Isolation, Total Synthesis, and Absolute Configuration Determination of Renoprotective Dimeric <i>N</i>-Acetyldopamine–Adenine Hybrids from the Insect <i>Aspongopus chinensis</i>

Ding, Wei-Yi; Yan, Yong‐Ming; Meng, Xiao-Hui; Nafie, Laurence A.; Xu, Te; Dukor, Rina K.; H, Qin; Cheng, Yong‐Xian

doi:10.1021/acs.orglett.0c01593

Cited by 27 publications

(21 citation statements)

References 27 publications

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“…As a consequence, the structure of 7 was identified as shown and named asponguanosine D. It is interesting that all the isolates are natural product hybrids. Such a phenomenon has been found in Aspongopus chinensis [20]. In combination with the previous reports, it could be seen that alkylation of nitrogen is common in insect derived natural products.…”

Section: Structure Elucidation Of the Compoundssupporting

confidence: 78%

Parvaxanthines D–F and Asponguanosines C and D, Racemic Natural Hybrids from the Insect Cyclopelta parva

et al. 2021

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Five new compounds including three pairs of enantiomeric xanthine analogues, parvaxanthines D–F (1–3), two new guanosine derivatives, asponguanosines C and D (6 and 7), along with two known adenine derivatives were isolated from the insect Cyclopelta parva. Racemic 1–3 were further separated by chiral HPLC. Their absolute configurations were assigned by spectroscopic and computational methods. It is interesting that all of these isolates are natural product hybrids. Antiviral, immunosuppressive, antitumor and anti-inflammatory properties of all the isolates were evaluated.

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Section: Structure Elucidation Of the Compoundssupporting

confidence: 78%

Parvaxanthines D–F and Asponguanosines C and D, Racemic Natural Hybrids from the Insect Cyclopelta parva

et al. 2021

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“…In this study, the hindwings of Anomala albopilosa (male) (Coleoptera: Scarabaeoidea, Scarabaeidae) were investigated by vibrational circular dichroism (VCD) spectroscopy. VCD spectroscopy is a chiroptical spectroscopy method that extends circular dichroism into the IR region. − In contrast to the IR spectra, which are less sensitive, the sign and intensity of a VCD peak provide clues that can be used to identify biopolymers with distinct supramolecular conformations . Accordingly, chiral composites can be identified from their VCD spectra.…”

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confidence: 99%

Mapping of Supramolecular Chirality in Insect Wings by Microscopic Vibrational Circular Dichroism Spectroscopy: Heterogeneity in Protein Distribution

Sato

Yamagishi

Shimizu³

et al. 2021

J. Phys. Chem. Lett.

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The supramolecular chirality of the hindwing of Anomala albopilosa (male) was investigated using a microscopic vibrational circular dichroism (VCD) system, denoted as MultiD-VCD. The source of intense infrared (IR) light for the system was a quantum cascade laser. Two-dimensional maps of IR and VCD spectra were taken by scanning the surface area (ca. 2 mm × 2 mm) of the insect hindwing tissue. The spectra ranged from 1500 to 1700 cm–1, and the maps have a spatial resolution of 100 μm. The distribution of proteins, including their supramolecular structures, was analyzed from the location-dependent spectral shape of the VCD bands assigned to amides I and II. The results revealed that the hindwing consists of segregated domains of proteins with different secondary structures: an α-helix (in one part of the membrane), a hybrid of α-helix and β-sheet (in another part of the membrane), and a coil (in a vein).

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“…In accordance of our previous computational study on absolute configurations assignments for natural products ( Cao et al, 2019 ; Ren et al, 2017 ; Xu et al, 2016 ). the electronic circular dichroism (ECD) calculations and vibrational circular dichroism (VCD) ( Mazzeo et al, 2013 ; Mándi and Kurtán, 2019 ; Mazzeo et al, 2017 ; Ding et al, 2020 ) were performed to clarify the absolute configuration of C-15 of 3 .…”

Section: Resultsmentioning

confidence: 99%

A Novel Azaphilone Muyophilone A From the Endophytic Fungus Muyocopron laterale 0307-2

et al. 2021

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Two known azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopic methods, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of azaphilone heterotrimers.

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Isolation, Total Synthesis, and Absolute Configuration Determination of Renoprotective Dimeric N-Acetyldopamine–Adenine Hybrids from the Insect Aspongopus chinensis

Cited by 27 publications

References 27 publications

Parvaxanthines D–F and Asponguanosines C and D, Racemic Natural Hybrids from the Insect Cyclopelta parva

Parvaxanthines D–F and Asponguanosines C and D, Racemic Natural Hybrids from the Insect Cyclopelta parva

Mapping of Supramolecular Chirality in Insect Wings by Microscopic Vibrational Circular Dichroism Spectroscopy: Heterogeneity in Protein Distribution

A Novel Azaphilone Muyophilone A From the Endophytic Fungus Muyocopron laterale 0307-2

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