Potent Antihyperuricemic Triterpenoids Based on Two Unprecedented Scaffolds from the Leaves of <i>Alstonia scholaris</i>

Hu, Bin‐Yuan; Zhao, Yun‐Li; Xiong, Deng-Sen; He, Yun; Zhou, Zhong-Shun; Zhu, Peifen; Wang, Zhaojie; Wang, Yongliang; Zhao, Li‐Xing; Luo, Xiao‐Dong

doi:10.1021/acs.orglett.1c01102

Cited by 20 publications

(13 citation statements)

References 29 publications

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“…Example 6 used the 13 C NMR and OR methods. There are many examples used with various combinations of the tools-for example, rare sesquiterpene (+)-3-ishwarone (115) was investigated using NMR, ORD, ECD, and VCD (Junior et al, 2014;Hu et al, 2021;Lee et al, 2021), and other examples include 116 and 117 (Cao et al, 2019;Cao et al, 2020b) (Figure 18A).…”

Section: Comprehensive Methods In Ac Determinationmentioning

confidence: 99%

Computational methods and points for attention in absolute configuration determination

Zhu

Nafie

2023

Front. Nat. Prod.

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With the rapid development of high performance computers and computational methods, including software, an increasing number of experimental chemists have tried to use computational methods such as optical rotation (OR, including the matrix model), optical rotatory dispersion (ORD), electronic circular dichroism (ECD or CD), vibrational circular dichroism (VCD), and magnetic shielding constants—nuclear magnetic resonance (NMR)—to explain and/or assign absolute configuration (AC) for various compounds. Such reports in the field of natural products have increased dramatically. However, every method has its range of application. This leads, in some cases, to incorrect conclusions by researchers who are not familiar with these methods. In this review, we provide experimental chemists and researchers with more computational details and suitable suggestions, and especially hope that this experience may help readers avoid computational pitfalls. Finally, we discuss the use of simplified models to replace original complex structures with a long side chain. The fundamental basis for using models to represent complex chiral compounds, such as in OR calculations, is the existence of conformation pairs with near canceling conformer contributions that justify the use of models rather than the original compounds. Using examples, we here introduce the transition state (TS) calculation, which may benefit readers in this area for use and mastery for their AC study. This review will summarize the general concepts involved in the study of AC determinations.

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Section: Comprehensive Methods In Ac Determinationmentioning

confidence: 99%

Computational methods and points for attention in absolute configuration determination

Zhu

Nafie

2023

Front. Nat. Prod.

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“…The promotion of UA excretion has been observed in MSU crystal-stimulated HK-2 cells treated with the triterpenoids Alstoscholarinoid A and B from Alstonia scholaris, which markedly downregulated GLUT9 and URAT1 expression [ 36 ].…”

Section: Beneficial Effect Of Bioactive Compounds In Gout and Hyperur...mentioning

confidence: 99%

Anti-Inflammatory and Hypouricemic Effect of Bioactive Compounds: Molecular Evidence and Potential Application in the Management of Gout

Scanu

Luisetto

Ramonda

et al. 2022

CIMB

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Gout is caused by the deposition of monosodium urate crystals in the joint and represents the most common form of inflammatory arthritis in men. Its prevalence is rising worldwide mainly due to the increase of risk factors associated with the disease, in particular hyperuricemia. Besides gout, hyperuricemia leads to an increased inflammatory state of the body with consequent increased risk of comorbidities such as cardiovascular diseases. Increasing evidence shows that bioactive compounds have a significant role in fighting inflammatory and immune chronic conditions. In gout and hyperuricemia, these molecules can exert their effects at two levels. They can either decrease serum uric acid concentrations or fight inflammation associated with monosodium urate crystals deposits and hyperuricemia. In this view, they might be considered valuable support to the pharmacological therapy and prevention of the disease. This review aims to provide an overview of the beneficial role of bioactive compounds in hyperuricemia, gout development, and inflammatory pathways of the disease.

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“…Alstoscholarinoids A (Scheme , 1 ) and B ( 2 ) are two rearranged pentacyclic triterpenoids isolated from the leaves of Alstonia scholaris , a plant historically used in “Dai” ethnopharmacology in China, by the Luo group in 2021 . Both compounds were reported to exhibit potent antihyperuricemic bioactivity by increasing the excretion of uric acid both in vitro and in vivo .…”

mentioning

confidence: 99%

Bioinspired Gram-Scale Synthesis of Alstoscholarinoid B

Luo

Shi

2023

Org. Lett.

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Potent Antihyperuricemic Triterpenoids Based on Two Unprecedented Scaffolds from the Leaves of Alstonia scholaris

Cited by 20 publications

References 29 publications

Computational methods and points for attention in absolute configuration determination

Computational methods and points for attention in absolute configuration determination

Anti-Inflammatory and Hypouricemic Effect of Bioactive Compounds: Molecular Evidence and Potential Application in the Management of Gout

Bioinspired Gram-Scale Synthesis of Alstoscholarinoid B

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