Two New Oxindole Alkaloid Glycosides from the Leaves of <i>Nauclea officinalis</i>

Liu, Fan; Huang, Xiao‐Jun; Fan, Chun‐Lin; Li, Guoqiang; Wu, Zhen‐Long; Li, Shuo‐Guo; He, Zhendan; Wang, Ying; Ye, Wen‐Cai

doi:10.1177/1934578x1501001218

Cited by 3 publications

(3 citation statements)

References 19 publications

(35 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, the 1 H and 13 C-NMR data of 5 and 6 were similar to those of nauclealomide A (Table 2). Thus, the planar structures of 5 , 6 were identical to that of nauclealomide A (Figure 1) [13]. The coupling constants of 3 J 20,21 ( J = 1.7 Hz) and 3 J 20,15 ( J = 5.8 Hz) suggested the presence of β/β/α orientation for H-15, H-20 and H-21 in 5 and 6 [15,16,17].…”

Section: Resultsmentioning

confidence: 92%

“…officinalis is widely used for the treatment of colds, fever, acute tonsillitis, sore throat, conjunctivitis, enteritis, dysentery, eczema and other ailments [1]. Previous phytochemical investigation had revealed that monoterpene indole alkaloids, which present a polycyclic skeleton with a tetrahydro-β-carboline ring, are the main components of this plant [2,3,4,5,6,7,8,9,10,11,12,13]. The complex ring system and diversity of stereostructure of these monoterpene indole alkaloids have attracted great interest for phytochemical studies.…”

Section: Introductionmentioning

confidence: 99%

“…The complex ring system and diversity of stereostructure of these monoterpene indole alkaloids have attracted great interest for phytochemical studies. As a part of our ongoing program to search for structurally unique alkaloids from the medicinal plants in southern China [5,13], we carried out the continuing investigation on the leaves of N . officinalis .…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Indole Alkaloids from the Leaves of Nauclea officinalis

et al. 2016

Self Cite

View full text Add to dashboard Cite

Three new indole alkaloids, named naucleamide G (1), and nauclealomide B and C (5 and 6), were isolated from the n-BuOH-soluble fraction of an EtOH extract of the leaves of Nauclea officinalis, together with three known alkaloids, paratunamide C (2), paratunamide D (3) and paratunamide A (4). The structures with absolute configurations of the new compounds were identified on the basis of 1D and 2D NMR, HRESIMS, acid hydrolysis and quantum chemical circular dichroism (CD) calculation. According to the structures of isolated indole alkaloids, their plausible biosynthetic pathway was deduced.

show abstract

Section: Resultsmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Indole Alkaloids from the Leaves of Nauclea officinalis

et al. 2016

Self Cite

View full text Add to dashboard Cite

show abstract

Spirooxindol‐1,3‐oxazine Alkaloids: Highly Potent and Selective Antitumor Agents Evolved from Iterative Structure Optimization

et al. 2022

View full text Add to dashboard Cite

Spirooxindole‐1,3‐oxazines are a small and structurally unique class of spirooxindole alkaloids. To date, only four of these compounds have been isolated from natural sources, and their biological properties remained unknown thus far. Dioxyreserpine is a synthetic spirooxindole‐1,3‐oxazine, that can readily be prepared from the Rauvolfia alkaloid (–)‐reserpine by catalytic photooxygenation. While dioxyreserpine itself was now identified as a moderately effective antitumoral agent, structurally modified analogs of it emerged as a new class of highly potent and selective growth inhibitors of various human cancers, including pancreatic cancers. Systematic structural optimization ultimately led to an inhibitor displaying low‐micromolar IC50‐values against six cancer cell lines as well as selective apoptosis induction in vitro.

show abstract

Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species

et al. 2022

View full text Add to dashboard Cite

Comprehensive phytochemical examination from different perspectives using preparative and analytical chromatographic techniques combined with spectroscopic/spectrometric methods of the so-called “yellow twig” Nauclea orientalis (L.) L. (Rubiaceae) led to the identification of 13 tryptamine-derived (=monoterpene-indole) alkaloids. The identified alkaloids comprise strictosamide and four of its glucosidic derivatives, three oxindole derivatives, and five yellow-colored angustine-type aglycones. Qualitative and quantitative HPLC analyses showed the enrichment of strictosamide in all studied organs. Based on these results, we performed metabolomic analyses of monoterpene-indole alkaloids and made a 1H NMR in vitro monitoring of enzymatic deglucosylation of strictosamide. A comparison of the stability of strictosamide and its enantiomer vincoside lactam by theoretical calculations was also performed revealing a slightly higher stability of vincoside lactam. Additionally, we conducted two different anti-feedant assays of strictosamide using larvae of the polyphageous moth Spodoptera littoralis Boisduval. The obtained results indicate that generally two different biosynthetic pathways are most likely responsible for the overall alkaloid composition in this plant. Strictosamide is the key compound in the broader pathway and most likely the source of the identified angustine-type aglycones, which may contribute significantly to the yellow color of the wood. Its cross-organ accumulation makes it likely that strictosamide is not only important as a reservoir for the further biosynthesis, but also acts in the plants’ defense strategy.

show abstract

Two New Oxindole Alkaloid Glycosides from the Leaves of Nauclea officinalis

Cited by 3 publications

References 19 publications

Indole Alkaloids from the Leaves of Nauclea officinalis

Indole Alkaloids from the Leaves of Nauclea officinalis

Spirooxindol‐1,3‐oxazine Alkaloids: Highly Potent and Selective Antitumor Agents Evolved from Iterative Structure Optimization

Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species

Contact Info

Product

Resources

About