Characterisation of alkaloids from some Australian Stephania (Menispermaceae) species

Blanchfield, Joanne T.; Sands, D. P. A.; Kennard, C. H. L.; Byriel, Karl A.; Kitching, William

doi:10.1016/s0031-9422(03)00240-1

Cited by 58 publications

(49 citation statements)

References 34 publications

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“…Additionally, the two methoxyl groups located at the other aromatic ring, positioning 9 and 10 were confirmed by the HMBC correlation of proton 11 and 12. The structure of compound 1 was finally confirmed by direct comparison of the major chemical shift 1 H and 13 C NMR of the isolated compound with the value reported by Joanne et al (2003).…”

Section: Resultsmentioning

confidence: 54%

“…This indicated that the dihedral angle between this proton and the adjacent CH proton must be very close to 180°. Correspondingly, the signal for the equatorial (geminal) proton (δ 3.27) was a dd pattern, with smaller vicinal coupling (J H-H = 3.65), suggesting a dihedral angle closer to 90° (Joanne et al, 2003). This was substantiation for the protoberberine system and these coupling constants necessitate an axially oriented H-13a.…”

Section: Resultsmentioning

confidence: 66%

“…The methylene proton H-8 displayed a pair doublets at δ 4.24 and 3.54 with the large between these signals ( 1 J H-H = 15.63 Hz) recommended geminal protons and the direct bond C-H correlation HMQC technique were established. So, the presence of deshielded, secluded methylene group is distinguishing of the bridge position (C-8) of protoberberine alkaloids (Joanne et al, 2003). The substantial down fielded shift of the 13 C signal of CH and CH 2 groups (δ 59.29 C-13a, 51.48 C-6, 53.96 C-8) indicated these carbons atom were adjacent to the nitrogen atom.…”

Section: Resultsmentioning

confidence: 97%

“…Additionally, the base peak at m/z 149 came from the fragment ion at m/z 296. The 400 MHz 1 H NMR (CDCl 3 ) spectrum (Table 1) of 2 indicated that compound 2 was aporphine alkaloids crebanine (Joanne et al, 2003). This fact was evidenced by the presence of signals for three protons on aromatic carbons.…”

Section: ------------------------------------------------------------mentioning

confidence: 96%

“…Based on above data, compound 2 was identified as crebanine. This compound has been isolated from S. sasakii and S. capitata (Joanne et al, 2003).…”

Section: ------------------------------------------------------------mentioning

confidence: 99%

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Antiproliferative Effects of Alkaloids Isolated from the Tuber of <i>Stephania venosa via</i> the Induction of Cell Cycle Arrest in Mammalian Cancer Cell Lines

Nantapap¹

2010

American Journal of Applied Sciences

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Approach:The research was carried out to extract, isolate, purify and elucidate structure of the active compound from the tuber S. venosa. Most of the solvent extracts and isolated compound were evaluated with kinds of mammalian cancer cell lines for investigation on antiproliferative effects. Results: Four alkaloids, tetrahydropalmatine (1), crebanine (2) O-methylbulbocapnine (3) and Nmethyltetrahydropalmatine (4) were isolated from the tuber of S. venosa. Charaterization of the compounds were carried out by extensive NMR studies using COSY, HMQC, HMBC and DEPT in addition to other spectroscopic methods. These compounds (1, 2 and 3) were showed evidence of the anticancer activities for cell proliferation inhibition in K562, K562/Adr, GLC4 and GLC4/Adr cell lines due to G0/G1 obstruction by compound 2 and 3 and negligible S phase arrest by compound 1. Conclusion:The result showed slightly increase in S phase by the effect of compound 1, beside the G0/G1 phase was blocked by compound 2 and 3.

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Section: Resultsmentioning

confidence: 54%

Section: Resultsmentioning

confidence: 66%

Section: Resultsmentioning

confidence: 97%

Section: ------------------------------------------------------------mentioning

confidence: 96%

“…Based on above data, compound 2 was identified as crebanine. This compound has been isolated from S. sasakii and S. capitata (Joanne et al, 2003).…”

Section: ------------------------------------------------------------mentioning

confidence: 99%

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Antiproliferative Effects of Alkaloids Isolated from the Tuber of <i>Stephania venosa via</i> the Induction of Cell Cycle Arrest in Mammalian Cancer Cell Lines

Nantapap¹

2010

American Journal of Applied Sciences

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Stereochemical assignment of three new benzylisoquinoline alkaloids from Phaeanthus vietnamensis by NMR study combined with CD spectroscopy

Hoàng

Diệp

et al. 2021

Magnetic Reson in Chemistry

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HPLC Analysis of Stephania rotunda Extracts and Correlation with Antiplasmodial Activity

Bory

Bun

Baghdikian

et al. 2012

Phytotherapy Research

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Stephania rotunda (Menispermaceae), a creeper commonly found in the mountainous areas of Cambodia, has been mainly used for the treatment of fever and malaria. Thus, the aim of this study is to investigate the chemical composition and antiplasmodial activity of different samples of S. rotunda and compare their antiplasmodial activity with their alkaloid content. Sixteen samples from different parts (roots, stem, and tuber) of S. rotunda were collected from four regions of Cambodia (Battambang, Pailin, Siem Reap, and Kampot). Reversed-phase HPLC was used to determine the content of three bioactive alkaloids (cepharanthine, tetrahydropalmatine, and xylopinine). These three alkaloids have been found in all samples from Battambang and Pailin (samples I-IX), whereas only tetrahydropalmatine was present in samples from Siem Reap and Kampot (samples X-XVI). The analyzed extracts were evaluated for their antiplasmodial activity on W2 strain of Plasmodium falciparum. Among them, 13 extracts were significantly active with inhibitory concentration 50 (IC(50) ) from 1.2 to 3.7 µg/mL and 2 extracts were moderately active (IC(50) = 6.1 and 10 µg/mL, respectively), whereas sample XI was not active (IC(50) = 19.6 µg/mL). A comparison between antiplasmodial activity and concentration of the three bioactive alkaloids in S. rotunda extracts has been realized.

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Characterisation of alkaloids from some Australian Stephania (Menispermaceae) species

Cited by 58 publications

References 34 publications

Antiproliferative Effects of Alkaloids Isolated from the Tuber of <i>Stephania venosa via</i> the Induction of Cell Cycle Arrest in Mammalian Cancer Cell Lines

Antiproliferative Effects of Alkaloids Isolated from the Tuber of <i>Stephania venosa via</i> the Induction of Cell Cycle Arrest in Mammalian Cancer Cell Lines

Stereochemical assignment of three new benzylisoquinoline alkaloids from Phaeanthus vietnamensis by NMR study combined with CD spectroscopy

HPLC Analysis of Stephania rotunda Extracts and Correlation with Antiplasmodial Activity

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