Chemistry of Indole Alkaloids Related to the Corynanthe-Type from Uncaria, Nauclea and Mitragyna Plants

Takayama, Hiromitsu; Kitajima, Mariko; Kogure, Noriyuki

doi:10.2174/138527205774370559

Cited by 42 publications

(15 citation statements)

References 80 publications

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“…6 Due to their antiproliferative, 7 antiparasitic, and antimicrobial 8,9 activities, some monoterpenoid indole alkaloids of the corynanthe type have been utilized as lead compounds in new drug development. 10 In contrast to the number of reports on chemical analysis and synthesis of these alkaloids, studies about their fragmentation behaviors on electrospray ionization (ESI) mass spectrometry are still lacking.…”

Section: Journal Of Mass Spectrometrymentioning

confidence: 99%

Identification of Indole Alkaloids in Nauclea Officinalis Using High-Performance Liquid Chromatography Coupled with Ion Trap and Time-of-Flight Mass Spectrometry

Qin

Zhang

et al. 2011

Eur J Mass Spectrom (Chichester)

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Indole alkaloids from Nauclea officinalis (Pierra ex Pitard) Merr are prospective agents for inflammation- related diseases. To speed up the process of discovering such bioactive compounds from natural origins, a mass spectrometry-based method was developed to screen N. officinalis for the presence of indole alkaloids. First, representative alkaloids were purified from herbs and analyzed using an ion trap (IT) mass spectrometer. Multi-stage mass spectra (MS(n))were utilized to establish the characteristic fragmentation pathways of indole alkaloids. It was shown that their fragmentation behaviors were correlated with the degree of unsaturation on ring-D of such alkaloids: if there is a double bond between C-3 and C-14, no fragments of ring cleavage are observed; otherwise, a fragment ion after reverse Diels-Alder cleavage of ring-D is observed as the base peak in their tandem mass spectrometry data. Then, herbal extracts of N. officinalis were analyzed using a combination of high- performance liquid chromatography (HPLC)/IT and HPLC/time-of-flight (ToF) systems. The structures of suspected alkaloids were deduced based on the accurate mass information from ToF and MS(n) from IT. Finally, a total of 10 indole and one indolizidine alkaloids were identified or tentatively characterized in extracts of N. officinalis. This work has demonstrated that the combination of MS(n) and ToF-MS can be used for rapid identification of monoterpenoid indole alkaloids in N. officinalis.

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Section: Journal Of Mass Spectrometrymentioning

confidence: 99%

Identification of Indole Alkaloids in Nauclea Officinalis Using High-Performance Liquid Chromatography Coupled with Ion Trap and Time-of-Flight Mass Spectrometry

Qin

Zhang

et al. 2011

Eur J Mass Spectrom (Chichester)

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“…The indole ring system is incorporated into a vast number of structurally diverse biologically active natural and synthetic compounds [147][148][149][150][151][152][153][154][155][156][157]. Consequently, the indole ring system has become an essential, or so called privileged, structural motif in many pharmaceutical agents [156,158].…”

Section: Indolesmentioning

confidence: 99%

“…149 Furthermore, Yamamoto and coworkers illustrated that o-(alkynyl)phenylisocyanates 159 could also be efficiently employed in a similar Pt(II)-catalyzed cycloisomerization reaction, serving as surrogates of the corresponding carbamate derivatives 160, to provide N-(alkoxycarbonyl)indoles 161 in moderate to excellent yields (Scheme 9.60) [219]. It is believed that a dual-role catalysis with the Pt(II) salt first triggered the initial intermolecular nucleophilic addition of alcohol to isocyanate 159, affording the key transient carbamate 160, which, upon a subsequent Pt(II)-catalyzed 5-endo-dig cyclization, generated the desired product 161.…”

Section: Synthesis Of Indoles Via Cycloisomerization Reactionsmentioning

confidence: 99%

Transition Metal‐Catalyzed Synthesis of Fused Five‐Membered Aromatic Heterocycles

Dudnik¹,

Gevorgyan²

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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“…It is worth to mention that depending on the subsequent steps, strictosidine is transformed to diverse MIA in different plant families as Apocynaceae, Loganiaceae, Rubiaceae, and Nyssaceae . Strictosidine is also involved in the formation of other glucoindole alkaloids characteristic of Rubiaceae as isodihydrocadambine …”

Section: Introductionmentioning

confidence: 99%

Strictosidine‐related enzymes involved in the alkaloid biosynthesis of Uncaria tomentosa root cultures grown under oxidative stress

Vera‐Reyes

Huerta-Heredia

Ponce-Noyola

et al. 2013

Biotechnology Progress

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The activity and gene expression of strictosidine-related enzymes in Uncaria tomentosa root cultures exposed to oxidative stress were studied. Elicitation with 0.2 mM hydrogen peroxide (H2 O2 ) or a combination of 0.8 mM buthionine sulfoximine and 0.2 mM jasmonic acid (BSO-JA) increased peroxidase activities by twofold at Day 8 and glutathione reductase by 1.4-fold at Day 5 in H2 O2 elicited cultures respect to the control. Production of monoterpenoid oxindole alkaloids (MOA), 3α-dihydrocadambine, and dolichantoside was stimulated after H2 O2 elicitation, reaching levels of 886.4 ± 23.6, 847.7 ± 25.4, and 87.5 ± 7.2 µg/g DW, at Day 8 which were 1.7-, 2.1-, and 2.3-fold higher relative to control. BSO-JA elicited cultures produced about twice alkaloids than H2 O2 -treated cultures, following a biphasic pattern with maxima at 0.5 and 8 days. Alkaloid production was preceded by increase in strictosidine synthase (STR) and strictosidine glucosidase (SGD) activities. After elicitation with H2 O2 or BSO-JA, the STR activity (pKat/mg protein) increased by 1.9-fold (93.8 ± 17.8 at 24 h) or 2.5-fold (102.4 ± 2.2 at 6 h) and the SGD activity (pKat/mg protein) by 2.8-fold (245.2 ± 14.4 at 6 h) or 4.2-fold (421.2 ± 1.8 at 18 h) relative to control. STR and SGD transcripts were upregulated after elicitation. H2 O2 -treated roots showed higher levels of STR at 48-192 h and SGD at 24-48 h, while BSO-JA treatments showed STR increased at 12 h and SGD at 24 h. Also, LC/ESI-MS confirmed the biosynthesis of dolichantoside from N-ω-methyltryptamine and secologanin by U. tomentosa protein extracts.

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Chemistry of Indole Alkaloids Related to the Corynanthe-Type from Uncaria, Nauclea and Mitragyna Plants

Cited by 42 publications

References 80 publications

Identification of Indole Alkaloids in Nauclea Officinalis Using High-Performance Liquid Chromatography Coupled with Ion Trap and Time-of-Flight Mass Spectrometry

Identification of Indole Alkaloids in Nauclea Officinalis Using High-Performance Liquid Chromatography Coupled with Ion Trap and Time-of-Flight Mass Spectrometry

Transition Metal‐Catalyzed Synthesis of Fused Five‐Membered Aromatic Heterocycles

Strictosidine‐related enzymes involved in the alkaloid biosynthesis of Uncaria tomentosa root cultures grown under oxidative stress

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