Benzopyrans

Publication Title: 
Biological & Pharmaceutical Bulletin

Gallic acid (GA) and chebulagic acid (CA) were isolated from the extract of a herbal medicine, kashi (myrobalans: the fruit of Terminalia chebula) as active principles that blocked the cytotoxic T lymphocyte (CTL)-mediated cytotoxicity. GA and CA inhibited the killing activity of CD8+ CTL clone at IC50 values of 30 microM and 50 microM, respectively. Granule exocytosis in response to anti-CD3 stimulation was also blocked by GA and CA at the equivalent concentrations.

Author(s): 
Hamada, S.
Kataoka, T.
Woo, J. T.
Yamada, A.
Yoshida, T.
Nishimura, T.
Otake, N.
Nagai, K.
Publication Title: 
Planta Medica

The bioassay-directed isolation of Terminalia chebula fruits afforded four human immunodeficiency virus type 1 (HIV-1) integrase inhibitors, gallic acid ( 1) and three galloyl glucoses ( 2 - 4). In addition, four flavonol glycoside gallates ( 5 - 8) from Euphorbia pekinensis containing the galloyl moiety also showed the inhibitory activity at a level comparable to those of 2 - 4.

Author(s): 
Ahn, Mi-Jeong
Kim, Chul Young
Lee, Ji Suk
Kim, Tae Gyun
Kim, Seung Hee
Lee, Chong-Kyo
Lee, Bo-Bin
Shin, Cha-Gyun
Huh, Hoon
Kim, Jinwoong
Publication Title: 
Arthritis and Rheumatism

OBJECTIVE: Chebulagic acid (CHE) from the immature seeds of Terminalia chebula was identified from a natural product library as a potent suppressor of T cell activity. This study examined the effectiveness of CHE against the onset and progression of collagen-induced arthritis (CIA) in mice. METHODS: Arthritis was induced in DBA/1J mice by subcutaneous immunization with bovine type II collagen on days 0 and 21. CHE was administered intraperitoneally for 3 weeks, either as prophylaxis (10 or 20 mg/kg) before disease onset or as therapy (20 mg/kg) after disease onset.

Author(s): 
Lee, Sang-Ik
Hyun, Pung-Mi
Kim, Seung-Hyung
Kim, Kyoung-Shin
Lee, Sang-Keun
Kim, Byoung-Soo
Maeng, Pil Jae
Lim, Jong-Soon
Publication Title: 
Journal of Separation Science

As a chromatographic column, the high-speed counter-current chromatography system was equipped with a preparative HPLC series, enabling the successful isolation of hydrolysable tannins from the fruits of Terminalia chebula, a traditional Chinese medicine. The two-phase solvent system was composed of n-hexane-ethyl acetate-methanol-water (1:20:1:20 v/v). As a result, 33.2 mg chebulagic and 15.8 mg chebulinic acids were obtained in one step from 300 mg of crude extract. Their purities were determined by HPLC to be 95.3 and 96.1%, respectively.

Author(s): 
Han, Quanbin
Song, Jingzheng
Qiao, Chunfeng
Wong, Lina
Xu, Hongxi
Publication Title: 
Bioscience, Biotechnology, and Biochemistry

Chebulagic acid, isolated form Terminalia chebula Retz, proved to be a reversible and non-competitive inhibitor of maltase with a K(i) value of 6.6 muM. The inhibitory influence of chebulagic acid on the maltase-glucoamylase complex was more potent than on the sucrase-isomaltase complex. The magnitude of alpha-glucosidase inhibition by chebulagic acid was greatly affected by its origin. These results show a use for chebulagic acid in managing type-2 diabetes.

Author(s): 
Gao, Hong
Huang, Yi-Na
Gao, Bo
Kawabata, Jun
Publication Title: 
Journal of Ethnopharmacology

ETHNOPHARMACOLOGICAL RELEVANCE: Terminalia chebula has an esteemed origin in Indian mythology; its fruits are used to treat many diseases such as digestive, diabetes, colic pain, chronic cough, sore throat, asthma, etc. AIM OF THE STUDY: The water or ethanolic extracts of the fruits were reported to have anti-oxidant, anti-inflammatory, anti-cancer and radio-protector properties. The present study is to isolate and identify the compounds that inhibit COX and 5-LOX, the key enzymes involved in inflammation and carcinogenesis.

Author(s): 
Reddy, D. Bharat
Reddy, T. C. M.
Jyotsna, G.
Sharan, Satish
Priya, Nalini
Lakshmipathi, V.
Reddanna, Pallu
Publication Title: 
Natural Product Communications

Abhayarishta is an Ayurvedic formulation prepared traditionally by the fermentation of the decoction of Terminalia chebula (pericarp), Vitis vinifera (fruits), Embelia ribes (fruits) and Madhuca indica (flowers). In the present communication, chemical changes occurring during fermentation in Abhayarishta have been studied for the purpose of its standardization. An HPLC-DAD method for quantitative estimation of selected marker constituents in the formulation has been developed and validated.

Author(s): 
Lal, Uma Ranjan
Tripathi, Shailendra Mani
Jachak, Sanjay M.
Bhutani, Kamlesh Kumar
Singh, Inder Pal
Publication Title: 
Natural Product Research

The aqueous extract of galls from Terminalia chebula Retz. (Combretaceae) was fractionated on Diaion and refractionated on octadecyl silica column. Six phenolic compounds were isolated and identified as gallic acid (1), punicalagin (2), isoterchebulin (3), 1,3,6-tri-O-galloyl-?-D-glucopyranose (4), chebulagic acid (5) and chebulinic acid (6). All of the compounds showed stronger 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and melanin inhibitory activities than ascorbic acid, butylated hydroxytoluene, ?-tocopherol, arbutin and kojic acid, the reference compounds.

Author(s): 
Manosroi, Aranya
Jantrawut, Pensak
Akazawa, Hiroyuki
Akihisa, Toshihiro
Manosroi, Jiradej
Publication Title: 
Journal of Virology

Herpes simplex virus 1 (HSV-1) is a common human pathogen that causes lifelong latent infection of sensory neurons. Non-nucleoside inhibitors that can limit HSV-1 recurrence are particularly useful in treating immunocompromised individuals or cases of emerging acyclovir-resistant strains of herpesvirus. We report that chebulagic acid (CHLA) and punicalagin (PUG), two hydrolyzable tannins isolated from the dried fruits of Terminalia chebula Retz. (Combretaceae), inhibit HSV-1 entry at noncytotoxic doses in A549 human lung cells.

Author(s): 
Lin, Liang-Tzung
Chen, Ting-Ying
Chung, Chueh-Yao
Noyce, Ryan S.
Grindley, T. Bruce
McCormick, Craig
Lin, Ta-Chen
Wang, Guey-Horng
Lin, Chun-Ching
Richardson, Christopher D.
Publication Title: 
Phytotherapy research: PTR

The fruit of Terminalia chebula Retz. (T. chebula), which is a member of the Combfreetaceae family, is used widely in Asian countries as a traditional folk medicine, and its extract has been reported to be an anticancer, antidiabetic and anticaries agent. In our previous study, chebulic acid isolated from T. chebula extract was confirmed to show antioxidant activity and protective action against endothelial cell dysfunction. In order to support the safety-in-use of the ethyl acetate (EtOAc)-soluble portion of a T.

Author(s): 
Kim, Ji-hoon
Koo, Yun-chang
Hong, Chung-Oui
Yang, Sung-Yong
Jun, Woojin
Lee, Kwang-Won

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