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1.
Bioorg Chem ; 142: 106962, 2024 01.
Artigo em Inglês | MEDLINE | ID: mdl-37992623

RESUMO

Two new dimeric Lycopodium alkaloids, casuattimines A and B (1 and 2), along with twelve previously undescribed Lycopodium alkaloids, casuattimines C-N (3-14), and eight known Lycopodium alkaloids, were isolated from Lycopodiastrum casuarinoides. Casuattimines A and B (1 and 2) are the first two ether-linked Lycopodium alkaloid dimers. Casuattimines C and D (3 and 4) are unique Lycopodium alkaloids characterized by a long fatty acid chain. Structural elucidation was achieved through HRESIMS, NMR, and electronic circular dichroism (ECD) calculations. In addition, the absolute configurations of compounds 7, 13, and 14 were determined by single crystal X-ray diffraction. Compounds 1, 2, and 4 demonstrated notable Cav3.1 channel inhibitory activities presenting IC50 values of 10.75 ± 1.02 µM, 9.33 ± 0.79 µM, and 7.14 ± 0.86 µM, respectively. The dynamics of compound 4 against the Cav3.1 channel and preliminary structure-activity relationships of these active Lycopodium alkaloids were also discussed.


Assuntos
Alcaloides , Lycopodiaceae , Lycopodium , Lycopodium/química , Estrutura Molecular , Inibidores da Colinesterase/farmacologia , Lycopodiaceae/química , Alcaloides/farmacologia , Alcaloides/química
2.
Chem Biodivers ; 21(4): e202400209, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38419385

RESUMO

One new fawcettimine-type Lycopodium alkaloid, hupertimine F (1), together with five known (2-6) Lycopodium alkaloids were isolated from Huperzia goebelii. The structure of 1 was elucidated by 1D and 2D NMR spectra, HRESIMS, and X-ray diffraction. Structurally, 1 represents the fourth example of Lycopodium alkaloids characterized by a 5/5/5/5/6 pentacyclic ring system with a 1-aza-7-oxabicyclo[2.2.1]heptane moiety. These known compounds 2, 3, 5, and 6 were isolated from H. goebelii for the first time. Compounds 1-6 were evaluated for acetylcholinesterase, butyrylcholinesterase and monoamine oxidase B inhibitory activities in vitro.


Assuntos
Alcaloides , Huperzia , Lycopodium , Huperzia/química , Lycopodium/química , Butirilcolinesterase , Acetilcolinesterase/química , Estrutura Molecular , Inibidores da Colinesterase/farmacologia , Inibidores da Colinesterase/química , Alcaloides/farmacologia , Alcaloides/química
3.
Phytochemistry ; 223: 114114, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38697240

RESUMO

Huperzia serrata, belonging to the Lycopodiaceae family, has been traditionally utilized for the management of treating rheumatic numbness, arthritic pain, dysmenorrhea, and contusions. This plant is a rich source of lycopodium alkaloids, some of which have demonstrated notable cholinesterase inhibitory activity. The objective of this study was to identify lycopodium alkaloids with cholinesterase inhibitory properties from H. serrata. The structures of these alkaloids were elucidated by HRESIMS, NMR (including a 1H-15N HMBC experiment), ECD methods and single-crystal X-ray diffraction. The inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were assessed using a modified Ellman's method. Consequently, sixteen lycopodium alkaloids (1-16), including ten previously undescribed ones named huperradines A-G and huperradines I-K (1-7 and 9-11), along with one previously undescribed naturally occurring compound, huperradine H (8), were isolated from H. serrata. Among these, compounds 7 and 1 exhibited potent and moderate AChE inhibition, with IC50 values of 0.876 ± 0.039 µM and 13.125 ± 0.521 µM, respectively. Our results suggest that huperradine G (7) may be a promising lead compound for the development of new AChE inhibitors for Alzheimer's disease.


Assuntos
Acetilcolinesterase , Alcaloides , Butirilcolinesterase , Inibidores da Colinesterase , Huperzia , Inibidores da Colinesterase/farmacologia , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Alcaloides/isolamento & purificação , Huperzia/química , Acetilcolinesterase/metabolismo , Acetilcolinesterase/efeitos dos fármacos , Butirilcolinesterase/metabolismo , Estrutura Molecular , Lycopodium/química , Relação Estrutura-Atividade , Relação Dose-Resposta a Droga
4.
Nat Prod Bioprospect ; 11(5): 557-564, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34089490

RESUMO

Three new clerodane-type diterpene glycosides, (5R,6S,8R,9S,10R)-6-O-[ß-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl]cleroda-3,13(16),14-diene (1), (5R,6S,8R,9S,10R,13S)-6-O-[ß-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl]-2-ox-oneocleroda-3,13-dien-15-ol (2), (5R,6S,8R,9S,10R)-6-O-[ß-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl]-(13E)-2-oxoneocleroda-3,14-dien-13-ol (3), together with two known compounds 4 and 5 were isolated from Dicranopteris pedata. The structures of these compounds were elucidated by detailed spectroscopic analysis, and the absolute configuration of compound 2 was determined by ECD calculations. In addition, compound 1 exhibited weak inhibitory activities against SMMC-7721, MCF-7 and SW480.

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