Phytotoxic Diterpenoids from Plants and Microorganisms

Wei, Wenjun; Li, Ya; Li, Hang-Ying; Ma, Kai-Liang; Wang, Liudi; Gao, Kun

doi:10.1002/cbdv.201900398

Cited by 6 publications

(6 citation statements)

References 62 publications

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“…As a result, five compounds were isolated from M. glyptostroboides . The structures of five compounds (compounds 1 – 5 ) were elucidated based on the 1 H and 13 C-NMR data, and comparison with relevant references [ 16 , 17 , 18 , 19 , 20 ]. The isolated compounds were identified as taxoquinone ( 1 ), sugiol ( 2 ), suginal ( 3 ), sandaracopimarinol ( 4 ), and sandaracopimaradien-19-ol ( 5 ) ( Figure 2 ).…”

Section: Resultsmentioning

confidence: 99%

“…Then, the bioassay-guided isolation of ethanol extract of M. glyptostroboides fruits allowed to isolate five pure compounds. The structures of these compounds were elucidated based on 1 H- and 13 C-NMR data by comparison with references [ 16 , 17 , 18 , 19 , 20 ]. As a result, compounds 1 – 3 were identified as taxoquinone, sugiol, and suginal, respectively, which are abietane-type diterpenoids.…”

Section: Discussionmentioning

confidence: 99%

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Anti-Amyloidogenic Effects of Metasequoia glyptostroboides Fruits and Its Active Constituents

Yeo

Lee

et al. 2023

Molecules

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Alzheimer’s disease (AD) is a serious neurodegenerative brain disease that interferes with daily life. The accumulation of beta-amyloid (Aβ), along with oxidative stress-inducing neurocellular apoptosis, has been considered one of the causes of AD. Thus, the purpose of this study is to find natural products that can reduce Aβ accumulation. The ethanol extract of Metasequoia glyptostroboides Hu & Cheng fruits (Cupressaceae) significantly reduced the aggregation of Aβ into oligomers and fibrils determined by Thioflavin T (ThT) assay. The solvent-partitioned ethyl acetate layer was further separated based on the bioassay-guided isolation method combined with the ThT assay. As a result, five compounds were isolated and elucidated as taxoquinone (1), sugiol (2), suginal (3), sandaracopimarinol (4), and sandaracopimaradien-19-ol (5) by comparing NMR data with references. All the compounds significantly reduced the aggregation of Aβ and enhanced the disaggregation of pre-formed Aβ aggregates in a dose-dependent manner. Furthermore, the inhibition of Aβ aggregation by the compounds protected PC12 cells from Aβ aggregate-induced toxicity. Among the five compounds, sandaracopimarinol (4) and sandaracopimaradien-19-ol (5) were the most effective. These results suggest that M. glyptostroboides and isolated five compounds have a potential for further study to be developed as anti-AD agents.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Anti-Amyloidogenic Effects of Metasequoia glyptostroboides Fruits and Its Active Constituents

Yeo

Lee

et al. 2023

Molecules

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“…Seven terpenoids isolated from Oryza sativa L. husks have antibacterial activity against four pathogenic fungi, such as Fusarium oxysporum Schl., and are phytotoxic to weeds such as barnyard grass (E. crus-galli) of rice fields (Gu et al 2019). Phytotoxic diterpenes inhibit seed germination and seedling growth, and cause disease symptoms in plant tissues and seedlings (Wei et al 2019). Strigolactone can induce colonization of parasitic plants in the Scrophulariaceae and arbuscular mycorrhizal fungi (AMF) (Bouwmeester et al 2007;Gomez-Roldan et al 2008).…”

Section: Other Compoundsmentioning

confidence: 99%

Allelopathy and allelobiosis: efficient and economical alternatives in agroecosystems

Han,

Yang,

Huang

et al. 2023

Plant Biol J

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Chemical interactions in plants often involve plant allelopathy and allelobiosis. Allelopathy is an ecological phenomenon leading to interference among organisms, while allelobiosis is the transmission of information among organisms. Crop failures and low yields caused by inappropriate management can be related to both allelopathy and allelobiosis. Therefore, research on these two phenomena and the role of chemical substances in both processes will help us to understand and upgrade agroecosystems. In this review, substances involved in allelopathy and allelobiosis in plants are summarized. The influence of environmental factors on the generation and spread of these substances is discussed, and relationships between allelopathy and allelobiosis in interspecific, intraspecific, plant–micro‐organism, plant–insect, and mechanisms, are summarized. Furthermore, recent results on allelopathy and allelobiosis in agroecosystem are summarized and will provide a reference for the future application of allelopathy and allelobiosis in agroecosystem.

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“…Fungal-derived diterpenoids are a large class of natural products that possess diverse structural scaffolds and bioactivities. − Psathyrella candolleana is an edible wild mushroom with medicinal potentials, such as an anticlastogenic effect against DNA damage . The previous chemical investigations of P.…”

Section: Introductionmentioning

confidence: 99%

Antibiotic Guanacastane Diterpenoids with Two New Skeletons from Psathyrella candolleana Uncovered by Semisolid and Liquid Media

Zhao

Yang

Zhou

et al. 2023

J. Agric. Food Chem.

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The culture of Psathyrella candolleana in host Dioscorea opposite medium produced seven new guanacastane diterpenoids, psayamin (1) as an unprecedented 5/7/6/6/6/6/7/5-fused octacyclic spiro scaffold both under liquid and semisolid conditions, psathins A−C (4−6) with a 5/7/6 tricyclic backbone by liquid medium, psathins D−E (7−8) as the same unprecedented skeletons of 5/6/7/6-fused tetracyclic or 6/7/6 tricyclic structures, and psathin F (9) with a 5/7/5/6 tetracyclic backbone by semisolid medium. The structures were elucidated by detailed spectroscopic analyses and those of 1 and 7 were determined by single-crystal X-ray crystallography. The semisolid culture led to four structure types of the guanacastane diterpenoid. Compound 5 showed antifungal activity against phytopathogen Fusarium incarnatum with a minimum inhibitory concentration (MIC) of 8 μg/mL, while compound 4 showed significant antifungal activity against Alternaria sp. with an MIC of 2 μg/mL. Compounds 1 and 8 also showed antifeedant activities against the silkworms with the feeding deterrence indices of 50%, at the concentrations of 50 μg/cm 2 . Compound 1 showed significant cytotoxicity with IC 50 at 10.87 ± 0.24−15.96 ± 0.30 μM and antiacetylcholinesterase activity with IC 50 at 37.3 μM. Also, compound 1 remarkably induced apoptosis of HL-60 at 10, 20 μM in a concentration-dependent manner. The spiral ring of 1 was vital in cytotoxicity and anti-acetylcholinesterase activity. The different media fermented by P. candolleana resulted in the chemical diversity of bioactive guanacastane diterpenoids and potential applications in the agricultural and food functions.

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Phytotoxic Diterpenoids from Plants and Microorganisms

Cited by 6 publications

References 62 publications

Anti-Amyloidogenic Effects of Metasequoia glyptostroboides Fruits and Its Active Constituents

Anti-Amyloidogenic Effects of Metasequoia glyptostroboides Fruits and Its Active Constituents

Allelopathy and allelobiosis: efficient and economical alternatives in agroecosystems

Antibiotic Guanacastane Diterpenoids with Two New Skeletons from Psathyrella candolleana Uncovered by Semisolid and Liquid Media

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