Alkaloid and iridoid glucosides from Palicourea luxurians (Rubiaceae: Palicoureeae) indicate tryptamine- and tryptophan-iridoid alkaloid formation apart the strictosidine pathway

Kornpointner, Christoph; Berger, Andreas; Traxler, Florian; Hadžiabdić, Azra; Massar, Magdalena; Matek, Joanna; Brecker, Lothar; Schinnerl, Johann

doi:10.1016/j.phytochem.2020.112296

Cited by 12 publications

(15 citation statements)

References 48 publications

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“…Species of the genus Palicourea (Rubiaceae: Palicoureeae) have been reported as rich sources of structurally diverse alkaloids indicative of varied biosynthetic capabilities (e.g. Achenbach et al 1995;Berger et al 2012Berger et al , 2015Berger et al , 2017Kornpointner et al 2020;Lopes et al 2004;Paul et al 2003). Cyclotides (Koehbach et al 2013), polyphenols, flavonoids (Berger et al 2016) and iridoids (Berger 2012;Lopes et al 2004) furthermore highlight the chemical diversity of Palicourea species.…”

Section: Taxonomy Of the Genus Palicoureamentioning

confidence: 99%

“…Javaniside is a MIA first reported from Alangium javanicum (Blume) Wangerin (Cornaceae; Ma and Hecht 2004) and was recently isolated from Palicourea luxurians (Rusby) Borhidi. It represents the only spirocyclic oxindole alkaloid reported from the genus Palicourea (Scheme 10, Kornpointner et al 2020; see also Berger et al 2021). Alkaloids with a spiro structure, i.e., two cycles fused at a central carbon, are compounds with various bioactivities, and are well-known from species of the genus Uncaria (Rubiaceae; e.g.…”

Section: Javanisidementioning

confidence: 99%

“…Muhammad et al 2001;Wang et al 2011). Kornpointner et al (2020) proposed two possible cyclisation reactions related to a Pictet-Spengler type reaction probably catalyzed by STR. A direct oxidation leads to the spiro-oxindole moieties in an earlier step of the biosynthesis.…”

Section: Javanisidementioning

confidence: 99%

“…The basics of the mechanism go back to Bailey (1987). Further saponification and lactam formation results in javaniside (Kornpointner et al 2020); STR: strictosidine synthase Alstrostines Alstrostines are a group of MIA possessing an unusual hexahydropyrrolo indole core and a tryptamine to secologanin ratio of 1:2. These compounds were first isolated and described from Alstonia rostrata C.E.C.…”

Section: Javanisidementioning

confidence: 99%

“…(Apocynaceae; Cai et al 2011) and subsequently found in a single species of Chassalia and Rudgea, both from tribe Palicoureeae (Schinnerl et al 2012). The derivatives alstrostine A, dehydrorudgeifoline and iso-alstrostine A were recently isolated from Palicourea luxurians (Kornpointner et al 2020), which represents the first record for the genus Palicourea. The reports from three single species out of three genera indicate that alstrostines are uncommon and of scattered occurrence in the tribe (see also Berger et al 2021).…”

Section: Javanisidementioning

confidence: 99%

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Alkaloid diversification in the genus Palicourea (Rubiaceae: Palicoureeae) viewed from a (retro-)biogenetic perspective

et al. 2021

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The species-rich genus Palicourea (Rubiaceae: Palicoureeae) is source of an intriguing diversity of alkaloids derived from tryptamine and its precursor tryptophan. So far simple tryptamine analogues, polypyrroloindoline, β-carboline, and, most importantly, monoterpene-indole, i.e., tryptamine-iridoid alkaloids of various structural types including javaniside, alstrostine and strictosidine derivatives have been identified. Here the diverse alkaloids that numerous studies have found in the genus are examined and organized according to their structures and biosynthetic groups. Using a parsimony-based approach that follows the concept of retro-biogenesis usually applied in synthetic chemistry, possible biosynthetic pathways are proposed and important steps and relationships between these alkaloids are highlighted. Understanding alkaloid diversification is of importance in studying the ecological significance and evolution of biosynthetic capabilities of the genus Palicourea, and should stimulate future investigations on the biochemical and genetic background.

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Section: Taxonomy Of the Genus Palicoureamentioning

confidence: 99%

Section: Javanisidementioning

confidence: 99%

Section: Javanisidementioning

confidence: 99%

Section: Javanisidementioning

confidence: 99%

Section: Javanisidementioning

confidence: 99%

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Alkaloid diversification in the genus Palicourea (Rubiaceae: Palicoureeae) viewed from a (retro-)biogenetic perspective

et al. 2021

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Privileged Biorenewable Secologanin‐Based Diversity‐Oriented Synthesis for Pseudo‐Natural Alkaloids: Uncovering Novel Neuroprotective and Antimalarial Frameworks

Zhu

Cai

et al. 2021

ChemSusChem

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Bioprivileged molecules hold great promise for supplementing petrochemicals in sustainable organic synthesis of a diverse bioactive products library. Secologanin, a biorenewable monoterpenoid glucoside with unique structural elements, is the key precursor for thousands of natural monoterpenoid alkaloids. Inspired by its inherent highly congested functional groups, a secologanin‐based diversity‐oriented synthesis (DOS) strategy for novel pseudo‐natural alkaloids was developed. All the reactive units of secologanin were involved in these operation simplicity protocols under mild reaction conditions, including the one‐step enantioselective transformation of exocyclic C8, C8/C11, and C8/C9/C10 as well as the chemoenzymatic manipulation of endocyclic C2/C6 via the attack by various nucleophiles. A combinatory scenario of the aforementioned reactions further provided diverse polycyclic products with multiple chiral centers. Preliminary activity screening of these newly constructed molecules led to the discovery of antimalarial and highly potent neuroprotective skeletons. The application of green biorenewable secologanin in diversity‐oriented pseudo‐natural monoterpenoid alkaloid synthesis might encourage the pursuit of valuable bioactive frameworks.

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Transcriptome and metabolome analysis revealed the changes of Geniposide and Crocin content in Gardenia jasminoides fruit

Chen²,

Zhang³

et al. 2023

Mol Biol Rep

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Alkaloid and iridoid glucosides from Palicourea luxurians (Rubiaceae: Palicoureeae) indicate tryptamine- and tryptophan-iridoid alkaloid formation apart the strictosidine pathway

Cited by 12 publications

References 48 publications

Alkaloid diversification in the genus Palicourea (Rubiaceae: Palicoureeae) viewed from a (retro-)biogenetic perspective

Alkaloid diversification in the genus Palicourea (Rubiaceae: Palicoureeae) viewed from a (retro-)biogenetic perspective

Privileged Biorenewable Secologanin‐Based Diversity‐Oriented Synthesis for Pseudo‐Natural Alkaloids: Uncovering Novel Neuroprotective and Antimalarial Frameworks

Transcriptome and metabolome analysis revealed the changes of Geniposide and Crocin content in Gardenia jasminoides fruit

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