Cytotoxic Alkaloids from the Roots ofTylophora atrofolliculata

Huang, Xueshi; Gao, Song; Fan, Li‐Hua; Yu, Steve S.‐F.; Liang, Xiao‐Tian

doi:10.1055/s-2004-818973

Cited by 38 publications

(8 citation statements)

References 6 publications

(12 reference statements)

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“…The MeOH extract (17.6 g) was suspended in H 2 O (200 mL) and extracted with chloroform and n-BuOH. The chloroform-soluble portion was subjected to silica gel column chromatography using the stepwise solvent system of chloroform-methanol (100 : 0 3 : 1 1 : 3) to yield 18 fractions (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). Active fraction 18 (98.4 mg) was chromatographed on a Sephadex LH-20 column eluted with methanolchloroform (2 : 3) to yield 5 fractions (19)(20)(21)(22)(23) Antiplasmodial Assay RPMI-1640 was supplemented with 25 mM N-(2-hydroxyethyl) piperazine-N′-2-ethanesulfonic acid (HEPES), 50 µg/mL hypoxanthine, 0.4% glucose and 5 µg/mL gentamicin.…”

Section: Methodsmentioning

confidence: 99%

“…The chloroform-soluble portion showed the most potent antimalarial activity. Bioassay-guided fractionation resulted in the isolation of a new seco-phenanthroindolizinetype alkaloid, compound 1, along with three previously known compounds, dehydrotylophorine (2), 11) dehydroantofine (3), 18) and tylophoridicine D (4). 19) In this paper, we report the structures of 1 and antimalarial activities of all four isolated compounds (Fig.…”

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confidence: 99%

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Antimalarial Phenanthroindolizine Alkaloids from Ficus septica

et al. 2016

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During the screening of antimalarial substances, MeOH extract from the twigs of Ficus septica was shown to have potent antimalarial activity. Bioassay-guided fractionation of a methanol extract of the twigs of F. septica led to the isolation of a new seco-phenanthroindolizine alkaloid and three known phenanthroindolizine alkaloids. Their structures were elucidated on the basis of NMR analysis. All isolated compounds were tested against Plasmodium falciparum. Compounds 2-4 displayed antimalarial activity against the 3D7 strain of P. falciparum with IC 50 values 0.028-0.42 µM, whereas a new compound 1 exhibited a moderate antimalarial activity.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Antimalarial Phenanthroindolizine Alkaloids from Ficus septica

et al. 2016

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“…Phenanthroindolizidine alkaloids are pentacyclic natural products isolated mainly from plants belonging to Cynanchum , Pergularia , Tylophora as well as some genera of the Asclepiadaceae [1]–[3]. For many years, these natural products and synthetic derivatives attract widespread attention for their extensively therapeutic activities, such as anticancer activity [4]–[8], anti-inflammatory activity [9]–[11], antibacterial activity [12]–[14], and so on.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation and Mechanism Studies of Deoxytylophorinine and Its Derivatives as Potential Anticancer Agents

Ren

et al. 2012

PLoS ONE

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Previous studies indicated that (+)-13a-(S)-Deoxytylophorinine (1) showed profound anti-cancer activities both in vitro and in vivo and could penetrate the blood brain barrier to distribute well in brain tissues. CNS toxicity, one of the main factors to hinder the development of phenanthroindolizidines, was not obviously found in 1. Based on its fascinating activities, thirty-four derivatives were designed, synthesized; their cytotoxic activities in vitro were tested to discover more excellent anticancer agents. Considering the distinctive mechanism of 1 and interesting SAR of deoxytylophorinine and its derivatives, the specific impacts of these compounds on cellular progress as cell signaling transduction pathways and cell cycle were proceeded with seven representative compounds. 1 as well as three most potent compounds, 9, 32, 33, and three less active compounds, 12, 16, 35, were selected to proform this study to have a relatively deep view of cancer cell growth-inhibitory characteristics. It was found that the expressions of phospho-Akt, Akt, phospho-ERK, and ERK in A549 cells were greater down-regulated by the potent compounds than by the less active compounds in the Western blot analysis. To the best of our knowledge, this is the first report describing phenanthroindolizidines alkaloids display influence on the crucial cell signaling proteins, ERK. Moreover, the expressions of cyclin A, cyclin D1 and CDK2 proteins depressed more dramatically when the cells were treated with 1, 9, 32, and 33. Then, these four excellent compounds were subjected to flow cytometric analysis, and an increase in S-phase was observed in A549 cells. Since the molecular level assay results of Western blot for phospho-Akt, Akt, phospho-ERK, ERK, and cyclins were relevant to the potency of compounds in cellular level, we speculated that this series of compounds exhibit anticancer activities through blocking PI3K and MAPK signaling transduction pathways and interfering with the cell cycle progression.

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“…8 Fragmentation pathway proposed to account for the CID spectra of tylophoridicine C ( 62 ) by positive ion FAB-MS. The structure of compound 62 was firstly elucidated to be (13a S ,14 S )-6,14-dihydroxy-3,7-dimethoxyphenanthroindolizidine N -oxide from T. atrofolliculata , also named as tylophoridicine C (Huang et al 2004 ), while its name of 3,6,7-trimethoxy-10-oxyphenanthroindolizidine for FAB-MS in the reference was incorrect (Xiang et al 2002 ) …”

Section: Key Spectroscopic Characteristics Of Pias and Pqasmentioning

confidence: 99%

Possible pharmaceutical applications can be developed from naturally occurring phenanthroindolizidine and phenanthroquinolizidine alkaloids

Jia

Zhao

et al. 2020

Phytochem Rev

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Naturally occurring phenanthroindolizidine and phenanthroquinolizidine alkaloids (PIAs and PQAs) are two small groups of herbal metabolites sharing a similar pentacyclic structure with a highly oxygenated phenanthrene moiety fused with a saturated or an unsaturated N -heterocycle (indolizidine/quinolizidine moieties). Natural PIAs and PQAs only could be obtained from finite plant families (such as Asclepiadaceae, Lauraceae and Urticaceae families, etc.). Up to date, more than one hundred natural PIAs, while only nine natural PQAs had been described. PIA and PQA analogues have been applied to the development of potent anticancer agents all along because of their excellent cytotoxic activity. However, in the last two decades, other great biological properties, such as anti-inflammatory and antiviral activities were revealed successively by different pharmacological assays. Especially because of their potent antiviral activity against coronavirus (TGEV, SARS CoV and MHV) and tobacco mosaic virus, PIA and PQA analogues have attracted much pharmaceutical attention again, some of them have been used to present interesting targets for total or semi synthesis, and structure–activity relationship (SAR) study for the development of antiviral agents. In this review, natural PIA and PQA analogues obtained in the last two decades with their herbal origins, key spectroscopic characteristics for structural identification, biological activity with possible SARs and application prospects were systematically summarized. We hope this paper can stimulate further investigations on PIA and PQA analogues as an important source for potential drug discovery.

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Cytotoxic Alkaloids from the Roots ofTylophora atrofolliculata

Cited by 38 publications

References 6 publications

Antimalarial Phenanthroindolizine Alkaloids from <i>Ficus septica</i>

Antimalarial Phenanthroindolizine Alkaloids from <i>Ficus septica</i>

Synthesis, Biological Evaluation and Mechanism Studies of Deoxytylophorinine and Its Derivatives as Potential Anticancer Agents

Possible pharmaceutical applications can be developed from naturally occurring phenanthroindolizidine and phenanthroquinolizidine alkaloids

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