A Bioactive Alkaloid from the Flowers of Trollius chinensis.

Wang, Ru Feng; Yang, Xiu Wei; Mei, Chao; Cai, Shao Qing; Li, Jian Nong; Shoyama, Yukihiro

doi:10.1002/chin.200444227

Cited by 13 publications

(27 citation statements)

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“…Compounds with pyrrolo[2,1-a]isoquinoline structure are reported to have hypotensive and anti-tumor activities (Mikhailovskii and Shklyaev, 1997) as well as antibacterial properties (Wang et al, 2004). Oleracein E (the antipode of trolline) has been reported to exhibit potent DPPH radical scavenging activity (Yang et al, 2009).…”

Section: Discussionmentioning

confidence: 99%

In silico physico-chemical evaluation, anti-inflammatory and mcf-7 breast cancer cell line growth inhibition effects of trolline isolated from Mirabilis jalapa

Sadiq¹,

Inuwa²,

Rehman³

et al. 2016

J. Med. Plants Res.

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The in silico simulations and predictions approach in evaluation of pharmacokinetic properties of new chemical entities (NCEs) is fast becoming an acceptable trend in natural products research and drug discovery. This paper focuses on the properties of trolline with respect to its anti-inflammatory and MCF-7 breast cancer cell line growth inhibition effects and an attempt to predict physico-chemical druglike properties in silico. The compound was isolated for the first time from aerial parts of Mirabilis jalapa and the structure was elucidated by 1D and 2D NMR, FTIR and mass spectroscopic analyses. The compound was screened for anti-inflammatory and anti-MCF-7 cell lines proliferation using chemoluminiscence oxidative burst and MTT assays respectively. Predictions on physico-chemical properties central to oral route drug administration were done using commercial software Admet predictor. Results show anti-inflammatory effects at IC 50 concentration of 53.8 µg/ml and 48% mortality of breast cancer cell lines at 50 µM concentration. Predictions suggest moderate solubility of 1.72 to 2.92 mg/ml across pH range of 1.6 to 6.8 in simulated solvent systems and effective jejunal permeability of 5.61 x 10 -4 cm/s. The compound was also predicted to be 60% unbound to plasma proteins and an LD 50 of 950 mg/kg in rats. The compound, trolline had clinically important bioactive effects, probably possess promising drug-like properties suitable for further high throughput screening.

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Section: Discussionmentioning

confidence: 99%

In silico physico-chemical evaluation, anti-inflammatory and mcf-7 breast cancer cell line growth inhibition effects of trolline isolated from Mirabilis jalapa

Sadiq¹,

Inuwa²,

Rehman³

et al. 2016

J. Med. Plants Res.

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“…A hydroxyl at C-7 of flavone skeleton, among others, is a characteristic of these two compounds ( Fig. In contrast, the compounds with a methoxy at C-7 constitute another subgroup of flavone C-glycosides which include isoswertisin and isoswertiajaponin [35] , as well as their derivatives. In contrast, the compounds with a methoxy at C-7 constitute another subgroup of flavone C-glycosides which include isoswertisin and isoswertiajaponin [35] , as well as their derivatives.…”

Section: Flavone C-glycosidesmentioning

confidence: 99%

“…2). Another group, including vanillic acid, protocatechuic acid, 4-hydroxybenzonic acid, methyl p-hydroxybenzoate [38] , proglobeflowery acid [35,55] and methyl 3, 4-dihydroxy-benzoate [43] are compounds with a free hydroxyl group. Another group, including vanillic acid, protocatechuic acid, 4-hydroxybenzonic acid, methyl p-hydroxybenzoate [38] , proglobeflowery acid [35,55] and methyl 3, 4-dihydroxy-benzoate [43] are compounds with a free hydroxyl group.…”

Section: Phenolic Acidsmentioning

confidence: 99%

“…These compounds are further classified into two groups, one group includes veratric acid [53] , benzoic acid [37] , methyl veratrate [38] , globeflowery acid, trollioside [35,45,54] and 4-(β-D-glucopyranosyloxy)-3-(3-methyl-2-butenyl)benzoic acid [45] are usually without a free hydroxyl group due to methylation and glycosidation. 3) in this laboratory, which demonstrated that trollioside could be hydrolyzed into globeflowery acid and glucose under acid conditions, and could also be hydrolyzed into proglobeflowery acid and glucose by cellulase [35] . It was deduced that some phenolic acids, for example, proglobeflowery acid and globeflowery acid may be interconvertible.…”

Section: Phenolic Acidsmentioning

confidence: 99%

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Investigation on Flos Trollii: Constituents and bioactivities

Yuan¹,

Wang²,

Xiu-wen³

et al. 2014

Chinese Journal of Natural Medicines

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Flos Trollii, the flowers of Trollius chinensis Bunge, has been widely used in Chinese and Mongolian medicine for its efficacy of heat-clearing and detoxification. This drug has both medicinal and edible applications, and has led to various pharmacognosy, natural product chemistry, and pharmacology studies. As a result, its chemical constituents and bioactivities have been well-characterized in recent years. Nevertheless, a couple of critical issues, such as the major effective components, are still unresolved. The present review summarizes research progress on this drug regarding the constituents and bioactivities based on investigations in these laboratories and the results reported in recent publications. In addition, the pending issues are discussed and constructive suggestions for further investigation are proposed.

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“…Por último, basados en trabajos publicados sobre pirroloisoquinoleínas, lactamas aisladas por primera vez en los años 80, poseedoras de interesantes propiedades antiinflamatorias, antitumorales y antimicrobianas (MOREAU et al, 2004;WANG et al, 2004), sintetizamos una serie de hexahidropirrolo-[2,1-a]isoquinolin-3-onas, vía doble ciclación intramolecular, mediante la reacción de condensación de Bischler-Napieralski, seguida de reducción de la imina generada. Los compuestos obtenidos mostraron una interesante actividad antibacteriana y antifúngica (MORENO et al, 2012) (Figura 8).…”

Section: ) (Figura 7)unclassified

Nuevos fármacos inspirados en Annonáceas

et al. 2014

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RESUMEN -Los metabolitos secundarios activos (MSA) juegan un papel importante en el descubrimiento de nuevos medicamentos. Moléculas naturales con esqueletos complejos, tales como las estatinas aisladas de Aspergillus terreus, o las acetogeninas específicas de la familia Annonaceae, no hubieran podido ser inventadas en ningún laboratorio. Los MSA aislados en Annonaceae, especialmente las acetogeninas y los alcaloides isoquinoleínicos, pueden ser considerados como fuente constante de inspiración para químicos, farmacólogos y para todos los investigadores interesados en el descubrimiento de una nueva familia de medicamentos. Terminos para indexacion: Annonaceae, acetogeninas, antitumorales, insecticidas, alcaloides isoquinoleínicos, dopaminérgicos, antimicrobianos. NEW MEDICINES INSPIRATED IN ANNONACEASABSTRACT -Active secondary metabolites (ASM) play a highly significant role in the drug discovery. Natural complex chemical skeleton such as statins isolated from Aspergillus terreus, or acetogenins specific from Annonaceae family, are not able to be invented in any laboratory. The ASM isolated from Annonaces, especially acetogenins and isoquinoline alkaloids should be considered as a source of continuous inspiration for the chemists, the pharmacologists and all researchers that are interested in discovering a new drug family. Los metabolitos secundarios (MS) han sido la principal fuente de diversidad química que ha dirigido el descubrimiento y desarrollo de nuevos agentes terapéuticos en el siglo pasado. Muchos productos de origen natural o análogos estructurales preparados por síntesis, han sido desarrollados con éxito para combatir enfermedades humanas en prácticamente todas las áreas terapéuticas. La época posterior al descubrimiento de la penicilina, durante la segunda guerra mundial, fue la más floreciente en cuanto a los esfuerzos dedicados por las empresas farmacéuticas al descubrimiento de nuevos metabolitos secundarios activos (MSA), moléculas de origen natural con interés terapéutico, centradas principalmente en la búsqueda de antibióticos (Figura 1).Pero estos esfuerzos no se dirigieron únicamente al desarrollo de compuestos antibacterianos o antifúngicos sino que también se amplió el objetivo a otras enfermedades no infecciosas. Así en los años 70, como ejemplo, se desarrollaron la mevastatina, aislada en cultivos de Penicillium citrinum y la lovastatina aislada a partir de un extracto del hongo Aspergillus terreus, como inhibidores de la biosíntesis de colesterol en el hígado, que son la base principal del tratamiento actual de las nuevas estatinas de síntesis (BAKER et al., 2007).Sin embargo, a pesar de estos éxitos indudables la gran industria farmacéutica disminuyó el interés por la investigación en productos naturales a lo largo de los años 90 y principios de la década del 2000, para focalizar la búsqueda de nuevos compuestos activos mediante el rastreo automatizado a gran escala (high throughpout screening, HTS) aplicados a librerías de compuestos generados por la química combinatoria (NEWMAN e C...

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A Bioactive Alkaloid from the Flowers of Trollius chinensis.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 13 publications

References 1 publication

In silico physico-chemical evaluation, anti-inflammatory and mcf-7 breast cancer cell line growth inhibition effects of trolline isolated from Mirabilis jalapa

In silico physico-chemical evaluation, anti-inflammatory and mcf-7 breast cancer cell line growth inhibition effects of trolline isolated from Mirabilis jalapa

Investigation on Flos Trollii: Constituents and bioactivities

Nuevos fármacos inspirados en Annonáceas

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