Two new apotirucallane-type isomeric triterpenoids from the root bark of Dictamnus dasycarpus with their anti-proliferative activity

Bai, Yuan-Yuan; Jin, Xing; Jia, Xian-hui; Tang, Wen-Zhao; Wang, Xiaojing; Zhao, Yunxue

doi:10.1016/j.phytol.2014.06.017

Cited by 15 publications

(6 citation statements)

References 9 publications

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“…The HMBC correlations ( Figure 2) between H-15 (δ H 5.44) and C-16 (δ C 35.9), C-17 (δ C 59.3) revealed the presence of a double bond between C-14 and C-15. All the data above indicated that the basic structure of 1 was similar to those of dictamnin B [17], except that the presence of 21-OCH 3 was replaced by 21-OCH 2 CH 3 and 26-CH 2 OH was replaced by 26-CH 3 in 1. This was additionally confirmed by the key HMBC correlations (Figure 2) from H- 21 (Figure 2) between the methyl proton signal H-26 (δ H 1.26) and H-27 (δ H 1.20) correlated with C-24 (δ C 78.4), C-25 (δ C 73.9), which indicated that the two methyl groups should be located at C-26 and C-27 position, respectively.…”

Section: Resultsmentioning

confidence: 80%

“…Compound 1 was obtained as a white amorphous powder. Its molecular formula was assigned as C 37 H 62 O 7 by high-resolution electrospray ionization mass spectra (HR-ESI-MS) ( Figure S7 [7,16,17]. Analysis of the HMBC spectrum ( Figure 2) demonstrated the isovaleryl ester group was located in C-3 by the cross-signal from H-3 (δ H 4.65) to C1 (δ C 174.6), H-4 (δ H 0.96) to C-3 (δ C 44.7) and C-2 (δ C 25.3), H-5 (δ H 0.96) to C-3 (δ C 44.7) and C-2 (δ C 25.3), and H-29 (δ H 1.09) and H-28 (δ H 0.86) to C-3 (δ C 79.7).…”

Section: Resultsmentioning

confidence: 99%

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Two New Apotirucallane-Type Triterpenoids from the Pericarp of Toona sinensis and Their Ability to Reduce Oxidative Stress in Rat Glomerular Mesangial Cells Cultured under High-Glucose Conditions

et al. 2020

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Hyperglycemia is a strong risk factor for chronic complications of diabetes. Hyperglycemic conditions foster not only the production of reactive oxygen species (ROS), but also the consumption of antioxidants, leading to oxidative stress and promoting the occurrence and progression of complications. During our continuous search for antioxidant constituents from the pericarp of Toona sinensis (A. Juss.) Roem, we isolated two previously unreported apotirucallane-type triterpenoids, toonasinensin A (1) and toonasinensin B (2), together with five known apotirucallane-type triterpenoids (3–7) and two known cycloartane-type triterpenoids (8–9) from the pericarp. Compounds 8–9 were obtained from T. sinensis for the first time. Their structures were characterized based on interpretation of spectroscopic data (1D, 2D NMR, high-resolution electrospray ionization mass spectra, HR-ESI-MS) and comparison to previous reports. Compounds (2, 4, 6, 7, and 9) were able to inhibit proliferation against rat glomerular mesangial cells (GMCs) cultured under high-glucose conditions within a concentration of 80 μM. Compounds (2, 6, and 7) were tested for antioxidant activity attributable to superoxide dismutase (SOD), malondialdehyde (MDA), and ROS in vitro, and the results showed that compounds (2, 6, and 7) could significantly increase the levels of SOD and reduce the levels of MDA and ROS. The current studies showed that apotirucallane-type triterpenoids (2, 6, and 7) might have the antioxidant effects against diabetic nephropathy.

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Section: Resultsmentioning

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Two New Apotirucallane-Type Triterpenoids from the Pericarp of Toona sinensis and Their Ability to Reduce Oxidative Stress in Rat Glomerular Mesangial Cells Cultured under High-Glucose Conditions

et al. 2020

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“…Xylogranatumine F (89) is C3 tigloyl and C21 ethoxy derivative of compound (81). Toonasinensin A (90) is C21 ethoxy, C26 hydroxy analog of previously reported Dictamnin A 89 . The hemiacetal group at C17 in previously reported 3α-acetoxy-21,23-epoxyapotirucall-14ene-7α,21R,24,25-tetrol 90 is replaced by lactone ring in Chisiamol G (91) making it a C21 carbonyl analog.…”

Section: Apoprotolimonoid/apotirucallanetriterpenoidmentioning

confidence: 98%

Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

Nandikol

Thulasiram

2022

Preprint

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Nature has bestowed us with abundant bioactive/drug molecules for various uses in our everyday life. One such group of plant specialized molecules is limonoids, which are structurally characterized as 4,4,8-trimethyl-17-furanyl steroidal skeleton. Limonoids are well known for their various biological activities such as potent anti-feedent, anti-cancer, anti-inflammatory, insecticidal, anti-diabetic, anti-viral, anti-microbial etc. These tetranortriterpenes are highly oxygenated and structurally diversified molecules majorly found in Meliaceae and Rutaceae and less frequently in the Cneoraceae families in the plant kingdom. Many of these plants have been used in traditional medicine from ages. One of the well-known limonoid, azadirachtin A is highly valued and widely popular for its outstanding insecticidal properties. Till date, nearly 2500 limonoids with over 35 unique carbon frameworks have been observed. In recent times, these molecules have dig a great interest among researchers due to their myriad biological properties. With the advancement of analytical techniques, the limonoid research is aced to explore more different molecules from their sources. In our review we cover all the Meliaceous limonoids isolated during July 2010 to Dec 2020. We found over 1502 new limonoids, which are reported from various Meliaceae plants after Jun 2010. We have classified them based on their skeletal structure rearrangements and functional groups into various classes such as protolimonoids, Apoprotolionoid, Azadirone, Vilasinin, Cedrelone, Havanensin, Trichilin, Nimbin, Salannin, Azadirachtin, Nimbolidin, Nimbolinin, Obacunol, Evodulone, Trijugin, Cipadesin, Andirobin, Mexicanolide, Phragmalin, Khayanolide, Preieurianin, Aphanamixoid, Nor Limonoid and N-containing derivatives. Further we have discussed their biological activities in detail.

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“…Moreover, limonin has also been found to induce apoptosis in IOMM-Lee and CH157MN meningioma cells, mainly by inhibiting Wnt5/β-catenin pathway [31]. Aside from this, limonin also has a good antiproliferative effect on lung cancer cells A549 (IC50 = 82.5 uM) [32]. Limonin can also suppress the growth of cervical carcinoma HeLa cells.…”

Section: Pharmacologymentioning

confidence: 99%

Limonin: A Review of Its Pharmacology, Toxicity, and Pharmacokinetics

et al. 2019

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Limonin is a natural tetracyclic triterpenoid compound, which widely exists in Euodia rutaecarpa (Juss.) Benth., Phellodendron chinense Schneid., and Coptis chinensis Franch. Its extensive pharmacological effects have attracted considerable attention in recent years. However, there is no systematic review focusing on the pharmacology, toxicity, and pharmacokinetics of limonin. Therefore, this review aimed to provide the latest information on the pharmacology, toxicity, and pharmacokinetics of limonin, exploring the therapeutic potential of this compound and looking for ways to improve efficacy and bioavailability. Limonin has a wide spectrum of pharmacological effects, including anti-cancer, anti-inflammatory and analgesic, anti-bacterial and anti-virus, anti-oxidation, liver protection properties. However, limonin has also been shown to lead to hepatotoxicity, renal toxicity, and genetic damage. Moreover, limonin also has complex impacts on hepatic metabolic enzyme. Pharmacokinetic studies have demonstrated that limonin has poor bioavailability, and the reduction, hydrolysis, and methylation are the main metabolic pathways of limonin. We also found that the position and group of the substituents of limonin are key in affecting pharmacological activity and bioavailability. However, some issues still exist, such as the mechanism of antioxidant activity of limonin not being clear. In addition, there are few studies on the toxicity mechanism of limonin, and the effects of limonin concentration on pharmacological effects and toxicity are not clear, and no researchers have reported any ways in which to reduce the toxicity of limonin. Therefore, future research directions include the mechanism of antioxidant activity of limonin, how the concentration of limonin affects pharmacological effects and toxicity, finding ways to reduce the toxicity of limonin, and structural modification of limonin—one of the key methods necessary to enhance pharmacological activity and bioavailability.

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Two new apotirucallane-type isomeric triterpenoids from the root bark of Dictamnus dasycarpus with their anti-proliferative activity

Cited by 15 publications

References 9 publications

Two New Apotirucallane-Type Triterpenoids from the Pericarp of Toona sinensis and Their Ability to Reduce Oxidative Stress in Rat Glomerular Mesangial Cells Cultured under High-Glucose Conditions

Two New Apotirucallane-Type Triterpenoids from the Pericarp of Toona sinensis and Their Ability to Reduce Oxidative Stress in Rat Glomerular Mesangial Cells Cultured under High-Glucose Conditions

Chemistry and Biology of Novel Meliaceae Limonoids

Limonin: A Review of Its Pharmacology, Toxicity, and Pharmacokinetics

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