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A Multifunctional Cytochrome P450 and a Meroterpenoid Cyclase in the Biosynthesis of Fungal Meroterpenoid Atlantinone B

Organic Letters, 2022
The biosynthetic gene cluster of atlantinone B (10) was discovered in Penicillium chrysogenum MT-40. A multifunctional cytochrome P450 (AtlD) encoded by the cluster is responsible for the formation of the unique lactone-bridged ring and the 16β-hydroxyl of atlantinone B, and a new terpene cyclase (AtlC) can unprecedentedly accept the demethylated ...
Bo-wen Qi   +11 more
openaire   +2 more sources

Biomimetic Synthesis of Meroterpenoids by Dearomatization‐Driven Polycyclization

open access: yesAngewandte Chemie - International Edition, 2019
AbstractA biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)‐derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA‐derived meroterpenoids is highly desirable to create a library of ...
Makoto Fujita   +2 more
exaly   +6 more sources

Biomimetic Total Synthesis of the Rubiginosin Meroterpenoids

Organic Letters, 2020
Total synthesis of the Rhododendron meroterpenoids rubiginosins A and G, which both contain unusual 6-6-6-4 ring systems, has been achieved using a bioinspired cascade approach. Stepwise synthesis of these natural products, and the related 6-6-5-4 meroterpenoids fastinoid B and rhodonoid B, from naturally occurring chromene precursors is also reported.
Laura Burchill   +3 more
openaire   +3 more sources

Total Synthesis of DMOA-Derived Meroterpenoids: Achieving Selectivity in the Synthesis of (+)-Berkeleyacetal D and (+)-Peniciacetal I.

Journal of the American Chemical Society
The synthesis of complex natural products requires efficient control over chemoselectivity, stereoselectivity, and regioselectivity. Berkeleyacetals, a subfamily of 3,5-dimethylorsellinic acid (DMOA)-derived meroterpenoids, pose substantial synthetic ...
Jianpeng Zhang   +3 more
semanticscholar   +1 more source

Artificial farnesol epoxidase enables a concise synthesis of meroterpenoids.

Science
Efficient asymmetric epoxidation reactions have been developed for both the head end and tail end double bonds of farnesol, greatly facilitating the synthesis of terpenoid natural products.
Jinxin Wang   +4 more
semanticscholar   +1 more source

Halogenated meroterpenoids with antifungal activities from the Deep-Sea-Derived fungus Acremonium sclerotigenum guided by the genomic and OSMAC strategy.

Bioorganic chemistry (Print)
Thirteen new meroterpenoids, acremorins A-M (1, 2, 4, 6, 7 and 9-16), together with three known analogues (3, 5 and 8) were isolated from the deep-sea-derived fungus Acremonium sclerotigenum LW14 guided by the genomic and OSMAC strategy. Their structures
Ruiyun Huo   +4 more
semanticscholar   +1 more source

The chemistry and biology of fungal meroterpenoids (2009–2019)

Organic & Biomolecular Chemistry, 2021
The structural features, biological activities, and fungal biodiversity of 1585 new meroterpenoids were comprehensively overviewed (2009–2019).
Minghua Jiang   +3 more
openaire   +2 more sources

Mining of Meroterpenoids with Anti-inflammatory Activity from the Mangrove Endophytic Fungus Talaromyces sp. JNQQJ-4 by Genome Analysis and Molecular Network Strategy.

Organic Letters
Talaromeroterpenoids A-G (1-7), seven new 3,5-dimethylorsellinic-acid-derived meroterpenoids, and two known analogues (8 and 9) were isolated from the mangrove endophytic fungus Talaromyces sp.
Gui-Min Wang   +7 more
semanticscholar   +1 more source

Formyl-phloroglucinol meroterpenoids with Nrf2 inhibitory activity from Eucalyptus globulus leaves.

Phytochemistry
Three previously undescribed formyl-phloroglucinol meroterpenoids eucalypglobulusals K-M (1-3), one phloroglucinol derivative (16), and sixteen known analogues were isolated from the petroleum ether extract of Eucalyptus globulus leaves.
Wei Liu   +8 more
semanticscholar   +1 more source

Baoslingzhines Q-X: Structurally previously undescribed trace phenolic meroterpenoids from Ganoderma lucidum and their biological activities toward renal fibrosis and cytotoxicity.

Phytochemistry
Eight previously undescribed phenolic meroterpenoids baoslingzhines Q-X (1-8) including three enantiomeric (±)-baoslingzhines Q-S (1-3) harboring a 2-methylbenzofuran moiety, two trinormeroterpenoids baoslingzhines T and U (4 and 5) containing a 5 ...
Yunyun Liu   +3 more
semanticscholar   +1 more source

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