Putative Identification of New Phragmaline-Type Limonoids from the Leaves of Swietenia macrophylla King: A Case Study Using Mass Spectrometry-Based Molecular Networking

被引:1
作者
Reis, Jose Diogo E. [1 ,2 ]
Gomes, Paulo Wender P. [3 ,4 ]
Sa, Paulo R. da C. [5 ]
Pamplona, Sonia das G. S. R. [1 ]
Yumiko Y. e Silva, Consuelo [1 ,6 ]
da Silva, Maria Fatima das G. F. [7 ]
Bishayee, Anupam [8 ]
da Silva, Milton Nascimento [1 ,2 ,6 ]
机构
[1] Fed Univ Para, Inst Exact & Nat Sci, Lab Liquid Chromatog, BR-66075110 Belem, Brazil
[2] Fed Univ Para, Inst Exact & Nat Sci, Chem Postgrad Program, BR-66075110 Belem, Brazil
[3] Univ Calif San Diego, Collaborat Mass Spectrometry Innovat Ctr, Skaggs Sch Pharm & Pharmaceut Sci, La Jolla, CA 92093 USA
[4] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, La Jolla, CA 92093 USA
[5] Fed Inst Para, Campus Castanhal, BR-68740970 Castanhal, Brazil
[6] Fed Univ Para, Inst Hlth Sci, Pharmaceut Sci Postgrad Program, BR-66075110 Belem, Brazil
[7] Univ Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, Brazil
[8] Lake Erie Coll Osteopath Med, Coll Osteopath Med, Bradenton, FL 16509 USA
关键词
limonoids; Meliaceae; mahogany; molecular networking; GNPS; mass spectrometry; ORTHO ESTERS; SEEDS; FRAGMENTATION; CONSTITUENTS; ANTIFEEDANTS; DIACETATE; MS/MS;
D O I
10.3390/molecules28227603
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Swietenia macrophylla King is a plant commonly known as Brazilian mahogany. The wood from its stem is highly prized for its exceptional quality, while its leaves are valued for their high content of phragmalin-type limonoids, a subclass of compounds known for their significant biological activities, including antimalarial, antitumor, antiviral, and anti-inflammatory properties. In this context, twelve isolated limonoids from S. macrophylla leaves were employed as standards in mass spectrometry-based molecular networking to unveil new potential mass spectrometry signatures for phragmalin-type limonoids. Consequently, ultra-performance liquid chromatography coupled with high-resolution mass spectrometry was utilized for data acquisition. Subsequently, the obtained data were analyzed using the Global Natural Products Social Molecular Networking platform based on spectral similarity. In summary, this study identified 24 new putative phragmalin-type limonoids for the first time in S. macrophylla. These compounds may prove valuable in guiding future drug development efforts, leveraging the already established biological activities associated with limonoids.
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页数:14
相关论文
共 64 条
[31]   Limonoids from the fruits of Swietenia macrophylla with inhibitory activity against H2O2-induced apoptosis in HUVECs [J].
Ma, Ya-Qian ;
Liu, Meng-Han ;
Jiang, Kun ;
Guo, Lan ;
Qu, Shi-Jin ;
Wan, Yi-Qun ;
Tan, Chang-Heng .
FITOTERAPIA, 2018, 129 :179-184
[32]   Mexicanolide-type limonoids from the seeds of Swietenia macrophylla [J].
Ma, Ya-Qian ;
Jiang, Kun ;
Deng, Yi ;
Guo, Lan ;
Wan, Yi-Qun ;
Tan, Chang-Heng .
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2018, 20 (04) :299-305
[33]  
Mak KK, 2021, Phytomedicine Plus, V1, P100018, DOI [10.1016/j.phyplu.2020.100018, DOI 10.1016/J.PHYPLU.2020.100018, 10.1016/j.phyplu.2020.100018]
[34]   Two new compounds from the roots of Swietenia macrophylla [J].
Mi, Cheng-Neng ;
Li, Wei ;
Chen, Hui-Qin ;
Wang, Jun ;
Cai, Cai-Hong ;
Li, Shao-Peng ;
Mei, Wen-Li ;
Dai, Hao-Fu .
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2019, 21 (10) :1005-1012
[35]  
Mi Cheng-neng, 2017, Journal of Tropical and Subtropical Botany, V25, P610, DOI 10.11926/jtsb.3754
[36]   Limonoids from Swietenia macrophylla and S-aubrevilleana [J].
Mootoo, BS ;
Ali, A ;
Motilal, R ;
Pingal, R ;
Ramlal, A ;
Khan, A ;
Reynolds, WF ;
McLean, S .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (11) :1514-1517
[37]   Multi-target antidiabetic mechanisms of mexicanolides from Swietenia humilis [J].
Ovalle-Magallanes, Berenice ;
Navarrete, Andres ;
Haddad, Pierre S. ;
Tovar, Armando R. ;
Noriega, Lilia G. ;
Tovar-Palacio, Claudia ;
Mata, Rachel .
PHYTOMEDICINE, 2019, 58
[38]   Phragmalin Limonoids from Swietenia macrophylla and Their Antifeedant Assay against Mahogany Predator [J].
Pamplona, Sonia G. S. R. ;
Arruda, Mara S. P. ;
Castro, Kelly C. F. ;
Silva, Consuelo Y. Y. e ;
Ferreira, Antonio G. ;
da Silva, Maria F. G. F. ;
Ohashi, Orlando S. ;
da Silva, Milton N. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2018, 29 (08) :1621-1629
[39]   Anticancer potential of limonoids from Swietenia macrophylla: Genotoxic, antiproliferative and proapoptotic effects towards human colorectal cancer [J].
Pinto, Laine C. ;
Mesquita, Felipe P. ;
Barreto, Leilane H. ;
Souza, Pedro F. N. ;
Ramos, Ingryd N. F. ;
Pinto, Adrielly V. U. ;
Soares, Bruno M. ;
Silva, Milton N. da ;
Burbano, Rommel M. R. ;
Montenegro, Raquel C. .
LIFE SCIENCES, 2021, 285
[40]   MZmine 2: Modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data [J].
Pluskal, Tomas ;
Castillo, Sandra ;
Villar-Briones, Alejandro ;
Oresic, Matej .
BMC BIOINFORMATICS, 2010, 11