Asperuloside

The molecular formula Cjg/f On contains eight double-bond equivalents, i.e. four more than those in the framework 1 known to be present. The 13C NMR spectrum shows two carboxy-CO 

The iridoid monoterpenoid part of the structure C-1-C-9-C-5-C-6-C-7 (B) is confirmed by the ////COSY plot  

The H and 13C signal assignments of glucopyranoside ring C are derived from the HH COSY and CH COSY diagram  

The assignment of all of the chemical shift values and coupling constants as derived from the measurements can be checked in structural formula D  

The natural product is the asperuloside described in the literature 40. The assignments for the carbon pairs C-1 /C-1, C-6 /C-1 and C-11 / CO (acetyl) have been interchanged. Deviations of 13C chemical shifts (CDC13-D20 40) from the values tabulated here [(CD3)2SO] are due mainly to sol-vent effects. Here the difference between the measurements a and d shows that the use of D20 exchange to locate the OH protons where the CH COSY plot is available is unnecessary since OH 

CH eorrelation maxima with the hydrogen atoms at 3h = 5.70, 5.54, 4.65, 3.55 and 3.22 finally establish the position of the additional CC double bond (C- 7/C-8, Table 45.1). Henee the basie strueture A of the aglyeone is now elear. 

The antiperiplanar coupling constant (8 Hz) of the protons V-H 5h = 4.49) and 2 -H Sh = 2.98) finally shows that a P-glucoside is involved. 

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Hydrogenolysis can be diminished by reduction at low temperature, Hydrogenaiion of asperuloside tetraacetate (28) over 5% Rh-on-C in ethyl acetate at 25 C gave mainly 29 accompanied by several hydrogenolysis products, but by starling at — 30 C and raising the temperature slowly toO C over 3 h, 29 was obtained quantitatively. The catalyst was reusable at least three times (13). 

Oldenlandia diffusa L. Bai Hua Shi Shi Cao (aerial part) Asperuloside, palderoside, desacetylasperuloside, beta-sitosterol, stigmasterol, ursolic acid, oldenlandoside.33 Treats mahgnant tumors, hepatomas, hepatomegaly, cancer of the cervix, esophagus, stimulates reticuloendothelial system. 

N.A. Asperuloside, flavonoids, alkanes, anthraquinones.107 A diuretic, for skin problems. 

N.A. Rubia tinctorum L. Anthraquinone derivatives, ruberythric acid, alzarin, purpurin, indoid, asperuloside, resin, calcium.99 Treat kidney and bladder stones. 

Asperuloside (= Asperulin Daphniphyllum macropodum PI3K (2) [laxative]... 

Indole alkaloids, borrerine and a dimmer borreverine, dihydroborrecapine and borrecoxine,asperuloside/ diacetyl-asperulosideic acid, feretoside, campesterol, stigmasterol, (3-sitosterol ... 

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