Lupane Triterpenes from the Leaves of Acanthopanax gracilistylus

Li, Xiaojun; Zou, Qin-Peng; Wang, Xiang; Kim, Kwan-Woo; Lu, Mao-Fang; Ko, Sung-Kwon; Yook, Chang‐Soo; Kim, Youn‐Chul; Liu, Xiangqian

doi:10.3390/molecules23010087

Cited by 16 publications

(11 citation statements)

References 16 publications

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“…C-6rha). The 13 C-NMR data for compound 2 agree with the literature data [23] corresponding to acangraciliside S. C-NMR data for compound 5 agree with the literature data [22] corresponding to acantrifoside A.…”

Section: Structural Identificationsupporting

confidence: 78%

Separation of Six Lupane-Type Triterpenoid Saponins from Leaves of Acanthopanax gracilistylus by HSCCC with Preparative-HPLC

Liu¹,

Luo²,

Wang³

et al. 2018

SDRP-JFST

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High efficiency and less solvent consumption are the essential requirements of high-speed counter current chromatography (HSCCC), especially for the preparation and purification of natural products. In this manuscript, an efficient HSCCC strategy with preparative high performance liquid chromatography (preparative-HPLC) was successfully developed to rapidly separate and purify six lupane-type triterpenoids (including acankoreoside C (1), acangraciliside S (2), acankoreoside B (3), acankoreoside D (4), acantrifoside A (5) and acankoreoside A (6)) from leaves of the A canthopanax gracilistylus. The effective separation was achieved using ethyl acetate-nbutanol-methanol-water (3:0.3:0.8:4, v/v/v/v) as the two-phase solvent system, in which the mobile phase was eluted at an optimized flow rate of 2.0 mL/min and a revolution speed of 900 rpm. HSCCC preparation was performed on 400 mg of crude sample yielding 5.3 mg of compound 3, 6.4 mg of compound 4, 10.6 mg of compound 5, 35.8 mg of compound 6 with purities of 95.6%, 96.3%, 96.1%, 97.2%, respectively, 17.2 mg of a mixture of compounds 1 and 2, which was further separated by preparative-HPLC yielding 5.9 mg of compound 1, and 4.5 mg of compound 2 with purities of 96.8% and 94.6%, respectively, as determined by HPLC at 210 nm. Their chemical structures were identified by nuclear magnetic resonance (NMR) technology. All compounds were evaluated for their anti-inflammatory activity with lipopolysaccharide (LPS)-induced RAW264.7 cell. The compounds 3 and 4 showed weakly inhibitory effect of nitric oxide (NO) production with low cytotoxicity.

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Section: Structural Identificationsupporting

confidence: 78%

Separation of Six Lupane-Type Triterpenoid Saponins from Leaves of Acanthopanax gracilistylus by HSCCC with Preparative-HPLC

Liu¹,

Luo²,

Wang³

et al. 2018

SDRP-JFST

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“…The 13 C NMR spectrum showed which seven methyl groups at [δc: 31.8 (C-23), 19.5 (C-28), 16.8 (C-25), 16.7 (C-26), 16.2 (C-24), 15.2 (C-27) and 22.2 (C-30)]; the signals due to an exomethylene group at [δc: 110.2 (C-29) and 152.0 (C-20)]; ten methylene, five methine and five quaternary carbons were assigned with the aid of DEPT 135º spectrum (Waliullah et al 2011). The deshielded singnal at δc 79.0 was due to C-3 with a hydroxyl group attached to it (Li et al 2018). The forgoing spectral analysis and comparison with reported data, led us to propose the structure of isolated compund as a pentacylic triterpenoid (Fig 2).…”

Section: Discussionmentioning

confidence: 73%

Triterpenoid compound from metanol extract of mangrove leaves (Sonneratia alba) and anti-cholesterol activity test

Musa

Bialangi

Situmeang³

et al. 2019

JPKim

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Mangrove plant (Sonneratia alba) is easily found in West and North Indonesia. Mangrove plant has the potential of being a herb medicine. Mangrove plant variously used in ethnomedicine to treat various deseases like wounds, diarrhea, and fever. In previously sutudy, leaf extract of mangrove plants reported have anti-cholesterol activity. This plant is widely used to treat various deseases like wounds, diarrhea, and fever. The purpose of this study was to isolate triterpenoid compound from the ethyl acetate fraction of mangrove leaves and anticholesterol activity test. Extraction was done by maceration method using methanol 96% as solvent. Isolation was carried out by column chromatography using a combination of n-hexane, ethyl acetate, and methanol solvents. The elucidation of the structure was determined by analysis of IR, 1 H-NMR, 13 C-NMR, 2D-NMR, and MS spectroscopies as well as by comparisons with the literature. Anticholesterol activity test was carried out in vitro. The results showed that triterpenoid compounds (lupeol) were able to reduce cholesterol from concentrations of 5, 10, 20, 40, 60, and 80 ppm are 13.7; 29.4; 49.0; 60,1; 70.2; and 77.0% respectively. Therefore, isolates compound (lupeol) have anti-cholesterol activity.

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“…2). It is also worth mentioning a C1‐hydroxyl derivative of ACK designated acangraciligenin S, isolated from the plant Acanthopanax gracilistylus 30 . Surprisingly, the structural analogy between BA and these compounds has not been underscored before, perhaps because they have a different stereochemistry at the C‐3 position.…”

Section: Ack and Related Sapogeninsmentioning

confidence: 99%

Acankoreagenin and acankoreosides, a family of lupane triterpenoids with anti‐inflammatory properties: an overview

Bailly¹

2021

Annals of the New York Academy of Sciences

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Acankoreagenin (ACK, also known as acankoreanogenin and HLEDA) and impressic acid are two lupane‐type triterpenes that can be isolated from various Acanthopanax and Schefflera species. They efficiently block activation of the NF‐κB signaling pathway and the release of proinflammatory cytokines and/or the action of inflammation mediators (HMGB1, iNOS, and NO). These effects are the basis for the antiviral and anticancer activities reported with these pentacyclic compounds or their various glycoside derivatives. More than 15 acankoreosides (Ack‐A to ‐O, and ‐R) and a few other mono‐ and bidesmosidic saponins (acantrifoside A and acangraciliside S) derive from the ACK aglycone. Compounds like Ack‐A and ‐B are remarkable anti‐inflammatory agents, inhibiting cytokine release from activated macrophages. Despite their effectiveness, ACK and impressic acid are far much less known and studied than the structurally related compounds betulinic acid and 23‐hydroxybetulinic acid (anemosapogenin). The structural differences (notably the R/S stereoisomerism of the 3‐hydroxyl group) and functional similarities of these compounds are discussed. The complete series of acankoreosides is presented for the first time. These natural products deserve further attention as anti‐inflammatory agents, and ACK is recommended as a template for the design of new anticancer and antiviral drugs.

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Lupane Triterpenes from the Leaves of Acanthopanax gracilistylus

Cited by 16 publications

References 16 publications

Separation of Six Lupane-Type Triterpenoid Saponins from Leaves of Acanthopanax gracilistylus by HSCCC with Preparative-HPLC

Separation of Six Lupane-Type Triterpenoid Saponins from Leaves of Acanthopanax gracilistylus by HSCCC with Preparative-HPLC

Triterpenoid compound from metanol extract of mangrove leaves (Sonneratia alba) and anti-cholesterol activity test

Acankoreagenin and acankoreosides, a family of lupane triterpenoids with anti‐inflammatory properties: an overview

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