Isolation and microbial transformation of tea sapogenin from seed pomace of Camellia oleifera with anti-inflammatory effects

Pingping SHEN , Xuewa JIANG , Jingling ZHANG , Jiayi WANG , Richa Raj , Guolong LI , Haixia GE , Weiwei WANG , Boyang YU , Jian ZHANG

Chinese Journal of Natural Medicines ›› 2024, Vol. 22 ›› Issue (3) : 280 -288.

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Chinese Journal of Natural Medicines ›› 2024, Vol. 22 ›› Issue (3) :280 -288. DOI: 10.1016/S1875-5364(24)60598-4
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Isolation and microbial transformation of tea sapogenin from seed pomace of Camellia oleifera with anti-inflammatory effects
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Abstract

In the current study, tea saponin, identified as the primary bioactive constituent in seed pomace of Camellia oleifera Abel., was meticulously extracted and hydrolyzed to yield five known sapogenins: 16-O-tiglogycamelliagnin B (a), camelliagnin A (b), 16-O-angeloybarringtogenol C (c), theasapogenol E (d), theasapogenol F (e). Subsequent biotransformation of compound a facilitated the isolation of six novel metabolites (a1a6). The anti-inflammatory potential of these compounds was assessed using pathogen-associated molecular patterns (PAMPs) and damage-associated molecular patterns molecules (DAMPs)-mediated cellular inflammation models. Notably, compounds b and a2 demonstrated significant inhibitory effects on both lipopolysaccharide (LPS) and high-mobility group box 1 (HMGB1)-induced inflammation, surpassing the efficacy of the standard anti-inflammatory agent, carbenoxolone. Conversely, compounds d, a3, and a6 selectivity targeted endogenous HMGB1-induced inflammation, showcasing a pronounced specificity. These results underscore the therapeutic promise of C. oleifera seed pomace-derived compounds as potent agents for the management of inflammatory diseases triggered by infections and tissue damage.

Keywords

Camellia oleifera / Seed pomace / Tea sapogenin / Microbial transformation / Damage-associated molecular patterns and Pathogen-associated molecular patterns / Anti-inflammatory activity

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Pingping SHEN, Xuewa JIANG, Jingling ZHANG, Jiayi WANG, Richa Raj, Guolong LI, Haixia GE, Weiwei WANG, Boyang YU, Jian ZHANG. Isolation and microbial transformation of tea sapogenin from seed pomace of Camellia oleifera with anti-inflammatory effects. Chinese Journal of Natural Medicines, 2024, 22(3): 280-288 DOI:10.1016/S1875-5364(24)60598-4

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References

[1]

Xiong J, Wan J, Ding PJ, et al. Camellianols A-G, barrigenol-like triterpenoids with PTP1B inhibitory effects from the endangered ornamental plant Camellia crapnelliana[J]. J Nat Prod, 2017, 80(11): 2874-2882.

[2]

Liu C, Chen L, Z He, Zhan Z, et al. Integration and potential application ability of culturable functional microorganism in oil tea Camellia[J]. Indian J Microbiol, 2021, 61(1): 1-9.

[3]

Kuo PC, Lin TC, Yang CW, et al. Bioactive saponin from tea seed pomace with inhibitory effects against Rhizoctonia solani[J]. J Agric Food Chem, 2010, 58(15): 8618.

[4]

Ye Y, Fang F, Li Y. Isolation of the sapogenin from defatted seeds of Camellia oleifera and its neuroprotective effects on dopaminergic neurons[J]. J Agric Food Chem, 2014, 62(26): 6175-6182.

[5]

Gong WY, Huang YW, Ji AB, et al. Optimisation of saponin extraction conditions with Camellia sinensis var. assamica seed and its application for a natural detergent[J]. J Sci Food Agric, 2018, 98: 2312-2319.

[6]

Cui C, Zong J, Sun Y, et al. Triterpenoid saponins from the genus Camellia: structures, biological activities, and molecular simulation for structure-activity relationship[J]. Food Funct, 2018, 9(6): 3069-3091.

[7]

Guo N, Tong T, Ren N, et al. Saponins from seeds of genus Camellia: phytochemistry and bioactivity[J]. Phytochemistry, 2018, 149: 42-55.

[8]

Chen Y, Yang C, Chang M, et al. Foam properties and detergent abilities of the saponins from Camellia oleifera[J]. Int J Mol Sci, 2010, 11(11): 4417-4425.

[9]

Qian W, Li XZ, Wu ZP, et al. Formulation of intumescent flame retardant coatings containing natural-based tea saponin[J]. J Agric Food Chem, 2015, 63(10): 2782-2788.

[10]

Darden D, Brakenridge S, Efron P, et al. Biomarker evidence of the persistent inflammation, immunosuppression and catabolism syndrome (PICS) in chronic critical illness (CCI) after surgical sepsis[J]. Ann Surg, 2021, 274(4): 664-673.

[11]

Zindel J, Kubes P. DAMPs, PAMPs, and LAMPs in immunity and sterile inflammation[J]. Annu Rev Pathol Mech, 2020, 15(1): 493-518.

[12]

Greenfield E, Beidelschies M, Tatro J, et al. Bacterial pathogen-associated molecular patterns stimulate biological activity of orthopaedic wear particles by activating cognate Toll-like receptors[J]. J Biol Chem, 2010, 285(42): 32378-32384.

[13]

Van Golen RF, Reiniers MJ, Marsman G, et al. The damage-associated molecular pattern HMGB1 is released early after clinical hepatic ischemia/reperfusion[J]. BBA-Mol Basis Dis, 2019, 1865(6): 1192-1200.

[14]

Pandya U, Egbuta C, Norman TA, et al. The biophysical interaction of the danger-associated molecular pattern (DAMP) calreticulin with the pattern-associated molecular pattern (PAMP) lipopolysaccharide[J]. Int J Mol Sci, 2019, 20(2): 408.

[15]

Bedini A, Baiula M, Vincelli G, et al. Inhibition of Toll-like receptor 4 (TLR4)-induced NF-κB activation by NOPr is lost in human glioblastoma cells chronically exposed to LPS[J]. Brain Behav Immun, 2013, 29: S18-S18.

[16]

Bhardwaj J, Chaudhary N, Seo HJ, et al. Immunomodulatory effect of tea saponin in immune T-cells and T-lymphoma cellsvia regulation of Th1, Th2 immune response and MAPK/ERK2 signaling pathway[J]. Immunopharm Immunot, 2014, 36(3): 202-210.

[17]

Chi X, Bi S, Xu W, et al. Oral administration of tea saponins to relive oxidative stress and immune suppression in chickens[J]. Poult Sci, 2017, 96(9): 3058-3067.

[18]

Shen PP, Wang WY, Xu SH, et al. Biotransformation of erythrodiol for new food supplements with anti-inflammatory properties[J]. J Agric Food Chem, 2020, 68(21): 5910-5916.

[19]

Zhou X, Shen P, Wang W, et al. Derivatization of soyasapogenol A through microbial transformation for potential anti-inflammatory food supplements[J]. J Agric Food Chem, 2021, 69(24): 6791-6798.

[20]

Yoshikawa M, Murakami T, Yoshizumi S, et al. Bioactive saponins and glycosides. V. Acylated polyhydroxyolean-12-ene triterpene oligoglycosides, camelliasaponins A1, A2, B1, B2, C1, and C2, from the seeds of Camellia japonica L.: structures and inhibitory activity on alcohol absorption[J]. Chem Pharm Bull, 1996, 44(10): 1899-1907.

[21]

Carrillo MR, Mitaine-Offer AC, Miyamoto T, et al. Oleanane-type glycosides from Pittosporum tenuifolium "variegatum" and P. tenuifolium "gold star"[J]. Phytochemistry, 2017, 140: 166-173.

[22]

Gao DF, Xu M, Zhao P, et al. Kaempferol acetylated glycosides from the seed cake of Camellia oleifera[J]. Food Chem, 2011, 124(2): 432-436.

[23]

Zhu CF, Zhang M, Tang QL, et al. Structure and activity of the Camellia oleifera sapogenin derivatives on growth and biofilm inhibition of Staphylococcus aureus and Escherichia coli[J]. J Agric Food Chem, 2019, 67(51): 14143-14151.

[24]

Morikawa T, Li N, Nagatomo A. Triterpene saponins with gastroprotective effects from tea seed (the seeds of Camellia sinensis)[J]. J Nat Prod, 2006, 69(2): 185-190.

[25]

Yu H, Chen YH, Cheng Z, et al. Anti-inflammatory oleanane-type triterpenoids produced by Nonomuraea sp. MYH522 through microbial transformation[J]. J Agric Food Chem, 2023, 71(8): 3777-3789.

[26]

Zhao W, Ning L, Zhang X, et al. Cancer chemopreventive theasaponin derivatives from the total tea seed saponin of Camellia sinensis[J]. J Funct Foods, 2015, 12: 192-198.

[27]

Jiang XW, Shen PP, Zhou J, et al. Microbial transformation and inhibitory effect assessment of uvaol derivates against LPS and HMGB1 induced NO production in RAW2647 macrophages[J]. Bioorg Med Chem Lett, 2022, 58: 128523.

[28]

Liu Y, Liu Z, Lu C, et al. Comprehensive identification of active triterpenoid metabolites in frankincense using a coupling strategy[J]. J Chromatogr B, 2014, 963: 90-98.

[29]

Yta B, Xha B, Jian S, et al. Comprehensive evaluation on tailor-made deep eutectic solvents (DESs) in extracting tea saponins from seed pomace of Camellia oleifera Abel[J]. Food Chem, 2020, 342: 128243.

[30]

Horiuchi T, Sakata N, Narumi Y, et al. Metformin directly binds the alarmin HMGB1 and inhibits its proinflammatory activity[J]. J Biol Chem, 2017, 292(20): 8436-8446.

Funding

National Nature Science Foundation of China(21302052)

“Program for New Century Excellent Talents in University” awarded to ZHANG Jian(NECT-11-0739)

Postgraduate Research & Practice Innovation Program of Jiangsu Province(SJKY19_0658)

Jiangsu Funding Program for Excellent Postdoctoral Talent, and “ Jiangsu Funding Program for Excellent Postdoctoral Talent” awarded to SHEN Pingping

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