ChemInform Abstract: Structure Characterization, Biomimetic Total Synthesis, and Optical Purity of Two New Pyrrolidine Alkaloids, Pandamarilactonine‐A and ‐B, Isolated from Pandanus amaryllifolius Roxb.

Takayama, Hiromitsu; Ichikawa, Tomotake; Kuwajima, Toshiyuki; Kitajima, Mariko; Seki, Hiroko; Aimi, Norio; Nonato, Maribel G.

doi:10.1002/chin.200101214

Cited by 2 publications

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“…2 the formation of the two lactone rings and the cyclization to a pyrrolidine ring in the co-occurring pandamarilactonine strongly suggests close structural relations to croomine (1). In this case the two characteristic terminal lactone rings were supposed to be derived from leucine via 4-hydroxy-4-methylglutamic acid, and the symmetrical central building block from a C 4 NC 4 dicarboxylic acid, probably derived from two glutamic acid units (Takayama et al 2000). Pandanamine was originally isolated from the leaves of Pandanus amaryllifolius Roxb.…”

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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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Structural classification and biological activities of Stemona alkaloids

Greger

2019

Phytochem Rev

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“…Phytochemical studies on the Pandanus species led to the isolation of essential oils [2], terpenes [3], lignans [3,4], and several phenolic compounds [4]. One interesting species is Pandanus amaryllifolius, owing to the isolation of alkaloids [5][6][7][8][9] which possess the novel C9-N-C9 pyrrolidine-type backbone unit. Some of these secondary metabolites have biological activities [1,4].…”

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Antitubercular triterpenes and phytosterols from Pandanus tectorius Soland. var. laevis

et al. 2007

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Bioassay-guided chromatographic purification of the antitubercular chloroform extract of Pandanus tectorius Soland. var. laevis leaves afforded a new tirucallane-type triterpene, 24,24-dimethyl-5 beta-tirucall-9(11),25-dien-3-one (1), squalene and a mixture of the phytosterols stigmasterol and beta-sitosterol. Microplate Alamar Blue Assay (MABA) showed that 1 inhibited the growth of Mycobacterium tuberculosis H(37)Rv with a MIC of 64 microg/mL, while squalene and the sterol mixture have MICs of 100 and 128 microg/mL, respectively.

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ChemInform Abstract: Structure Characterization, Biomimetic Total Synthesis, and Optical Purity of Two New Pyrrolidine Alkaloids, Pandamarilactonine‐A and ‐B, Isolated from Pandanus amaryllifolius Roxb.

Cited by 2 publications

References 1 publication

Structural classification and biological activities of Stemona alkaloids

Structural classification and biological activities of Stemona alkaloids

Antitubercular triterpenes and phytosterols from Pandanus tectorius Soland. var. laevis

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