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Cytotoxic sesquiterpenoids from Ligularia pleurocaulis

Published on May 1, 2016in Phytochemistry2.90
· DOI :10.1016/j.phytochem.2016.02.010
Guang-Bo Xie1
Estimated H-index: 1
(University of Electronic Science and Technology of China),
Ya Xie1
Estimated H-index: 1
(University of Electronic Science and Technology of China)
+ 1 AuthorsZhi-Xiang Zhu1
Estimated H-index: 1
(Beijing University of Chinese Medicine)
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Abstract
Abstract The phytochemical investigation of whole plants of Ligularia pleurocaulis led to isolation of five sesquiterpenoids, including an eremophilenolide dimer named biligupleurolide, along with eight known sesquiterpenoids. Their structures were determined by spectroscopic methods including 2D NMR techniques, and the structures of biligupleurolide and ligupleurolide were confirmed by X-ray diffraction analysis. All of the isolated compounds were tested for their cytotoxic activity against three cancer cell lines (HepG2, A549 and MCF-7), and biligupleurolide showed moderate inhibitory activities, with IC 50 values of 5.2, 5.6 and 8.4 μM against MCF-7, HepG2 and A549, respectively.
  • References (23)
  • Citations (3)
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References23
Newest
Published on Jan 1, 2015in Pharmacognosy Magazine1.26
Jin Tian1
Estimated H-index: 1
(University of Electronic Science and Technology of China),
Guangbo Xie1
Estimated H-index: 1
(University of Electronic Science and Technology of China)
+ 1 AuthorsTie-Nan Li1
Estimated H-index: 1
(University of Electronic Science and Technology of China)
Background: Ligularia kangtingensis , a species from the genus Ligularia (Compositae), is an indigenous plant in Southwest China and more than 20 species in this genus have been used as folk medicines in China. Objective: The chemical constituents of the whole plant of L. kangtingensis were studied. Materials and Methods: The dried whole plants were extracted with ethanol. Its chemical constituents were mainly isolated and purified by silica gel and Sephadex LH-20 column chromatography and their...
Published on Sep 1, 2014in Chirality1.93
Guangbo Xie1
Estimated H-index: 1
(University of Electronic Science and Technology of China),
Jin Tian1
Estimated H-index: 1
(University of Electronic Science and Technology of China)
+ 2 AuthorsTibor Kurtán32
Estimated H-index: 32
(University of Debrecen)
A chiral tetralin norsesquiterpenoid, ligukangtinol, was isolated from the plant Ligularia kangtingensis. Its planar structure was determined by extensive analysis of spectroscopic data (MS, IR, and NMR), and (1S,3R) absolute configuration of the tetralin ring was established by TDDFT-ECD calculations of the solution conformers. Conformational analysis and ECD calculations proved that the semiempirical helicity rules of 6-hydroxytetralins correlating the 1Lb Cotton effect and P/M helicity of the...
Published on Jun 27, 2014in Journal of Natural Products4.26
Jian-Jun Chen9
Estimated H-index: 9
,
Chao-Jun Chen1
Estimated H-index: 1
+ 2 AuthorsKun Gao18
Estimated H-index: 18
Five new highly oxygenated eremophilane-type sesquiterpenoids, possessing C19 (1 and 2), C15 (3 and 4), and C14 (8) skeletons, along with eight known eremophilenolides were obtained from the aerial parts of Ligularia sagitta. The absolute configuration of 1 was assigned by X-ray diffraction analysis and that of 3 by ECD spectroscopy. Compounds 1–10 were evaluated for their antibacterial activities against Staphyloccocus aureus, Bacillus subtilis, Escherichia coli, Bacillus cereus, and Erwinia ca...
Published on Sep 1, 2013in Tetrahedron2.38
Yoshinori Saito12
Estimated H-index: 12
(Tokushima Bunri University),
Mizuho Taniguchi1
Estimated H-index: 1
(Tokushima Bunri University)
+ 5 AuthorsMotoo Tori31
Estimated H-index: 31
(Tokushima Bunri University)
Four new compounds, rearranged noreremophilan-8,6-olide, rearranged dinoreremophilanone, epoxy gamma-lactone, and 2 alpha-hydroxyermophil-11-en-9-one, along with eremophilenolides related to ligularol and other known terpenoids, were isolated from Ligularia virgaurea (ligularol type) collected from the northern Sichuan Province of China. Three of the new compounds had degraded and unique structures. The absolute configuration of 2 alpha-hydroxyermophil-11-en-9-one was determined on the basis of ...
Published on Jan 1, 2012in Records of Natural Products1.21
Shaosong Liu4
Estimated H-index: 4
,
Chunhua Lu12
Estimated H-index: 12
+ 2 Authors沈月毛4
Estimated H-index: 4
Key Grant of the Chinese Ministry of Education [306010]; National Ocean 863 Foundation of China [2006AA092410]
Published on Aug 1, 2011in Natural Products and Bioprospecting
Jun-Li Yang11
Estimated H-index: 11
(Lanzhou University),
Rui Wang9
Estimated H-index: 9
(CAS: Chinese Academy of Sciences),
Yan-Ping Shi27
Estimated H-index: 27
(CAS: Chinese Academy of Sciences)
Ligularia, an important genus of the Compositae family, has captured the interest of natural product chemists for years. Phytochemical investigations on the title genus have led to isolation of hundreds of secondary metabolites with various skeletons. Herein, we summarized the chemical constituents of this genus and their biological activities over the past few decades. Open image in new window
Published on Sep 1, 2008in Helvetica Chimica Acta1.39
Cai-Fang Wang1
Estimated H-index: 1
(Zhengzhou University),
Yu Zhao21
Estimated H-index: 21
(ZJU: Zhejiang University)
+ 1 AuthorsZhen-Zhong Zhang1
Estimated H-index: 1
(Zhengzhou University)
Two new eremophilane-type sesquiterpenoids eremophil-6-en-11-ol (1) and (7α,9α,10α)-9,10-epoxy-eremophilan-11-ol (2), together with a known eremophilane-type (6α,8α)-6,8-dihydroxyeremophil-7(11)-en-12-oic acid 12,8-lactone (3) were isolated from the rhizomes of Ligularia veitchiana. The structures of 1 and 2 were established by spectral analysis including 1H- and 13C-NMR, HSQC, HMBC, and HR-ESI-MS data. The compounds 1 and 3 were assessed against lung-cancer (A549) and stomach-cancer (BCG823) ce...
Published on Jan 1, 2008in Fitoterapia2.43
Amira Arciniegas10
Estimated H-index: 10
(UNAM: National Autonomous University of Mexico),
Ana L. Pérez-Castorena11
Estimated H-index: 11
(UNAM: National Autonomous University of Mexico)
+ 3 AuthorsAlfonso Romo de Vivar16
Estimated H-index: 16
(UNAM: National Autonomous University of Mexico)
Abstract The new eremophilanolide 1 , the known eremophilane derivatives 2 and 3 , already described as part of mixtures, the known compounds hyperin, 2″-acetylhyperin and two calenduladiol esters were isolated from Roldana lineolata . Their structures were determined by spectroscopic methods. Compounds 1 and 2 as well as their acetylated and oxidized derivatives were tested against several fungi strains. Eremophilanolide 1 showed a mild activity against Trichophyton mentagrophytes .
Published on Jan 1, 2008in Acta Crystallographica Section A1.88
George M. Sheldrick50
Estimated H-index: 50
(GAU: University of Göttingen)
An account is given of the development of the SHELX system of computer programs from SHELX-76 to the present day. In addition to identifying useful innovations that have come into general use through their implementation in SHELX, a critical analysis is presented of the less-successful features, missed opportunities and desirable improvements for future releases of the software. An attempt is made to understand how a program originally designed for photographic intensity data, punched cards and ...
Published on Feb 1, 2006in Bulletin of the Chemical Society of Japan4.43
Hajime Nagano16
Estimated H-index: 16
,
Yukiko Iwazaki3
Estimated H-index: 3
+ 3 AuthorsRyo Hanai17
Estimated H-index: 17
Intra-specific diversity of Ligularia pleurocaulis was examined from both chemical and genetic aspects, using furanoeremophilanes as the chemical index and the nucleotide sequences in the atpB-rbcL and the ITS1 regions as the genetic index. Four samples of L. pleurocaulis were collected in northwestern Yunnan, and six in southwestern Sichuan. From the ethanol extracts of the roots of all of the samples, four compounds, 6 beta-angeloyloxy- and 6 beta-tigloyloxy-furanoeremophil-1(10)-enes, and 6 b...
Cited By3
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Published on 2019in Natural Product Communications0.55
Motoo Tori31
Estimated H-index: 31
(Tokushima Bunri University),
Yoshinori Saito12
Estimated H-index: 12
(Nagasaki University)
+ 1 AuthorsChiaki Kuroda17
Estimated H-index: 17
(Rikkyo University)
Chemical constituents of Cremanthodium angustifolium, C. brunneopilosum, C. campanulatum, C. daochengense, C. discoideum, C. ellisii, C. helianthus, C. lineare, C. nobile, C. potaninii, C. principi...
Published on Dec 1, 2018in Chinese Journal of Natural Medicines1.77
Guo-Xun Yang1
Estimated H-index: 1
(Fudan University),
Guang-Lei Ma1
Estimated H-index: 1
(Fudan University)
+ 3 AuthorsJin-Feng Hu1
Estimated H-index: 1
(Fudan University)
Abstract In this review, we intensively focus on the advances in research of natural products (NPs) discovery carried out by domestic scholars in China from 2015 through 2017. In general, a total of 1811 publications (1479 in English and 332 in Chinese) were accumulated regarding newly isolated NPs from plants, microorganisms, and marine sources. As a result, 277 selected papers concerning naturally occurring compounds with extraordinary frameworks, origins, and promising activities were discuss...
Published on Jun 1, 2018in Phytochemistry2.90
Hong-Hua Wu5
Estimated H-index: 5
(Tianjin University of Traditional Chinese Medicine),
Xu Deng2
Estimated H-index: 2
(Tianjin University of Traditional Chinese Medicine)
+ 8 AuthorsYan-Tong Xu5
Estimated H-index: 5
(Tianjin University of Traditional Chinese Medicine)
Abstract Dinardokanshones C–E, three sesquiterpenoid dimers comprising an unusual nornardosinane-type sesquiterpenoid core and an aristolane-type sesquiterpenoid unit conjugated by an extra pyran or furan ring, together with monomeric sesquiterpenoids isonardoeudesmols A–D and nardoeudesmol D, were isolated from the underground parts of Nardostachys jatamansi DC. Structures of the eight compounds were elucidated by analysis of the extensive spectroscopic data, and their absolute configurations w...
Published on Mar 1, 2017in Natural Product Communications0.55
Feng-Ming Qi7
Estimated H-index: 7
(Lanzhou University),
Le-Le Dong6
Estimated H-index: 6
(Lanzhou University)
+ 5 AuthorsDong-Qing Fei5
Estimated H-index: 5
(Lanzhou University)