Stereochemical investigation and total synthesis of inuloidin, a biologically active sesquiterpenoid from Heterotheca inuloides

Kamatani, Jumpei; Iwadate, Takehiro; Tajima, Reiko; Kimoto, Hideaki; Yamada, Yoichi M. A.; Masuoka, Noriyoshi; Kubo, Isao; Nihei, Keiji

doi:10.1016/j.tet.2014.03.057

Cited by 6 publications

(5 citation statements)

References 21 publications

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“…Thus, these findings were in agreement with previous results that established that the configuration of (+)-(4 S )-7-hydroxy-3,4-dihydrocadalene [(+)-3-hydroxy-α-calacorene] from G. hirsutum is the opposite of that of the compound isolated from H. inuloides. The 4 R configuration has also been recently proven for inuloidin, a cadinene isolated from H. inuloides …”

Section: Resultssupporting

confidence: 58%

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Cadinane-Type Sesquiterpenoids from Heterotheca inuloides: Absolute Configuration and Anti-inflammatory Activity

Egas¹,

Toscano²,

Linares³

et al. 2015

J. Nat. Prod.

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Eight cadinane-type sesquiterpenoids (1-8) together with some triterpenoids, flavonoids, and sterols were isolated from the aerial parts of Heterotheca inuloides. The structures of the new compounds (1-4) were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis. The structures of the new (1-3) and the known (5-7) sesquiterpenoids were confirmed by X-ray crystallography. The absolute configurations of metabolites 2-5 were determined by comparing their experimental and calculated electronic circular dichroism spectra and confirmed via refinement of the Flack parameter using anomalous X-ray scattering from the oxygen atoms and chemical correlation methods. The sesquiterpenoids were evaluated for their anti-inflammatory potential by applying the TPA-induced mouse ear edema model. The results revealed that some of these metabolites exhibit moderate anti-inflammatory activity. At a dose of 228 μg/ear compound 1 showed 43.14 ± 8.09% inhibition on ear edema, indicating an IC50 > 228 μg/ear.

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Section: Resultssupporting

confidence: 58%

“…25 The 4R configuration has also been recently proven for inuloidin, a cadinene isolated from H. inuloides. 26 X-ray crystal structures of the known compounds 4methoxyisocadalene (6) and 3,7-dihydroxy-3(4H)-isocadalen-4-one (7) (not previously reported) were determined and are shown in Figures 7 and 8, respectively.…”

mentioning

confidence: 89%

Cadinane-Type Sesquiterpenoids from Heterotheca inuloides: Absolute Configuration and Anti-inflammatory Activity

Egas¹,

Toscano²,

Linares³

et al. 2015

J. Nat. Prod.

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“…Natural materials, like plants, bacteria, fungi, yeast, have been used for the synthesis of silver nanoparticles [ 40 ]. The dried flower of Heterotheca inuloides , which is called “arnica”, has been used in Mexican traditional medicine to treat inflammatory discomfort [ 43 , 44 ].…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Silver Nanoparticles on Orthodontic Elastomeric Modules: Evaluation of Mechanical and Antibacterial Properties

et al. 2017

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In the present study, silver nanoparticles (AgNPs) were synthesized in situ on orthodontic elastomeric modules (OEM) using silver nitrate salts as metal-ion precursors and extract of the plant Hetheroteca inuloides (H. inuloides) as bioreductant via a simple and eco-friendly method. The synthesized AgNPs were characterized by UV-visible spectroscopy; scanning electron microscopy-energy-dispersive spectroscopy (SEM-EDS) and transmission electron microscopy (TEM). The surface plasmon resonance peak found at 472 nm confirmed the formation of AgNPs. SEM and TEM images reveal that the particles are quasi-spherical. The EDS analysis of the AgNPs confirmed the presence of elemental silver. The antibacterial properties of OEM with AgNPs were evaluated against the clinical isolates Streptococcus mutans, Lactobacillus casei, Staphylococcus aureus and Escherichia coli using agar diffusion tests. The physical properties were evaluated by a universal testing machine. OEM with AgNPs had shown inhibition halos for all microorganisms in comparison with OEM control. Physical properties increased with respect to the control group. The results suggest the potential of the material to combat dental biofilm and in turn decrease the incidence of demineralization in dental enamel, ensuring their performance in patients with orthodontic treatment.

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“…Thus, we theorized that these substances may exhibit fungicidal effects, and the phytochemistry of infected H. tiliaceus was further analyzed. gossyvertin (11), 36 isohemigossypol (12), 37 inuloidin (13), 38 7-hydroxy-3,4-dihydrocadalin (14), 39 (lR,4R)-7-hydroxycalamenene (15), 40 7-hydroxy-1,2-dihydrocadalene ( 16), 41 7hydroxycadalenal (17), 42 mansonone C (18), 42 parvifloral A (19), 43 syriacusin A (20), 43 7-hydroxycadalene (21), 42 hibisceusin D (22), 34 thespesilactam (23), 44 and mansonone D (24), 42 were separated from the infected stems of the plant (Figure 1). Compounds 1−24 represented a class of cadinanetype sesquiterpenoids, including diverse planar structures, and showed remarkable antifungal activities.…”

Section: ■ Introductionmentioning

confidence: 99%

Discovery of Cadinane-Type Sesquiterpenoids from the Infected Stems of Hibiscus tiliaceus as Potential Agrochemical Fungicides

Chen,

Xu,

Yang

et al. 2024

J. Agric. Food Chem.

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Ten new cadinane-type sesquiterpenoids, named hibisceusins I−R (1−10), along with 14 known sesquiterpenoids (11−24), were acquired from the tainted stems of Hibiscus tiliaceus. Their structures were identified via spectroscopic analysis, onedimensional (1D) and two-dimensional (2D) NMR, and computer-assisted structure elucidation techniques, including infrared (IR) and mass spectrometry (MS) data. Additionally, subsequent DP4/DP4+ probability methods were used to resolve 3′s relative configurations by comparing their experimental values to the predicted NMR data. The absolute configurations of compounds 1−4 were measured through electronic circular dichroism (ECD) spectra. The ability of all isolates to inhibit the growth of five phytopathogenic fungi (Rhizopus stolonifer, Verticillium dahliae Kleb., Thanatephorus cucumeris, Fusarium oxysporum Schltdl., and F. oxysporum HK-27) was evaluated. Aldehydated sesquiterpenoids (1, 6−9, 11, 12, and 22) and a known sesquiterpenoid quinine (18) exhibited significant inhibitory activities against V. dahliae, T. cucumeris, F. oxysporum, and F. oxysporum HK-27 with minimum inhibitory concentration (MIC) values of 2.5−50 μg/mL, but all isolates remained inactive against R. stolonifer. Moreover, the effects of the isolates on the mycelial morphology were watched through scanning electron microscopy. This study revealed that aldehydated cadinane-type sesquiterpenoids could be used as novel antifungal molecules to develop agrochemical fungicides in plant protection.

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Stereochemical investigation and total synthesis of inuloidin, a biologically active sesquiterpenoid from Heterotheca inuloides

Cited by 6 publications

References 21 publications

Cadinane-Type Sesquiterpenoids from Heterotheca inuloides: Absolute Configuration and Anti-inflammatory Activity

Cadinane-Type Sesquiterpenoids from Heterotheca inuloides: Absolute Configuration and Anti-inflammatory Activity

Biosynthesis of Silver Nanoparticles on Orthodontic Elastomeric Modules: Evaluation of Mechanical and Antibacterial Properties

Discovery of Cadinane-Type Sesquiterpenoids from the Infected Stems of Hibiscus tiliaceus as Potential Agrochemical Fungicides

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