Six new sulfur-containing bis-iridoid glucosides, saprosmosides A-F (1-6), were isolated from the leaves of Saprosma scortechinii. From the stems of this same plant, two new iridoid glucosides, 3,4-dihydro-3-methoxypaederoside (8) and 10-O-benzoyldeacetylasperulosidic acid (12), were isolated. Their structures were elucidated by means of chemical, NMR, and mass spectroscopic methods. Additionally, 11 known iridoid glucosides were isolated and characterized as deacetylasperuloside, asperuloside, paederoside (7), deacetylasperulosidic acid (9), scandoside, asperulosidic acid, 10-acetylscandoside, paederosidic acid (10), 6-epi-paederosidic acid (11), methylpaederosidate, and monotropein. The structures of the new bis-iridoid glucosides were formed by intermolecular esterification between the glucose and carboxyl groups of three monomeric iridoid glucosides (7, 9, and 10).
Saprosma scortechinii BL. KING & GAMBLE, a rubiaceous plant endemic in the Malay Peninsula, 1) is also known as 'sekentut', a local name associated with the unpleasant and fetid odor emitted by the bruised plant tissues. In the traditional medicinal system of Malaysia, the roots are employed in decoctions to treat fever by the native communities, while the young leaves are also eaten as a vegetable.2) Our previous studies on the plant have resulted in the isolation of six sulfur-containing bis-iridoid glucosides (saprosmosides A-F) and 13 iridoid glucosides.3) On-going studies on the same plant materials have resulted in the isolation of two new bisiridoid glucosides, a new iridoid glucoside, and seven new anthraquinones, in addition to three known compounds. We wish to report herein the isolation and structural elucidation of these compounds. Results and DiscussionDried leaves and stems were separately extracted with methanol, and the resulting extracts were subjected to solvent-solvent partitioning. A combination of column chromatography followed by further purification led to the isolation of two new bis-iridoid glucosides (1 and 2) and a new iridoid glucoside (3) from the leaves, and seven new anthraquinones (4-10) from the stems, in addition to three known compounds identified as 6-O-acetylscandoside, The 1 H-and 13 C-NMR spectra ( ; 8-19-1 Nanakuma, Jyounanku, Fukuoka 814-0180, Japan. Received February 18, 2002; accepted May 8, 2002 A further investigation of the leaves and stems of Saprosma scortechinii afforded 13 compounds, of which 10 are new compounds. These were elucidated as the bis-iridoid glucosides, saprosmosides G (1) and H (2), the iridoid glucoside, 6-O-epi-acetylscandoside (3), and the anthraquinones, 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone (4), 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-b b-primeveroside (5), 1,3-dihydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-b b-primeveroside (6), 1,3,6-trihydroxy-2-methoxymethyl-9,10-anthraquinone (7), 1-methoxy-3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (8), 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-b b-primeveroside (9), and 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (10). Structure assignments for all compounds were established by means of mass and NMR spectroscopies, chemical methods, and comparison with published data. The new anthraquinones were derivatives of munjistin and lucidin.
Saprosma scortechinii BL. KING & GAMBLE, a rubiaceous plant endemic in the Malay Peninsula, 1) is also known as 'sekentut', a local name associated with the unpleasant and fetid odor emitted by the bruised plant tissues. In the traditional medicinal system of Malaysia, the roots are employed in decoctions to treat fever by the native communities, while the young leaves are also eaten as a vegetable.2) Our previous studies on the plant have resulted in the isolation of six sulfur-containing bis-iridoid glucosides (saprosmosides A-F) and 13 iridoid glucosides.3) On-going studies on the same plant materials have resulted in the isolation of two new bisiridoid glucosides, a new iridoid glucoside, and seven new anthraquinones, in addition to three known compounds. We wish to report herein the isolation and structural elucidation of these compounds. Results and DiscussionDried leaves and stems were separately extracted with methanol, and the resulting extracts were subjected to solvent-solvent partitioning. A combination of column chromatography followed by further purification led to the isolation of two new bis-iridoid glucosides (1 and 2) and a new iridoid glucoside (3) from the leaves, and seven new anthraquinones (4-10) from the stems, in addition to three known compounds identified as 6-O-acetylscandoside, The 1 H-and 13 C-NMR spectra ( ; 8-19-1 Nanakuma, Jyounanku, Fukuoka 814-0180, Japan. Received February 18, 2002; accepted May 8, 2002 A further investigation of the leaves and stems of Saprosma scortechinii afforded 13 compounds, of which 10 are new compounds. These were elucidated as the bis-iridoid glucosides, saprosmosides G (1) and H (2), the iridoid glucoside, 6-O-epi-acetylscandoside (3), and the anthraquinones, 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone (4), 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-b b-primeveroside (5), 1,3-dihydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-b b-primeveroside (6), 1,3,6-trihydroxy-2-methoxymethyl-9,10-anthraquinone (7), 1-methoxy-3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (8), 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-b b-primeveroside (9), and 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (10). Structure assignments for all compounds were established by means of mass and NMR spectroscopies, chemical methods, and comparison with published data. The new anthraquinones were derivatives of munjistin and lucidin.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.