Chebulinic acid

Phyllanthus emblica L. Ye Gan Zi (whole plant) Chebulinic acid, mucic acid, alpha-leucodelphinidin, vitamin C.3330,7 For conjuctivitis, diarrhea, abdominal tumors, nephritis, urogenital ailments. 

Terminalia chebula Retz. He Zi (Myrobalans) (leaf, fruit) Chebulic acid, fatty oil, tannins, ellagic acid, chebulinic acid.49-450 An astringent in diarrhea, enterorrhagia, metrorrhagia, metritis, leukorrhea. 

Other tannins of this type (Fig. 12.6) contain modified acids such as chebulagic acid (18) andpedunculagin (19), and the brevilagins 1 (20) and 2 (21) which are normally considered ellagitannins (Haslam, 1979). When the galloyl groups are in the diaxial position, radical coupling can occur to produce compounds such as chebulinic acid (22) (Fig. 12.7). 

Fig. 12.7. Biogenesis of chebulinic acid (modified from Haslam, 1974).

Yoshida, T, Fujii, R. Okuda, T. (1980). Revised structure of chebulinic acid and chebulagic acid. Chemical and Pharmaceutical Bulletin, 28, 3713-3715. 

No evidence has yet been obtained to show that dimeric products are formed by oxidative coupling of the monomeric species such as was noted in Class 2B (vide supra). However, brief comment should be made on two phenolic metabolites, isolated early in the studies of the ellagitannins chebulinic acid (91,140) and chebulagic acid (91) (Table 7.2.9). It is clear from biogenetic considerations that these are phenolic metabolites very probably derived by further oxidative ring fission of one aryl ring in a precursor such as geraniin (51). 

Chebulinic acid Terminalia chebula )8-l,3,6-trigalloyl chebulic acid linked 2,4 to D-glucopyranose 140, 91... 

Uddin M, Haslam E 1967 Gallotannins. Part 15. Some observations on the structure of chebulinic acid and its derivatives. J Chem Soc (C) 2381-2384... 

Scheme 14. Proposed pathways of biosynthesis of chebulinic acid (56) and chebulagic acid (57) from P-penta-o-galloyl-D-glucose (11), 81). Hydrolysis of (56 and 57) to give...

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