Sains Malaysiana 51(6)(2022): 1725-1732

http://doi.org/10.17576/jsm-2022-5106-10

(+)-Neocadambine A and (-)-Nauclederine Isolated from the Bark of Neolamarckia cadamba (Rubiaceae) as Natural Advanced Glycation End Products (AGEs) Inhibitors

((+)-Neocadambine A dan (-)-Nauclederine Diasingkan daripada Kulit Neolamarckia cadamba (Rubiaceae) sebagai Perencat Produk Akhir Glisasi Lanjutan Semula Jadi (AGEs))

NOOR AIMI OTHMAN¹, SOOK YEE LIEW^2,*, PATRICIA BLANCHARD³, SÉVERINE DERBRɳ, SOON-LIM CHONG¹, ABDUL MANAF ALI⁴ & KHALIJAH AWANG^1,5

¹Department of Chemistry, Faculty of Science, Universiti Malaya, 50603 Kuala Lumpur, Federal Territory, Malaysia

²Chemistry Division, Centre for Foundation Studies in Science, Universiti Malaya, 50603 Kuala Lumpur, Federal Territory, Malaysia

³Sonas, EA921, Department of Pharmacy, Faculty of Health Sciences, University of Angers,

16 Bd Daviers, 49045, Angers cedex 01, France

⁴Faculty of Bioresources and Food Industry, Universiti Sultan Zainal Abidin, 22200 Besut, Terengganu Darul Iman, Malaysia

⁵Centre for Natural Products and Drug Discovery (CENAR), Universiti Malaya, 50603 Kuala Lumpur, Federal Territory, Malaysia

Received: 29 March 2021/Accepted: 25 October 2021

ABSTRACT

The phytochemical study on the dichloromethane extract of Neolamarckia cadamba (Roxb.) Bosser has afforded two indole alkaloids, (+)-neocadambine A (1) and (-)-nauclederine (2). Their structures were confirmed by extensive spectroscopic analysis and by comparing with the reported data. (+)-Neocadambine A (1) and (-)-nauclederine (2) exhibited potent inhibition activity of advanced glycation end products (AGEs) with IC₅₀ values of 1.2 and 0.95 mM, respectively, while the latter was almost two times more potent than the standard, aminoguanidine (1.8 mM). This is the first report on the compounds isolated from this plant with AGEs inhibition activity. In addition, (-)-nauclederine (2) was isolated for the first time in the genus of Neolamarckia. Complete ¹H-NMR and ¹³C-NMR of compound 2 were also reported.

Keywords: Advanced glycation end products; indole alkaloid; (-)-nauclederine; (+)-neocadambine A; Neolamarckia cadamba

ABSTRAK

Kajian fitokimia ke atas ekstrak dikloromethana bagi Neolamarckia cadamba (Roxb.) Bosser telah menghasilkan dua alkaloid indola, (+)-neocadambine A (1) dan (-)-nauclederine (2). Strukturnya dikenal pasti melalui pelbagai analisis spektroskopi dan perbandingan dengan data yang telah dilaporkan. (+)-Neocadambine A (1) dan (-)-nauclederine (2) menunjukkan aktiviti perencatan kuat terhadap produk akhir glisasi lanjutan (AGE) dengan nilai IC₅₀ masing-masing 1.2 dan 0.95 mM sementara (-)-nauclederine (2) hampir dua kali ganda lebih kuat daripada piawai, aminoguanidine (1.8 mM). Ini adalah laporan pertama mengenai sebatian yang diasingkan daripada tumbuhan ini dengan aktiviti perencatan terhadap AGE. Selain itu, (-)-nauclederine (2) diasingkan untuk pertama kalinya dalam genus Neolamarckia. ¹H-NMR dan ¹³C-NMR yang lengkap bagi sebatian 2 juga dilaporkan.

Kata kunci: Alkaloid indola; (-)-nauclederine; (+)-neocadambine A; Neolamarckia cadamba; produk akhir glisasi lanjutan

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^*Corresponding author; email: joeyliew5382@um.edu.my