Phytochemical Studies on <i>Stemona</i> Plants: Isolation of New Tuberostemonine and Stemofoline Alkaloids

Sastraruji, Thanapat; Jatisatienr, Araya; Issakul, Kritchaya; Pyne, Stephen G.; Ung, Alison T.; Lie, Wilford; Williams, Morwenna C.

doi:10.1177/1934578x0600101001

Cited by 8 publications

(16 citation statements)

References 16 publications

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“…The known compound 3c was isolated as a yellow brown gum; R f 0.14 (CH 2 Cl 2 -MeOH, 96:4). 1 H NMR data (CDCl 3 , 400 MHz) and 13 C NMR data (CDCl 3 , 100 MHz) were consistent with these of a previous report [19].…”

Section: Resultssupporting

confidence: 90%

“…Based on these data, the structure of 3b was determined as (11Z, 6 R)-1 0 ,2 0 -didehydro-6-hydroxystemofoline. While the structure of the known compound 3c was identified by comparing its 1 H and 13 C NMR spectroscopic data with those reported [19]. It was significant to note that the biohydroxylation reactions of the stemofolines alkaloids (1a, 2a and 3a) occurred at a relatively unactivated site (C-6) on these caged substrates rather than at more chemically activated sites (for example, sites a to N or O or at an allylic position).…”

Section: Discussionmentioning

confidence: 99%

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Oxidative biotransformation of stemofoline alkaloids

Phaya

Chalom

Ingkaninan

et al. 2021

Artificial Cells, Nanomedicine, and Biotechnology

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Biotransformations of stemofoline (1a), (2 0 S)-hydroxystemofoline (2a), (11Z)-1 0 ,2 0-didehydrostemofoline (3a) and stemocurtisine (4) were studied through fermentation with Cunninghamella elegans TISTR 3370. Three new stemofoline derivatives; 6 R-hydroxystemofoline (1b), (2 0 S, 6 R)-dihydroxystemofoline (2b) and (11Z,6R)-1 0 ,2 0-didehydro-6-hydroxystemofoline (3b), together with the known compound 1 0 ,2 0didehydrostemofoline-N-oxide (3c), were produced by C-hydroxylation and N-oxidation reactions. Stemocurtisine was not biotransformed under these conditions. The transformed product 1b was four times more potent (IC 50 ¼ 11.01 ± 1.49 mM) than its precursor 1a (IC 50 ¼ 45.1 ± 5.46 mM) as an inhibitor against acetylcholinesterase.

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Section: Resultssupporting

confidence: 90%

Section: Discussionmentioning

confidence: 99%

Oxidative biotransformation of stemofoline alkaloids

Phaya

Chalom

Ingkaninan

et al. 2021

Artificial Cells, Nanomedicine, and Biotechnology

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“…Additional oxidations lead to hydroxy groups in ring B at C-6 (6bhydroxystemofoline (162)) and C-8 (stemoburkilline (181)), and in ring D at C-16 (16-hydroxystemofoline (172), as well as to the formation of the N-oxide 175. In stemofolinoside (178) a b-glucopyranosyl moiety is attached to C-5, representing the first glycosylated Stemona alkaloid (Sastraruji et al 2005).…”

Section: Stemofoline-type Derivatives (I)mentioning

confidence: 99%

Structural classification and biological activities of Stemona alkaloids

Greger

2019

Phytochem Rev

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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.

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“…The NOESY correlations between H−3 and H−15α and Η−14 and the two H-5 protons, and Η−15β (Figure 2, see Figure 1 for the definition of 15α and 15β) indicated the βconfiguration of H−3, opposite that found in all previous naturally occurring croomine-like alkaloids (Pilli et al, 2005;Greger, 2006). This C-3 configuration is rare and has been only found in two tuberostemonines, tuberostemonine A 6 (Schinnerl et al, 2005(Schinnerl et al, , 2007 and tuberostemonine M (Sastraruji, 2006).…”

Section: Resultsmentioning

confidence: 88%