated as oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 1 ) and oleanolic acid 3‐O‐α‐L ‐arabinopyranosyl(1→3)‐α‐L ‐rhamnopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 2 ). The four known compounds were identified as oleanolic acid 3‐O‐α‐L ‐arabinopyranoside ( 3 ), oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→4)‐α‐L ‐arabinopyranoside ( 4 ), hederasaponin B ( 5 ), and hederacholchiside E ( 6 ) on the basis of chemical and spectral evidences. Compound 4 is reported for the first time from the Anemone genus, while the other three known compounds have been already found in this plant.     

Highly Polar Triterpenoid Saponins from the Roots of Saponaria officinalis L.

Five new triterpenoid saponins, including 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐β‐d ‐glucopyranosyl‐(1→3)‐β‐d ‐xylopyranosyl‐(1→4)‐α‐l ‐rhamnopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)‐(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 1 ), 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐(6‐O‐acetyl)‐β‐d ‐glucopyranosyl‐(1→3)‐[β‐d ‐xylopyranosyl‐(1→4)]‐α‐l ‐rhamnopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)‐(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 2 ), 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐β‐d ‐xylopyranosyl‐(1→4)‐α‐l ‐rhamnopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)‐(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 3 ), 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐β‐d ‐glucopyranosyl‐(1→3)‐β‐d ‐xylopyranosyl‐(1→4)‐α‐l ‐rhamnopyranosyl‐(1→2)‐[(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 4 ), 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐(6‐O‐acetyl)‐β‐d ‐glucopyranosyl‐(1→3)‐[β‐d ‐xylopyranosyl‐(1→4)]‐α‐l ‐rhamnopyranosyl‐(1→2)‐[(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 5 ) together with two known congeners, saponariosides A ( 6 ) and B ( 7 ) were isolated from the roots of Saponaria officinalis L. Their structures were elucidated by extensive spectroscopic methods, including 1D‐ (¹H, ¹³C) and 2D‐NMR (DQF‐COSY, TOCSY, HSQC, and HMBC) experiments, HR‐ESI‐MS, and acid hydrolysis.     

New Polyoxygenated Triterpenoids from Stachyurus himalaicus var. himalaicus

Two new polyoxygenated triterpenoids, stachlic acid A (= (2α,3β)‐2,3,23,29‐tetrahydroxyolean‐12‐en‐28‐oic acid; 1 ) and stachlic acid B (= (2α,3α)‐2,29‐dihydroxy‐3,23‐[(1,1‐dimethylmethylene)dioxy]olean‐12‐ene‐28‐oic acid; 2 ), were isolated from Stachyurus himalaicus var. himalaicus. Their structures were established by means of extensive spectroscopic studies and chemical evidence. The purified product 1 was found to have moderate in vitro cytotoxic activity against human Hela cells.     

Triterpenoids from the stems of Kadsura ananosma

An extensive study of the triterpenoids produced by the stems of Kadsura ananosma, has led to the isolation of eleven new ones, kadnanolactones A-I (1-4, 7-11) and kadnanosic acids A (5) and B (6), and six known analogues. Their structures were elucidated mainly by comprehensive spectroscopic analysis, and DFT computational methods were applied to validate the stereochemistry of an epoxide in compound 7. All triterpenoids were evaluated for their cytotoxicity against HL-60, SMMC-7721, A-549, PANC-1, and SK-BR-3 human cancer cells.