A Review on the Phytochemistry, Pharmacology, Pharmacokinetics and Toxicology of Geniposide, a Natural Product

Shan, Mingqiu; Yu, Sheng; Yan, Hui; Guo, Sheng; Xiao, Wei; Wang, Zhenzhong; Zhang, Li; Ding, Anwei; Wu, Qinan; Li, Sam Fong Yau

doi:10.3390/molecules22101689

Cited by 93 publications

(66 citation statements)

References 152 publications

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“…It was previously shown to inhibit 5-lipoxygenase [33] and the tumor-promoting factor P-glycoprotein [34] and have anti-angiogenic activity [35] and potential antiasthma properties [36]. Additionally, geniposide was shown recently to protect against sepsis-induced myocardial dysfunction by activating AMPKα to suppress myocardial reactive oxygen species (ROS) accumulation [37]. It is present in nearly 40 species belonging to various families, especially the Rubiaceae, among which the most representative are Tinospora capillipes (native to China), Paederia scandens (native to China), Cornus officinalis (native to China, Japan, Korea), Eucommia ulmoides (native to China), Lantana camara (weed native to Mexico, Central America, the Caribbean, and tropical South America), Paratinospora sagittata (present in southern Taiwanese and mainland Chinese disjunction), Artemisia capillaries (Chinese medicinal herb), Plantago asiatica (native to China, Japan, Korea), Rehmannia glutinosa (native to China), Plantago depressa (native to China, Korea, Himalayas), and Gardenia jasminoides (native to Vietnam, Southern China, Korea, Taiwan, Japan, Myanmar, India, and Bangladesh).…”

Section: Resultsmentioning

confidence: 99%

Virtual Screening of Natural Products against Type II Transmembrane Serine Protease (TMPRSS2), the Priming Agent of Coronavirus 2 (SARS-CoV-2)

et al. 2020

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Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has caused about 2 million infections and is responsible for more than 100,000 deaths worldwide. To date, there is no specific drug registered to combat the disease it causes, named coronavirus disease 2019 . In the current study, we used an in silico approach to screen natural compounds to find potent inhibitors of the host enzyme transmembrane protease serine 2 (TMPRSS2). This enzyme facilitates viral particle entry into host cells, and its inhibition blocks virus fusion with angiotensin-converting enzyme 2 (ACE2). This, in turn, restricts SARS-CoV-2 pathogenesis. A three-dimensional structure of TMPRSS2 was built using SWISS-MODEL and validated by RAMPAGE. The natural compounds library Natural Product Activity and Species Source (NPASS), containing 30,927 compounds, was screened against the target protein. Two techniques were used in the Molecular Operating Environment (MOE) for this purpose, i.e., a ligand-based pharmacophore approach and a molecular docking-based screening. In total, 2140 compounds with pharmacophoric features were retained using the first approach. Using the second approach, 85 compounds with molecular docking comparable to or greater than that of the standard inhibitor (camostat mesylate) were identified. The top 12 compounds with the most favorable structural features were studied for physicochemical and ADMET (absorption, distribution, metabolism, excretion, toxicity) properties. The low-molecular-weight compound NPC306344 showed significant interaction with the active site residues of TMPRSS2, with a binding energy score of −14.69. Further in vitro and in vivo validation is needed to study and develop an anti-COVID-19 drug based on the structures of the most promising compounds identified in this study.

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Section: Resultsmentioning

confidence: 99%

Virtual Screening of Natural Products against Type II Transmembrane Serine Protease (TMPRSS2), the Priming Agent of Coronavirus 2 (SARS-CoV-2)

et al. 2020

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“…Geniposide is isolated from medicinal herbs for cholestasis such as Gardenia jasminoides Ellis. Geniposide has many beneficial effects including anti‐inflammation and hepatoprotection . It protects against ANIT‐induced cholestasis and d ‐GlaN/LPS hepatotoxicity .…”

Section: Paradoxical Hepatoprotection and Hepatotoxicity With Herbal mentioning

confidence: 99%

“…Geniposide has many beneficial effects including anti-inflammation and hepatoprotection. 102 It protects F I G U R E 4 TRG5 activation by OA could cause both hepatoprotection and hepatotoxicity. A, d-GlaN/LPS-induced liver injury is associated with cholestasis, and low dose of OA (90 mg/kg, po × 4 d) showed hepatoprotection 37 ; B, high dose of OA (1000 μmoles, 451 mg/kg, po × 10 d) produced cholestatic liver injury as showed in arrows 18 ; C, OA (91 mg/kg, sc × 1 d) produced apparent cell proliferation, and mitotic cells are shown in arrows 27 OA Hepatoprotection Hepatotoxicity TGR5 Cell Proliferation…”

Section: Par Adoxic Al Hepatoprotec Tion and Hepatotoxi Cit Y With mentioning

confidence: 99%

Oleanolic acid reprograms the liver to protect against hepatotoxicants, but is hepatotoxic at high doses

Liu

Lü

et al. 2018

Liver International

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Oleanolic acid (OA) is a triterpenoid that exists widely in fruits, vegetables and medicinal herbs. OA is included in some dietary supplements and is used as a complementary and alternative medicine (CAM) in China, India, Asia, the USA and European countries. OA is effective in protecting against various hepatotoxicants, and one of the protective mechanisms is reprogramming the liver to activate the nuclear factor erythroid 2-related factor 2 (Nrf2). OA derivatives, such as CDDO-Im and CDDO-Me, are even more potent Nrf2 activators. OA has recently been shown to also activate the Takeda G-protein-coupled receptor (TGR5). However, whereas a low dose of OA is hepatoprotective, higher doses and long-term use of OA can produce liver injury, characterized by cholestasis. This paradoxical hepatotoxic effect occurs not only for OA, but also for other OA-type triterpenoids. Dose and length of time of OA exposure differentiate the ability of OA to produce hepatoprotection vs hepatotoxicity. Hepatotoxicity produced by herbs is increasingly recognized and is of global concern. Given the appealing nature of OA in dietary supplements and its use as an alternative medicine around the world, as well as the development of OA derivatives (CDDO-Im and CDDO-Me) as therapeutics, it is important to understand not only that they program the liver to protect against hepatotoxic chemicals, but also how they produce hepatotoxicity.

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“…A previous study revealed that 6,8-di-C-β-d-glucopyranosyl-luteolin (lucenin-2) is weakly or not cytotoxic against five cancer cell lines [28]. Therefore, iridoids might be responsible for the cytotoxic effect on neutrophils, since some of these metabolites have been described as antiproliferative agents [29]. No toxicity study was found in the literature on banana inflorescences; however, previous bioassays have shown that its incorporation in rat diets might modulate serum cholesterol and glucose [8].…”

Section: Discussionmentioning

confidence: 99%

NOx-, IL-1β-, TNF-α-, and IL-6-Inhibiting Effects and Trypanocidal Activity of Banana (Musa acuminata) Bracts and Flowers: UPLC-HRESI-MS Detection of Phenylpropanoid Sucrose Esters

et al. 2019

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Banana inflorescences are a byproduct of banana cultivation consumed in various regions of Brazil as a non-conventional food. This byproduct represents an alternative food supply that can contribute to the resolution of nutritional problems and hunger. This product is also used in Asia as a traditional remedy for the treatment of various illnesses such as bronchitis and dysentery. However, there is a lack of chemical and pharmacological data to support its consumption as a functional food. Therefore, this work aimed to study the anti-inflammatory action of Musa acuminata blossom by quantifying the cytokine levels (NO x , IL-1β, TNF-α, and IL-6) in peritoneal neutrophils, and to study its antiparasitic activities using the intracellular forms of T. cruzi, L. amazonensis, and L. infantum. This work also aimed to establish the chemical profile of the inflorescence using UPLC-ESI-MS analysis. Flowers and the crude bract extracts were partitioned in dichloromethane and n-butanol to afford four fractions (FDCM, FNBU, BDCM, and BNBU). FDCM showed moderate trypanocidal activity and promising anti-inflammatory properties by inhibiting IL-1β, TNF-α, and IL-6. BDCM significantly inhibited the secretion of TNF-α, while BNBU was active against IL-6 and NO x . LCMS data of these fractions revealed an unprecedented presence of arylpropanoid sucroses alongside flavonoids, triterpenes, benzofurans, stilbenes, and iridoids. The obtained results revealed that banana inflorescences could be used as an anti-inflammatory food ingredient to control inflammatory diseases.

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A Review on the Phytochemistry, Pharmacology, Pharmacokinetics and Toxicology of Geniposide, a Natural Product

Cited by 93 publications

References 152 publications

Virtual Screening of Natural Products against Type II Transmembrane Serine Protease (TMPRSS2), the Priming Agent of Coronavirus 2 (SARS-CoV-2)

Virtual Screening of Natural Products against Type II Transmembrane Serine Protease (TMPRSS2), the Priming Agent of Coronavirus 2 (SARS-CoV-2)

Oleanolic acid reprograms the liver to protect against hepatotoxicants, but is hepatotoxic at high doses

NOx-, IL-1β-, TNF-α-, and IL-6-Inhibiting Effects and Trypanocidal Activity of Banana (Musa acuminata) Bracts and Flowers: UPLC-HRESI-MS Detection of Phenylpropanoid Sucrose Esters

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