Myrotheciumones: Bicyclic cytotoxic lactones isolated from an endophytic fungus of Ajuga decumbens

Lin, Ting; Wang, Guanghui; Shan, Wenjun; Zeng, Deqiang; Ding, Rong; Jiang, Xin; Zhu, Dan; Liu, Xiaoxuan; Yang, Shuiyuan; Chen, Haifeng

doi:10.1016/j.bmcl.2014.04.016

Cited by 29 publications

(20 citation statements)

References 42 publications

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“…The results showed that Ajudecumin A (35) and Ajudecumin C (37) exhibited moderate cytotoxic activities against MCF-7 cell lines with IC50 values of 19.4 and 12.5 μM, respectively [18]. Myrotheciumone A isolated from endophytic fungus of A. decumbens exhibited in vitro cytotoxicity and apoptosic activity [49].…”

Section: Figurementioning

confidence: 99%

Advance of the Chemical Components and Biological Activities of Ajuga Decumbens Thunb

Olatunde

Yang

Yong

et al. 2019

BJSTR

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is an annual herbaceous flowering plant, which grow to 10-30 cm height with white villous on the young parts of the stem, numerous basal leaves longer than stem leaves, floral leaves are bractlike and lanceolate, with funnel-shape calyx and corolla tubular, straight, basally slightly swollen. Flowering starts from March and lasts to the end of July. The fruiting season starts from May and continues till November [16]. Bioactive Compounds Isolated from A. decumbensThere are bioactive compounds isolated from A. decumbens, including diterpenoids, iridoid glycosides, triterpenoids, sesquiterpenoids, phytoecdysteroids, withanolides and other essential compounds, which are responsible for its effective biological activities. Diterpenoids:A. decumbens is highly rich in diterpenoids as other Ajuga species, diterpenoids from A. decumbens are of two groups that are neoclerodane and abietane [11,[17][18]. Eight diterpenoids were isolated from ethanol extract of A. decumbens, including Ajugacumbins A (1), Ajugacumbins B (2), Ajugacumbins C (3), Ajugacumbins D (4), Ajugamarins A2 (5), Ajugamarins G1(6), Ajugamarins H1(7) and Ajugamarins F4 (8) [19][20]. Min et al. also isolated Ajugacumbins E (9) and Ajugacumbins F (10) for the first time [21]. Ajugacumbins G (11) was isolated from A. decumbens [22]. Amano et al. isolated Ajugatakasins A (12), Ajugatakasins B (13), Ajugaside A (14), Ajugapitin (Clerodendrin D) (15) and Dihydroajugamarin (16) from the extract of A. decumbens [23].

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Section: Figurementioning

confidence: 99%

Advance of the Chemical Components and Biological Activities of Ajuga Decumbens Thunb

Olatunde

Yang

Yong

et al. 2019

BJSTR

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“…There are two similar species also found in the same general geographical location, Ajuga nipponensis Makino and Ajuga taiwanensis Nakai ex Murata [1,2]. Modern pharmacological research indicates that 8-O-acetylharpagide in A. decumbens has various pharmacological activities, such as antitumoral, antiviral, and anti-inflammatory [3][4][5]. A pharmacokinetics study was performed to quantitatively investigate the absorption, distribution, metabolism, and excretion (ADME) of 8-O-acetylharpagide in vivo and also focus on the metabolic mechanism, interaction within a complex drug system, and dynamic investigation of the material basis of the drug's effect [6,7].…”

Section: Introductionmentioning

confidence: 99%

Pharmacokinetics of 8-O-acetylharpagide in mouse blood by UPLC–MS/MS

Chen

Huang

Zheng

et al. 2019

Acta Chromatographica

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Acetylharpagide is the main active component of the herb Ajuga decumbens, which possesses anti-tumor, antivirus, and anti-inflammation properties. In this study, ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) was used to measure the concentration of 8-O-acetylharpagide in mouse blood, with subsequent investigation of the pharmacokinetics of the drug after intravenous or oral administration. Shanzhiside methyl ester was used as an internal standard, and the acetonitrile precipitation method was used to process the blood samples. Chromatographic separation was achieved using an ultra-performance liquid chromatography ethylene-bridged hybrid (UPLC BEH) column (2.1 mm × 50 mm, 1.7 μm) with a gradient methanol-water mobile phase (containing 0.1% formic acid). The flow rate was 0.4 mL/min, and the elution time was 5.0 min. 8-O-Acetylharpagide was quantitatively measured using electrospray ionization (ESI) tandem mass spectrometry in multiple reaction monitoring (MRM) mode with positive ionization. The result indicated that, within the range of 5-500 ng/mL, the linearity of 8-O-acetylharpagide in mouse blood was satisfactory (r > 0.995), and the lower limit of quantification (LLOQ) was 5 ng/mL. Intra-day precision relative standard deviation (RSD) of 8-O-acetylharpagide in blood was lower than 9%, and the inter-day precision RSD was lower than 13%. The accuracy range was between 94.3% and 107.1%, average recovery was higher than 91.3%, and the matrix effect was between 100.8% and 110.8%. This analytical method was sensitive and fast with good selectivity and was successfully applied to perform pharmacokinetic studies of 8-O-acetylharpagide in mice. The bioavailability of 8-O-acetylharpagide was 10.8%, and the analysis of the primary pharmacokinetic parameters after oral and intravenous administration indicated that 8-O-acetylharpagide had a significant first pass effect after oral administration.

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“…Our endeavor on the application of Cp 2 Ti(III)Cl-promoted epoxide opening followed by a concomitant radical cyclization reaction has emerged as a versatile approach for natural product synthesis . Several groups including ours have been using this strategy for the synthesis of many biologically and pharmacologically important natural products. , To further peregrinate over this strategy, we planned a synthetic approach for the synthesis of secondary metabolites pestalotiolactone A ( 1 , Scheme ), isolated by Proksch et al in 2017 from anexic culture of endophytic fungus Pestalotiopsis species obtained from fruits of Drepanocarpus lunatus (Fabaceae) and myrotheciumone A ( 2 ), isolated by Lin et al in 2014 from Myrothecium roridum , an endophytic fungus of the medicinal herb plant Ajuga decumbens . Pestalotiolactone A did not show significant antibacterial and anticancer activity against L5178Y mouse lymphoma cell line .…”

Section: Introductionmentioning

confidence: 99%

Cp₂TiCl-Mediated Reductive Cyclization: Total Synthesis of Pestalotiolactone A, Myrotheciumone A, and Scabrol A

Begum

Chakraborty

2021

J. Org. Chem.

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The first stereoselective total syntheses of fungal secondary metabolites monoterpenoid (+)-pestalotiolactone A, meroterpenoid (−)-myrotheciumone A, and iridoid lactone (+)-scabrol A have been accomplished in an expedient unified approach starting from D-(+)-malic acid employing an epoxide opening-radical cyclization protocol initiated by Cp 2 Ti(III)Cl as a key step to assemble the core bicyclic lactone moieties of these molecules with complete diastereoselective control. Finally, the deoxygenation and methylation delivered the target natural products.

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Myrotheciumones: Bicyclic cytotoxic lactones isolated from an endophytic fungus of Ajuga decumbens

Cited by 29 publications

References 42 publications

Advance of the Chemical Components and Biological Activities of Ajuga Decumbens Thunb

Advance of the Chemical Components and Biological Activities of Ajuga Decumbens Thunb

Pharmacokinetics of 8-O-acetylharpagide in mouse blood by UPLC–MS/MS

Cp₂TiCl-Mediated Reductive Cyclization: Total Synthesis of Pestalotiolactone A, Myrotheciumone A, and Scabrol A

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Myrotheciumones: Bicyclic cytotoxic lactones isolated from an endophytic fungus of Ajuga decumbens

Cited by 29 publications

References 42 publications

Advance of the Chemical Components and Biological Activities of Ajuga Decumbens Thunb

Advance of the Chemical Components and Biological Activities of Ajuga Decumbens Thunb

Pharmacokinetics of 8-O-acetylharpagide in mouse blood by UPLC–MS/MS

Cp2TiCl-Mediated Reductive Cyclization: Total Synthesis of Pestalotiolactone A, Myrotheciumone A, and Scabrol A

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Cp₂TiCl-Mediated Reductive Cyclization: Total Synthesis of Pestalotiolactone A, Myrotheciumone A, and Scabrol A