Phytochemical Studies on Stemona burkillii Prain:  Two New Dihydrostemofoline Alkaloids

Mungkornasawakul, Pitchaya; Pyne, Stephen G.; Jatisatienr, Araya; Lie, Wilford; Ung, Alison T.; Issakul, Kritchaya; Sawatwanich, Auntika; Supyen, Damrat; Jatisatienr, C.

doi:10.1021/np049791z

Cited by 29 publications

(85 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All samples of S. collinsiae collected in different localities of Thailand uniformly showed a predominance of didehydrostemofoline (173), indicating a species-specific chemical character. The closely related S. burkillii can be distinguished by an accumulation of stemofoline (160) (Mungkornasawakul et al 2004b;Schinnerl et al 2007). By contrast, the alkaloid profiles of S. kerrii were characterized by pyridoazepine derivatives, especially by a predominance of stemokerrine (183).…”

Section: Chemotaxonomymentioning

confidence: 99%

Structural classification and biological activities of Stemona alkaloids

Greger

2019

Phytochem Rev

View full text Add to dashboard Cite

Stemona alkaloids represent a unique class of natural products exclusively known from the three genera Stemona, Stichoneuron, and Croomia of the monocotyledonous family Stemonaceae. Structurally they are characterized by a central pyrroloazepine core usually linked with two butyrolactone rings. The great diversity, comprising 215 derivatives, is created by the formation of additional CC linkages and oxygen bridges together with ring cleavages and eliminations of the lactone rings. Based on biosynthetic considerations they can be grouped into three structural types represented by the croomine, stichoneurine, and protostemonine skeleton. Due to the formation of characteristic terminal lactone rings and the central pyrrolidine ring pandanamine and pandamarilactonine, isolated from Stichoneuron calcicola, were suggested to represent biogenetic precursors. The taxonomically complex S. tuberosa group can be clearly segregated by the formation of stichoneurines, while the other Stemona species are characterized by protostemonine derivatives. Croomine derivatives are more widespread found in both groups and in the genus Croomia. Of chemotaxonomic significance are the different transformations of protostemonine into stemofolines with a cage-type structure or into pyridoazepines characterized by a six-membered piperidine ring. Stimulated by the great interest in the antitussive activity of Stemona alkaloids, differences in transport mechanisms and potencies via different administrative routes were investigated. Follow-up studies on the significant insecticidal activities focused on the mode of action by using biochemical and electrophysiological approaches. Screening for acetylcholinesterase inhibitory properties revealed a much higher potency for stemofoline derivatives compared to pyridoazepines, but showed also significant activity for isomers of stenine with a stichoneurine skeleton. Evaluating synergistic growth inhibitory effects with cancer chemotherapeutic agents stemofoline exhibited the most potent effect in the reversal of permeability glycoprotein-mediated multidrug resistance. The anti-inflammatory activity of some derivatives was identified as an inhibition of the expression of inflammatory mediators. Comparing the diverse bioactivities of Stemona alkaloids stemofoline-type derivatives are the most versatile compounds representing promising lead structures for further development as commercial agents in agriculture and medicine.

show abstract

Section: Chemotaxonomymentioning

confidence: 99%

Structural classification and biological activities of Stemona alkaloids

Greger

2019

Phytochem Rev

View full text Add to dashboard Cite

show abstract

“…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). The relative small J 11,12 value for 3 (1.3 Hz) and the ROESY correlations between H-12 and H-17, as well as the correlation between H-11 and H-17, are consistent with the relative 11S,12S configurations assigned to compound 3.…”

Section: Resultsmentioning

confidence: 99%

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

Self Cite

View full text Add to dashboard Cite

. 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

show abstract

“…(11S,12R)-Dihydrostemofoline (63) was isolated from the root extract of S. burkillii. 30 Its structure and relative configuration were determined via spectroscopic data and from comparison with synthetic (11S,12S)-dihydrostemofoline by syn hydrogenation of stemofoline.…”

Section: Stemofoline Groupmentioning

confidence: 99%

“…Their epimeric nature was confirmed after oxidation of (2 0 S)-hydroxystemofoline (66) to the corresponding ketone, followed by sodium borohydride reduction, which afforded a 62 : 38 mixture of (2 0 S)-hydroxystemofoline (66) and (2 0 R)-hydroxystemofoline (65). 31 2 0 -Hydroxystemofoline was also isolated from roots of S. curtisii, 19 S. cochinchinensis 19 and S. burkillii, 30 while the 2 0 S alkaloid (66) was also isolated from S. aphylla. 29 Additionally, (3 0 R)-stemofolenol (67) and (3 0 S)-stemofolenol (68) were also found in the above-mentioned unidentified Stemona species as a 1 : 1 mixture by thin-layer chromatography.…”

Section: Stemofoline Groupmentioning

confidence: 99%

See 1 more Smart Citation

The chemistry of Stemona alkaloids: An update

2010

View full text Add to dashboard Cite

In the review period, 97 new representatives of Stemona alkaloids were described, bringing the total reported so far to 139. In this review, we discuss their isolation, structural elucidation, structural classification, biological activities, semi-synthesis and total syntheses. These alkaloids are classified into seven groups displaying either a pyrrolo[1,2-a]azepine or a pyrido[1,2-a]azepine core, and a miscellaneous group comprising those alkaloids without these structural motifs, together with those that are the sole representative of a new group. It displays a ring A pyrrole unit, and its relative stereochemistry resembles that of tuberostemonine J (5), except for H-18 which is proposed to be aoriented in epi-bisdehydroneotuberostemonine J (10) while it is b-oriented in tuberostemonine J (5) and in most of the other Stemona alkaloids bearing the a-methyl-g-butyrolactone moiety attached to C-3. Its absolute chemical structure was claimed to have been established by X-ray crystallographic analysis. 1 9a-Bisdehydrotuberostemonine (11) also displays a pyrrole ring and it was isolated from the roots of S. tuberosa. 15 Its structure was assigned as the 9a epimer of bisdehydrotuberostemonine, also known as didehydrotuberostemonine, 4 by Fig. 2 Stemona alkaloids of the stenine group (1-14).

show abstract

Phytochemical Studies on Stemona burkillii Prain: Two New Dihydrostemofoline Alkaloids

Cited by 29 publications

References 8 publications

Structural classification and biological activities of Stemona alkaloids

Structural classification and biological activities of Stemona alkaloids

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

The chemistry of Stemona alkaloids: An update

Contact Info

Product

Resources

About