Rapid screening of unprecedented sesquiterpenes with distinctive ring skeletons from <i>Daphne aurantiaca</i> employing an integrated strategy

Dong, Shu-Hui; Han, Jinling; Chang, Xiaohong; Lian, Mei-Ya; Li, Xiaoxue; Bai, Ming; Huang, Xiao‐Xiao; Song, Shao‐Jiang

doi:10.1039/d3qo00902e

Cited by 10 publications

(7 citation statements)

References 49 publications

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“…Our efforts to determine the relative stereochemistry of C-6′ were unsuccessful because of the conformation flexibility of C-6′ and the long distance between C-6′ and C-2′ and 3′. Therefore, the calculated NMR chemical shifts of two possible diastereomers 8a and 8b were subjected to custom DP4+ analysis with the experimental values. , The statistical results indicated the structural equivalence of 8 and 8b (100% probability). The specific rotation of (2′ R , 3′ R , 6′ S )- 8 was calculated as +40.9; from a comparison of the experimental value of 8 [[α] D 20 +36.0 (c 1.00, MeOH)], the absolute configuration of 8 was determined to be 2′ R , 3′ R , 6′ S .…”

Section: Resultsmentioning

confidence: 99%

“…The conformers with a Boltzmann population of over 1% were further geometry optimized at the B3LYP/6-31G(d) level, and subsequently, the Gauge-Independent Atomic Orbital (GIAO) calculations of magnetic shielding tensors were accomplished by DFT at the mPW1PW91/6-311+G(d,p) level with the PCM model in the Gaussian 09 package. The OR values were calculated using Gaussian 09 by the time-dependent density functional theory method at the b3lyp/tzvp level in MeOH, of which the given wavelength was 589.3 nm. − …”

Section: Methodsmentioning

confidence: 99%

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Bioassay-Guided and DeepSAT-Driven Precise Mining of Monoterpenoid Coumarin Derivatives with Antifeedant Effects from the Leaves of Ailanthus altissima

Duan,

Wang,

Lian

et al. 2024

J. Agric. Food Chem.

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Demand for the exploration of botanical pesticides continues to increase due to the detrimental effects of synthetic chemicals on human health and the environment and the development of resistance by pests. Under the guidance of a bioactivity-guided approach and HSQC-based DeepSAT, 16 coumarin derivatives were discovered from the leaves of Ailanthus altissima (Mill.) Swingle, including seven undescribed monoterpenoid coumarins, three undescribed monoterpenoid phenylpropanoids, and two new coumarin derivatives. The structure and configurations of these compounds were established and validated via extensive spectroscopic analysis, acetonide analysis, and quantum chemical calculations. Biologically, 5 exhibited significant antifeedant activity toward the Plutella xylostella. Moreover, tyrosinase being closely related to the growth and development of larva, the inhibitory potentials of 5 against tyrosinase was evaluated in vitro and in silico. The bioactivity evaluation results highlight the prospect of 5 as a novel category of botanical insecticide.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Bioassay-Guided and DeepSAT-Driven Precise Mining of Monoterpenoid Coumarin Derivatives with Antifeedant Effects from the Leaves of Ailanthus altissima

Duan,

Wang,

Lian

et al. 2024

J. Agric. Food Chem.

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“…Intermediates Ia and Ib might undergo alkene isomerization [11] and oxidative cleavage of the C-4/5 bond to produce diketo intermediates IIa andIIb [32] , from which vital intermediatesIIIa and IIIb could be formed through selective keto-enol tautomerism, reduction, and oxidative cleavage. IIIa andIIIb were then transformed into the crucial intermediatesIVa and IVb by a aldol condensation [33] to furnish the bicyclo[3.3.1]nonane core. Moreover, IVa andIVb were likely transformed to intermediates Va andVb by redox reaction [34] , which would undergo esterification to finally generate (-)-2 and (+)-2 .…”

Section: Resultsmentioning

confidence: 99%

Discovery of sesquiterpenoids from Chloranthus henryi Hemsl. var. hupehensis (Pamp.)K. F. Wu and their anti-inflammatory activity by suppression of the IKBα/NF-κB p65 signaling pathway

Liu,

Wang,

Wang

et al. 2024

Preprint

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The phytochemical investigation of the roots of Chloranthus henryi Hemsl. var. hupehensis (Pamp.) K. F. Wu led to the isolation and identification of 23 structurally diverse sesquiterpenes and their dimer, including a new eudesmane sesquiterpenoid dimer, nineteen new sesquiterpenoids and three known sesquiterpenoids. Among the isolates, 1 was a rare sesquiterpenoid dimer formed by assembling two highly rearranged eudesmane-type sesquiterpenes through a unique oxygen bridge (C-11–O–C-8′). It is worth noting that rearranged eudesmane type sesquiterpenoid dimers containing an oxygen bridge are rarely isolated from nature. (+)-2 and (−)-2 were a pair of new skeleton sesquiterpenoids with a remarkable 6/6/5 tricyclic ring framework including one γ-lactone ring and the bicyclo[3.3.1]nonane core. Their structures and absolute configurations were determined by spectroscopic analysis, single-crystal X-ray diffraction analysis, and quantum chemical calculation. Moreover, all the isolated compounds were evaluated for their potential anti-inflammatory activity using an LPS-induced BV-2 cell microglial. Among them, 18 suppressed TNF-α and IL-1β expression with EC50 values of 6.81 µM and 2.76 µM, respectively, indicating its excellent efficacy in inhibiting inflammatory factors production. In subsequent mechanism studies, compounds 3, 17, and 18 could reduce the production of IL-1β and TNF-α by inhibiting the activation of IKBα/p65 pathway.

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“…It is suggested that daphaulides A 10 and E 11 , from Daphne aurantiaca , are also derived from cleaved guaiane sesquiterpenoid precursors. 9 …”

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Hill,

Sutherland

2023

Nat. Prod. Rep.

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Rapid screening of unprecedented sesquiterpenes with distinctive ring skeletons from Daphne aurantiaca employing an integrated strategy

Abstract: Guaiane-type sesquiterpenoids are well-known in medicinal chemistry of natural products, but the unprecedented sesquiterpenoid scaffold furnished by forming unexpected carbon-carbon linkages or occurring startling cracking deserves expected to be further...

Cited by 10 publications

References 49 publications

Bioassay-Guided and DeepSAT-Driven Precise Mining of Monoterpenoid Coumarin Derivatives with Antifeedant Effects from the Leaves of Ailanthus altissima

Bioassay-Guided and DeepSAT-Driven Precise Mining of Monoterpenoid Coumarin Derivatives with Antifeedant Effects from the Leaves of Ailanthus altissima

Discovery of sesquiterpenoids from Chloranthus henryi Hemsl. var. hupehensis (Pamp.)K. F. Wu and their anti-inflammatory activity by suppression of the IKBα/NF-κB p65 signaling pathway

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