Structurally diverse triterpenes obtained from the fruits of <i>Ziziphus jujuba</i> Mill. as inflammation inhibitors by NF-κB signaling pathway

Ruan, Jing; Sun, Fan; Hao, Mimi; Han, Lifeng; Yu, Haiyang; Lin, Fanyou; Wang, Limin; Cao, Guohao; Zhang, Yi; Wang, Tao

doi:10.1039/d1fo00117e

Cited by 14 publications

(5 citation statements)

References 33 publications

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“…2-O-Trans-p-coumaroyl maslinic and 3-oxo-urs-12-en-28-oic acids had no inhibitory effect on RAW 246.7 cell activity at 5 µM and inhibited the production of NO, both of which were passed. The NF-κB signaling pathway exhibited anti-inflammatory activity by downregulating the expression of inflammatory factors [ 33 ]. Another study reported that triterpenoid saponins moderately inhibited the release of the proinflammatory cytokine TNF-αin LPS-induced RAW 246.7 macrophages [ 48 ].…”

Section: Resultsmentioning

confidence: 99%

Triterpenoids in Jujube: A Review of Composition, Content Diversity, Pharmacological Effects, Synthetic Pathway, and Variation during Domestication

Pan

Zhao

Liu

et al. 2023

Plants

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Chinese jujube (Ziziphus jujuba Mill.) and its wild ancestor, sour jujube (Z. acidojujuba C.Y. Cheng & M.J. Liu), is a Ziziphus genus in the Rhamnaceae family. ZJ and ZA are rich in a variety of active ingredients, with triterpenoids being a unique active ingredient, which are present in the fruit, leaves, branches, and roots. More than 120 triterpenoids have been identified in ZJ and ZA, and have various biological activities, such as betulinic and ursolic acids with anticancer, antioxidant, antibacterial, and antiviral activities, and ceanothic, alphitolic, and zizyberanalic acids with anti-inflammatory activities. The MVP pathway is a synthetic pathway for triterpenoids in ZJ and ZA, and 23 genes of the MVP pathway are known to regulate triterpene synthesis in ZJ and ZA. In order to better understand the basic situation of triterpenoids in ZJ and ZA, this paper reviews the types, content dynamic changes, activities, pharmacokinetics, triterpenoid synthesis pathways, and the effects of domestication on triterpenoids in ZJ and ZA, and provides some ideas for the future research of triterpenoids in ZJ and ZA. In addition, there are many types of ZJ and ZA triterpenoids, and most of the studies on their activities are on lupane- and ursane-type triterpenes, while the activities of the ceanothane-type and saponin are less studied and need additional research.

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Section: Resultsmentioning

confidence: 99%

Triterpenoids in Jujube: A Review of Composition, Content Diversity, Pharmacological Effects, Synthetic Pathway, and Variation during Domestication

Pan

Zhao

Liu

et al. 2023

Plants

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“…Compounds 9 – 15 were identified by comparing the spectroscopic data with those reported in literature. The effects of compounds 1 – 15 on LPS-stimulated NO release were measured by using Griess reaction in RAW 264.7 cells 24 . Compounds 2, 3, 7 , and 12 – 15 significantly inhibited NO release at 50 µM ( Table 4 and Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The LPS treated RAW 264.7 cells were analyzed by Western blot using a previously reported method [24]. The protein concentrations in the supernatants and tissues were quantified with a bicinchoninic acid protein assay kit.…”

Section: Western Blot Analysismentioning

confidence: 99%

NO Release Inhibitory Activity of Flavonoids from Aesculus Wilsonii Seeds through MAPK (P38), NF-κB, and STAT3 Cross-Talk Signaling Pathways

et al. 2022

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The flavonoid constituents of Aesculus wilsonii, a source of the Chinese medicinal drug Suo Luo Zi, and their in vitro anti-inflammatory effects were investigated. Fifteen flavonoids, including aeswilflavonosides IA–IC (1–3) and aeswilflavonosides IIA–IIE (4–8), along with seven known derivatives were isolated from a seed extract. Their structures were elucidated by extensive spectroscopic methods, acid and alkaline hydrolysis, and calculated electronic circular dichroism (ECD) spectra. Among them, compounds 3 and 7 possess a 5-[2-(carboxymethyl)-5-oxocyclopent-yl]pent-3-enylate or oleuropeoylate substituent, respectively, which are rarely reported in flavonoids. Compounds 2, 3, 7, and 1215 were found to inhibit lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 cell lines. In a mechanistic assay, the flavonoid glycosides 2, 3, and 7 reduced the expressions of interleukin-6 (IL-6) and tumor necrosis factor (TNF-α) induced by LPS. Further investigations suggest that 2 and 3 down-regulate the protein expression of TNF-α and IL-6 by inhibiting the phosphorylation of p38. Compound 7 was found to reduce the production of inducible nitric oxide synthase (iNOS), and the secrection of TNF-α and IL-6 through inhibiting nuclear factor kappa-light-chain-enhancer of activated B (NF-κB) signaling pathway. Compounds 2, 3 and 7 possessed moderate inhibitory activity on the expression of signal transducer and activator of transcription 3 (STAT3). Taken together, the data indicate that the flavonoid glycosides of A. wilsonii seeds exhibit NO release inhibitory activity through mitogen-activated protein kinase (p38) [MAPK (p38)], NF-κB and STAT3 cross-talk signaling pathways.

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“…Indeed, altered intracellular calcium concentration can act as a crucial signal for T cell proliferation and activation [37][38][39][40]. In a previous study, ALA was shown to inhibit the nuclear factor-kappa B (NF-κB) pathway [41]. As with intracellular calcium signaling, the NF-κB pathway is associated with immune cell activity, proliferation, and differentiation, whereas the pathway proteins are engaged in activities such as epithelial cell differentiation or apoptosis [42].…”

Section: Discussionmentioning

confidence: 99%

Anti-Inflammatory Effects of Alphitolic Acid Isolated from Agrimonia coreana Nakai Extracts Are Mediated via the Inhibition of ICRAC Activity in T Cells

Park,

Lee,

Nam

et al. 2023

IJMS

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Agrimonia pilosa Ledeb., an important medicinal herb in traditional East Asian medicine, is primarily used to treat abdominal pain, dysentery, and hemostasis. There are ten other reported species of Agrimonia plants, including Agrimonia coreana Nakai—a naturally growing species in South Korea—and Agrimonia eupatoria Linn. Although recent studies have isolated numerous active constituents and investigated their effects, the medicinal utility of this herb is not yet fully explored. Through patch-clamp recording, a previous study reported that Agrimonia plant extracts inhibit the function of Ca2+ release-activated Ca2+ channels (CRACs). Herein, we aimed to identify and isolate the main compounds in A. coreana responsible for CRAC inhibition while assessing the anti-inflammatory effects mediated by this inhibition. We demonstrated for the first time that alphitolic acid isolated from A. coreana has a dose-dependent inhibitory effect on CRAC activity and, thus, an inhibitory effect on intracellular calcium increase. Furthermore, analysis of human CD4+ T cell proliferation via the carboxyfluorescein diacetate succinimidyl ester method revealed that alphitolic acid inhibited T cell proliferation in a concentration-dependent manner. Our findings provide a theoretical basis for the potential therapeutic use of alphitolic acid in the treatment of inflammatory diseases.

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Structurally diverse triterpenes obtained from the fruits of Ziziphus jujuba Mill. as inflammation inhibitors by NF-κB signaling pathway

Abstract: Twenty-nine triterpenes were obtained from the fruits of Ziziphus jujuba Mill. by using various chromatography and the stereo-structures were confirmed by spectroscopic methods. Among them, 2α,3β,20-trihydroxylupane-28-oic acid (1) was identified...

Cited by 14 publications

References 33 publications

Triterpenoids in Jujube: A Review of Composition, Content Diversity, Pharmacological Effects, Synthetic Pathway, and Variation during Domestication

Triterpenoids in Jujube: A Review of Composition, Content Diversity, Pharmacological Effects, Synthetic Pathway, and Variation during Domestication

NO Release Inhibitory Activity of Flavonoids from Aesculus Wilsonii Seeds through MAPK (P38), NF-κB, and STAT3 Cross-Talk Signaling Pathways

Anti-Inflammatory Effects of Alphitolic Acid Isolated from Agrimonia coreana Nakai Extracts Are Mediated via the Inhibition of ICRAC Activity in T Cells

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