Acetylcholinesterase Inhibitory Alkaloids from the Whole Plants of <i>Zephyranthes carinata</i>

Zhan, Guanqun; Zhou, Junfei; Liu, Junjun; Huang, Jinfeng; Zhang, Hanqi; Liu, Rong; Yao, Guangmin

doi:10.1021/acs.jnatprod.7b00301

Cited by 36 publications

(14 citation statements)

References 39 publications

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“…By changing the electrophile to MeI, the total synthesis of zephycarinatine D ( 1 b ) was accomplished in 52 % in three steps with a small amount of removable diene 14 . All the spectroscopic data were in agreement with those of the natural zephycarinatines C and D reported in the literature [2] {zephycarinatine C:

{([], α)}_{D}^{26} =

+141 ( c =0.060, MeOH); lit. [ α ] D =+108 ( c =0.14, MeOH), zephycarinatine D:

{([], α)}_{D}^{26} =

+172 ( c =0.15, MeOH); lit.…”

Section: Resultssupporting

confidence: 86%

Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso‐Cyclization

et al. 2020

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We report herein a nonbiomimetic strategy for the total synthesis of the plicamine‐type alkaloids zephycarinatines C and D. The key feature of the synthesis is a stereoselective reductive radical ipso‐cyclization using visible‐light‐mediated photoredox catalysis. This cyclization enabled the construction of a 6,6‐spirocyclic core structure through the addition of a carbon‐centered radical onto the aromatic ring. Biological evaluation of zephycarinatines and their derivatives revealed that the synthetic derivative with a keto group displays moderate inhibitory activity against LPS‐induced NO production. This approach could offer future opportunities to expand the chemical diversity of plicamine‐type alkaloids as well as providing useful intermediates for their syntheses.

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{([], α)}_{D}^{26} =

+141 ( c =0.060, MeOH); lit. [ α ] D =+108 ( c =0.14, MeOH), zephycarinatine D:

{([], α)}_{D}^{26} =

+172 ( c =0.15, MeOH); lit.…”

Section: Resultssupporting

confidence: 86%

Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso‐Cyclization

et al. 2020

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“…The chemical structure of these alkaloids was determined by extensive spectroscopic analyses, and absolute configuration of 20 and 21 was confirmed by single crystal X-ray diffraction analysis. Zephycarinatines A ( 74 ), B ( 75 ), and G ( 76 ) represent the first examples of 12-acetylplicamine, N -deformyl- seco -plicamine, and 4a- epi -plicamine alkaloids, respectively [ 69 ]. Narciclasine-4- O- β - d- xylopyranoside ( 51 ), a new narciclasine glycoside, was isolated from the whole plant of Zephyranthes minuta .…”

Section: Occurrence Of Amaryllidaceae Alkaloidsmentioning

confidence: 99%

“…New lycorine derivatives ( 22 ) displayed moderate AChE inhibition (IC 50 = 35.61 ± 1.90 μM) compared to carinatine (IC 50 > 200 μM). The aromatic C-ring in lycorine-sort alkaloids may be essential for their activity against AChE [ 69 ]. Oxoincartine ( 23 ) was inactive against both cholinesterases (AChE and BChE) [ 70 ].…”

Section: Pharmacological Properties Of Novel Amaryllidaceae Alkalomentioning

confidence: 99%

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Biosynthesis and Biological Activities of Newly Discovered Amaryllidaceae Alkaloids

Koirala

Mérindol

et al. 2020

Molecules

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Alkaloids are an important group of specialized nitrogen metabolites with a wide range of biochemical and pharmacological effects. Since the first publication on lycorine in 1877, more than 650 alkaloids have been extracted from Amaryllidaceae bulbous plants and clustered together as the Amaryllidaceae alkaloids (AAs) family. AAs are specifically remarkable for their diverse pharmaceutical properties, as exemplified by the success of galantamine used to treat the symptoms of Alzheimer’s disease. This review addresses the isolation, biological, and structure activity of AAs discovered from January 2015 to August 2020, supporting their therapeutic interest.

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“…The experimental shifts were plotted against the calculated shifts, and least-squares fit lines was confirmed. The calculated shifts for 2a and 2b were corrected by the slope and intercept to get the corrected 13 C shifts ( Table 1 ), and the differences between the corrected and experimental 13 C NMR chemical shifts were analyzed [ 23 , 24 ]. The result showed that the correlation coefficient R 2 of 2a (0.9966) was higher than that of 2b (0.9926) ( Figures S21 and S22 ).…”

Section: Resultsmentioning

confidence: 99%

Two New Terpenoids from Talaromyces purpurogenus

et al. 2018

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A new sesquiterpenoid 9,10-diolhinokiic acid (1) and a new diterpenoid roussoellol C (2), together with 4 known compounds, were isolated from the extracts of laboratory cultures of marine-derived fungus Talaromyces purpurogenus. 9,10-diolhinokiic acid is the first thujopsene-type sesquiterpenoid containing a 9,10-diol moiety, and roussoellol C possesses a novel tetracyclic fusicoccane framework with an unexpected hydroxyl at C-4. These new structures were confirmed by spectroscopic data, chemical method, NMR data calculations and electronic circular dichroism (ECD) calculations. The selected compounds were evaluated for cytotoxicities against five human cancer cell lines, including SW480, HL-60, A549, MCF-7, and SMMC-7721 and the IC50 values of compound 2 against MCF-7 and 3 against HL-60 cells were 6.5 and 7.9 μM, respectively.

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Acetylcholinesterase Inhibitory Alkaloids from the Whole Plants of Zephyranthes carinata

Cited by 36 publications

References 39 publications

Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso‐Cyclization

Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso‐Cyclization

Biosynthesis and Biological Activities of Newly Discovered Amaryllidaceae Alkaloids

Two New Terpenoids from Talaromyces purpurogenus

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