Flueggenines A and B, Two Novel C,C-Linked Dimeric Indolizidine Alkaloids from Flueggea virosa

Gan, Li‐She; Fan, Cheng-Qi; Yang, Sheng‐Ping; Wu, Yan; Lin, Liping; Ding, Jian; Yue, Jian‐Min

doi:10.1021/ol060551f

Cited by 62 publications

(43 citation statements)

References 20 publications

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“…2D NMR experiments allowed to propose a structure consisting of one norsecurinine unit and three dihydronorsecurinine units connected in the order C12-C15 0 , C14-C15 00 , and C12 00 -C15 000 . By analogy with flueggenines C (50) and D (51), and fluevirosine D (55), the same relative stereochemistry was proposed. In addition, these four compounds shared the same ECD spectra profiles and therefore the same absolute stereochemistry was proposed, as depicted.…”

Section: Flueggenine a (48)mentioning

confidence: 93%

“…51 Its molecular formula was determined as C 24 H 26 N 2 O 4 by HRESIMS (m/z 406.1871 [M þ ]). As commonly observed in these series, the IR spectrum displayed the typical a,b-unsaturated g-lactone bands.…”

Section: Fluegginementioning

confidence: 99%

“…The same negative Cotton effect at l 265 nm allowed the authors to assign the configurations at C9 and C9 0 as S, and the absolute configuration was assigned as depicted. 51 Its molecular formula was assigned as C 24 H 28 N 2 O 5 on the basis of the 13 C NMR spectra and the MS spectra. Interestingly, in addition to the typical butenolide signals, the IR spectrum displayed a band attributed to a carboxylate function, which was correlated with the carbon at 173.9 ppm in the 13 C NMR spectrum.…”

Section: Fluegginementioning

confidence: 99%

“…Final incorporation of the last unit (C12 0 -C15 00 ) leads to fluevirosinine A (56). The priority order between flueggenine C (50) and D (51) was not established, if any. However, condensation of two flueggenine D units could also be considered.…”

Section: Biosynthesis Of Norsecurinine-based Oligomersmentioning

confidence: 99%

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The Securinega Alkaloids

Chirkin

Atkatlian

Porée

2015

The Alkaloids: Chemistry and Biology

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Section: Flueggenine a (48)mentioning

confidence: 93%

Section: Fluegginementioning

confidence: 99%

Section: Fluegginementioning

confidence: 99%

Section: Biosynthesis Of Norsecurinine-based Oligomersmentioning

confidence: 99%

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The Securinega Alkaloids

Chirkin

Atkatlian

Porée

2015

The Alkaloids: Chemistry and Biology

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“…Previous chemical studies of F. virosa showed that tannins, flavonoids, saponins [4,7,10] , resin, glycosides, glycerin carbohydrate, anthraquine, steroids [4] , alkaloids [7,11] , cardiac glycosides [4,7] , anthraquinone [7] , norsecurinine [13] , pipecolinic acid [14] , bergenin [8,9] , 14, 15-epoxynorsecurinine, norsecurinine [15] , virosecurinine [16,17] , viroallosecurinine [17] , friedelin, friedelan-3α-ol, friedelan-3β-ol, lupeol, glochidonol, glochilocudiol, betulonic acid and sitosterol [18] were chemical constituent of F. virosa. As part of our ongoing project on the discovery of new anti-cancer agents from F. virosa.…”

Section: Introductionmentioning

confidence: 99%

Identification and Antiproliferative Activity Evaluation of a Series of Triterpenoids Isolated from Flueggea virosa (Roxb. ex Willd.)

Monkodkaew¹,

Loetchutinat²,

Nuntasaen³

et al. 2009

American J. of Applied Sciences

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Problem statement: Medicinal plants derived anticancer were now being subjects of many research groups especially, the secondary metabolite triterpenoids trees which had enormous potential to inspire and influence modern antiproliferative research. The study aimed to investigate the chemical constitution and their potential use as antiproliferative activity of purified compounds derived from F. virosa. Approach: The F. virosa was selected and percolated with hexane, ethyl acetate, acetone and methanol. The extracts were purified and elucidated chemical structures. Furthermore, the isolated compounds were tested for biological activity. The bioassays were performed on two cancer cell lines, adriamycin-sensitive erythroleukemia cells (K562) and adriamycin-resistant erythroleukemia cells (K562/Adr) which overexpressed P-glycoprotein (MDR1/ABCB1). Results: Friedelin (1), epifriedelanol (3), stigmasterol (4) and betulinic acid (5) were isolated from the leaves and twigs of F. virosa. The molecular structures of these compounds were determined using several spectroscopic methods. The compounds i.e., 1, a chemically modified compound 1 heptanolide (2), 3 and 4 showed a limited cytotoxic activity towards human cancer cell lines mainly due to a low aqueous solubility which prevented their use in cell viability assays. Interestingly, compound 5 exhibited a high cytotoxicity characterized by an effective concentration value (IC 50 ) equal to 9.7±2.1 µg.mL −1 (21.2±4.6 µM) and 7.1±0.7 µg.mL −1 (15.5±1.5 µM) for K562and K562/Adr, respectively. Moreover, the antiproliferative activity of compound 5 was independent of the multidrug resistance phenotype exhibited by the K562/Adr cell line suggesting that compound 5 was not the effluxes out of the K562/Adr cells by MDR1 (ABCB1). Conclusion: The results clearly showed that the betulinic acid of the four isolated compounds from F. virosa could be considered as high potential source of cytotoxic activity.

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Securinega Alkaloids: Complex Structures, Potent Bioactivities, and Efficient Total Syntheses

Wehlauch

Gademann

2017

Asian J Org Chem

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The Securinega alkaloids feature a compact tetracyclic structural framework and can be divided into four subclasses characterized by either a bridged [2.2.2]‐ or a [3.2.1]‐bicyclic core with two homologous series in each subclass. In the last two decades, many innovative strategies to chemically access the Securinega alkaloids have been developed. This Focus Review discusses the selected structures and syntheses of representative members of the Securinega alkaloids. Ring‐closing metathesis has enabled the syntheses of securinine and norsecurinine, and different cycloaddition approaches were key to the syntheses of nirurine and virosaines A and B. Virosine A was accessed through a Vilsmeier–Haack/Mannich reaction cascade. A bio‐inspired vinylogous Mannich reaction has enabled the synthesis of allosecurinine and this strategy has been extended by an intramolecular 1,6‐addition to obtain bubbialidine and secu′amamine E. A rearrangement process of the latter two alkaloids has furnished allonorsecurinine and allosecurinine, respectively. Finally, an expanded model for the biogenesis of the Securinega alkaloid subclasses is discussed.

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Flueggenines A and B, Two Novel C,C-Linked Dimeric Indolizidine Alkaloids from Flueggea virosa

Cited by 62 publications

References 20 publications

The Securinega Alkaloids

The Securinega Alkaloids

Identification and Antiproliferative Activity Evaluation of a Series of Triterpenoids Isolated from Flueggea virosa (Roxb. ex Willd.)

Securinega Alkaloids: Complex Structures, Potent Bioactivities, and Efficient Total Syntheses

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