Non-targeted analysis of vulgarisins by using collisional dissociation mass spectrometry for the discovery of analogues from Prunella vulgaris

Ma, Fengwei; Lou, Hua‐Yong; Ge, Yonghui; Li, Jinyu; Chen, Chao; Xu, Su; Tang, Lei; Pan, Weidong

doi:10.1007/s00216-021-03615-x

Cited by 6 publications

(2 citation statements)

References 21 publications

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“…236 Vulgarisins A-F (288-293), six new diterpenoids with an unprecedented 5/6/4/5 fused tetracyclic skeleton, were isolated from the medicinal plant Prunella vulgaris. [237][238][239] The structures of compounds 286, 288, and 289 were determined by single crystal X-ray diffraction analysis. The biosynthetic pathways of 286-293 were proposed, and these compounds could be derived from geranylgeranyl diphosphate Natural Product Reports Review (GGPP); furthermore, the pathways may subsequently involve cation-induced cyclization to produce a cyclobutane skeleton.…”

Section: Diterpenoidsmentioning

confidence: 99%

[2 + 2]-Cycloaddition-derived cyclobutane natural products: structural diversity, sources, bioactivities, and biomimetic syntheses

et al. 2023

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Section: Diterpenoidsmentioning

confidence: 99%

[2 + 2]-Cycloaddition-derived cyclobutane natural products: structural diversity, sources, bioactivities, and biomimetic syntheses

et al. 2023

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“…They were identified as vulgarisin A-F by comparing their spectroscopic data with the literature. [34][35][36]…”

Section: Papermentioning

confidence: 99%

Vulgarisin-type diterpenoids from self-heal (Prunella vulgaris) and their neuroprotective effects against ischemia/reperfusion (I/R) via a mitochondria-related pathway

Deng

Lou

et al. 2022

Food Funct.

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Divergent Total Syntheses of (+)‐Vulgarisins A–E

Rao

et al. 2023

Angewandte Chemie

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The asymmetric total syntheses of (+)‐vulgarisins A–E, which share a rare and highly oxygenated [5‐6‐4‐5] tetracyclic core structure that were isolated from P. vulgaris Linn., have been described for the first time in a divergent manner. Key transformations include: 1) a catalytic asymmetric intramolecular cyclopropanation to forge the A ring bearing desired stereochemistry at C14; 2) a one‐pot borylation/conjugate addition process for creation of the C1−C11 bond; 3) a Wolff ring contraction to assemble the bicyclo[3.2.0]heptane subunit (CD rings); and 4) a stereocontrolled pinacol cyclization for construction of the central B ring of the natural products.

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Non-targeted analysis of vulgarisins by using collisional dissociation mass spectrometry for the discovery of analogues from Prunella vulgaris

Cited by 6 publications

References 21 publications

[2 + 2]-Cycloaddition-derived cyclobutane natural products: structural diversity, sources, bioactivities, and biomimetic syntheses

[2 + 2]-Cycloaddition-derived cyclobutane natural products: structural diversity, sources, bioactivities, and biomimetic syntheses

Vulgarisin-type diterpenoids from self-heal (Prunella vulgaris) and their neuroprotective effects against ischemia/reperfusion (I/R) via a mitochondria-related pathway

Divergent Total Syntheses of (+)‐Vulgarisins A–E

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