Alkaloids of Haplophyllum leptomerum. I. The structure of leptomerine

Akhmedzhanova, V. I.; Bessonova, I. A.; Yunusov, S. Yu.

doi:10.1007/bf00574586

Cited by 5 publications

(6 citation statements)

References 3 publications

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“…7 ( t R = 15.4 min) and Fr. 9 ( t R = 19.3 min) were identified as two 4-quinolinone alkaloids, leiokinine A ( 1 , 5.8 mg) [ 3 ] and leptomerine ( 2 , 16.0 mg) [ 13 ], respectively. Fractions Fr.…”

Section: Resultsmentioning

confidence: 99%

“…The alkaloids maculine, flindersiamine, kokusaginine, leptomerine, leiokinine A and skimmianine identified in this work were previously isolated from other Esenbeckia species [ 1 , 17 , 18 , 19 ]. The alkaloids leptomerine and skimmianine have already been isolated from Haplophyllum heptomerum (Rutaceae) in 1986 [ 13 ]. However, this is the first occurrence of leptomerine and skimmianine in Esenbeckia leiocarpa (Engl.).…”

Section: Resultsmentioning

confidence: 99%

“…1 H-NMR [CDCl 3 , δ (ppm), J (Hz)]: δ 1.60 (m, H-C1’), 1.60 (m, H-C2’), 0.85 (t, H-C3’), 6.36 (s, H-C3), 8.41 (dd, H-C5), 7.34 (t, H-C6), 7.52 (d, H-C7), 7.63 (d, H-C8), 3.77 (s, H-N-CH 3 ). 13 C-NMR [CDCl 3 ]: δ 27.6 (C-1’), 27.6 (C-2’), 11.6 (C-3’), 109.0 (C-3), 177.23 (C-4), 142.14 (C-5), 126.57 (C-6), 123.70 (C-7), 132.18 (C-8), 115.9 (C-9), 126.7 (C-10), 34.4 (N- C H 3 ) [ 13 ].…”

Section: Methodsmentioning

confidence: 99%

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Alkaloids from Stems of Esenbeckia leiocarpa Engl. (Rutaceae) as Potential Treatment for Alzheimer Disease

et al. 2010

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Esenbeckia leiocarpa Engl. (Rutaceae), popularly known as guarantã, goiabeira, is a native tree from Brazil. Bioactivity-guided fractionation of the ethanol stems extract afforded the isolation of six alkaloids: leiokinine A, leptomerine, kokusaginine, skimmianine, maculine and flindersiamine. All isolated compounds were tested for acetyl cholinesterase inhibition, in vitro and displayed anticholinesterasic activity. The alkaloid leptomerine showed the highest activity (IC50 = 2.5 μM), similar to that of the reference compound galanthamine (IC50 = 1.7 μM). The results showed for the first time the presence of alkaloids leptomerine and skimmianine in E. leiocarpa (Engl.) with potent anticholinesterasic activity.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Alkaloids from Stems of Esenbeckia leiocarpa Engl. (Rutaceae) as Potential Treatment for Alzheimer Disease

et al. 2010

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“…Alkaloids have been reported as the most representative compounds in the genus, and they are also of the utmost importance from a chemosystematic standpoint [ 114 ]. Skimmianine is the most reported compound of this class in the genus, followed by γ-fagarine [ 44 , 45 , 46 , 49 , 51 , 52 , 53 , 54 , 57 , 58 , 66 , 73 , 75 , 77 , 78 , 80 , 81 , 82 , 85 , 86 , 87 , 89 , 90 , 95 , 97 , 98 , 101 , 106 , 108 , 111 ]. Coumarins were also quite present in the Haplophyllum genus, in particular scopoletin [ 56 , 58 , 62 , 68 , 84 , 91 , 98 , 111 ].…”

Section: Phytochemistrymentioning

confidence: 99%

“…with a problematic classification are desirable in the future since the distribution of these flavonoids might be of help for their correct classification. The other classes of natural compounds observed in the Haplophyllum genus were triterpenoids with β-sitosterol as the major compound [ 47 , 49 , 67 , 80 , 99 ] and lignans with diphyllin as the major compound [ 49 , 51 , 58 , 65 , 96 , 106 , 111 ] together with some phenolic acid derivatives. These classes have little chemotaxonomic relevance since they can be biosynthesized by many other plant genera and species such as those belonging to the Araucariaceae [ 4 ], Lamiaceae [ 122 ], and Orobanchaceae [ 123 ] families.…”

Section: Phytochemistrymentioning

confidence: 99%

The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities—A Review

et al. 2021

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Herein, a comprehensive review is given focusing on the chemical profiles of the essential oils (EOs), non-volatile compounds, ethnobotany, and biological activities of different Haplophyllum (Rutaceae family) species. To gather the relevant data, all the scientific databases, including Scopus, ISI-WOS (Institute of Scientific Information-Web of Science), and PubMed and highly esteemed publishers such as Elsevier, Springer, Taylor and Francis, etc., were systematically retrieved and reviewed. A wide array of valuable groups of natural compounds, e.g., terpenoids, coumarins, alkaloids, lignans, flavonoids, and organic acids have been isolated and subsequently characterized in different organic extracts of a number of Haplophyllum species. In addition, some remarkable antimicrobial, antifungal, anti-inflammatory, anticancer, cytotoxic, antileishmanial, and antialgal effects as well as promising remedial therapeutic properties have been well-documented for some species of the genus Haplophyllum.

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Two New α‐Glucosidase Inhibitors from Haplophyllum tuberculatum: Inhibition Kinetics and Mechanistic Insights Through in Vitro and in Silico Approaches

Shah,

Ullah,

Halim

et al. 2024

Chemistry & Biodiversity

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Two new (1, 2) and nine known (3‐11) compounds were isolated from the rutaceous plant Haplophyllum tuberculatum and characterised by extensive NMR spectroscopic techniques and HR‐ESI‐MS. After structural elucidation, nine compounds were evaluated for their ability to inhibit α‐glucosidase, a target for the treatment of type‐2 diabetes. Among them, three compounds (7, 5 and 1) exhibited noteable inhbition with IC50 values of 3.42 ± 0.12, 5.79 ± 0.28, and 6.75 ± 1.18 μM, respectively, while the remaining six compounds (2‐4, 6, 8, and 9) had moderate activity with IC50 values ranging from 12.14 ± 0.35 to 24.60 ± 0.57 μM, compared to the standard drug acarbose (IC50 = 875.75 ± 1.24 μM). A kinetic study of compounds 5 and 7 showed that they exhibited competitive inhibition with Ki values of 4.82 ± 0.0036 and 3.92 ± 0.0062 µM, respectively. Furthermore, a structure‐based prediction of the compounds’ binding mode suggested that these inhibitors fitted exceptionally well within the active site of the target enzyme, α‐glucosidase, forming multiple hydrogen and hydrophobic interactions with its active site residues.

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Alkaloids of Haplophyllum leptomerum. I. The structure of leptomerine

Cited by 5 publications

References 3 publications

Alkaloids from Stems of Esenbeckia leiocarpa Engl. (Rutaceae) as Potential Treatment for Alzheimer Disease

Alkaloids from Stems of Esenbeckia leiocarpa Engl. (Rutaceae) as Potential Treatment for Alzheimer Disease

The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities—A Review

Two New α‐Glucosidase Inhibitors from Haplophyllum tuberculatum: Inhibition Kinetics and Mechanistic Insights Through in Vitro and in Silico Approaches

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