Structure elucidation of a new cycloartane triterpene glycoside from <i>Souliea vaginata</i> by NMR

Wu, Haifeng; Zhu, Yindi; Sun, Zhonghao; Ma, Guoxu; Xu, Xudong; Liu, Yilin; Luo, Zheng‐Hong; Zou, Qiongyu; Zhao, Zhigang

doi:10.1002/mrc.4497

Cited by 9 publications

(3 citation statements)

References 18 publications

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“…Compounds 1-12 were isolated from S. vaginata similarly to our previous reported studies [15][16][17][18][19][20][21]. Scheme 1 outlines the general synthetic procedure leading to six derivatives 1a, 13 and 13a-d including two new ones (13b-c).…”

Section: Chemistrymentioning

confidence: 83%

“…Such glycosides show various biological effects, including anti-HIV, cytotoxic, anti-acetylcholinesterase, and neuroprotective activities [11][12][13][14]. In our previous investigation on this species, we isolated a series of new cycloartane triterpene glycosides [15][16][17][18][19][20][21]. Herein, twelve known cycloartane triterpenoids with four different skeletons, beesioside I (1), beesioside K (2), soulieoside M (3), beesioside M (4), soulieoside N (5), soulieoside R (6), soulieoside Q (7), beesioside O (8), (20S,24S)-15αacetoxy-16β,24;20,24-diepoxy-3β-(β-D-xylopyranosyloxy)-9,19-cyclolanostane-18,25-diol (9), soulieoside S (10), soulieoside O (11), and soulieoside P (12) (Fig.…”

Section: Introductionmentioning

confidence: 99%

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Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity

Yang

et al. 2019

European Journal of Medicinal Chemistry

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In this study, 12 known cycloartane triterpenoids (1-12) with four different skeletons isolated from the roots of Souliea vaginata were screened for the first time for in vitro anti-HIV activity using AZT as a standard. Among the compounds, beesioside I (1) showed the highest potency against HIV-1 NL4-3 with an EC 50 value of 2.32 μM (CC 50 > 40 μM). Preliminary structure-activity relationship (SAR) studies on 1 indicated that simple modification of its aglycone (13) could significantly influence the antiviral activity. Particularly, the introduction of an acyl group at the C-3 position of 13 led to significant improvement in both anti-HIV potency and selectivity index. Among all synthetically modified derivatives, compound 13g was the most potent compound with an EC 50 value of 0.025 μM and TI value greater than 800, comparable to those of 3-O-(3′,3′dimethylsuccinyl)-betulinic acid (DSB, bevirimat). Other analogues exhibited strong to weak inhibition of HIV-1 replication in MT-4 cells. The length, carboxylic terminus, and C-3′ dimethyl substitution of the C-3 side chain substantially affected the anti-HIV activity. Finally, compound 13g was an effective agent against HIV with high potential for further investigation.

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Section: Chemistrymentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity

Yang

et al. 2019

European Journal of Medicinal Chemistry

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“…Inorganic acids are used as catalysts in traditional processes [1] . In recent years, a variety of activator systems for the acylation of catalyzed carboxylic acids have been developed, including poly-phosphoric acid [2] , hydrogen uoride [3] , tri uoromethanesulfonic acid [4] , mesylate/phosphorus pentoxide [5] , and Lewis acid [6] . Intramolecular acylation is a common reaction in organic synthesis, especially in the synthesis of heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

An efficient synthesis of isoxepac and 2-ethylanthraquinone via intramolecular acylation catalyzed by chloroaluminate ionic liquids with P2O5

Wang

Zhang

et al. 2022

Preprint

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Acylation reaction directly using carboxylic acid as an acylation agent is the most ideal acylation method but demands rigorous reaction conditions. In this study, an efficient method was used in synthesizing isoxepac and 2-ethylanthraquinone from electron-poor substrates through intramolecular acylation catalyzed by chloroaluminate ionic liquids with P2O5. The condition optimization experiment was carried out, and the yield of isoxepac was improved to 82.7%. By studying the catalyzed intramolecular acylation of 2-(4-ethylbenzoyl) benzoic acid to obtain 2-ethylanthraquinone, the universality of chloroaluminate ionic liquids with P2O5 as catalysts for intramolecular acylation was confirmed. Compared with the original process, using ionic liquids catalysts in catalytic reactions can effectively reduce the amount of waste acid and water produced by post-treatment.

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Orbital Occupancy Modulation to Optimize Intermediate Absorption for Efficient Electrocatalysts in Water Electrolysis and Zinc–Ethanol–Air Battery

Ye,

Xu,

et al. 2024

Advanced Materials

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Spin engineering is a promising way to modulate the interaction between the transition metal d‐orbital and the reaction intermediates and thus enhance the catalytic kinetics. Herein, we report an innovative strategy to modulate the spin state of Co by regulating its coordinating environment. We first prepared o‐c‐CoSe2‐Ni as pre‐catalyst, then in situ EIS and in situ Raman spectroscopy were employed to prove phase transition, and CoOOH/Co3O4 was formed on the surface as active sites. In hybrid water electrolysis, the voltage has a negative shift, and in zinc–ethanol–air battery, the charging voltage was lowered and the cycling stability was greatly increased. Coordinated atom substitution and crystalline symmetry change were combined to regulate the absorption ability of reaction intermediates with balanced optimal adsorption. Coordinated atom substitution weakens the adsorption while the crystalline symmetry change strengthens the adsorption. Importantly, the tetrahedral sites were introduced by Ni doping which enables the co‐existence of four‐coordinated sites and six‐coordination sites in o‐c‐CoSe2‐Ni. The dz2 + dx2‐y2 orbital occupancy decreased after the atomic substitution, while increased after replacing the CoSe6‐Oh field with CoSe6‐Oh/CoSe4‐Td caused by the Ni doping. This work explored a new direction for the preparation of efficient catalysts for water electrolysis and innovative zinc–ethanol–air battery.This article is protected by copyright. All rights reserved

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Structure elucidation of a new cycloartane triterpene glycoside from Souliea vaginata by NMR

Cited by 9 publications

References 18 publications

Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity

Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity

An efficient synthesis of isoxepac and 2-ethylanthraquinone via intramolecular acylation catalyzed by chloroaluminate ionic liquids with P2O5

Orbital Occupancy Modulation to Optimize Intermediate Absorption for Efficient Electrocatalysts in Water Electrolysis and Zinc–Ethanol–Air Battery

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Structure elucidation of a new cycloartane triterpene glycoside from Souliea vaginata by NMR

Cited by 9 publications

References 18 publications

Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity

Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity

﻿An efficient synthesis of isoxepac and 2-ethylanthraquinone via intramolecular acylation catalyzed by chloroaluminate ionic liquids with P2O5

Orbital Occupancy Modulation to Optimize Intermediate Absorption for Efficient Electrocatalysts in Water Electrolysis and Zinc–Ethanol–Air Battery

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About

An efficient synthesis of isoxepac and 2-ethylanthraquinone via intramolecular acylation catalyzed by chloroaluminate ionic liquids with P2O5