Clerodane diterpenoids with anti-inflammatory and synergistic antibacterial activities from <i>Tinospora crispa</i>

Five new polychlorinated bibenzyls (1–5) along with 3 known compounds (6–8) were isolated from the stems and leaves of Rhododendronminutiflorum. The chemical structures of all the isolates were determined by spectroscopic methods, and compounds 1 and 2 were further verified by single-crystal X-ray diffraction analyses. Compounds 1–5 were halogenated compounds which bear three to five chlorine atoms in their chemical structures. Biologically, compounds 2, 5 and 6 showed varying degrees of toxicity toward the Asian citrus psyllid (Diaphorinacitri) with LD50 values 27.15, 17.02 and 16.20 mg/L, respectively. These values were comparable to the positive control matrine (LD50 = 11.86 mg/L), which were calculated using observations on day 6. Meanwhile, compound 4 had α-glucosidase inhibitory activity with IC50 value of 17.87 ± 0.74 μM. Graphical Abstract

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“…The instruments, materials and reagents used in this study were consistent with those reported in the literature [13,20].…”

Section: General Experimental Proceduressupporting

confidence: 54%

New polychlorinated bibenzyls from Rhododendron minutiflorum

Zhu

Deng

Tao

et al. 2023

Nat. Prod. Bioprospect.

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“…Therefore, NO inhibitors were considered a promising direction for anti-inflammatory drug research [ 39 ]. Recently, several diterpenes with decalin skeleton have been reported to have significant NO inhibitory activity [ 40 , 41 , 42 ]. Among diterpenes, tinopanoid M, a clerodane diterpenoid isolated from Tinospora crispa, exerts good anti-inflammatory effects by reducing the expression of various pro-inflammatory factors and modulating multiple inflammatory pathways [ 41 ].…”

Section: Discussionmentioning

confidence: 99%

Talaroacids A–D and Talaromarane A, Diterpenoids with Anti-Inflammatory Activities from Mangrove Endophytic Fungus Talaromyces sp. JNQQJ-4

Wang,

Wu,

et al. 2024

IJMS

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Five new diterpenes including four diterpenes with 1,2,3,4,4a,5,6,8a-octalin skeleton talaroacids A–D (1–4) and an isopimarane diterpenoid talaromarane A (5) were isolated from the mangrove endophytic fungus Talaromyces sp. JNQQJ-4. Their structures and absolute configurations were determined by analysis of high-resolution electrospray ionization mass spectroscopy (HRESIMS), 1D/2D Nuclear Magnetic Resonance (NMR) spectra, single-crystal X-ray diffraction, quantum chemical calculation, and electronic circular dichroism (ECD). Talaromarane A (5) contains a rare 2-oxabicyclo [3.2.1] octan moiety in isopimarane diterpenoids. In bioassays, compounds 1, 2, 4, and 5 displayed significant anti-inflammatory activities with the IC50 value from 4.59 to 21.60 μM.

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“…NO Inhibitory Activity and Cytotoxicity on BV-2 Cells. The inhibitory activity of all the isolated compounds on nitric oxide (NO) release was tested by the method described in previous reports 25,26 with minor modifications. In short, 100 μL medium containing 4 × 10 4 BV-2 cells was transferred to each well of the 96-well plate.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Quassinoids from Picrasma chinensis with Insecticidal Activity against Adults and Larvae of Diaphorina citri Kuwayama and Neuroprotective Effect

Fan

Han

Deng

et al. 2022

J. Agric. Food Chem.

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Eleven new tetracyclic quassinoids, picrachinensin A−K (1−11), along with six known congeners, were isolated from the stems and leaves of Picrasma chinensis. Their structures were elucidated by integrated multiple spectroscopic techniques, singlecrystal X-ray diffraction analysis, and electronic circular dichroism. Notably, compounds 3 and 4 are a pair of undescribed epimers, and 8 and 9 are unusual quassinoids with a hydroxymethyl group at C-13. Biologically, compound 7 exhibited insecticidal activity on both adults and larvae of Diaphorina citri Kuwayama even more effectively than the positive control (abamectin), with an LD 50 of 55.69 mg/L for adults and a corrected mortality rate of 30.42 ± 2.78% for larvae (100 mg/L). According to preliminary structure− activity relationship investigations, the hydroxymethyl at the C-13 position of quassinoids was beneficial for their insecticidal activity. In addition, compounds 1, 4, and 12 exhibited excellent neuroprotective effect against H 2 O 2 -induced oxidative injury on SH-SY5Y cells, with more potent activity than the positive control (Trolox), and all the compounds exhibited no cytotoxicity to SH-SY5Y and BV-2 cells at the indicated concentrations.

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Clerodane diterpenoids with anti-inflammatory and synergistic antibacterial activities from Tinospora crispa

Abstract: Ten new and four known clerodane diterpenoids were isolated from the vine and leaves of Tinospora crispa. The chemical structures and absolute stereochemical configurations of all the compounds were established...

Cited by 8 publications

References 47 publications

New polychlorinated bibenzyls from Rhododendron minutiflorum

New polychlorinated bibenzyls from Rhododendron minutiflorum

Talaroacids A–D and Talaromarane A, Diterpenoids with Anti-Inflammatory Activities from Mangrove Endophytic Fungus Talaromyces sp. JNQQJ-4

Quassinoids from Picrasma chinensis with Insecticidal Activity against Adults and Larvae of Diaphorina citri Kuwayama and Neuroprotective Effect

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