Antifungal Abietane-Type Diterpenes from the Cones of Taxodium distichum Rich

Kusumoto, Norihisa; Ashitani, Tatsuya; Murayama, Tetsuya; Ogiyama, Koichi; Takahashi, Koetsu

doi:10.1007/s10886-010-9875-2

Cited by 51 publications

(41 citation statements)

References 21 publications

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“…The results suggest that the antiprotozoal activity depends on oxygenated and dehydrogenated chromophoric systems through rings B and C since dehydroabietane ( 1 ), without oxygen functions in ring B and C as well as dehydrogenations in ring B, had no activity against all protozoal strains. The structural analysis of the diterpenes 2 – 5 allow us to conclude that the quinone-structure at C6, C7, C11 and C12 apparently increases the antiprotozoal activity as well as the antifungal and antibacterial activities of several abietane-type diterpene quinones [17]. Quinones should not be the only chemical group required for antiprotozoal activity.…”

Section: Resultsmentioning

confidence: 99%

In Vitro Antiprotozoal Activity of Abietane Diterpenoids Isolated from Plectranthus barbatus Andr.

Mothana

Alsaid

Al-Musayeib

et al. 2014

IJMS

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Chromatographic separation of the n-hexane extract of the aerial part of Plectranthus barbatus led to the isolation of five abietane-type diterpenes: dehydroabietane (1); 5,6-didehydro-7-hydroxy-taxodone (2); taxodione (3); 20-deoxocarnosol (4) and 6α,11,12,-trihydroxy-7β,20-epoxy-8,11,13-abietatriene (5). The structures were determined using spectroscopic methods including one- and two-dimensional NMR methods. Compounds (1)–(3) and (5) are isolated here for the first time from the genus Plectranthus. The isolated abietane-type diterpenes tested in vitro for their antiprotozoal activity against erythrocytic schizonts of Plasmodium falciparum, intracellular amastigotes of Leishmania infantum and Trypanosoma cruzi and free trypomastigotes of T. brucei. Cytotoxicity was determined against fibroblast cell line MRC-5. Compound (2) 5,6-didehydro-7-hydroxy-taxodone showed remarkable activity with acceptable selectivity against P. falciparum (IC50 9.2 μM, SI 10.4) and T. brucei (IC50 1.9 μM, SI 50.5). Compounds (3)–(5) exhibited non-specific antiprotozoal activity due to high cytotoxicity. Compound (1) dehydroabietane showed no antiprotozoal potential.

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Section: Resultsmentioning

confidence: 99%

In Vitro Antiprotozoal Activity of Abietane Diterpenoids Isolated from Plectranthus barbatus Andr.

Mothana

Alsaid

Al-Musayeib

et al. 2014

IJMS

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“…T. distichum is a coniferous tree whose biological activities have been rarely evaluated31. T. distichum cones showed antifungal and antitermitic activities3233, but whether other parts of the plant have antiviral activity is unknown. We screened the extracts of cones, leaves and stems of T. distichum for anti-influenza virus activity, and the stem exhibited the best effectiveness against influenza A virus (data not shown).…”

Section: Discussionmentioning

confidence: 99%

An extract from Taxodium distichum targets hemagglutinin- and neuraminidase-related activities of influenza virus in vitro

Hsieh

Chen

Lin

et al. 2016

Sci Rep

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Influenza virus remains an emerging virus and causes pandemics with high levels of fatality. After screening different plant extracts with potential anti-influenza activity, a water extract of Taxodium distichum stems (TDSWex) showed excellent activity against influenza viruses. The EC50 of TDSWex was 0.051 ± 0.024 mg/mL against influenza virus A/WSN/33. TDSWex had excellent antiviral efficacy against various strains of human influenza A and B viruses, particularly oseltamivir-resistant clinical isolates and a swine-origin influenza strain. We observed that the synthesis of viral RNA and protein were inhibited in the presence of TDSWex. The results of the time-of-addition assay suggested that TDSWex inhibited viral entry and budding. In the hemagglutination inhibition assay, TDSWex inhibited the hemagglutination of red blood cells, implying that the extract targeted hemagglutin-related functions such as viral entry. In the attachment and penetration assay, TDSWex showed antiviral activity with EC50s of 0.045 ± 0.026 and 0.012 ± 0.003 mg/mL, respectively. In addition, TDSWex blocked neuraminidase activity. We conclude that TDSWex has bimodal activities against both hemagglutinin and neuraminidase during viral replication.

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“…Thus, mycelial growth inhibition tests were performed according to a previously published method (Kusumoto et al. ) with some modification to take the sample volatility into consideration.…”

Section: Methodsmentioning

confidence: 99%

Antifungal properties of terpenoids in Picea abies against Heterobasidion parviporum

et al. 2014

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Summary The antifungal properties of 14 major oleoresin‐constitutive terpenoids of Norway spruce (Picea abies) against Heterobasidion parviporum were evaluated in vitro at three gradient concentrations, 0.1, 0.2 and 0.4 μmol/cm2, on potato dextrose agar medium. Eight monoterpene hydrocarbons (+)‐ and (−)‐α‐pinene, (−)‐β‐pinene, (+)‐3‐carene, myrcene, (+)‐ and (−)‐limonene, terpinolene; four oxygenated monoterpenes α‐terpineol, terpinen‐4‐ol, 1,8‐cineole, bornyl acetate; and two resin acids abietic acid and dehydroabietic acid were selected. Abietic and dehydroabietic acids showed the highest antifungal activities at all concentrations. Among oxygenated monoterpenes, bornyl acetate and α‐terpineol showed antifungal activity at the highest concentration. Among monoterpene hydrocarbons, (+)‐α‐pinene showed similar activity to terpinen‐4‐ol and 1,8‐cineole at the highest concentration; however, it was lower than α‐terpineol and bornyl acetate. Other monoterpene hydrocarbons inhibited mycelial growth by <10%. Re‐extraction of medium surfaces after the test period revealed that most α‐terpineol and terpinen‐4‐ol remained unchanged on the surface but monoterpene hydrocarbons completely disappeared. However, notable fungal transformed products were observed on surfaces applied with 1,8‐cineole and bornyl acetate. Thus, mycelial growth inhibition of monoterpenoids might be caused by complex functions such as biodegradation and/or detoxification by interaction between mycelium and compound. These results provide a basis for future studies considering the role of chemodiversity in the comprehensive chemical defence of P. abies.

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Antifungal Abietane-Type Diterpenes from the Cones of Taxodium distichum Rich

Cited by 51 publications

References 21 publications

In Vitro Antiprotozoal Activity of Abietane Diterpenoids Isolated from Plectranthus barbatus Andr.

In Vitro Antiprotozoal Activity of Abietane Diterpenoids Isolated from Plectranthus barbatus Andr.

An extract from Taxodium distichum targets hemagglutinin- and neuraminidase-related activities of influenza virus in vitro

Antifungal properties of terpenoids in Picea abies against Heterobasidion parviporum

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