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1.
Cipadonoid A ( 1), a novel limonoid with an unprecedented skeleton, was isolated from the leaves of Cipadessa cinerasecns. Its structure and relative configuration were determined by spectroscopic analysis and computer modeling. 1 represents a new type of limonoid, characterized by a rearranged tetrahydropyranyl ring B incorporating usually exocyclic C-30. A possible biosynthetic pathway of 1 was also proposed. 相似文献
2.
Nine new phragmalin-type limonoid orthoesters, tabulalides F-N (1-9), together with three known compounds, tabulalides C and D, and tabularisin N (10-12), were isolated from the stem bark of Chukrasia tabularis var. velutina. Extensive spectroscopic technologies were applied to elucidate the structures of these new compounds, including the application of circular dichroism (CD) exciton chirality method for the determination of the absolute configurations of 1 and 2. Tabulalide F (1) has a rare orthoisobutylate moiety in phragmalin-type limonoid orthoesters. These compounds were evaluated for cytotoxic activity against five human cancer cell lines in vitro. Tabulalide G (2) exhibits moderate cytotoxic activity against MCF-7 with IC(50) value of 20.4 μmol/l, and other compounds have weak inhibitory effects on the growth of tested tumor cells. 相似文献
3.
Yan Yu-Xin Yan Li-Jun Wang Yong-Chao Qiu Ming-Hua 《Chemistry of Natural Compounds》2022,58(3):482-484
Chemistry of Natural Compounds - A new limonoid, 3-acetoxy-7-(2′-methylpropenoyl)-vilasinin lactone (1), together with a known analogue, 3-acetoxy-7-tigloylvilasinin lactone (2), was isolated... 相似文献
4.
Seven rings A,B-seco limonoids 1-7 were isolated from the EtOH extract of the seed of Aphanamixis polystachya. Their structures were identified as rohituka-7 (1), dregeana-1 (2), rohituka-15 (3), Tr-B (4), rohituka-3 (5), rohituka-5 (6), and rohituka-14 (7) by MS and NMR spectroscopy. The complete assignment of proton and carbon signals was achieved by 1D and 2D NMR experiments including DEPT, HSQC, 1H--1H COSY, HMBC, and NOESY. 相似文献
5.
Four new limonoid derivatives, 1-O-methylichangensin (1), sudachinoid A (2), B (3), and C (4) were isolated from the seeds of Citrus sudachi, together with the known compounds ichangensin, obacunone, obacunoic acid and limonin, and the structures of the new compounds were elucidated based on spectroscopic and chemical evidence. 相似文献
6.
Limonoids from the root of Dictamnus radicis cortex 总被引:1,自引:0,他引:1
Chemical investigation of the roots of Dictamnus radicis Cortex led to the isolation of a new limonoid isodictamdiol (1) and a known dictamdiol (2), the first 5S/9S-type degraded limonoids, together with other six known limonoids (3-8). The chemical structures were identified on the basis of modern spectroscopic methods, including IR, MS, NMR ((1)H-NMR, (13)C-NMR, (1)H-(1)H COSY, HMQC, HMBC, NOESY). Additionally, the absolute configurations of limonoid isodictamdiol (1) and dictamdiol (2) were separately elucidated by single crystal X-ray diffraction, as well as their circular dichroism spectra. Furthermore, all compounds were evaluated for antibacterial activity against three bacterial cultures. 相似文献
7.
A new limonoid, named Citriolide-A (1), along with the known structurally related compounds 2-5, was isolated from the liposoluble extract of the seeds of Citrus reticulata Blanco. The structure of Citriolide-A (1) was elucidated by means of EI, 1D- and 2D-NMR techniques. Compounds 1, 2 and 4 exhibited medium cytotoxicity against P-388 and A-549 cell lines. 相似文献
8.
Two new limonoids, munronolide (1) and munronolide 21-O-beta-D-glucopyranoside (2), were isolated from the whole plant of Munronia henryi (Meliaceae). Their structures have been elucidated on the basis of spectroscopic and chemical methods. The D-glucose moiety attached to C-21 position of limonoid is firstly reported. 相似文献
9.
Markus Bacher Günter Brader Harald Greger Otmar Hofer 《Magnetic resonance in chemistry : MRC》2010,48(1):83-88
Phytochemical analysis of different organs of the rutaceaeous plant Severinia buxifolia led to the isolation of a new limonoid, a new acridone alkaloid, and a new flavone. Structure elucidation and signal assignment were achieved by the extensive use of 1D and 2D NMR experiments (selective 1D NOE, COSY, NOESY, HSQC, HMBC). Copyright © 2009 John Wiley & Sons, Ltd. 相似文献
10.
《Magnetic resonance in chemistry : MRC》2003,41(2):139-142
Bioassay‐guided fractionation of the methanol extract of Odontadenia macrantha afforded a new limonoid, odontadenin A (1) and two known triterpenoids, lupeol (2) and α‐amyrin (3). The structure of 1 was established on the basis of 1D and 2D NMR and high‐resolution fast atom bombardment mass spectrometric data. The new compound was found to possess moderate cytotoxicity against A2780, the ovarian cancer cell line. Copyright © 2003 John Wiley & Sons, Ltd. 相似文献
11.
Two new limonoids, chukrasone A (1) incorporating a highly rearranged A/B ring system and chukrasone B (2) possessing the first 16,19-dinor limonoid backbone with an extended C3 unit at C-15, were isolated from Chukrasia tabularis. Their structures were characterized on the basis of detailed spectroscopic analysis. Compounds 1 and 2 exhibited potential inhibition of the delayed rectifier (I(K)) K(+) current. 相似文献
12.
One new limonoid of the phragmalin type (1) named Swietenine J with nine known compounds methyl-6-β-hydroxy angolensate (2), 1-O-acetylkhayanolide A(3), Khayanolide E (4), Khayalactone (5), Khayanone (6), 1-O-Acetylkhayanolide B (7), 1-O-Deacetylkhayanolide E (8), Khayanolide A (9), Khayanolide B (10) were isolated from Swietenia macrophylla. The structure of 1 was elucidated on the basis of 1D and 2D- NMR spectroscopic analysis. 相似文献
13.
Zhou H Hamazaki A Fontana JD Takahashi H Wandscheer CB Fukuyama Y 《Chemical & pharmaceutical bulletin》2005,53(10):1362-1365
Three new C-seco limonoids (1-3) and one new tetracyclic limonoid (4) were isolated from a methanol extract of the ripe fruits of Melia azedarach collected in Curitiba, Brazil, and their structures were elucidated by spectroscopic data analysis and comparison of spectral data with those of the previously known compounds. Among the limonoids isolated in the present study, compounds 3 and 4 exhibited significant inhibitory activity against HeLa S3 cancer cells, whereas 1 and 2 showed weak cytotoxicity. 相似文献
14.
An enantioselective and short approach to the synthesis of limonoids has been applied successfully to the simplest limonoid, 2. The carbon atoms of the tetracyclic framework were assembled in a single operation from the acylsilane 3 and the acetylenic sulfone 4 to form the chiral epoxide 5. Successive cationic and free-radical cyclizations starting with 5 generated the tetracyclic intermediates 9a, which was transformed into limonoid 2 by a sequence consisting of (1) oxidative cleavage of the exocyclic double bond, (2) stereoselective alpha-methylation, (3) furyl attachment, and (4) introduction of a 16-keto function. 相似文献
15.
A new pentanortriterpenoid, 1-O-methylclausenolide ( 1 ) and a known limonoid, zapoterin ( 4 ) were isolated from the stem bark of Clausena excavata (Rutaceae). Their structures were elucidated by spectral analysis and chemical transformation. 相似文献
16.
Jianxun Zhu Xiaofeng Lu Xiaona Fan Ruibo Wu Hongjuan Diao Rongmin Yu Hanhong Xu Jiachen Zi 《中国化学快报》2018,29(8):1261-1263
Azadiramide A (1), a new salannin-class limonoid alkaloid, inhibits growth of human breast cancer MDA-MB-231 cell line with IC50 value of 2.70±0.63 μmol/L. 相似文献
17.
Trangmolins A–F with an Unprecedented Structural Plasticity of the Rings A and B: New Insight into Limonoid Biosynthesis 下载免费PDF全文
Wanshan Li Prof. Dr. Li Shen Dr. Torsten Bruhn Dr. Patchara Pedpradab Prof. Dr. Jun Wu Prof. Dr. Gerhard Bringmann 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(33):11719-11727
The absolute stereostructures of trangmolins A–F ( 1 – 6 ), limonoids with three new and one known topologies of the rings A and B, were unambiguously determined by NMR spectroscopic investigations, single‐crystal XRD analysis, and quantum‐chemical electronic circular dichroism calculations. Compounds 1 – 3 contain a hexahydro‐1H‐inden‐4‐one motif, compound 4 comprises a hexahydro‐2,6‐methanobenzofuran‐7‐one cage, and compound 5 consists of a hexahydro‐2H‐2,8‐epoxychromene scaffold. The C1?C30 linkage in 1 – 3 and the C3?C30 connection in 4 form two unprecedented types of ring A/B‐fused carbobicyclic cores: viii and ix . The oxidative cleavage of the C2?C3 bond in 5 and heterocyclization in 4 and 5 constitute the unprecedented tricyclic 6/6/5 ring A/B1/B2‐ and 6/5/6 ring A1A2/B‐fused topologies, respectively, which are uncovered, for the first time, in the construction of limonoid architectures. The diverse cyclization patterns of 1 – 6 reveal an unparalleled structural plasticity of rings A and B in limonoid biosynthesis. 相似文献
18.
Jun-Lin Yin Ying-Tong DiXin Fang En-De LiuHai-Yang Liu Hong-Ping HeShun-Lin Li Shi-Fei Li Xiao-Jiang Hao 《Tetrahedron letters》2011,52(24):3083-3085
Tabulvelutin A (1), the first 19-nor limonoid incorporating a unique 7,10-γ-lactone, together with a biosynthetically related limonoid tabulvelutin B (2) was isolated from the stem bark of Chukrasia tabularis var. velutina. Their structures were elucidated by extensive spectroscopic analysis and chemical computation. The insecticidal activity of compounds 1 and 2 was also assessed. 相似文献
19.
Yunpeng Sun Letian Cui Qiurong Li Pengfei Tang Yongyi Li Wenjun Xu Jun Luo Lingyi Kong 《中国化学快报》2022,33(1):516-518
Mufolinin A(1), a ring A-seco rearranged limonoid with an unprecedented ethyl at C-10 and novel 6/6/6/5 fused-ring skeleton, together with three new potential precursors(ring A-seco limonoids, 2–4) were isolated from Munronia unifoliolata. Their structures and absolute configurations were confirmed by nuclear magnetic resonance(NMR), high resolution electrospray ionization mass spectroscopy(HRESIMS), X-ray crystallography, electronic circular dichroism(ECD) calculations and NMR calculations with... 相似文献