Phukettosides A–E, mono- and bis-iridoid glycosides, from the leaves of Morinda umbellata L

Kaweetripob, Wirongrong; Thongnest, Sanit; Boonsombat, Jutatip; Batsomboon, Paratchata; Salae, Abdul-Wahab; Prawat, Hunsa; Mahidol, Chulabhorn; Ruchirawat, Somsak

doi:10.1016/j.phytochem.2023.113890

Phytochemistry

2023

DOI: 10.1016/j.phytochem.2023.113890

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Phukettosides A–E, mono- and bis-iridoid glycosides, from the leaves of Morinda umbellata L

Wirongrong Kaweetripob,

Sanit Thongnest,

Jutatip Boonsombat

et al.

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Cited by 3 publications

References 51 publications

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Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

Jongsomjainuk,

Boonsombat,

Thongnest

et al. 2023

Nat. Prod. Bioprospect.

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Four highly oxidized pimarane diterpenoids were isolated from Kaempferia takensis rhizomes. Kaemtakols A–C possess a tetracyclic ring with either a fused tetrahydropyran or tetrahydrofuran motif. Kaemtakol D has an unusual rearranged A/B ring spiro-bridged pimarane framework with a C-10 spirocyclic junction and an adjacent 1-methyltricyclo[3.2.1.02,7]octene ring. Structural characterization was achieved using spectroscopic analysis, DP4 + and ECD calculations, as well as X-ray crystallography, and their putative biosynthetic pathways have been proposed. Kaemtakol B showed significant potency in inhibiting nitric oxide production with an IC50 value of 0.69 μM. Molecular docking provided some perspectives on the action of kaemtakol B on iNOS protein. Graphical Abstract

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Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

Jongsomjainuk,

Boonsombat,

Thongnest

et al. 2023

Nat. Prod. Bioprospect.

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Chemical constituents of Ulmus pumila L. and their chemotaxonomic significance

Hu,

Liu,

et al. 2024

Biochemical Systematics and Ecology

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Bis-Iridoids: Occurrence, Chemophenetic Evaluation and Biological Activities—A Review

Frezza,

Venditti,

De Vita

et al. 2024

Molecules

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In this work, the first review paper about bis-iridoids was presented. In particular, their detailed occurrence, chemophenetic evaluation and biological activities were reported. To the best of our knowledge, two hundred and eighty-eight bis-iridoids have been evidenced so far, bearing different structural features, with the link between two seco-iridoids sub-units as the major one. Different types of base structures have been found, with catalpol, loganin, paederosidic acid, olesoide methyl ester, secoxyloganin and loganetin as the major ones. Even bis-irdioids with non-conventional structures like intra-cyclized and non-alkene six rings have been reported. Some of these compounds have been individuated as chemophenetic markers at different levels, such as cantleyoside, laciniatosides, sylvestrosides, GI-3, GI-5, oleonuezhenide, (Z)-aldosecologanin and centauroside. Only one hundred and fifty-nine bis-iridoids have been tested for their biological effects, including enzymatic, antioxidant, antimicrobial, antitumoral and anti-inflammatory. Sylvestroside I was the compound with the highest number of biological tests, whereas cantleyoside was the compound with the highest number of specific biological tests. Bis-iridoids have not always shown activity, and when active, their effectiveness values have been both higher and lower than the positive controls, if present. All these aspects have been deeply discussed in this paper, which also shows some critical issues and even suggests possible arguments for future research, since there is still a lot unknown about bis-iridoids.

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Phukettosides A–E, mono- and bis-iridoid glycosides, from the leaves of Morinda umbellata L

Cited by 3 publications

References 51 publications

Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

Chemical constituents of Ulmus pumila L. and their chemotaxonomic significance

Bis-Iridoids: Occurrence, Chemophenetic Evaluation and Biological Activities—A Review

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