Monoterpenoid indole alkaloids from Alstonia rostrata

Bao, Ming; Zeng, Chun‐Xia; Qu, Yuanzhi; Kong, Lingmei; Liu, Yaping; Cai, Xiang‐Hai; Luo, Xiao‐Dong

doi:10.1007/s13659-012-0019-y

Cited by 9 publications

(4 citation statements)

References 19 publications

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“…Further alkaloids identified by HRESIMS and 13 C and 1 H NMR included 15-hydroxyangustilobine A ( 2 ), , 6,7-seco-angustilobine B ( 3 ), , 6,7-seco-19,20-α-epoxyangustilobine B ( 4 ), , alstrostine E ( 5 ), alstrostine C ( 6 ), alstrostine D ( 7 ), 12-methoxyechitamidine ( 8 ), and 19-oxo-12-methoxyechitamidine ( 9 ). All data identifying compounds 2 to 9 are reported as Supporting Information.…”

Section: Resultsmentioning

confidence: 99%

Alstoboonine, an Ulean-Type Indole Alkaloid from Alstonia boonei Leaves

Grimm,

Börner,

Addotey

et al. 2023

J. Nat. Prod.

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Alstonia boonei De Wild is a common plant in West Africa used in traditional medicine for various indications. While the stem bark has frequently been investigated, not much is known about the phytochemistry and bioactivity of the leaves. Within the current study, the major alkaloids of a hydroethanolic leaf extract were therefore isolated and characterized by MS, NMR, and ECD. This led to the identification of alstoboonine 1, a new ulean-type alkaloid, along with eight previously reported indole alkaloids, 15-hydroxyangustilobine A (2), 6,7-seco-angustilobine B (3), 6,7-seco-19,20-α-epoxyangustilobine B (4), alstrostine E (5), alstrostine C (6), alstrostine D (7), 12-methoxyechitamidine (8), and 19-oxo-12-methoxyechitamidine (9). 1 was moderately active in vitro against Plasmodium falciparum NF54 (IC50 6.9 μM), but inactive against other protozoan parasites (Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani). No significant cytotoxic effects were observed in L6 rat skeletal myoblast cells and MCF-7 breast cancer cells. Similarly, compounds 3 to 9 did not show cytotoxicity in MCF-7 cells. Due to the reported traditional use of the plant as an anthelmintic, the major alkaloids 2, 5, 6, and 8 were tested against the nematode Caenorhabditis elegans. Nematicidal effects were observed for 6 (LC50 400 μM), whereas 2, 5, and 8 were inactive.

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Section: Resultsmentioning

confidence: 99%

Alstoboonine, an Ulean-Type Indole Alkaloid from Alstonia boonei Leaves

Grimm,

Börner,

Addotey

et al. 2023

J. Nat. Prod.

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“…Alstrostines C-F ( 27 – 30 ) ( Figure 6 ) were isolated from the leaves and twigs of Chinese A. rostrata [ 38 ]. Compounds 27 – 30 showed a characteristic UV absorption at 326, 275 and 214 nm, which indicated the presence of an indole alkaloid with a β-anilineacrylate system.…”

Section: Alstoniamentioning

confidence: 99%

“…The chemical structure elucidation was confirmed by 1D and 2D NMR. Compounds 27 – 30 showed weak cytotoxicity against five human cancer cells, breast (SK-BR-3), human myeloid leukemia (HL-60), pancreatic (PANC-1), hepatocellular carcinoma (SMMC-7721) and lung (A-549) cells, with IC 50 values > 40 μM [ 38 ].…”

Section: Alstoniamentioning

confidence: 99%

“…Five MIAs, 11-hydroxy-6,7-epoxy-8-oxo-vincadifformine ( 31), 14-chloro-15-hydroxyvinca difformine (32), perakine N 4 -oxide (33), raucaffrinoline N 4 -oxide (34), and vinorine N 1 ,N 4dioxide (35) (Figure 7) have been reported from A. yunnanensis. Additionally, three compounds, 11-methoxy-6,7-epoxy-8-oxovincadifformine (36), vinorine N4-oxide (37) and vinorine (38) have also been found from the same plant [39]. The chemical structures were established based on 1D and 2D ( 1 H-1 H-COSY, HMQC, HMBC, and ROESY) NMR spectroscopy.…”

Section: Alstoniamentioning

confidence: 99%

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Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

et al. 2021

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By the end of the twentieth century, the interest in natural compounds as probable sources of drugs has declined and was replaced by other strategies such as molecular target-based drug discovery. However, in the recent times, natural compounds regained their position as extremely important source drug leads. Indole-containing compounds are under clinical use which includes vinblastine and vincristine (anticancer), atevirdine (anti-HIV), yohimbine (erectile dysfunction), reserpine (antihypertension), ajmalicine (vascular disorders), ajmaline (anti-arrhythmic), vincamine (vasodilator), etc. Monoterpene Indole Alkaloids (MIAs) deserve the curiosity and attention of researchers due to their chemical diversity and biological activities. These compounds were considered as an impending source of drug-lead. In this review 444 compounds, were identified from six genera belonging to the family Apocynaceae, will be discussed. These genera (Alstonia, Rauvolfia, Kopsia, Ervatamia, and Tabernaemontana, and Rhazya) consist of 400 members and represent 20% of Apocynaceae species. Only 30 (7.5%) species were investigated, whereas the rest are promising to be investigated. Eleven bioactivities, including antibacterial, antifungal, anti-inflammatory and immunosuppressant activities, were reported. Whereas cytotoxic effect represents 47% of the reported activities. Convincingly, the genera selected in this review are a wealthy source for future anticancer drug lead.

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Preakuammicine: A Long‐Awaited Missing Link in the Biosynthesis of Monoterpene Indole Alkaloids

et al. 2016

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(16S)-Preakuammicine has been considered a key intermediate in the biosynthesis of monoterpene indole alkaloids since the 1970s. Indeed, preakuammicine plays a crucial role in the biosynthesis of type II and type III monoterpene indole alkaloids and strychnine. In this paper, we disclose the unprecedented biomimetic transformation of akuammiline into (16R)-acetylpreakuammicine, which ultimately gives mechanistic in-

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Monoterpenoid indole alkaloids from Alstonia rostrata

Cited by 9 publications

References 19 publications

Alstoboonine, an Ulean-Type Indole Alkaloid from Alstonia boonei Leaves

Alstoboonine, an Ulean-Type Indole Alkaloid from Alstonia boonei Leaves

Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

Preakuammicine: A Long‐Awaited Missing Link in the Biosynthesis of Monoterpene Indole Alkaloids

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