THE CHEMICAL CONSTITUTION OF A CHINESE DRUG“HWAI-HUA-ME”(槐花米)——PART Ⅰ.HWAI-HUA-MENINE-A(or SORPHORINE A).

Hwai-Hua-Me has long been used as insecticide,dye-stuff,nutriment,heamosta- tic agent as well as remedies for haemorrhoids and brain hyperemia (apoplexy). Hitherto six substances have been isolated by the author from a sample ob- tainable in Shanghai. The presant paper deals with the study of Sorphorine-A,a yellowish crystal- line subtance.The yield is about 14%.The sample was first extracted with dilute alcohol,then washed with ether,acetone and petroleum ether,and the Product was recrystallized from alcohol and hot water,and then reated with methyl alcohol and ether mixture in order to remove Sorphorn-B,Sorphorin-C & etc.The substance thus obtained gives the following: m.p.180-182°(bulbing),185-188°(Changing forom),199-203°(Sintering with plastic appearance) and decomposing at 245-250°). a_D²⁴=+12°(0.5% C₂H₅OH);+5°(% CH₃OH). Mol.formula:C₂₉H₃₆O₁₇. Crystallization of water:7.16;7.33%;CH₂₉H-(36)O₁₇·3H₂O. Crystallizion of methyl alcohol:4.86%,C₂₉H₃₆O₁₇·CH₃OH. Crystallization of ethyl alcohol:6.57%,C₂₉H₃₆O₁₇·C₂H₅OH. Solubility:cold water(1:60,000);boiling water (1:167). cold methyl alcohol(1:1,080);boiling methyl alcohol(111:100). cold ethyl alcohol(1:600);boiling ethyl alcohol(3:5). cold acetone(1:600);boiling acetone(1:350). Pyridine(1:12). cold dioxan(1:12);boiling dioxan(1:15). cold ethyl acetate(trace);boiling ethyl acetate(small). cold amyl alcohol(slightly);hot amyl alcohol(slightly). Reactions:1.Tollen's reagent:black ppt. 2.Fehling's solution:no reaction. 3.HCl+Mg+C₂H₅OH:reddish purple coloration. 4.HAC+Mg+C₂H₅OH:greenish fluorescence. 5.Hydrolysis(1:100 HCl): a.yellowish brown crystals(yield 59%),306-308°(blackens),310-311° (melts),C₁₇H₁₃₍₁₄₎O₉₍₁₀₎. b.acetone Insoluble osazone:m.p.215-217°(D). c.acetone soluble osazone:m.p.188-189. 6.FeCl₃ solution:dark green solution. 7.Lead acetate solution:Lemon-yellow ppt. 8.Basic lead acetate solution:yellowish Orange ppt. 9.Hydrolyzed product:yellowish brown crystal. a.FeCl₃ solotion:bark green solution. b.Lead acetate:yellowish orange ppt. c.Tollen's reagent:black ppt. d.Fehling's solution:no reaction. e.Acetate,C₂₇₍₂₈₎ H₂₃₍₂₄₎O₁₄:m.p.198-203°,CH₃CO%=44.4%;hydro- lyzed with KOH,give greenish yellow crystals,yield about 98% with m.p.310-312°(D). f.Methyated:(1)m.p.300-302° greenish yellow. (2)m.p.151-152° slight yellowish white. The spectrophotometric determination: As show in Fig.Vl (1) Hwai-hua-menine-A exhibits absorption at E_1cm^1% 258 mμ =353;E_1cm^1% 364 mμ=277.8(95% ethyl alcohol+1% 0.2N HAC),(Conc.1.551 mg/100CC.)(Beckman DU). (2) aglucone of Hwai-Hua-Menine-A exhibits absorpotion at: E_1cm^1% 258 mμ=660;E_1c%^1% 375 mμ=550. The paper chromatography determination: Solvent:n-butanol:acetic acid:water=4:1:5 for 10 hours. R_f.=0.68 (0.71-0.72) Aglucone:R_f=0.75.(0.73) Acetic acid:water(6:4 V/V), R_f.=0.71,0.72;Aglucone:R_f=0 The active Oh-groug of aglucone(Tschugajiff Zerrmettinoff's method 26.8%.) The mixed m.p.of rutin(obtained from leaf and stem of Fagoyprum esculentuni, Moench 蕎麦茎叶) and Hwai-Hua-Menine-A:154°(contract),180-190°(syrup), 240-250°(D). It may be concluded from the above results,that the compound is neither rutin, nor its homologues.