The Stemona Alkaloids

Pilli, Ronaldo A.; Rosso, Giovanni; Oliveira, Maria da Conceição Ferreira de

doi:10.1016/s1099-4831(05)62002-0

Cited by 71 publications

(111 citation statements)

References 67 publications

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“…While compound 4 had the same molecular formula, and related structure features, to isoprotostemonine 2 and protostemonine there were notable differences in their NMR spectroscopic data (Wang et al, 2007). The aforementioned two known alkaloids had very similar However, we have tentatively assign the 3R, 18S, 20R configuration to 4 since the 18S configuration is the most commonly found absolute configuration of the Stemona alkaloids (Greger 2006;Kongkiatpaiboon, 2001;Pilli et al, 2010Pilli et al, , 2005. The lack of a NOESY correlations between the OMe group and the protons on the C-ring was consistent the Econfiguration of the C-11−C-12 alkene.…”

Section: Resultsmentioning

confidence: 83%

“…The ROESY correlations between H-18 and H-19and; H-19 and H-20; and H-19 and H-22 stereocentres from molecular modelling and ROESY NMR studies. However, we have tentatively assign the 3S, 18S, 20S configuration to 3 since this is the most commonly found absolute configuration of the Stemona alkaloids (Greger 2006;Kongkiatpaiboon, 2001;Pilli et al, 2010Pilli et al, , 2005. The configurations assigned to C-11 and C-12 in 3 were based on ROESY correlations and the magnitude of J 11,12 when compared to the known Stemona alkaloids 11S,12S-saxorumamide (ROESY correlation between H-12 and H-17, and J 11,12 = 2.0 Hz) and 11S,12R-isosaxorumamide (ROESY correlation between H-10 and H-13, and J 11,12 = 6.9 Hz) (Wang et al, 2007) and related dihydrostemofoline alkaloids (Mungkornasawakul et al, 2004b).…”

Section: Resultsmentioning

confidence: 87%

“…Extracts of the roots of the Stemona species have been used in traditional medicine to treat the symptoms of bronchitis, pertussis and tuberculosis and as anti-parasitics on humans and animals (Greger, 2006;Kongkiatpaiboon, 2001, Pilli et al, 2010, 2005. More than 190 unique Stemona alkaloids have been isolated, some of these have significant antitussive activity (Chung et al, 2003;Lin et al, 2008aLin et al, , 2008bLin et al, , 2006Xu et al, 2010Xu et al, , 2006Yang et al, 2009;Zhou et al, 2009;), as well as insect toxicity, antifeedant, and repellent activities (Brem et al, 2002;Jiwajinda et al, 2001;Kaltenegger et al, 2003;Kongkiatpaiboon et al, 2013Kongkiatpaiboon et al, , 2012Mungkornasawakul et al, 2009Mungkornasawakul et al, , 2004aPhattharaphan et al, 2010;Sanguanpong and Hummel, 2008;Sakata et al, 1978;Tang et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

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Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities

Ramli

Pudjiastuti

Tjahjandaric

et al. 2015

Phytochemistry Letters

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. Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities. Phytochemistry Letters, Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities AbstractTwo new protostemonine-type alkaloids, javastemonine A and B (3 and 4) have been isolated from the root extracts of Stemona javanica together with four known Stemona alkaloids, 13-demethoxy-11(S*),12(R*)-dihydroprotostemonine (1), isoprotostemonine (2), protostemonine and isomaistemonine. The structures and relative configurations of the new alkaloids were determined by spectroscopic analysis. The alkaloids 1 and 2 and protostemonine showed moderated antiplasmodial activities against the Plasmodium falciparum strains, TM4 (IC50 values of 17.7 ± 3.7, 16.8 ± 5.4, 16.0 ± 4.2 μg/mL, respectively) and K1 (IC50 values of 16.8 ± 3.1, 14.1 ± 3.7, 11.9 ± 3.3 μg/mL, respectively). These compounds showed no significant cytotoxicities against KB or Vero cells or acetylcholinesterase inhibitory activities. Disciplines Medicine and Health Sciences | Social and Behavioral Sciences Publication DetailsRamli, R., Pudjiastuti, P., Tjahjandaric, T. S., Lie, W., Rattanajak, R., Kamchonwongapaisan, S. & Pyne, S. G. values of 17.7 ± 3.7, 16.8 ± 5.4, 16.0 ± 4.2 µg/mL, respectively) and K1 (IC 50 values of 16.8 ± 3.1, 14.1 ± 3.7, 11.9 ± 3.3 µg/mL, respectively). These compounds showed no significant cytotoxicities against KB or Vero cells or acetylcholinesterase inhibitory activities.2

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Section: Resultsmentioning

confidence: 83%

Section: Resultsmentioning

confidence: 87%

Section: Introductionmentioning

confidence: 99%

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Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities

Ramli

Pudjiastuti

Tjahjandaric

et al. 2015

Phytochemistry Letters

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“…The mass-to-charge ratios of 127.038 and 376.248 were identified as protonated 5-HMF and stemonine, which are the chemical markers of Rehmannia glutinosa and Stemona sessilifolia, respectively [18,19]. The protonated ions of m/z 271.061 were identical to the molecular weight of baicalein from Scutellaria baicalensis.…”

Section: Dart-ms Analysis Of Pm104mentioning

confidence: 97%

Effects of Gwaruhaengryeon-hwan on COPD and Particulate Matter Induced Lung Injury on a Mouse Model

Lee¹,

Yang²,

Yeeran³

et al. 2017

J Int Korean Med

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Chronic obstructive pulmonary disease (COPD), which is characterized by airway obstruction, leads to, as the two major forms of COPD, chronic bronchitis and emphysema. This study was conducted to evaluate the effects of herbal formula, PM014, in a murine model of COPD. Balb/c mice were treated once with each herb extract in PM014 or PM014 mixture via an oral injection. Lipopolysaccharide (LPS) or elastase/LPS were administrated to the mice to induce a disease that resembles COPD. PM014 treatment significantly attenuated the increased accumulation of immune cells in bronchoalveolar lavage fluid (BALF) compared to control mice. In addition, the TNF-α and IL-6 levels in BALF were decreased in the PM014 mice. Furthermore, histological analysis demonstrated that PM014 attenuated the hazardous effects of lung inflammation. These data suggest that PM014 exerts beneficial effects against forms of COPD such as lung inflammation.

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“…The root extracts have also been used in the treatment of various respiratory diseases and have been used as anticough agents in China and Japan [Greger, 2006;Pilli et al 2000Pilli et al , 2005Pilli et al , 2010. To date over 130 different Stemona alkaloids have been isolated with the majority of alkaloids having the pyrrolo[1,2-a]azepine base structure [Pilli et al 2010].…”

Section: Introductionmentioning

confidence: 99%

6-Hydroxy-5,6-seco-stemocurtisine: A novel seco-stemocurtisine-type alkaloid

Mungkornasawakul

Pyne

Willis

et al. 2013

Phytochemistry Letters

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Lie, W. (2013). 6-Hydroxy-5,6-seco-stemocurtisine: a novel seco-stemocurtisine-type alkaloid. Phytochemistry Letters, 6 (4), 602-605.6-Hydroxy-5,6-seco-stemocurtisine: a novel seco-stemocurtisine-type alkaloid AbstractA novel seco-stemocurtisine-type alkaloid, 6-hydroxy-5,6-seco-stemocurtisine was isolated from the aerial parts of Stemona curtisii (Stemonaceae) collected from Trang Province in Thailand. The unprecedented 5,6-seco-pyrido[1,2-a] azepine structure was elucidated by 2D NMR analysis and a single crystal X-ray crystallographic analysis. (C) 2013 Phytochemical Society of Europe. The unprecedented 5,6-seco-pyrido[1,2-a]azepine structure was elucidated by 2D NMR analysis and a single crystal X-ray crystallographic analysis. 6-Hydroxy-5,6-seco-stemocurtisine: A novel seco-stemocurtisine-

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The Stemona Alkaloids

Cited by 71 publications

References 67 publications

Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities

Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities

Effects of Gwaruhaengryeon-hwan on COPD and Particulate Matter Induced Lung Injury on a Mouse Model

6-Hydroxy-5,6-seco-stemocurtisine: A novel seco-stemocurtisine-type alkaloid

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