Four New C19-Diterpenoid Alkaloids from Aconitum nagarum Stapf

Four new aconitine-type C₁₉-diterpenoid alkaloids, were isolated from the roots of Aconitum nagarum Stapf which were named as nagarutines A–D ( 1–4 ), together with eleven known compounds ( 5–15 ). The structures of the compounds were identified by IR, HR-ESI-MS, 1D and 2D NMR spectra. All compounds were tested for the inhibitory effect on LPS induced NO production in RAW 264.7 macrophages, compound 7 showed moderate anti-inflammatory activity effect and Inhibition rate is about 44.50%.     

Five New C19‐Diterpenoid Alkaloids from Delphinium tianshanicum W.T.Wang

Five new diterpenoid alkaloids, tianshanitines A‐E ( 1  –  5 ), along with ten known compounds ( 6  –  15 ), were isolated from the EtOH extracts of the whole plant of Delphinium tianshanicum W.T.Wang . Their structures were determined based on extensive spectroscopic analyses, including 1D‐ and 2D‐NMR, HR‐ESI‐MS, and the structure of tianshanitine C ( 3 ) was confirmed by X‐ray diffraction analysis. Tianshanitine A ( 1 ) is the first example of natural diterpenoid alkaloid containing a benzoyl group at C(1) position. Tianshanitine B ( 2 ) is a rare natural diterpenoid alkaloid bearing a OH group at C(16) position. Compounds 1  –  5 , 6 , 8 , 10 , 12 and 14 were evaluated for cytotoxicity against HCT116, MCF‐7 and HepG2 human cancer cell lines.     

C19-、C20-二萜生物碱抗肿瘤活性研究进展

二萜生物碱具有较高的药理活性和药用价值,一直以来为药理学家和临床医生所重视,但对于其抗肿瘤作用的报道却并不多见,主要集中于 C19-、C20- 二萜生物碱。综述近 10 年来 C19-、C20- 二萜生物碱抗肿瘤作用的基础及临床研究进展,并对当前研究存在的不足提出见解,为进一步研究及应用提供参考。     

Alkaloids from Delphinium pentagynum

Aerial parts of a collection of Delphinium pentagynum Lam. from Niebla, Southern Spain, furnished one diterpene alkaloid, 2-dehydrodeacetylheterophylloidine, two norditerpene alkaloids, 14-demethyl-14-isobutyrylanhweidelphinine and 14-demethyl-14-acetylanhweidelphinine, the known alkaloids 14-deacetylnudicauline, methyllycaconitine, 14-deacetyl-14-isobutyrylnudicauline, 14-acetylbrowniine, browniine, delcosine, lycoctonine, 18-methoxygadesine, neoline, karakoline and the aporphine alkaloid magnoflorine. Structures of the alkaloids were established by MS, 1D and 2-D NMR techniques.     

直距翠雀花中的降二萜生物碱

从直距翟雀花（Ｄｅｌｈｉｎｉｕｍ ｏｒｔｈｏｃｅｎｔｒｕｎ Ｆｒａｎｃｈ．）全草的甲醇提取物中分离得到了３个降二萜生物碱,通过ＮＭＲ,ＭＳ等波谱分析将其结构鉴定为７,１０－二羟基８,１、４,１６三甲氧基１９,２０－二去氢乌头烷（７β,８β,１４α,１６β）（１）,２０－乙基－２,３－二去氢－６,１０二羟基－７,８－二氧亚甲菜－１,１４,１６－三甲氧基乌头烷（１α,６β,１４α,１６β）（２）和翼北     

C19-Diterpenoid alkaloids from Aconitum richardsonianum

Three new aconitine-type C₁₉-diterpenoid alkaloids, richardsonines A-C (1–3), were isolated from the roots of Aconitum richardsonianum Lauener, together with seventeen known compounds (4–20). Their structures were elucidated by extensive spectroscopic analysis, and the absolute stereochemistry of 1 was confirmed by X-ray crystallography. Compounds 2, 5, 8 and 9 were rare C₁₉-diterpenoid alkaloids bearing an OH group at C-16. Isolated compounds were evaluated for inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated neuroinflammatory responses in BV-2 microglial cells. Compounds 3 and 7 showed weak antineuroinflammatory effects with inhibition rates of 35.32 ± 2.29% and 39.94 ± 2.50%, respectively, at a concentration of 100 µM.     

秦岭翠雀花中生物碱成分的研究

从秦岭翠雀花(Delphinium giraldii Diels)全草中分得14个已知生物碱：tongolinine(1)、氨茴酰牛扁碱(anthranoyllycoctonine)(2)、牛扁碱(1ycoctonine)(3)、dihydrogadesine(4)、tatsiensine(5)、siwanine A(6)、delsemine A(7)、delsemine B(8)、甲基牛扁碱(methyllycaconitine)(9)、ajacine(10)、delajacine(11)、delsoline(12)、滇乌碱(yunaconitine)(13)和查斯曼宁(chasmanine)(14)。应用光谱和与已知品对照TLC法鉴定了所有化合物的结构。     

Four New Diterpenoid Alkaloids from The Roots of Aconitum coreanum

Four new hetisine‐type C₂₀‐diterpenoid alkaloids, named as coreanines A–D ( 1 – 4 ), were isolated from the roots of Aconitum coreanum, together with thirteen known alkaloids ( 5 – 17 ). Their structures were elucidated by extensive spectroscopic methods including IR, HR‐ESI‐MS and NMR techniques. All the isolated compounds were screened for the acetylcholinesterase (AChE) inhibitory effects, and none of them showed considerable inhibitory activity.     

Four New Diterpenoid Alkaloids from the Roots of Aconitum carmichaelii

Aconitum carmichaelii Debeaux is a widely used traditional Chinese medicine and an important source of clinical drugs, of which the parent and lateral roots are known as ‘Chuanwu’ and ‘Fuzi’, respectively. Four new C₁₉‐diterpenoid alkaloids, carmichasines A – D ( 1 – 4 ), were isolated from the roots of Aconitum carmichaelii, together with twelve known compounds ( 5 – 16 ). Their structures were elucidated via spectroscopic analyses, including HR‐ESI‐MS, IR, and NMR. Carmichasine A ( 1 ) is the first natural C₁₉‐diterpenoid alkaloid possessing a cyano group. Most of the diterpenoid alkaloids isolated were C₁₉‐category, which might provide further clues for understanding the chemotaxonomic significance of this plant. The cytotoxicity of the new compounds was also investigated against several human cancer cell lines, including MCF‐7, HCT116, A549, and 786‐0, and none of them showed considerable cytotoxic activity.     

Honatisine, a novel diterpenoid alkaloid, and six known alkaloids from Delphinium honanense and their cytotoxic activity

A novel diterpene alkaloid named honatisine (1) has been isolated from the whole plants of Delphinium honanense, along with six known alkaloids, siwanine E (2), isoatisine (3), atisine (4), delcorinine (5), uraphine (6), and nordhagenine A (7). Their structures were deduced on the basis of their spectral data. All of them were evaluated by a SRB assay for their cytotoxicity, and compound 1 showed a significant cytotoxic activity (IC(50) =3.16 μM) against the MCF-7 cell line.     

Uraline,a New Norditerpenoid Alkaloid from Aerial Parts of <Emphasis Type="Italic">Delphinium uralense</Emphasis> Nevski

Uraline, a new norditerpenoid alkaloid, was isolated from aerial parts of Delphinium uralense. The structure of 1α,7,8-trihydroxy-6β,14α,16β-trimethoxy-18-N-(2-methyl)succinylanthranoyloxyaconane was ascribed to the new compound on the basis of ¹H and ¹³C NMR, IR, and mass spectra. The known alkaloids methyllycaconitine and delcorine were also isolated from the plant.__________Translated from Bioorganicheskaya Khimiya, Vol. 31, No. 4, 2005, pp. 425–429.Original Russian Text Copyright © 2005 by Gabbasov, Tsyrlina, Spirikhin, Danilov, Yunusov.     

Norditerpenoid Alkaloids from Aconitum spicatum Stapf

To search for pharmacologically and structurally interesting substances from traditional Chinese medicines, we Investigated the chemical compounds of Aconitum spicatum Stapf. Two new nordlterpenold alkaloids, namely spicatlne A （compound 1） and splcatine B （compound 2）, as well as 11 known norditerpenoid alkaloids were Isolated from the CHCIs portion of the 90% ethanol extract of the roots of A. spicatum. The structures of the alkaloids were characterized on the basis of their spectral data. One of the Isolated compounds showed significant cytotoxic activities （IC50 values 〈 200μmol/l.） against the HL-60 cell line.     

Two New Diterpenoid Alkaloids from Spiraea japonica L.f.var. Fortunei (Planchon) Rehd.

Two new hetisine-type C20-diterpenoid alkaloids named spiraqine (1) and 6-hydroxylspiraqine (2), and four known alkaloids, namely spiredine (3), spiradine A (4), spiradine B (5), and spirasine Ⅴ/Ⅵ (6),were isolated from Spiraea japonica L. f. var. fortunei (Planchon) Rehd. The structures of the alkaloids were elucidated using nuclear magnetic resonance analysis (1H-NMR, 13C-NMR, DEPT, HMQC, and HMBC) and mass spectrometry data.     

A New Cytotoxic Carbazole Alkaloid and Two New Other Alkaloids from Clausena excavata

One new carbazole alkaloid, excavatine A ( 1 ), and two additional new alkaloids, excavatine B ( 2 ) and excavatine C ( 3 ), were isolated from the stems and leaves of Clausena excavata Burm .f. (Rutaceae). Their structures were determined on the basis of detailed spectroscopic analyses, especially 2D‐NMR and HR‐EI‐MS data. Compounds 1 – 3 were tested for their cytotoxic activities against A549, HeLa, and BGC‐823 cancer cell lines, and for their antimicrobial activities against Candida albicans and Staphylococcus aureus. Only 1 exhibited cytotoxicity against A549 and HeLa cell lines with the IC₅₀ values of 5.25 and 1.91 μg/ml, respectively.     

Norditerpenoid alkaloids from Delphinium species

From the aerial parts of four Delphinium species 11 known and 3 new norditerpenoid alkaloids have been isolated: from D. dissectum Huth: delavaine A/B, deoxylycoctonine, methyllycaconitine; new: 10-hydroxymethyllycaconitine; from D. excelsum Reichenb.: delcaroline, delectinine, delterine, methyllycaconitine; new: 10-hydroxymethyllycaconitine, 18-O-methyldelterine and 10-hydroxynudicaulidine; from D. grandiflorum L.: delcosine, deltatsine, grandiflorine, methyllycaconitine; from D. triste Fisch.: delcosine, macrocentridine, 14-dehydrodelcosine. The structures of the new alkaloids were established on the basis of MS, 1H, 13C, DEPT, homonuclear COSY, HMQC and HMBC NMR spectroscopic techniques.     

Two New Diterpenoid Alkaloids from Spiraea japonica L. f. var.fortunei （Planchon） Rehd.

Two new hetisine-type C20-diterpenoid alkaloids named spiraqine (1) and 6-hydroxylspiraqine (2), and four known alkaloids, namely spiredine (3), spiradine A (4), spiradine B (5), and spirasine V/VI (6),were isolated from Spiraea japonica L. f. var.fortunei (Planchon) Rehd. The structures of the alkaloids were elucidated using nuclear magnetic resonance analysis (1H-NMR, ^13C-NMR, DEPT, HMQC, and HMBC) and mass spectrometry data.     

A Study on the Alkaloidal Components from Delphinium gyalanura Marq. et Shaw

From the roots of Delphinium gyalanum Marq. et Shaw native to China, a pair of new regioisomeric diterpenoid alkaloids as a mixture, named gyalanine A and B, was isolated whose structures were shown to be 4 and 5, respectively, on the basis of spectral data. The known diterpenoid alkaloids, delsemine A(1) and B(2), methyllycaconitine (3) and lycoctonine, were also obtained.     

Matrine-Type Alkaloids from the Seeds of Sophora alopecuroides and Their Potential Anti-inflammatory Activities

Three new matrine-type alkaloids, 8β-hydroxyoxysophoridine ( 1 ), 9β-hydroxysophoridine ( 2 ), 9β-hydroxyisosophocarpine ( 3 ), together with one known analog, 11,12-dehydromatrine ( 4 ), were isolated from the seeds of Sophora alopecuroides L. The structures of new compounds were elucidated using extensive spectroscopic techniques including the experimental and calculated ECD data. The anti-inflammatory activities of all the isolates on NO production in RAW 264.7 cells stimulated by lipopolysaccharide were evaluated. Among them, 8β-hydroxyoxysophoridine ( 1 ) showed a significant inhibitory effect with an IC₅₀ value of 18.26 μM.     

叉角翠雀花,四川毛茛科一新种

描述了自四川发现的毛茛科翠雀属一新种,叉角翠雀花。此新种的萼片具叉状角状突起而与弯距翠雀花有亲缘关系,但其叶片3深裂,下面无毛,花3~5朵排列成伞房花序,花梗被白色短柔毛,无腺毛,萼距稍向下弯曲,花瓣不2裂,而与弯距翠雀花相区别。     

Three new C19-diterpenoid alkaloids from Delphinium tianshanicum W. T. Wang

Three new C₁₉-diterpenoid alkaloids, tianshanisine (1), tianshanine (2) and tianshanidine (3), together with six known C₁₉-diterpenoid alkaloids (4–9) were isolated from the whole herb of Delphinium tianshanicum W. T. Wang. Their structures were established on the basis of spectroscopic analyses, including HR-ESI-MS and 1D and 2D NMR.