Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata

doi:10.3390/molecules28186664

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	Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata
	Traxler,Florian; Zhang,Haoqi; Mahavorasirikul,Wiratchanee; Krivanek,Katharina; Cai,Xiang-Hai; Aiyakool,Wichai; Pfeiffer,Martin; Brecker,Lothar; Schinnerl,Johann
	2023
发表期刊	MOLECULES
ISSN	1420-3049
卷号	28 期号:18 页码:6664
摘要	Phytochemical investigation of the two Tabernaemontana species (Apocynaceae) T. peduncularis Wall. and T. divaricata (L.) R.Br. ex Roem. & Schult. indicated closely related biosynthetic pathways leading to lipophilic and hydrophilic alkaloids. In total, 18 specialized metabolites comprising indole-derived alkaloid aglycones, three oxindole-derived alkaloid glycosides, and two iridoid glucosides could be identified in the studied species. Among the alkaloids, the two Iboga-type alkaloids 3,7-coronaridine isoindolenine, coronaridine 3,4-iminium and a javaniside derivative bearing a glucuronic acid, named javanuronic acid, could be described by spectroscopic and spectrometric methods for the first time. A docking experiment using alpha-fold was performed to generate a protein model of the enzyme 7-deoxyloganetic acid glucosyl transferase. Performed bioassays exhibited a growth reduction of neonate Spodoptera littoralis larvae and reduced cell viability of HepG2 cells of the extracts containing Iboga alkaloids, whilst the javaniside derivatives containing hydrophilic fraction did not show any effects. These findings indicate a high flexibility in the formation of bioactive indole alkaloid aglycones by Tabernaemontana species and also evidence similar accumulation trends in both species as well as indicate that biosynthetic routes leading to oxindole alkaloids like javanisides are more widespread than reported. Furthermore, the incorporation of the three novel compounds into potential biosynthetic pathways is discussed.
关键词	Apocynaceae Tabernaemontana peduncularis Tabernaemontana divaricata javaniside indole alkaloid glucuronide alkaloid MONOTERPENE INDOLE ALKALOIDS BISINDOLE ALKALOIDS ALANGIUM-JAVANICUM STEM BARK GLYCOSIDES OXIDATION LOGANIN LEAVES GENUS
DOI	10.3390/molecules28186664
WOS记录号	WOS:001078455000001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/75041
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Traxler,Florian,Zhang,Haoqi,Mahavorasirikul,Wiratchanee,et al. Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata[J]. MOLECULES,2023,28(18):6664.
APA	Traxler,Florian.,Zhang,Haoqi.,Mahavorasirikul,Wiratchanee.,Krivanek,Katharina.,Cai,Xiang-Hai.,...&Schinnerl,Johann.(2023).Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata.MOLECULES,28(18),6664.
MLA	Traxler,Florian,et al."Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata".MOLECULES 28.18(2023):6664.

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