Labdane diterpene lactones of Vitex pubescens and their antileukemic properties

Anwar, Lenny; Efdi, Mai; Ninomiya, Masayuki; Ibrahim, S. A.; Putra, Deddi Prima; Tanaka, Kaori; Koketsu, Mamoru

doi:10.1007/s00044-017-1937-3

Cited by 7 publications

(4 citation statements)

References 20 publications

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“…Alternative routes to furan formation have been proposed, and involve the formation and subsequent loss of a 9,13epoxy bridge in conjunction with an additional oxidation of C-15 or C-16 (Henderson and McCrindle, 1969;Zerbe et al, 2014). It seems, however, that the presence of the C-9 hydroxyl (and by extension the 9,13-epoxy bridge) is not essential for furan or lactone ring formation as multiple furan-and lactone-bearing diterpenoids without C-9 hydroxylation exist (Smith et al, 1982;Omosa et al, 2014;Anwar et al, 2017). Nevertheless, a potential intermediate of this alternative route was identified in the present study as a major product of VacTPS2 when coupled with VacTPS1 (3a), and similar compounds are often encountered in other furan/lactone diterpenoid-producing species (Ono et al, 1999;Tesso and K€ onig, 2004;Kulkarni et al, 2013).…”

Section: Identification Of a Cyp Capable Of Peregrinol Oxidationmentioning

confidence: 99%

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

et al. 2018

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Summary Vitex agnus‐castus L. (Lamiaceae) is a medicinal plant historically used throughout the Mediterranean region to treat menstrual cycle disorders, and is still used today as a clinically effective treatment for premenstrual syndrome. The pharmaceutical activity of the plant extract is linked to its ability to lower prolactin levels. This feature has been attributed to the presence of dopaminergic diterpenoids that can bind to dopamine receptors in the pituitary gland. Phytochemical analyses of V. agnus‐castus show that it contains an enormous array of structurally related diterpenoids and, as such, holds potential as a rich source of new dopaminergic drugs. The present work investigated the localisation and biosynthesis of diterpenoids in V. agnus‐castus. With the assistance of matrix‐assisted laser desorption ionisation‐mass spectrometry imaging (MALDI‐MSI), diterpenoids were localised to trichomes on the surface of fruit and leaves. Analysis of a trichome‐specific transcriptome database, coupled with expression studies, identified seven candidate genes involved in diterpenoid biosynthesis: three class II diterpene synthases (diTPSs); three class I diTPSs; and a cytochrome P450 (CYP). Combinatorial assays of the diTPSs resulted in the formation of a range of different diterpenes that can account for several of the backbones of bioactive diterpenoids observed in V. agnus‐castus. The identified CYP, VacCYP76BK1, was found to catalyse 16‐hydroxylation of the diol‐diterpene, peregrinol, to labd‐13Z‐ene‐9,15,16‐triol when expressed in Saccharomyces cerevisiae. Notably, this product is a potential intermediate in the biosynthetic pathway towards bioactive furan‐ and lactone‐containing diterpenoids that are present in this species.

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Section: Identification Of a Cyp Capable Of Peregrinol Oxidationmentioning

confidence: 99%

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

et al. 2018

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“…The downeld C-3 in 4 indicated the formation of an oxygen bridge between C-3 and C-19. 20,21 The cross-peaks of H-3/H 3 -18 in the NOESY spectrum of compound 4 (Fig. S32, ESI †) indicated the same orientations of H-3 and CH 3 -18.…”

Section: Resultsmentioning

confidence: 98%

ent-Rosane diterpenoids from Euphorbia milii showing an Epstein–Barr virus lytic replication assay

Liu

Tan

et al. 2017

RSC Adv.

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“…Phenolic compounds commonly found in this genus are vanillic acid, ferulic acid, p-coumaric acid, 3,4-dihydroxybenzoate acid, casticin, caffeic acid, gallic acid, chlorogenic acid, isochlorogenic acid, vitexin [21][22][23][24][25]. Vitex pinnata Linn is a plant species from the Vitex genus with a wide range of phenolic compounds, such as methyl p-hydroxybenzoate, vicioside, apigenin, retusin, and kaemferol trimethyl ether [26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Antioxidant Activity-Guided Isolation of Phenolic Compounds from Leaves of Vitex pinnata (Lamiaceae)

Faisal

Efdi

Itam

et al. 2022

CSIJ

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The aim of this study is to isolate phenolic compounds from the ethyl acetate fraction of the leaves of V. pinnata Linn, which have antioxidant properties, guided by a TLC-Bioautography (Thin-layer chromatography) with a reagent of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH). The TLC-antioxidant bioautography technique has several advantages. It does not require a long time in testing, the sample used is small, and it can potentially obtain promising antioxidant-positive compounds.The isolation process led to obtaining two phenolic compounds. The UV-Vis, FTIR, and NMR spectrum analysis showed that the compounds were (1) p-hydroxybenzoate and (2) luteolin. Further antioxidant evaluation by DPPH assay showed a potential radical scavenging DPPH of luteolin (2) with an IC50 of 1.56±0.18 µg/mL.

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Labdane diterpene lactones of Vitex pubescens and their antileukemic properties

Cited by 7 publications

References 20 publications

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

ent-Rosane diterpenoids from Euphorbia milii showing an Epstein–Barr virus lytic replication assay

Antioxidant Activity-Guided Isolation of Phenolic Compounds from Leaves of Vitex pinnata (Lamiaceae)

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