Quaternary Alkaloids of<i>Tinospora capillipes</i>

Chang, Hung‐Chun; El-Fishawy, Ahlam M.; Slatkin, David J.; Schiff, Paul L.

doi:10.1055/s-2007-969629

Cited by 21 publications

(12 citation statements)

References 7 publications

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“…These data indicated that the three alkaloids lost a methyl radical in MS 2 15 Since the formation of such a methylenedioxy group only occurs when two methoxy groups are vicinal to each other, fragment A can be used as a diagnostic ion. Although the exact positions of methoxy groups cannot be fully elucidated by MS n analysis, it is rather rare to find a methoxy group at a position other than C-2, C-3, C-9 and C10, especially in Tinospora.…”

Section: Protoberberine-type Alkaloidsmentioning

confidence: 95%

“…1 Up to now, three major groups of compounds including protoberberine and aporphine alkaloids, clerodane-type diterpenes and botanic steroids have been reported as bioactive components from this herb. [2][3][4][5] Modern pharmacological studies have shown that ethanolic extracts of Jin-Guo-Lan possess broader bioactivities, such as antibiosis, anti-inflammatory and antiviral effects. 6,7 It is well accepted that the bioactivities of TCM are not the effect of a single compound or a class of compounds, but the synergistic effects of all the components, major and minor, in the herbs.…”

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confidence: 99%

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Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin‐Guo‐Lan (Tinospora sagittata and Tinospora capillipes) by high‐performance liquid chromatography/electrospray ionization with multistage mass spectrometry

Zhang

Shi

et al. 2006

Rapid Comm Mass Spectrometry

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This study sought to determine the primary components (isoquinoline alkaloids, diterpenoids and steroids) in crude extracts of the Chinese herb Jin-Guo-Lan, prepared from the roots of Tinospora sagittata and T. capillipes, by liquid chromatography/electrospray ionization multistage mass spectrometry coupled with diode-array detection (LC-DAD/ESI-MS(n)). After separation on a reversed-phase C(18) column using gradient elution, positive and negative ESI-MS experiments were performed. In positive ion mode, the three types of compounds showed very different characteristic ions: strong [M](+) or [M+H](+) ions were observed for isoquinoline alkaloids; [M+NH(4)](+) and/or [M+H-CO(2)](+) for diterpenoids; [M+H-nH(2)O](+) (n=1-3) for steroids. These adduct ions and/or fragments were used to deduce the mass and categories of known and unknown components in crude extracts, and their structures were further confirmed by ESI-MS(n) in positive ion mode. Moreover, UV absorption peaks obtained from DAD provided useful functional group information to aid the MS(n)-based identification. As a result, 11 compounds were unambiguously identified by comparing with standard compounds and 13 compounds were tentatively identified or deduced according to their MS(n) data. Two of these compounds (13-hydroxycolumbamine and 13-hydroxyjatrorrhizine) were found to be new compounds and another one (13-hydroxypalmatine) was detected for the first time as a natural product. In addition, a [M-*CH(3)-H(2)O](*+) ion in MS(2) of [M](+) after in-source collision-induced dissociation was used to differentiate positional isomers of protoberberine alkaloids, columbamine and jatrorrhizine. Although the roots of T. sagittata and T. capillipes contain almost identical compounds, the content of the compounds in them is dramatically different, suggesting the necessity for further comparison of the bioactivities of the two species.

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Section: Protoberberine-type Alkaloidsmentioning

confidence: 95%

mentioning

confidence: 99%

Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin‐Guo‐Lan (Tinospora sagittata and Tinospora capillipes) by high‐performance liquid chromatography/electrospray ionization with multistage mass spectrometry

Zhang

Shi

et al. 2006

Rapid Comm Mass Spectrometry

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“…Alkaloid 3 had been obtained earlier from Fissistigma balansae [13], Tinospora capillipes [14], Thalictrum foliolosum [15] and Corydalis tashiroi [16]. 4 has been reported from several plants, for example, Corydalis tashiroi [16], Fissistigma glaucescens [17], and Uvaria lucida [18].…”

Section: Resultsmentioning

confidence: 99%

Chemical constituents of Polyalthia parviflora stem

2007

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“…Contemporary pharmacological studies have confirmed that Radix Tinosporae possesses anti-inflammatory activities in vitro (Ma et al, 2002;Li et al, 2003Li et al, , 2004. The chemical constituents of Radix Tinosporae mainly include diterpenoid lactone, protoberberine alkaloids, aporphine alkaloids and botanic steroids, among which diterpenoid lactones and alkaloids are considered important bioactive constituents (Huang and Zhu, 1957;Chang et al, 1984;Song et al, 1988). Phytochemical studies in our laboratory showed that columbamine, jatrorrhizine, palmatine and menisperine are major diterpenoid lactones and alkaloids compounds in Radix Tinosporae.…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory and anti-nociceptive activities of compounds from Tinospora sagittata (Oliv.) Gagnep.

Liu

Shi

et al. 2010

Arch. Pharm. Res.

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Radix Tinosporae is a herb widely used in traditional Chinese medicine for the treatment of various inflammatory diseases. In the present study, its anti-inflammatory and antinociceptive activities were investigated. The ethanol extract of Radix Tinosporae exhibited significant inhibitory effects on xylene-induced ear edema and acetic acid-induced writhing in mice. Using bioassay-guided fractionation, the n-butanol fraction was determined as the active fraction. Further purification of the most active n-butanol fraction led to the isolation of three compounds, palmatine, columbamine and columbinyl glucoside. All three compounds showed inhibitory activities on xylene-induced ear edema, but only palmatine and columbamine exhibited significant inhibitory effects on acetic acid-induced writhing. In addition, palmatine and columbamine markedly inhibited in vitro production of nitric oxide and nuclear factor-kappaB activation in RAW264.7 macrophage cells in response to lipopolysaccharide or tumor necrosis factor alpha stimulation. These results provide justification for the utilization of Radix Tinosporae in Chinese folk medicine for the treatment of inflammatory diseases.

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Quaternary Alkaloids ofTinospora capillipes

Abstract: Extracts of the roots of TINOSPORA CAPILLIPES Gagnep. (Menispertnaceae) afforded the quaternary protoberberine alkaloids palmatine, jatrorrhizine, columbamine, stepharanine and dehydrodiscretamine and the quaternary aporphine alkaloids menisperine and magnoflorine.

Cited by 21 publications

References 7 publications

Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin‐Guo‐Lan (Tinospora sagittata and Tinospora capillipes) by high‐performance liquid chromatography/electrospray ionization with multistage mass spectrometry

Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin‐Guo‐Lan (Tinospora sagittata and Tinospora capillipes) by high‐performance liquid chromatography/electrospray ionization with multistage mass spectrometry

Chemical constituents of Polyalthia parviflora stem

Anti-inflammatory and anti-nociceptive activities of compounds from Tinospora sagittata (Oliv.) Gagnep.

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