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
来源
MOLECULES | 2023年 / 28卷 / 22期
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.
引用
收藏
页数:14
相关论文
共 64 条
[1]   Rings B,D-seco limonoids from the leaves of Swietenia mahogani [J].
Abdelgaleil, SAM ;
Doe, M ;
Morimoto, Y ;
Nakatani, M .
PHYTOCHEMISTRY, 2006, 67 (05) :452-458
[2]   Rings B,D-seco limonoid antifeedants from Swietenia mahogani [J].
Abdelgaleil, Samir A. M. ;
Doe, Matsumi ;
Nakatani, Munehiro .
PHYTOCHEMISTRY, 2013, 96 :312-317
[3]   Integration of Molecular Networking and In-Silico MS/MS Fragmentation for Natural Products Dereplication [J].
Allard, Pierre-Marie ;
Peresse, Tiphaine ;
Bisson, Jonathan ;
Gindro, Katia ;
Marcourt, Laurence ;
Van Cuong Pham ;
Roussi, Fanny ;
Litaudon, Marc ;
Wolfender, Jean-Luc .
ANALYTICAL CHEMISTRY, 2016, 88 (06) :3317-3323
[4]  
[Anonymous], 2002, Mogno na Amazonia Brasileira: Ecologia e Perspectivas de Manejo
[5]   BIOLOGICAL-ACTIVITY OF LIMONOIDS FROM THE RUTALES [J].
CHAMPAGNE, DE ;
KOUL, O ;
ISMAN, MB ;
SCUDDER, GGE ;
TOWERS, GHN .
PHYTOCHEMISTRY, 1992, 31 (02) :377-394
[6]   ISOLATION OF SWIETENOLIDE DIACETATE FROM SWIETENIA-MACROPHYLLA [J].
CHAN, KC ;
TANG, TS ;
TOH, HT .
PHYTOCHEMISTRY, 1976, 15 (03) :429-430
[7]   A new phragmalin-type limonoid and anti-inflammatory constituents from the fruits of Swietenia macrophylla [J].
Chen, Jih-Jung ;
Huang, Sheng-Shiou ;
Liao, Chang-Hui ;
Wei, Dau-Chang ;
Sung, Ping-Jyun ;
Wang, Tai-Chi ;
Cheng, Ming-Jen .
FOOD CHEMISTRY, 2010, 120 (02) :379-384
[8]   Limonoids from the Seeds of Swietenia macrophylla and Their Anti-Inflammatory Activities [J].
Chen, Li-Chai ;
Liao, Hsiang-Ruei ;
Chen, Pei-Yu ;
Kuo, Wen-Lung ;
Chang, Tsung-Hsien ;
Sung, Ping-Jyun ;
Wen, Zhi-Hong ;
Chen, Jih-Jung .
MOLECULES, 2015, 20 (10) :18551-18564
[9]  
Cheng YB, 2014, PLANTA MED, V80, P1449
[10]   Limonoids from the Seeds of Swietenia macrophylla with Inhibitory Activity against Dengue Virus 2 [J].
Cheng, Yuan-Bin ;
Chien, Yi-Ting ;
Lee, Jin-Ching ;
Tseng, Chin-Kai ;
Wang, Hui-Chun ;
Lo, I-Wen ;
Wu, Yi-Hung ;
Wang, Sheng-Yang ;
Wu, Yang-Chang ;
Chang, Fang-Rong .
JOURNAL OF NATURAL PRODUCTS, 2014, 77 (11) :2367-2374