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1.
Chem Biodivers ; : e202401339, 2024 Sep 25.
Artigo em Inglês | MEDLINE | ID: mdl-39319522

RESUMO

Eighteen aromatic abietane-type diterpenes, including three previously unreported compounds, Salkanoids A-C (1-3), were isolated from the roots of Salvia prattii. Their stuctures were extensively elucidated using 1D/2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS) data, and ECD calculation. Among these, compounds 1, 6 and 7 belong to a class of diterpenes featuring a [5, 5]-oxaspirolactones moiety, a rare structure isolated from the Salvia plants. All the isolates were assessed for their protective effects against alcoholic liver disease using ethanol-induced AML-12 cell lines. The findings revealed that compounds 2, 5, 8 and 15 demonstrated potential protective activity.

2.
ACS Omega ; 9(32): 34869-34879, 2024 Aug 13.
Artigo em Inglês | MEDLINE | ID: mdl-39157111

RESUMO

In this study, eight lindenane-type sesquiterpene dimers, including five previously undescribed sesquiterpene dimers (1-5), were isolated from the roots of Chloranthus fortunei, and their structures were elucidated using 1D/2D NMR, HRESIMS, and ECD calculations. Compound 1 presents the second example of a type of novel 8,9-seco lindenane-type sesquiterpene dimer, considered a product of 8/9-diketone oxidation. Compounds 2 and 3 represent the third and fourth examples, respectively, of this kind of C-11 methine dimer. Furthermore, compound 4 was considered as an artifact generated from the radical reaction of a known compound chlojaponilide F (6), which was explained by the density functional theory quantum calculation. All isolates were evaluated for their protective activity against the LPS-induced pulmonary epithelial cell line with compound 7 exhibiting the most potent bioactivity. Further in vitro biological evaluation demonstrated that 7 reduced the production of reactive oxygen species and interleukin-1ß, further regulated by the expression of the NLRP3. These results show that compound 7 exhibits therapeutic potential for lung inflammatory diseases.

3.
Molecules ; 29(4)2024 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-38398659

RESUMO

In our research on naturally occurring sesquiterpenes, eight shizukaol-type dimers, one chlorahololide-type dimer, and one sarcanolide-type dimer were isolated from the roots of Chloranthus fortunei. As the project was implemented, we accidentally discovered that shizukaol-type dimers can be converted into peroxidized chlorahololide-type dimers. This potential change was discovered after simulations of the changes in corresponding shizukaols showed that three peroxide products were generated (1-3), indicating that peroxidation reactions occurred. HPLC-HR-MS analysis results obtained for the shizukaol derivatives further demonstrate that the reaction occurred, and the type of substituent of small organic ester moieties at positions C-15' and C-13' of unit B were not decisively related to the reaction. Quantum chemical calculations of the mode dimer further demonstrated this phenomenon. The highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy of the precursor and production revealed the advantageous yield of 4ß-hydroperoxyl production. Additionally, the potential reaction mechanism was speculated and validated using the free energy in the reaction which successfully explained the feasibility of the reaction. Finally, the anti-inflammatory activity of the precursors and products was evaluated, and the products of peroxidation showed better anti-inflammatory activity.


Assuntos
Artefatos , Sesquiterpenos , Anti-Inflamatórios/farmacologia , Sesquiterpenos/química
4.
Fitoterapia ; 173: 105788, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38141880

RESUMO

As our ongoing searching for the bioactive natural terpenoids, nine ent-kauranoids (1-9), including three previously undescribed ones (1, 2, and 9), were isolated from the aerial parts of Isodon amethystoides. Their structures were elucidated on the basis of spectroscopic data analysis, including NMR, MS, and ECD. Compounds 1 and 2 were a pair of tautomeric compounds, which was confirmed by the HPLC analysis and low temperature NMR testing. The underlying mechanism of the tautomer was proposed as an intramolecular SN2 reaction, which was explained by quantum chemical calculation. The HOMO-LUMO gap and the free energy revealed the spontaneous of the tautomeric of the 1 and 2. Additionally, the similar phenomena were also found in the two groups of known compounds 3 and 4 and 6 and 7, respectively. Apart from the tautomer, compounds 3 and 4 can be hydrolyzed into 5 through ester hydrolysis in CDCl3, while compounds 6, 7 can be hydrolyzed into 8 through ester hydrolysis. These phenomena were also confirmed through HPLC analysis and low temperature nuclear magnetic resonance tests and the mechanism was studied using quantum chemical calculation.


Assuntos
Antineoplásicos Fitogênicos , Diterpenos do Tipo Caurano , Isodon , Estrutura Molecular , Isodon/química , Componentes Aéreos da Planta/química , Ésteres , Ensaios de Seleção de Medicamentos Antitumorais
5.
Phytochemistry ; 214: 113819, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37572737

RESUMO

Eleven previously unreported compounds (1-11), including five diterpenoids (1-5) and six sesquiterpenoids (6-11), together with two known diterpenoids (12-13), have been isolated from the roots of Salvia prattii. Their structures were comprehensively elucidated through spectroscopic methods, and their configurations were established using computational 13C nuclear magnetic resonance and electronic circular dichroism. Compound 1 was found to be an abietane-type diterpenoid with a novel rearrangement generated from the cleavage of the C-4/5 chemical bond, 20-methyl shift, and the rearrangement of the C-10 side chain. Compounds 2-3 were the third and fourth examples of arrangement seco-norabietanes with a spiro-lactone ring. We evaluated all compounds for their protective effects against alcoholic liver diseases (ALD). Compound 2 exhibited potential protective activity and hence can be used as a novel anti-ALD candidate.


Assuntos
Diterpenos , Salvia , Terpenos/farmacologia , Estrutura Molecular , Salvia/química , Diterpenos/farmacologia , Diterpenos/química , Abietanos/farmacologia , Abietanos/química
6.
Phytochemistry ; 202: 113308, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-35817204

RESUMO

Four undescribed trimethylated acylphloroglucinol meroterpenoids, hyjapones A-D, along with seven known analogues, were isolated from Hypericum japonicum Thunb. Hyjapone A represents the first example of a double norflavesones-caryophyllene hybrid featuring a rare 6/6/9/4/6/6 hexacyclic frame. Hyjapone D was isolated as a natural product for the first time. Their structures and absolute configurations were established by comprehensive spectroscopic data analyses and electronic circular dichroism (ECD) calculations. The anti-inflammatory activities of all compounds were evaluated using lipopolysaccharide-induced RAW264.7 cells. Hyperjapone A showed more pronounced anti-inflammatory effect through reducing the production of nitric oxide (IC50 value of 11.32 ± 2.10 µM) and proinflammatory cytokines. In addition, the mechanistic studies revealed hyperjapone A inhibited LPS-induced activation of nuclear factor-κB.


Assuntos
Hypericum , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Hypericum/química , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Células RAW 264.7
7.
Chin J Nat Med ; 18(8): 582-593, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-32768165

RESUMO

Camptotheca acuminata produces camptothecin (CPT), a monoterpene indole alkaloid (MIA) that is widely used in the treatment of lung, colorectal, cervical, and ovarian cancers. Its biosynthesis pathway has attracted significant attention, but the regulation of CPT biosynthesis by the APETALA2/ethylene-responsive factor (AP2/ERF) transcription factors (TFs) remains unclear. In this study, a systematic analysis of the AP2/ERF TFs family in C. acuminata was performed, including phylogeny, gene structure, conserved motifs, and gene expression profiles in different tissues and organs (immature bark, cotyledons, young flower, immature fruit, mature fruit, mature leaf, roots, upper stem, and lower stem) of C. acuminata. A total of 198 AP2/ERF genes were identified and divided into five relatively conserved subfamilies, including AP2 (26 genes), DREB (61 genes), ERF (92 genes), RAV (18 genes), and Soloist (one gene). The combination of gene expression patterns in different C. acuminata tissues and organs, the phylogenetic tree, the co-expression analysis with biosynthetic genes, and the analysis of promoter sequences of key enzymes genes involved in CPT biosynthesis pathways revealed that eight AP2/ERF TFs in C. acuminata might be involved in CPT synthesis regulation, which exhibit relatively high expression levels in the upper stem or immature bark. Among these, four genes (CacAP2/ERF123, CacAP2/ERF125, CacAP2/ERF126, and CacAP2/ERF127) belong to the ERF-B2 subgroup; two genes (CacAP2/ERF149 and CacAP2/ERF152) belong to the ERF-B3 subgroup; and two more genes (CacAP2/ERF095 and CacAP2/ERF096) belong to the DREB-A6 subgroup. These results provide a foundation for future functional characterization of the AP2/ERF genes to enhance the biosynthesis of CPT compounds of C. acuminata.


Assuntos
Camptotheca/genética , Camptotecina/biossíntese , Genoma de Planta , Plantas Medicinais/genética , Fatores de Transcrição/genética , Perfilação da Expressão Gênica , Regulação da Expressão Gênica de Plantas , Estudo de Associação Genômica Ampla , Filogenia , Proteínas de Plantas/genética
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