Sessilifoliamine A and sessilifoliamide J: new alkaloids from Stemona sessilifolia

Hitotsuyanagi, Yukio; Takeda, Erika; Fukaya, Haruhiko; Takeya, Koichi

doi:10.1016/j.tetlet.2008.10.042

Cited by 25 publications

(35 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tuberostemospiroline (16), tuberostemospironine (17), and stemo-lactam R (18) deviate by the loss of lactone ring C, and stemona-amine A (15) by an additional butyrolactone ring fused with the azepane ring at C-5-C-6. In the case of stemona-lactam J (13) the seven-membered azepane ring B is contracted to a sixmembered piperidine-2-one ring (Hitotsuyanagi et al 2008).…”

Section: Croominesmentioning

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: Croominesmentioning

confidence: 99%

Structural classification and biological activities of Stemona alkaloids

Greger

2019

Phytochem Rev

View full text Add to dashboard Cite

show abstract

“…For the appended lactone/pyrrolidine moiety, the anti-stereochemistry is characteristic, as can be seen from Figure 1, however, both syn [e.g. sessilifoliamide J [5] (1) and croomine (2)] and anti [e.g. tuberspironine (3) and dehydrocroomine (4)] stereochemistries are found in the spirolactone/pyrrolidine moieties.…”

Section: Introductionmentioning

confidence: 91%

Towards Stereochemical Control: Two Approaches for the Highly anti‐Diastereoselective Construction of the Spirolactone Moieties of Some Stemona Alkaloids

2012

View full text Add to dashboard Cite

Some Stemona alkaloids belonging to the tuberostemospironine group possess a spirolactone moiety with anti-configuration (C-9/C-9a). In this paper, we describe two approaches to this structural unity. By using bromine atom as a traceless directing group, the SmI 2 -mediated reductive coupling of ketone 6 and β-bromomethacrylate proceeded with complete anti-diastereoselectivity. In the absence of an α-directing (chelation) group, the one-pot reaction of the ketone derived from alcohol 15 with the organozinc reagent generated from bromomethacrylate afforded spiro-α-methylene-γ-lactone derivative 16 as a single diastereomer. These two highly diastereoselective methods would find application in the synthesis of stemona alkaloids containing anti-configured spiro-lactone/pyrrolidine moieties. In addition, on the basis of our previous work, the total synthesis of (−)-9-epi-11-demethylsessilifoliamide J (11), and an improved synthesis of (−)-9,11-di-epi-sessilifoliamide J (9) were accomplished.

show abstract

“…The building block-based strategy has achieved great success in the symmetric synthesis of piperidine ring-containing heterocycles [37]. In recent years, we have been engaged in the development of synthetic [41]. The six-membered piperidin-2-one ring present in sessilifoliamide J is unique among the known Stemona alkaloids.…”

Section: Building Block 2: the Asymmetric Syntheses Of 9-epi-sessilifmentioning

confidence: 99%

Efficient asymmetric syntheses of alkaloids and medicinally relevant molecules based on heterocyclic chiral building blocks

Wang

Huang

2014

Pure and Applied Chemistry

View full text Add to dashboard Cite

In this report, we present recent progress in synthetic methodologies based on three heterocyclic chiral building blocks developed from our laboratories. The potential of these chiral building block-based methods in the concise asymmetric synthesis of alkaloids and medicinally interesting molecules has been demonstrated by the total syntheses of 8-aza-prostaglandin E 1 , 11-hydroxylated analogues of the lead compounds CP-734432 and PF-04475270, (+)-castanospermine, (+)-1-epi-castanospermine, 7-deoxy-6-epi-castanospermine as well as 9-epi-sessilifoliamide J.

show abstract

Sessilifoliamine A and sessilifoliamide J: new alkaloids from Stemona sessilifolia

Cited by 25 publications

References 10 publications

Structural classification and biological activities of Stemona alkaloids

Structural classification and biological activities of Stemona alkaloids

Towards Stereochemical Control: Two Approaches for the Highly anti‐Diastereoselective Construction of the Spirolactone Moieties of Some Stemona Alkaloids

Efficient asymmetric syntheses of alkaloids and medicinally relevant molecules based on heterocyclic chiral building blocks

Contact Info

Product

Resources

About