Complex scaffold remodeling in plant triterpene biosynthesis

Science, Journal Year: 2023, Volume and Issue: 379(6630), P. 361 - 368

Published: Jan. 26, 2023

Triterpenes with complex scaffold modifications are widespread in the plant kingdom. Limonoids an exemplary family that responsible for bitter taste citrus (e.g., limonin) and active constituents of neem oil, a widely used bioinsecticide azadirachtin). Despite commercial value limonoids, complete biosynthetic route has not been described. We report discovery 22 enzymes, including pair neofunctionalized sterol isomerases, catalyze 12 distinct reactions total biosynthesis kihadalactone A azadirone, products bear signature limonoid furan. These results enable access to valuable limonoids provide template reconstitution triterpene pathways plants require multiple skeletal rearrangements oxidations.

Language: Английский

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Divergent Total Syntheses of Phragmalin and Khayanolide-Type Limonoids: A Torquoselective Interrupted Nazarov Approach

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 8, 2025

The asymmetric and divergent total syntheses of two phragmalin (moluccensins G H) khayanolide-type (krishnolide F khayseneganin F) limonoids were disclosed, which employed a torquoselective interrupted Nazarov cyclization as the key step. Taken together with Liebeskind-Srogl coupling, benzoin condensation, bidirectional acyloin rearrangements, our strategy would simplify synthetic design both facilitate their modular syntheses. Moreover, described approach also provides additional insights into biosynthetic relationships between these distinct skeletons.

Language: Английский

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Bioactive limonoids from Carapa guianensis seeds oil and the sustainable use of its by-products

Current Research in Toxicology, Journal Year: 2023, Volume and Issue: 4, P. 100104 - 100104

Published: Jan. 1, 2023

Carapa guianensis (Andiroba, Meliaceae) is considered a multipurpose tree. In Brazil, Indigenous people have used it as insect repellent and in the treatment of various diseases. Most biological activities popular uses are attributed to limonoids, which highly oxygenated tetranortriterpenoids. More than 300 limonoids been described Meliaceae family. Limonoids from Andiroba oil shown high anti-inflammatory anti-allergic vivo, by inhibiting platelet activating factors many inflammatory mediators such IL-5, IL-1β TNF-α. It also reduced T lymphocytes, eosinophils mast cells. corroboration with wide use oil, no significant cytotoxicity or genotoxicity vivo was reported. This promotes apoptosis gastric cancer cell line (ACP02) at concentrations, without showing mutagenic effects, suggested increase body's nonspecific resistance adaptive capacity stressors, exhibit some antioxidant activity, protect against oxidative DNA damages. Recently, new methodologies toxicological assays applied. They include chemico, vitro, silico ex procedures, take place substitute laboratory animals. by-products sustainable production processes fertilizers soil conditioners, raw material for soap production, biodegradable surfactants an alternative natural source polymer order reduce environmental impacts. review reinforces relevance highlights its ability add value minimize possible risks health Amazonian population.

Language: Английский

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Sesquiterpenoids from Meliaceae Family and Their Biological Activities

Molecules, Journal Year: 2023, Volume and Issue: 28(12), P. 4874 - 4874

Published: June 20, 2023

Sesquiterpenoids, an important class of natural products possessing three isoprene-derived units, are widely distributed across plants and have a variety biological activities. All sesquiterpenoids derived from farnesyl pyrophosphate (FPP), biosynthesis precursor that can form various carbon skeletons. In order to provide reference for further research development these compounds, this review focused on the increasing number isolated volatile found be produced by Meliaceae family between 1968 2023. The related articles were collected SciFinder, Google Scholar, PubMed. According literature review, several studies started more than 55 years plant’s stem barks, twigs, leaves, flowers, seeds, pericarps, where approximately 413 sesquiterpenoid compounds groups such as eudesmane, aromadendrane, cadinane, guaiane, bisabolane, furanoeremophilane, humulene, germacrane, oppositane-type identified with some minor products. Additionally, hypothetical route was identified, eudesmane-type reported 27% total compounds. antimicrobial, antidiabetic, antioxidant, antiplasmodial, antiviral, cytotoxic activities major constituent essential oil also evaluated. result showed fundamental using in traditional medicine discovery new drugs.

Language: Английский

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Unusual Secondary Metabolites from the Mangrove Ecosystems: Structures, Bioactivities, Chemical, and Bio-Syntheses

Marine Drugs, Journal Year: 2022, Volume and Issue: 20(8), P. 535 - 535

Published: Aug. 20, 2022

Mangrove ecosystems are widely distributed in the intertidal zone of tropical and subtropical estuaries or coasts, containing abundant biological communities, for example, mangrove plants diverse groups microorganisms, featuring various bioactive secondary metabolites. We surveyed literature from 2010 to 2022, resulting a collection 134 metabolites, classified them into two major families terms sources 15 subfamilies according chemical structures. To highlight structural diversity bioactivities ecosystem-associated we presented structures, bioactivities, biosynthesis, syntheses.

Language: Английский

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Limonoids: Advances in Extraction, Characterization, and Applications

Food Reviews International, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 62

Published: Feb. 4, 2025

Language: Английский

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Nephroprotective effects of substances of medicine food homology and traditional Chinese medicine phytochemicals against acute kidney injury

Frontiers in Pharmacology, Journal Year: 2025, Volume and Issue: 16

Published: Feb. 19, 2025

Acute kidney injury (AKI) represents significant medical challenges due to its elevated rates of morbidity and mortality, with limited therapeutic options currently available. Hence, the exploration novel medicinal treatments for AKI management remains vital. Substances medicine food homology (SMFH), referring substances having characteristics both medicine, have been applied in China thousands years.They could be used daily diets body conditioning. Traditional Chinese (TCM), naturally derived components demonstrated effectiveness, presents distinctive benefits treatment. Numerous studies shown that SMFH TCM phytochemicals function satisfactorily nephroprotective effects a effect on alleviating as well complications. In this review, pathogenesis was illustrated. We concentrated against tried summarize underlying mechanisms various kinds AKI, highlighting crucial phytochemical prevention therapy. Besides, strategies globalization are analysed. This review comprehensively reveals exhibit promising potential intervention by targeting signal pathways targets, which would contribute AKI's cognition, preventive treatments, global promotion.

Language: Английский

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Comparative genomics provides insights into the biogeographic and biochemical diversity of meliaceous species

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: March 17, 2025

Meliaceous plants such as Azadirachta indica (neem) and Melia azedarach (chinaberry) contain large amounts of limonoids with unique anti-insect activities. However, genes responsible for downstream modifications are not well known. Here, we improve the genome assemblies neem chinaberry to telomere-to-telomere (T2T) level. Allopatric speciation two is confirmed by lineage-specific inversion chromosome 12 in lineage. We further identify BAHD-acetyltransferases (ATs) (MaAT8824 MaAT1704) that catalyse acetylation at both C-12 C-3 hydroxyl groups limonoids, whereas syntenic copy (AiAT0635) does possess this activity. A critical N-terminal region (SAGAVP) crucial AiAT0635, swapping it into MaAT8824 version (CHRSSG) can endow Our improved provide insights allopatric neem, limonoid biosynthesis chemical diversity meliaceous plants. Biosynthetic pathway after azadirone still unclear. authors report genomes tree reveal acetyltransferases determine structure species.

Language: Английский

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Novel Secondary Metabolites from Mangrove Flora: Chemistry and Bioactivity

Reference series in phytochemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 17

Published: Jan. 1, 2025

Language: Английский

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Three new limonoids with high oxidation from the fruits of Aglaia edulis

Journal of Asian Natural Products Research, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 7

Published: April 11, 2025

Agledulines L-N (1 - 3), three previously undescribed limonoids with the A/D-ring-seco structural characteristics and high degree oxidation, along reported compounds (4 6), were isolated from fruits of Aglaia edulis. The structures 1 3 elucidated by NMR data, HRESIMS, ECD spectra, circular dichroism exciton chirality method. furan rings in 2 oxidized to γ-hydroxy-butene lactone moiety, tautomerism hemiacetal C-21 contributed disappearance signals segments. biological evaluation showed that had no anti-inflammatory activity inhibiting NO release LPS-activated RAW264.7 macrophages.

Language: Английский

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