Accurate Identification of Bioactive Meliaceae Limonoids by UHPLC-MS/MS Based Structure-Fragment Relationships (SFRs).
Accurate Identification of Bioactive Meliaceae Limonoids by UHPLC-MS/MS Based Structure-Fragment Relationships (SFRs).
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DOI：
10.1021/acsomega.1c03697
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发表时间：
2021-10-12
期刊：
影响因子：
4.1
通讯作者：
Thulasiram HV
中科院分区：
文献类型：
--
作者：
Mulani FA;Nandikol SS;Haldar S;Thulasiram HV
Limonoids are bioactive plant specialized metabolites found in the Meliaceae family. The basic limonoids, i.e., azadiradione, epoxyazadiradione, and gedunin have been exploited for various bioactivities and therefore are the potential drug leads for tomorrow. However, their low abundance, structural similarity, and lack of adequate mass fragmentation data have hampered their accurate identification and quantification from various sources. In the present study, basic limonoids such as azadirone, azadiradione, epoxyazadiradione, and gedunin isolated from Neem were utilized for the synthesis of their derivatives and isotopologs. A total of 30 one compounds were used in this study among which five were isolated, two were biotransformed, and 24 were synthesized. Among the synthesized compounds nine are novel compounds including six deuterated analogs/isotopologs which are (1,3-2H)-1,2-dihydro-3β-hydroxyazadiradione (9), (1,3,16-2H)-1,2-dihydro-3β-16β-dihydroxyazadiradione (10), 3β-hydroxyazadiradione (11), 3β-16β-dihydroxyazadiradione (12), (3-2H)-3β-hydroxyazadiradione (13), (3,16-2H)-3β-16β-dihydroxyazadiradione (14), (1,3,7-2H)-1,2-dihydro-3β-hydroxy-7-deacetylazadiradione (15), 1,2,20,21,22,23-hexahydroazadiradione (17), and (1,3-2H)-1,2-dihydro-3β-hydroxygedunin (29). These limonoids along with their semisynthesized derivatives were subjected to ultra high performance liquid chromatography mass spectrometry (UHPLC–MS/MS) and the fragmentation pathway was established based on structure–fragment relationships (SFRs), utilizing high resolution MS/MS data. We have developed a most reliable and easily reproducible protocol describing in depth analysis of SFRs based on the structural modifications and synthesis of isotopologs. Also, the MS/MS fragment library of these basic limonoids generated in this study acts as a fingerprint for accurate identification and quantification of limonoids by MS/MS analysis in various plant tissue extracts, phytopharmaceutical formulations and biological samples.
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影响因子：
5.3
作者：
Aarthy T;Mulani FA;Pandreka A;Kumar A;Nandikol SS;Haldar S;Thulasiram HV
通讯作者：
Thulasiram HV
影响因子：
6.1
作者：
Jaiswal, Rakesh;Kuhnert, Nikolai
通讯作者：
Kuhnert, Nikolai
影响因子：
8.8
作者：
De Rosso, M.;Tonidandel, L.;Flamini, R.
通讯作者：
Flamini, R.
影响因子：
7.4
作者：
Garcia-Reyes, Juan F.;Molina-Diaz, Antonio;Fernandez-Alba, Amadeo R.
通讯作者：
Fernandez-Alba, Amadeo R.
影响因子：
9.8
作者：
Haldar, Saikat;Kolet, Swati P.;Thulasiram, Hirekodathakallu V.
通讯作者：
Thulasiram, Hirekodathakallu V.