3-Epicabraleahydroxylactone and Other Triterpenoids from Camellia Oil and Their Inhibitory Effects on Epstein-Barr Virus Activation

Akihisa, Toshihiro; Tokuda, Harukuni; Ukiya, Motohiko; Suzuki, Toshie; Enjo, Fumio; Koike, Kazuo; Nikaido, Tamotsu; Nishino, Hoyoku

doi:10.1248/cpb.52.153

Cited by 64 publications

(29 citation statements)

References 22 publications

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“…: Yanagimoto Micro Mp apparatus; uncorrected. IR Spectra: Perkin-Elmer Spectrum One FT-IR spectrophotometer in KBr pellets; in cm (7) [15], uvaol (17) [16], and erythrodiol (18) [16] were used as the reference specimens.…”

Section: Experimental Partmentioning

confidence: 99%

“…Fr. B1 was subjected to HPLC (system IV) to yield (23E)-23-dehydro-25-hydroxydammarenolic acid (3; 45.0 mg; t R 29.7 min) [19], isofouquierol (10; 9.0 mg; t R 33.6) [20], cabralealactone (13; 29.2 mg; t R 27.9 min) [15] [21], 19-dehydroxycecropiacic acid (14; 53.2 mg; t R 12.9 min), 19-dehydroxycecropiacic acid 3-O-methyl ester (15; 24.2 mg, t R 19.2 min), and 1b,16a-dihydroxyeudesm-4(14)-ene (20; 12.5 mg; t R 3.3 min) [22]. A portion of Fr.…”

Section: Experimental Partmentioning

confidence: 99%

“…A portion of Fr. B2 (885 mg) was subjected to HPLC (system II) to afford dammarenolic acid (1, 716 mg; t R 16.5 min) [6], dammarenolic acid methyl ester (2, 20.0 mg; t R 36.0 min) [21], eichlerianic acid (4; 27.9 mg; t R 15.3 min) [6] [15], and ursonic acid (16; 66.3 mg; t R 25.2 min) [6]. A portion of Fr.…”

Section: Experimental Partmentioning

confidence: 99%

“…A portion of Fr. B3 (558 mg) was subjected to HPLC (system II) to give dammarenediol I (6; 48.1 mg; t R 18.2 min) [17], dammarenediol II (7; 153.7 mg; t R 19.2 min) [15], ocotillone (12; 22.9 mg; t R 11.7 min) [6], uvaol (17; 9.9 mg; t R 30.6 min) [16], and erythrodiol (18; 11.1 mg; t R 32.0 min) [16]. Fr.…”

Section: Experimental Partmentioning

confidence: 99%

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Antitumor‐Promoting Effects and Cytotoxic Activities of Dammar Resin Triterpenoids and Their Derivatives

Ukiya

Kikuchi

Tokuda

et al. 2010

Chemistry & Biodiversity

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Nineteen known triterpenoids, 1-19, and one known sesquiterpenoid, 20, were isolated from dammar resin obtained from Shorea javanica K. & V. (Dipterocarpaceae). One of the acidic triterpenoids, dammarenolic acid (1), was converted to fourteen derivatives, namely, an alcohol, 21, an aldehyde, 22, and twelve L-amino acid conjugates, 23-34. Compounds 1-34 were examined for their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol 13-acetate (TPA) in Raji cells, a known primary screening test for antitumor promoters. All of the compounds tested, except for compounds 4, 5, 12-14, 16, and 17, showed inhibitory effects against EBV-EA activation with potencies either comparable with or stronger than that of beta-carotene, a known natural antitumor promoter. In addition, (20S)-20-hydroxy-3,4-secodammara-4(28),24-dien-3-al (22) exhibited inhibitory effects on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as promoter. Furthermore, evaluation of the cytotoxic activities of compounds 1-34 against human cancer cell lines showed that reduction (i.e., 21 and 22) or conjugation with L-amino acids (i.e., 23-34) of compound 1 enhanced the cytotoxicity against human melanoma cell line CRL1579.

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Section: Experimental Partmentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 99%

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Antitumor‐Promoting Effects and Cytotoxic Activities of Dammar Resin Triterpenoids and Their Derivatives

Ukiya

Kikuchi

Tokuda

et al. 2010

Chemistry & Biodiversity

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“…CJ oil has a long history of use as a cosmetic protectant to keep skin and hair healthy and as a soothing agent. It has been reported that Camellia japonica possesses a variety of biological activities, including antibacterial activity (13), inhibitor of human immunodeficiency virus type 1 protease (14), Epstein-Barr virus inhibitor (15), anti-metastasis activity (16), antioxidant activity (17,18), inhibitor of human type I pro-collagen production (19), and anti-allergic responses (20). Despite its wide spread use, there have been no studies that have examined the effects of CJ oil on inflammation-associated gene expression.…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory activity of Camellia japonica oil

Kim

Jung²,

Shin³

et al. 2012

BMB Reports

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Camellia japonica oil (CJ oil) has been used traditionally in EastAsia to nourish and soothe the skin as well as help restore the elasticity of skin. CJ oil has also been used on all types of bleeding instances. However, little is known about its anti-inflammatory effects. Therefore, the anti-inflammatory effects of CJ oil and its mechanisms of action were investigated. CJ oil inhibited LPS-induced production of NO, PGE2, and TNF-α in RAW264.7 cells. In addition, expression of COX-2 and iNOS genes was reduced. To evaluate the mechanism of the anti-inflammatory activity of CJ oil, LPS-induced activation of AP-1 and NF-κB promoters was found to be significantly reduced by CJ oil. LPS-induced phosphorylation of IκBα, ERK, p38, and JNK was also attenuated. Our results indicate that CJ oil exerts anti-inflammatory effects by downregulating the expression of iNOS and COX-2 genes through inhibition of NF-κB and AP-1 signaling. [BMB reports 2012; 45(3): 177-182]

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New Dipterocarpol‐Based Molecules with α‐Glucosidase Inhibitory and Hypoglycemic Activity

Smirnova,

Galimova,

Sapozhnikova

et al. 2023

ChemBioChem

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Dammarane triterpenoids are affordable and bioactive natural metabolites with great structural potential, which makes them attractive sources for drug development. The aim of the study was to investigate the potency of new dipterocarpol derivatives for the treatment of diabetes. Two dammaranes (dipterocarpol and its 20(24)‐diene derivative) were modified by a Claisen‐Schmidt aldol condensation to afford C2(E)‐arylidenes in good yields. The majority of the synthesized compounds exhibited an excellent‐to‐moderate inhibitory effect toward α‐glucosidase (from S. saccharomyces), among them eight compounds showed IC50 values less than 10 μM. 3‐Oxo‐dammarane‐2(E)‐benzylidenes (holding p‐hydroxy‐ 3 l and p‐carbonyl‐ 3 m substituents) demonstrated the most potent α‐glucosidase inhibition with IC50 0.753 and 0.204 μM, being 232‐ and 857‐times more active than acarbose (IC50 174.90 μM), and a high level of NO inhibition in Raw 264.7 cells with IC50 of 1.75 and 4.57 μM, respectively. An in vivo testing of compound 3 m (in a dose of 20 mg/kg) on a model of streptozotocin‐induced T1DM in rats showed a pronounced hypoglycemic activity, the ability to reduce effectively the processes of lipid peroxidation in liver tissue and decrease the excretion of glucose and pyruvic acid in the urine. Compound 3 m reduced the death of diabetic rats and preserved their motor activity.

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3-Epicabraleahydroxylactone and Other Triterpenoids from Camellia Oil and Their Inhibitory Effects on Epstein-Barr Virus Activation

Cited by 64 publications

References 22 publications

Antitumor‐Promoting Effects and Cytotoxic Activities of Dammar Resin Triterpenoids and Their Derivatives

Antitumor‐Promoting Effects and Cytotoxic Activities of Dammar Resin Triterpenoids and Their Derivatives

Anti-inflammatory activity of Camellia japonica oil

New Dipterocarpol‐Based Molecules with α‐Glucosidase Inhibitory and Hypoglycemic Activity

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