Tellimagrandine

During the synthesis of tellimagrandin, debenzylation was accomplished over 10% Pd/C in dry THE The mixture was purged six times with hydrogen and stirred at room temperature under 1 atm of hydrogen for 48 hours and finally purged with argon.67... 

Figure 3-17. Biosynthesis of Tellimagrandin II (3.103) and Comusiin E (3.104) from pentagalloylglucose (3.102) by polyphenol oxidases of the laccase class.

Niemetz, R., and Gross, G. G., 2003, Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves, Phytochem. 62 301-306. 

More complex ellagitannins, such as the natural compounds tellimagrandin I (162) [117], sanguiin H-5 [18], pedunculagin [118], and coriariin A (166) (Scheme 41) [119, 120] have also been synthesized by the lead tetraacetate oxidative coupling procedure, with the same favorable stereoselective (S)-biaryl bond formation. 

Procyanidin B3 (= Catechin (4a —>8) catechin) (procyanidin dimer) Procyanidin B4 (catechin (4a — 8)epicatechin) (procyanidin dimer) Tellimagrandin I (= 4,5 Hexahydroxydiphenoyl 2,3-digalloylglucose) (ellagitannin)... 

Figure 4.15 Oxidative coupling of two molecules tellimagrandin II to cornusiin E by the laccase-type tellimagrandin 11 02 oxidoreductase from Tellima grandiflora.

Niemetz, R. and Gross, G.G. (2003b) Ellagitannin biosynthesis laccase-catalyzed dimerization of tellimagrandin II to cornusiin E in Tellima grandiflora. Phytochemistry, 64,1197-1201. 

Niemetz, R., Schilling, G. and Gross, G.G. (2001) Ellagitannin biosynthesis oxidation of pentagalloylglucose to tellimagrandin II by an enzyme from Tellima grandiflora leaves. Chem. Commun., 35-6. 

SHIOTA, S., SHIMIZU, M., MIZUSHIMA, T., ITO, H., HATANO, T., YOSHIDA, T., TSUCHIYA, T., Restoration of effectiveness of beta-lactams on methicillin-resistant Staphylococcus aureus by tellimagrandin I from rose red, FEMS Microbiol. Lett.,2000,185, 135-138. 

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