Two new triterpenoids from the roots of <i>Pinus densiflora</i>

Otaka, Junnosuke; Komatsu, Masabumi; Miyazaki, Yasumasa; Futamura, Yushi; Osada, Hiroyuki

doi:10.1080/09168451.2016.1263149

Cited by 5 publications

(4 citation statements)

References 21 publications

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“…It indicated the presence of one double bond, a methoxy, and an oxirane ring at C‐12, C‐3, and C‐29/31 of 2 , respectively. A comparison of the NMR data of 2 with olean‐12‐en [53–58] revealed that the structures of the two compounds were very similar except for the presence of methoxy at C‐3 and oxirane at C‐29 position; consequently, new compound 2 was identified as a 3 β ‐methoxy‐29(31)‐oxirane olean‐12‐ene ( Supporting Information Figure S4‐S6).…”

Section: Resultsmentioning

confidence: 99%

Biological Activity and Phytochemical Analysis of Dicranum scoparium against the Bacterial Disease for Honey Bee

Karaoğlu

Yaylı

Erik

et al. 2022

Chemistry & Biodiversity

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Bacterial diseases, such as American Foulbrood (AFB) and European Foulbrood (EFB), are known to have catastrophic effects on honey bees (if left to spread, can wipe out entire colonies), leading to severe financial losses in the beekeeping industry. The aim of this study was to evaluate the pharmacological properties of methanol extract and its fractions (ethyl acetate, hexane, water) derived from Dicranum scoparium Hedw., which could be utilized as a potential drug to prevent the bacterial diseases (AFB and EFB) affecting the honey bees. For this purpose, crude methanol extract and ethyl acetate/hexane/water fractions were prepared from the aerial part of D. scoparium, collected from Trabzon province. Bio‐guided fractionation of the extract and its fractions led to the first‐time isolation of five compounds. The structure of all compounds was elucidated by nuclear magnetic resonance (NMR) spectroscopy, ultraviolet (UV) spectral analysis, Fourier‐transform infrared spectroscopy (FT‐IR), liquid chromatography quadrupole time‐of‐flight mass spectroscopy (LC‐QToF‐MS), and by comparison of their NMR data with that of literature. The analysis of these compounds revealed significant antibacterial and sporicidal activities against bacteria causing larval diseases in honey bees. The antibacterial activity of these compounds ranged from 0.6 to 60 μg/mL against AFB and EFB causing bacteria. Therefore, the natural raw extract and fractions of D. scoparium could be used as potential therapeutic agents against bacterial agents affecting honey bees.

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Section: Resultsmentioning

confidence: 99%

Biological Activity and Phytochemical Analysis of Dicranum scoparium against the Bacterial Disease for Honey Bee

Karaoğlu

Yaylı

Erik

et al. 2022

Chemistry & Biodiversity

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“…The characterization of P. merkusii bark resulted in three triterpenoids (C1, C3, and C5) and two steroids (C2 and C4). In previous research, triterpenoids and steroids have been linearly detected in the Pinaceae family (Zullo and Adam 2002;Le Milbeau et al 2013;Otaka et al 2016). Compound C1 has been reported in Pinus bark, i.e., P. armandii (Fang et al 1991;Fang and Cheng 1992), P. luchuensis (Yamamoto et al 2011), P. contorta (Rowe et al 1972), P. strobus (Zinkel and Evans 1972), P. radiata (Weston 1973), P. taiwanensis (Cheng and Chao 1979), and P. roxburghii (Labib et al 2018), while compound C5 been reported in the bark of P. lambertiana (Rowe 1964).…”

Section: Chemotaxonomic Significancementioning

confidence: 96%

Triterpenoids and steroids from the bark of Pinus merkusii (Pinaceae)

Masendra

Ashitani

Takahashi

et al. 2018

BioRes

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Serratene triterpenoids are considered chemotaxonomy compounds from the Pinaceae family, within the Pinus genus. However, no studies have been conducted on the constituents of serratene triterpenoids of Pinus merkusii. P. merkusii is the only pine species native to Southeast Asia, including Indonesia. This study aimed to investigate the use of triterpenoids and steroids from the bark of P. merkusii as chemotaxonomic biomarkers. Five lipophilic extractives, including three triterpenoids (3β-methoxyserratt-14-en-21-one (C1), 3α,21β- dimethoxy-D14-serratene (C3), serrate-14-en-3β,21β-diol (C5)), and two steroids (stigmast-4-en-3-one (C2) and β-sitosterol (C4)), were isolated from the n-hexane extract of the bark of P. merkusii using column chromatography and thin–layer chromatography. The structures of the triterpenoids and steroids were characterized on the basis of their spectroscopic data. The discovery of serratene triterpenoids and steroids in P. merkusii bark characterizes this species as being in chemical accordance with other species of the Pinus genus and Pinaceae family.

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“…In addition, root terpenoids play a crucial role in the defense against herbivores and pathogens ( Sharma et al., 2017 ; Lackus et al., 2018 ). Previous studies have analyzed the VOCs of Pinus species including Pinus tabuliformis, Pinus bungeana, Cedrus deodara, Pinus thunbergii ( Ji and Ji, 2021 ) , Pinus densiflora ( Otaka et al., 2017 ), Pinus halepensis ( Blanch et al., 2007 ), Pinus mugo ( Celiński et al., 2015 ), Pinus sylvestris ( Szmigielski et al., 2011 ), Pinus massoniana ( Quan and Ding, 2017 ), with a majority of the studies focusing on needles rather than roots.…”

Section: Introductionmentioning

confidence: 99%

“…While few studies have focused on root terpenoids in tree species ( Kleiber et al., 2017 ; Otaka et al., 2017 ; Quan and Ding, 2017 ; Chang et al., 2021 ), there is a complete lack of knowledge on the relationship between root terpenoids and water deficit conditions. More importantly, it is currently unknown whether terpenoid biosynthesis mitigates or alleviates drought stress in tree species Pinus strobus .…”

Section: Introductionmentioning

confidence: 99%

Short-term severe drought influences root volatile biosynthesis in eastern white pine (Pinus strobus L)

et al. 2022

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Climate change-related drought stress is expected to shift carbon partitioning toward volatile organic compound (VOC) biosynthesis. The effect of drought stress on VOC synthesis remains unknown in several tree species. Therefore, we exposed eastern white pine (Pinus strobus) plants to severe drought for 32 days and performed physiological analysis (chlorophyll content, leaf water content, and root/shoot index), biochemical analysis (non-structural carbohydrates, proline, lipid peroxidation, and antioxidant assay), and total root VOC analysis. Drought stress decreased the relative water and soil moisture contents. Root proline accumulation and antioxidant activity increased significantly, whereas leaf chlorophyll synthesis and fresh weight decreased significantly in drought-treated plants. A non-significant increase in sugar accumulation (leaves and roots), proline accumulation (leaves), antioxidant activity (leaves), and lipid peroxidation (leaves and roots) was observed in drought-treated plants. Drought stress caused a non-significant decline in root/shoot ratio and starch accumulation (leaves and roots) and caused a significant increase in root abscisic acid content. Drought-treated plants showed an increase in overall monoterpene synthesis (16%) and decline in total sesquiterpene synthesis (3%). Our findings provide an overall assessment of the different responses of VOC synthesis to severe water deficit that may help unravel the molecular mechanisms underlying drought tolerance in P. strobus.

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Two new triterpenoids from the roots of Pinus densiflora

Cited by 5 publications

References 21 publications

Biological Activity and Phytochemical Analysis of Dicranum scoparium against the Bacterial Disease for Honey Bee

Biological Activity and Phytochemical Analysis of Dicranum scoparium against the Bacterial Disease for Honey Bee

Triterpenoids and steroids from the bark of Pinus merkusii (Pinaceae)

Short-term severe drought influences root volatile biosynthesis in eastern white pine (Pinus strobus L)

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