Discovery and characterization of pentacyclic triterpenoid acids in Styrax as potent and reversible pancreatic lipase inhibitors

Wang, Lu; Guan, Xiao-Qing; He, Rong-Jing; Huo, Pengchao; Qin, Weiwei; Cui, Longtao; Hu, Qing; Hou, Jie; Mamat, Mihreay; Jia, Shou-Ning; Tang, Hui; Ge, Guangbo

doi:10.1016/j.jff.2020.104159

Cited by 14 publications

(9 citation statements)

References 70 publications

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“…In addition, it also has assorted pharmacological effects, e.g., antibacterial (Wang et al, 2010;, insecticidal (Imam, 2013), antidepressant (Min et al, 2018), inhibiting abnormal excitation of uterine smooth muscle (Wang et al, 2014), anti-prostate cancer cells (Atmaca et al, 2020), promoting wound healing (Ocsel et al, 2012) and hepatoprotective (Suzek et al, 2016), which will not be discussed in this article. (Wang et al, 2012b;Gurbuz et al, 2013;Peng et al, 2013) Carvone (Wang et al, 2012b;Peng et al, 2012;Peng et al, 2013) (-)-α-Terpineol Gurbuz et al ( 2013) Terpinen-4-ol (Peng et al, 2012;Gurbuz et al, 2013) Linalool oxide (Furanoid) (Wang et al, 2012b;Gurbuz et al, 2013;Peng et al, 2013) α-Pinene (Wang et al, 2012b;Peng et al, 2012;Gurbuz et al, 2013;Peng et al, 2013;Park 2014) β-pinene (Wang et al, 2012b;Peng et al, 2012;Gurbuz et al, 2013; Huang et al, 2019) Pentacyclic triterpenoids Oleanic acid Wang et al, 2020b;Wang et al, 2020c;Zhang et al, 2020) Oleanonic acid Wang et al, 2020b;Wang et al, 2020c;Zhang et al, 2020) Betulinic acid (Wang et al, 2020b;Wang et al, 2020c;Zhang et al, 2020) Corosolic acid (Wang et al, 2020b;Wang et al, 2020c;…”

Section: Pharmacological Activitiesmentioning

confidence: 99%

“…ST is rich in terpenoids ( Table 2 ), which have pharmacological effects such as anti-inflammatory, hypolipidemic and hypotensive, and are classified by structure into monoterpenes (36–63) ( Figure 4A ), sesquiterpenes (64–73) ( Figure 4B ), diterpenes (74–77) ( Figure 4C ) and pentacyclic triterpenes (78–84) ( Figure 4D ). These seven pentacyclic triterpenoids including oleanolic acid (78), oleanolone acid (79), betulinic acid (80), corosolic acid (81), maslinic acid (82), epibetulinic acid (83) and betulonic acid (84) are not only widely used as food additives, but also efficiently inhibit Human carboxylesterase 1A1 (hCES1A) and Pancreatic lipase (PL) activities ( Wang et al, 2020b ; Wang et al, 2020c ; Zhang et al, 2020 ). Thereby ST could be a potential drug for the treatment of obesity and obesity-related metabolic disorders such as stoke and coronary heart disease, which is a hot research topic at the moment.…”

Section: Phytochemical Constituentsmentioning

confidence: 99%

“…ST contains five pentacyclic triterpenoid acids, which have a strong inhibitory effect on pancreatic lipase, with IC50 values ranging from 0.49 to 6.35 μm. Among them, oleanonic acid and betulonic acid are the most effective two pancreatic lipase inhibitors, and they have a strong inhibitory effect on pancreatic lipase in a reversible and mixed manner, revealing the chemical composition of ST for the treatment of lipid metabolic diseases such as coronary heart disease ( Wang et al, 2020b ). ⑥ Anti-apoptosis of cardiomyocytes …”

Section: Pharmacological Activitiesmentioning

confidence: 99%

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Storax, A Promising Botanical Medicine for Treating Cardio-Cerebrovascular Diseases: A Review

Yuan

et al. 2021

Front. Pharmacol.

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In recent years, the incidence and mortality of cardio-cerebrovascular diseases have been increasing year by year, which has become global burden and challenge. Based on the holistic thinking of “brain disease affects the heart” and “heart disease affects the brain,” as well as the characteristics of multi-target and multi-path effects of Chinese medicine, Chinese medicine is more advantageous in the treatment of cardio-cerebrovascular diseases. As a botanical medicine, storax is known for its resuscitation, filth avoidance and pain-relieving effects in the treatment of cardio-cerebrovascular diseases. By reviewing and collating the relevant domestic and international literature in the past 10 years, we have sorted out an overview of the medicinal parts, traditional uses and chemical composition of storax. For the first time, based on the idea of “cerebral and cardiac simultaneous treatment,” the pharmacological activities and mechanisms of heart and brain protection of storax for treating cardio-cerebrovascular diseases were summarized and analyzed, showing that storax has the pharmacological effects of anti-cerebral ischemia, regulation of blood-brain barrier, bidirectional regulation of the central nervous system, anti-myocardial ischemia, anti-arrhythmia, anti-thrombosis and anti-platelet aggregation. It mainly exerts its protective effects on the brain and heart through mechanisms such as inhibition of inflammatory immune factors, anti-oxidative stress, anti-apoptosis, pro-neovascularization and regulation of NO release. On the basis of the current findings and limitations, the future research strategies and perspectives of storax are proposed, with a view to providing a reference for further application and development of this medicine, as well as contributing new thoughts and visions for the clinical application of “treating brain-heart synchronously”.

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Section: Pharmacological Activitiesmentioning

confidence: 99%

Section: Phytochemical Constituentsmentioning

confidence: 99%

Section: Pharmacological Activitiesmentioning

confidence: 99%

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Storax, A Promising Botanical Medicine for Treating Cardio-Cerebrovascular Diseases: A Review

Yuan

et al. 2021

Front. Pharmacol.

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“…According to the method reported in the previous literature, with a slight modification, the type of inhibition of PL by active peptides was determined ( 29 , 30 ). The peptide (0.8 mg/mL, final concentration) was reacted with different concentrations (0, 5, 10, 15, 20 mg/mL) of PL for 10 min, then 10 mM p NPB was added for 10 min.…”

Section: Methodsmentioning

confidence: 99%

Efficient screening of pancreatic lipase inhibitors from cod meat hydrolysate through ligand fishing strategy

Tian

Liu²,

Wang³

et al. 2022

Front. Nutr.

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Obesity has become an increasingly serious public health problem. Pancreatic lipase (PL) is identified as a ideal target for the prevention and treatment of obesity. Orlistat, the only approved PL inhibitor (PLI), is a powerful weight loss drug but has many side effects. Therefore, there is an urgent need to discover powerful PLIs with high safety. Protein hydrolysate has been demonstrated to be a treasure trove of PLIs, but recognizing responsible functional peptides from them is like looking for a needle in a haystack. In this work, we synthesized and optimized a PL ligand fishing model (PLLFM) using magnetic nanoparticles (MNPs), then PLLFM was used to quickly fish out potential PLIs from the Cod meat hydrolysate (CMH). Finally, two new PLIs, GSPPPSG and KLEGDLK were identified with IC50 of 0.60 and 1.08 mg/mL, respectively. The Lineweaver-Burk diagram showed that GSPPPSG is a non-competitively dominant mixed-type PLI, whereas KLEGDLK is a competitive inhibitory-type PLI. Moreover, molecular docking suggested that both peptides can stably bind to the key amino acid residues of the PL active site, mainly through hydrogen bonding, hydrophobic, and electrostatic interactions. In general, we not only established a method to rapidly fish out potential PLIs from protein hydrolysate, but also provided safe and efficient lead compounds for the development of novel diet foods or drugs.

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“…Betulonic acid ( 1 ) is a pentacyclic triterpene belonging to the lupane group isolated from many plants. − As one of the most important oxo-derivatives of betulin, betulonic acid exhibits a broad spectrum of biological activities, such as anti-inflammatory, antimelanoma, antiviral, and antioxidant activities. , Additionally, betulonic acid can serve as a key pharmaceutical intermediate for the production of new drugs. It has attracted significant interest in the pharmaceutical, cosmetic, and food industries …”

mentioning

confidence: 99%

Biotransformation of Betulonic Acid by the Fungus Rhizopus arrhizus CGMCC 3.868 and Antineuroinflammatory Activity of the Biotransformation Products

Song

Chu

et al. 2021

J. Nat. Prod.

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Biotransformation of betulonic acid (1) by Rhizopus arrhizus CGMCC 3.868 resulted in the production of 16 new (3, 5, 6, and 9–21) and five known compounds. Structures of the new compounds were established by analysis of spectroscopic data. Hydroxylation, acetylation, oxygenation, glycosylation, and addition reactions involved the C-20–C-29 double bond. Antineuroinflammatory activities of the obtained compounds in NO production were tested in lipopolysaccharides-induced BV-2 cells. Compared with the substrate betulonic acid, biotransformation products 3, 8, 9, 14, and 21 exhibited an improved inhibitory effect, with IC50 values of 10.26, 11.09, 5.38, 1.55, and 4.69 μM, lower than that of the positive control, N G-monomethyl-l-arginine.

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Discovery and characterization of pentacyclic triterpenoid acids in Styrax as potent and reversible pancreatic lipase inhibitors

Cited by 14 publications

References 70 publications

Storax, A Promising Botanical Medicine for Treating Cardio-Cerebrovascular Diseases: A Review

Storax, A Promising Botanical Medicine for Treating Cardio-Cerebrovascular Diseases: A Review

Efficient screening of pancreatic lipase inhibitors from cod meat hydrolysate through ligand fishing strategy

Biotransformation of Betulonic Acid by the Fungus Rhizopus arrhizus CGMCC 3.868 and Antineuroinflammatory Activity of the Biotransformation Products

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