Anti-Aging Activities and LC-MS Analysis of Chrysophyllum cainito Leaves Extract

Authors

  • Parichat Thepthong Innovative Material Chemistry for Environment Center, Department of Chemistry, Faculty of Science and Digital Innovation, Thaksin University, Phattalung 93210, Thailand
  • Netnapa Chana Innovative Material Chemistry for Environment Center, Department of Chemistry, Faculty of Science and Digital Innovation, Thaksin University, Phattalung 93210, Thailand
  • Maliwan Noonmai Department of Chemistry, Faculty of Science and Digital Innovation, Thaksin University, Phattalung 93210, Thailand
  • Wipawee Boonsri Department of Chemistry, Faculty of Science and Digital Innovation, Thaksin University, Phattalung 93210, Thailand
  • Nisakorn Saewan School of Cosmetic Science, Mae Fah Luang University, Chiang Rai 57100, Thailand

DOI:

https://doi.org/10.48048/tis.2024.8375

Keywords:

Chrysophyllum cainito, Leaves, Antioxidant, Anti-tyrosinase, Anti-collagenase, Cell proliferation, LC-MS

Abstract

Star apple (Chrysophyllum cainito L.), or Apple-nam in Thai, is a medium-sized tree in the Sapotaceae family. It is native to Middle America and distributed in Thailand and Southeast Asia. It has antioxidation, anti-inflammatory and anti-diabetic properties. The active compounds in star apples are flavonoids. This research aimed to study the biological activities and chemical constituents of crude extract and active fractions from the leaves of star apples. The leaf powder was defatted with dichloromethane and further extracted with ethanol using ultrasound-assisted extraction. The ethanol extract was separated by quick column chromatography given 7 fractions (CCE1-CCE7). The total phenolic content and antioxidant activity of the extract and chromatographic fractions were determined. The active fractions were further studied for tyrosinase inhibition, collagenase inhibition and cell proliferation properties. The result showed that the highest total phenolic content was observed in ethanol extract. The high polar fraction, CCE6, displayed the highest antioxidation activity with radical scavenging of 0.34 ± 0.01 mg AAE/mL in the DPPH assay and a FRAP value of 1.36 ± 0.01 mg AAE/mL in the FRAP assay. The CCE6 also exhibited the highest anti-tyrosinase and anti-collagenase activities with a percentage of 67.14 ± 1.34 and 70.32 ± 2.88, respectively and showed the best activity in cell proliferation with a percentage of 24.68 ± 2.94. The analysis of the components using the negative ionization LC-MS technique revealed that gallic acid and quercetin-3-galactoside are the major constituents in the ethanol extract. While the fraction CCE6 showed glucosyl (2E,6E,10x)-10,11-dihydroxy-2,6-farnesadienoate and p-mentha-1,3,5,8-tetraene as the predominant compounds.

HIGHLIGHTS

  • The ethanol extract was prepared using ultrasound-assisted extraction.
  • The first report of tyrosinase and collagenase inhibition, as well as cell proliferation properties, of the cainito leaves extract and chromatographic fractions.
  • The major components of the ethanol extract of cainito leaves in Thailand and its active fraction by LC-MS technique were reported for the first time.

GRAPHICAL ABSTRACT

Downloads

Download data is not yet available.

References

M Chaudhary, A Khan and M Gupta. Skin ageing: Pathophysiology and current market treatment approaches. Curr. Aging Sci. 2020; 13, 22-30.

M Cavinato, B Waltenberger, G Baraldo, CVC Grade, H Stuppner and P Jansen-Durr. Plant extracts and natural compounds used against UVB-induced photoaging. Biogerontology 2017; 18, 499-516.

C Lia, Y Fua, H Daia, Q Wangc, R Gaod and Y Zhang. Recent progress in preventive effect of collagen peptides on photoaging skin and action mechanism. Food Sci. Hum. Wellness 2022; 11, 218-29.

X Xu, A Liu, S Hu, I Ares, MR Martínez-Larrañaga, X Wang, M Martínez, A Anadón and MA Martínez. Synthetic phenolic antioxidants: Metabolism, hazards and mechanism of action. Food Chem. 2021; 353, 129488.

NM Mostafa, AM Mostafa, ML Ashour and SS Elhady. Neuroprotective effects of black pepper cold-pressed oil on scopolamine-induced oxidative stress and memory impairment in rats. Antioxidants 2021; 10, 1993.

K Farhadi, F Esmaeilzadeh, M Hatami, M Forough and R Molaie. Determination of phenolic compounds content and antioxidant activity in skin, pulp, seed, cane and leaf of five native grape cultivars in West Azerbaijan province, Iran. Food Chem. 2016; 199, 847-55.

U Phetkul, A Vongkul, K Chaichan, S Paosen, SP Voravuthikunchai, M Daus and S Maungchanbur. Isolation and structural elucidation of coumarin and flavonoids from Citrus grandis Linn. (Tubtim Siam pomelo) and their biological activities. Trends Sci. 2024; 21, 7129.

H Speisky, F Shahidi, AC Camargo and J Fuentes. Revisiting the oxidation of flavonoids: Loss, conservation or enhancement of their antioxidant properties. Antioxidants 2022; 11, 133.

HV Doan and TP Le. Chrysophyllum cainito: A tropical fruit with multiple health benefits. Evid. Based Complement. Alternat. Med. 2020; 2020, 7259267.

XD Luo, MJ Basile and EJ Kennely. Polyphenolic antioxidants from the fruits of Chrysophyllum cainito L. (star apple). J. Agr. Food Chem. 2002; 50, 1379-82.

S Shailajan and D Gurjar. Pharmacognostic and phytochemical evaluation of Chrysophyllum cainito Linn. leaves. Int. J. Pharm. Sci. Rev. Res. 2014; 26, 106-11.

IY Ningsih, S Zulaikhah, MA Hidayat and B Kuswandi. Antioxidant activity of various kenitu (Chrysophyllum cainito L.) leaves extracts from Jember, Indonesia. Agr. Agr. Sci. Procedia 2016; 9, 378-85.

W Vichit and N Saewan. Antioxidant activities and cytotoxicity of Thai pigmented rice. Int. J. Pharm. Pharm. 2015; 7, 329-34.

T Kuda and T Yano. Changes of radical-scavenging capacity and ferrous reducing power in chub mackerel Scomber japonicus and Pacific saury Cololabis saira during 4 C storage and retorting. LWT Food Sci. Tech. 2009; 42, 1070-5.

N Rangkadilok, S Sitthimonchai, L Worasuttayangkurn, C Mahidol, M Ruchirawat and J Satayavivad. Evaluation of free radical scavenging and antityrosinase activities of standardized longan fruit extract. Food Chem. Toxicol. 2007; 45, 328-36.

N Saewan, A Thakam, A Jintaisong and K Kittigowitana. Anti-tyrosinase and cytotoxicity activities of curcumin-metal complexes. Int. J. Pharm. Pharm. Sci. 2014; 6, 270-3.

N Saewan, A Jimtaisong, N Panyachariwat and P Chaiwut. In vitro and in vivo anti-aging effect of coffee berry nanoliposomes. Molecules 2023; 28, 6830.

J Ma, H Yang, MJ Basile and EJ Kennelly. Analysis of polyphenolic antioxidants from the fruits of three pouteria species by selected ion monitoring liquid chromatography-mass spectrometry. J. Agr. Food Chem. 2004; 52, 5873-8.

O López-Fernández, R Domínguez, M Pateiro, PES Munekata, G Rocchetti and JM Lorenzo. Determination of polyphenols using liquid chromatography-tandem mass spectrometry technique (LC-MS/MS): A review. Antioxidants 2020; 9, 479.

IY Ningsih, S Zulaikhah, MA Hidayataand and B Kuswandi. Antioxidant activity of various Kenitu (Chrysophyllum cainito L.) leaves extracts from Jember, Indonesia. Agr. Agr. Sci Procedia 2016; 9, 378-85.

BY Sin and HP Kim. Inhibition of collagenase by naturally-occurring flavonoids. Arch. Pharm. Res. 2005; 28, 1152-5.

GS Sim, BC Lee, HS Cho, JW Lee, JH Kim, DH Lee, JH Kim, HB Pyo, DC Moon, KW Oh, YP Yun and JT Hong. Structure-activity relationship of antioxidative property of flavonoids and inhibitory effect on matrix metalloproteinase activity in UVA-irradiated human dermal fibroblast. Arch. Pharm. Res. 2007; 30, 290-8.

A Singh, V Bajpai, S Kumar, K Rai Sharma and B Kumar. Profiling of gallic and ellagic acid derivatives in different plant parts of Terminalia arjuna by HPLC-ESI-QTOF-MS/MS. Nat. Prod. Commun. 2016; 11, 239-44.

Y Zhang, H Xiong, X Xu, X Xue, M Liu, S Xu, H Liu, Y Gao, H Zhang and X Li. Compounds identification in Semen Cuscutae by ultra-high-performance liquid chromatography (UPLCs) coupled to electrospray ionization mass spectrometry. Molecules 2018; 23, 1199.

B Ma’arif, KHP Putra, MS ‘Arifin, Rukiana, R Amiruddin, WS Bhagawan, A Suryadinata, FR Inayatilah, R Muti’ah and A Aditama. Metabolite profiling and activity study of ethanol extract of Chrysophyllum cainito L. leaves in increasing bone density in male mice. Thai J. Pharmaceut. Sci. 2022; 46, 69-74.

Downloads

Published

2024-10-15