Bing‐Chao Yan

ORCID: 0000-0002-9739-5234
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Research Areas
  • Bioactive Natural Diterpenoids Research
  • Microbial Natural Products and Biosynthesis
  • Plant-based Medicinal Research
  • Marine Sponges and Natural Products
  • Biological Activity of Diterpenoids and Biflavonoids
  • Phytochemistry and Biological Activities
  • Traditional and Medicinal Uses of Annonaceae
  • Plant biochemistry and biosynthesis
  • Fungal Biology and Applications
  • Sesquiterpenes and Asteraceae Studies
  • Natural product bioactivities and synthesis
  • Crystallization and Solubility Studies
  • X-ray Diffraction in Crystallography
  • Phytochemistry and Bioactivity Studies
  • Steroid Chemistry and Biochemistry
  • Plant-derived Lignans Synthesis and Bioactivity
  • Synthetic Organic Chemistry Methods
  • Microbial Metabolism and Applications
  • Alkaloids: synthesis and pharmacology
  • Oxidative Organic Chemistry Reactions
  • Autophagy in Disease and Therapy
  • Immune Response and Inflammation
  • Advanced Synthetic Organic Chemistry
  • Traditional Chinese Medicine Analysis
  • Plant Pathogens and Fungal Diseases

Kunming Institute of Botany
2015-2024

Chinese Academy of Sciences
2015-2024

University of Chinese Academy of Sciences
2014-2024

Shanghai Institute of Organic Chemistry
2021

Kunming University
2018

State Council of the People's Republic of China
2018

Phomopchalasins A (1) and B (2), two novel cytochalasans with unprecedented carbon skeletons, phomopchalasin C (3), containing a rare hydroperoxyl motif, were obtained from the endophytic fungus Phomopsis sp. shj2, which was first isolated Isodon eriocalyx var. laxiflora. Their structures elucidated by extensive spectroscopic analyses, electronic circular dichroism (ECD) calculation, X-ray crystallographic analysis. Notably, 1 possessed an 5/6/5/8-fused tetracyclic ring system, 2 featured...

10.1021/acs.orglett.6b00214 article EN Organic Letters 2016-02-16

Isopenicins A–C (1–3), three novel meroterpenoids possessing two types of unprecedented terpenoid-polyketide hybrid skeletons, were isolated from the cultures Penicillium sp. sh18. Their structures determined through synergetic use extensive spectroscopic analysis, quantum-chemical calculation with ANN–PRA and X-ray crystallographic analysis. Additionally, inhibitory activities these compounds on Wnt/β-catenin signaling pathway evaluated, 1 was identified as a potent inhibitor Wnt pathway.

10.1021/acs.orglett.8b04020 article EN Organic Letters 2019-01-14

Abstract Cyclobutanes are distributed widely in a large class of natural products featuring diverse pharmaceutical activities and intricate structural frameworks. The [2 + 2] cycloaddition is unequivocally the primary most commonly used method for synthesizing cyclobutanes. In this review, we have summarized application with different reaction mechanisms chemical synthesis selected cyclobutane-containing over past decade. Graphical

10.1007/s13659-024-00457-9 article EN cc-by Natural Products and Bioprospecting 2024-06-11

Glutinosasins A–D (1–4), four novel 8,14- seco - ent -kaurane diterpenoids featuring an β -carbonyl enol moiety, along with glutinosasin E (5), a new diterpenoid, were isolated from the aerial part of Isodon glutinosus ....

10.1039/d5qo00356c article EN Organic Chemistry Frontiers 2025-01-01

(-)-Isoscopariusin A was isolated from the aerial parts of Isodon scoparius. Chemical synthesis and spectroscopic analysis established its structure as an unsymmetrical meroditerpenoid bearing a sterically congested 6/6/4 tricyclic carbon skeleton with seven continuous stereocenters. gram-scale achieved in 12 steps commercially available (+)-sclareolide. cobalt catalyzed, hydrogen atom transfer-based olefin isomerization used to prepare trisubstituted alkene, which underwent stereoselective...

10.1002/anie.202100288 article EN Angewandte Chemie International Edition 2021-02-23

Exploitation of key protected wild plant resources makes great sense, but their limited populations become the major barrier. A particular strategy for breaking this barrier was inspired by exploration a resource-saving fungal endophyte Penicillium sp. DG23, which inhabits Schisandra macrocarpa. Chemical studies on cultures strain afforded eight novel indole diterpenoids, schipenindolenes A-H (1-8), belonging to six diverse skeleton types. Importantly, semisyntheses suggested some...

10.1002/anie.202313859 article EN Angewandte Chemie International Edition 2023-12-06

Scospirosins A (1) and B (2), two unprecedented spiro ent-clerodane dimers with 6/6/10/6 6/6/6/6/6 ring systems, respectively, were isolated from Isodon scoparius. Their structures unambiguously established by spectroscopic, X-ray crystallographic, chemical approaches. bioinspired protecting-group-free strategy for their synthesis was achieved on a gram scale featured the application of green methods, including neat reaction, sensitized photooxygenation, electrochemical oxidation. 2...

10.1021/acs.orglett.1c01724 article EN Organic Letters 2021-06-25

Natural products possessing unique scaffolds may have antiviral activity but their complex structures hinder facile synthesis. A pharmacophore-oriented semisynthesis approach was applied to (-)-maoelactone (1) and oridonin (2) for the discovery of anti-SARS-CoV-2 agents. The Wolff rearrangement/lactonization cascade (WRLC) reaction developed construct unprecedented maoelactone-type scaffold during 1. Further mechanistic study suggested a concerted mechanism rearrangement water-assisted...

10.1002/anie.202201684 article EN Angewandte Chemie International Edition 2022-04-29

Penicilfuranone A (1), a novel furancarboxylic acid, and its proposed biosynthetic precursor, gregatin (2), were isolated from the cultures of fungus Penicillium sp. sh18 endophytic to stems Isodon eriocalyx var. laxiflora guided by HPLC-MS. X-ray crystallography was applied structure determination acid for first time, allowing unambiguous assignment 1. displays significant antifibrotic effect in activated hepatic stellate cells via negative regulation transforming growth factor-β...

10.1021/acs.jnatprod.5b00814 article EN Journal of Natural Products 2015-12-18

Phomopsischalins A−C (1–3), two classes of polycyclic-fused cytochalasins, were discovered from Phomopsis sp. shj2. Compound 2 is the first example a cytochalasin accelerating lysosome function in transcription factor EB-independent manner.

10.1039/d3qo00252g article EN Organic Chemistry Frontiers 2023-01-01

Rugosiformisin A, a skeleton-rearranged abietane-type diterpenoid with spiro[4.5]decane motif, was isolated from Isodon rugosiformis. Its structure unambiguously established via NMR spectroscopic analysis and single-crystal X-ray diffraction. A bioinspired asymmetric synthesis of rugosiformisin achieved in 15 steps 2.7% overall yield. The features an iridium-catalyzed polyene cyclization semipinacol rearrangement.

10.1021/acs.orglett.2c02834 article EN Organic Letters 2022-10-26

The plants of the genus Isodon and schisandraceae family are two economically medicinally important phytogroups, research chemical constituents from these phytogroups has been recognized as one most outstanding achievements in natrural product recently. So far, over 1200 diterpenoids classified into 11 different groups have reported species more than 200 schinortriterpenoids (SNTs) involving 20 skeletons isolated species. Their diverse scffolds significant bioactivities aroused great...

10.6023/cjoc201806002 article EN Chinese Journal of Organic Chemistry 2018-01-01

Isoxerophilusins A (1) and B (2), two unprecedented diterpene heterodimers biogenetically from ent-atisanes abietanes, were isolated the rhizomes of Isodon xerophilus. Their structures determined by extensive spectroscopic analysis single-crystal X-ray diffraction. Selective esterification 1 generated 11 new derivatives. All derivatives showed excellent α-glucosidase inhibitory activity in comparison to acarbose. Compounds 12 13 demonstrated significant inhibition against with IC50 values...

10.1021/acs.orglett.4c02095 article EN Organic Letters 2024-07-15

(+)-Isoscopariusins B (1) and C (2), two meroditerpenoids containing a 6/6/4 tricyclic carbon skeleton seven continuous stereocenters, were identified from Isodon scoparius. The structures determined by nuclear magnetic resonance analysis concise biomimetic syntheses readily available alkene 5 in six steps, respectively. An intermolecular [2+2] photocycloaddition with cooperative catalysis of Lewis acid an Ir photocatalyst was used to construct cyclobutane core four stereogenic centers.

10.1021/acs.orglett.3c00742 article EN Organic Letters 2023-04-21

Maoeriocalysin A, an unprecedented 4,5-seco-3,5-cyclo-7,20-epoxy-<italic>ent</italic>-kauranoid, together with three rare 9,10-seco-<italic>ent</italic>-kauranoids, maoeriocalysins B–D, were isolated.

10.1039/c8qo01007b article EN Organic Chemistry Frontiers 2018-11-06

Eight new diterpenoids (1-8) with varied structures were isolated from the aerial parts of Isodon xerophilus. Among them, xerophilsin A (1) was found to be an unusual meroditerpenoid representing a hybrid ent-kauranoid and long-chain aliphatic ester, xerophilsins B-D (2-4) are dimeric ent-kauranoids, while E-H (5-8) ent-kauranoids. The 1-8 elucidated mainly through analyses their spectroscopic data. absolute configurations 2, 6, 8 confirmed by single-crystal X-ray diffraction, configuration...

10.1021/acs.jnatprod.0c00983 article EN Journal of Natural Products 2020-12-16
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