Chemical Constituents of Celastrus rugosus

Ying, You‐Min; Zhang, Caixue; Yu, Kai-Ming; Fang, Cheng-An; Xiang, Jia‐Gui; Wang, Fa-Song; Wang, Zhen; Zhang, Wei; Shan, Wei‐Guang; Zhan, Zha‐Jun

doi:10.1007/s10600-017-2060-x

Cited by 6 publications

(3 citation statements)

References 10 publications

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“…orbiculatus were isolated to yield six diterpenoids ( 1 – 6 ), nine triterpenoids ( 7 – 15 ), and two steroids ( 16 and 17 ) using various column chromatography. Their chemical structures were elucidated as (+)-7-deoxynimbidiol ( 1 ) [ 38 ], nimbidiol ( 2 ) [ 39 ], celaphanol A ( 4 ) [ 39 ], (+)-ferruginol ( 5 ) [ 40 ], dehydroabietic acid ( 6 ) [ 41 ], lupenone ( 7 ) [ 42 ], lupeol ( 8 ) [ 42 ], betulin ( 9 ) [ 43 ], 2 β ,3 β -dihydroxylup-20(29)-ene ( 10 ) [ 44 ], 3 β -caffeoyloxylup-20(29)-en-6 α -ol ( 11 ) [ 45 ], lup-20(29)-en-28-ol-3 β -yl caffeate ( 12 ) [ 43 ], dammarenediol II 3-caffeate ( 13 ) [ 46 ], β -amyrin ( 14 ) [ 47 ], α -amyrin ( 15 ) [ 47 ], sitostenon ( 16 ) [ 48 ], and ergone ( 17 ) [ 49 ], compared to previous reported spectroscopic data, NMR, MS, and optical rotation values. Among these, 13 compounds ( 3 , 5 – 13 , and 15 – 17 ) containing compound 3 determined as novel podocarpane trinorditerpenoid based on HRESIMS and NMR data were first reported from C .…”

Section: Resultsmentioning

confidence: 99%

Anti-Inflammatory Activity of Diterpenoids fromCelastrus orbiculatusin Lipopolysaccharide-Stimulated RAW264.7 Cells

Jang

Kim

Park

et al. 2020

Journal of Immunology Research

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Celastrus orbiculatus Thunb has been known as an ethnopharmacological medicinal plant for antitumor, anti-inflammatory, and analgesic effects. Although various pharmacological studies of C. orbiculatus extract has been reported, an anti-inflammatory mechanism study of their phytochemical constituents has not been fully elucidated. In this study, compounds 1–17, including undescribed podocarpane-type trinorditerpenoid (3), were purified from C. orbiculatus and their chemical structure were determined by high-resolution electrospray ionization mass (HRESIMS) and nuclear magnetic resonance (NMR) spectroscopic data. To investigate the anti-inflammatory activity of compounds 1–17, nitric oxide (NO) secretion was evaluated in LPS-treated murine macrophages, RAW264.7 cells. Among compounds 1–17, deoxynimbidiol (1) and new trinorditerpenoid (3) showed the most potent inhibitory effects (IC50: 4.9 and 12.6 μM, respectively) on lipopolysaccharide- (LPS-) stimulated NO releases as well as proinflammatory mediators, such as inducible nitric oxide (iNOS), cyclooxygenase- (COX-) 2, interleukin- (IL-) 1β, IL-6, and tumor necrosis factor- (TNF-) α. Its inhibitory activity of proinflammatory mediators is contributed by suppressing the activation of nuclear transcription factor- (NF-) κB and mitogen-activated protein kinase (MAPK) signaling cascades including p65, inhibition of NF-κB (IκB), extracellular signal-regulated kinase (ERK), c-Jun NH2-terminal kinase (JNK), and p38. Therefore, these results demonstrated that diterpenoids 1 and 3 obtained from C. orbiculatus may be considered a potential candidate for the treatment of inflammatory diseases.

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Section: Resultsmentioning

confidence: 99%

Anti-Inflammatory Activity of Diterpenoids fromCelastrus orbiculatusin Lipopolysaccharide-Stimulated RAW264.7 Cells

Jang

Kim

Park

et al. 2020

Journal of Immunology Research

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“…We are also reporting the presence of 3-oxo-friedelan-20α-oic acid ( 2 ) in the plant, S . torvum for the first time, although the compound has previously been reported in a number of plant species [ 44 – 46 ].…”

Section: Discussionmentioning

confidence: 99%

Bioactive triterpenoids from Solanum torvum fruits with antifungal, resistance modulatory and anti-biofilm formation activities against fluconazole-resistant candida albicans strains

et al. 2021

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Vulvovaginal candidiasis (VVC) is the second most common vaginal infection that affects women of reproductive age. Its increased occurrence and associated treatment cost coupled to the rise in resistance of the causative pathogen to current antifungal therapies has necessitated the need for the discovery and development of novel effective antifungal agents for the treatment of the disease. We report in this study the anti-Candida albicans activity of Solanum torvum 70% ethanol fruit extract (STF), fractions and some isolated compounds against four (4) fluconazole-resistant strains of C. albicans. We further report on the effect of the isolated compounds on the antifungal activity of fluconazole and voriconazole in the resistant isolates as well as their inhibitory effect on C. albicans biofilm formation. STF was fractionated using n-hexane, chloroform (CHCl3) and ethyl acetate (EtOAc) to obtain four respective major fractions, which were then evaluated for anti-C. albicans activity using the microbroth dilution method. The whole extract and fractions recorded MICs that ranged from 0.25 to 16.00 mg/mL. From the most active fraction, STF- CHCl3 (MIC = 0.25–1.00 mg/mL), four (4) known compounds were isolated as Betulinic acid, 3-oxo-friedelan-20α-oic acid, Sitosterol-3-β-D-glucopyranoside and Oleanolic acid. The compounds demonstrated considerably higher antifungal activity (0.016 to 0.512 mg/mL) than the extract and fractions and caused a concentration-dependent anti-biofilm formation activity. They also increased the sensitivity of the C. albicans isolates to fluconazole. This is the first report of 3-oxo-friedelan-20α-oic acid in the plant as well as the first report of betulinic acid, sitosterol-3-β-D-glucopyranoside and oleanolic acid from the fruits of S. torvum. The present study has demonstrated the anti-C. albicans activity of the constituents of S. torvum ethanol fruit extract and also shown that the constituents possess anti-biofilm formation and resistance modulatory activities against fluconazole-resistant clinical C. albicans isolates.

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“…In addition, two aromatic proton signals assignable to a symmetrically 1,3,4,5-tetrasubstituted phenyl ring (δ H 6.73 (2H, s)) were present, as were two proton signals of a trans double bond (δ H 7.50 (1H, d, J = 15.8 Hz) and 6.35 (1H, d, J = 15.8 Hz)), which indicated the presence of a sinapinoyl moiety. 10,11 The 13 C NMR spectrum of 1 revealed 33 carbon resonances, which were assigned on the basis of chemical shift values and HMQC data to three methoxyls, one methene, fifteen methines and fourteen quaternary carbons plus two carbonyls at δ C 182.6 and 166.4. The data mentioned above indicated that 1 was a flavone glycoside bearing an unusual sinapinoyl moiety.…”

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confidence: 99%