本研究探討山茱萸果實及野生番石榴葉之降血糖活性成分,山茱萸為降血糖藥物六味地黃丸之其中一味,野生番石榴則常被用為民間之降血糖藥物,故針對山茱萸果實及番石榴葉作進一步的活性成分探討。經各種層析管柱及不同溶媒系統分離純化後,共分離出二十八個化合物。山茱萸果實之70 % acetone/H2O萃取物於n-BuOH層分離出十一個化合物,分別為quercetin 3-O-β-D-glucuronide (1)、quercetin 3-O-β-D-(6″-n-butyl glucuronide) (2)、epicatechin 3-O-gallate (3)、loganin (4)、(7R)-n-butyl morroniside (5)、gallic acid (6)、caffeic acid (7)、caftaric acid monomethyl ester (8)、cornuside (11)、2-butoxybutandioic acid (12);於hexane層分離出兩個化合物oleanolic acid (9)、β-sitosterol (10),其中compound 8、12為首次由天然物中分離出之成分。另外,從野生番石榴葉之70 % acetone/H2O萃取物共分離十六個化合物,其中自乙酸乙酯層萃取物分離出quercetin (13)、quercerin 3-O-β-D-galactopytanoside (14)、quercetin 3-O-α-L-arabinofuranoside (15)、quercerin 3-O-β-D-xylopyranoside (16)、quercetin 3-O-β-D-glucuronide (17)、gallic acid (20)、protocatehuic acid (21)、p-coumaric acid (22)、ferulic acid (23)、strictinin (24)、isostrictinin (25)、casuarinin (26)、1,2,3,4,6-penta-O-galloyl-β-D-glucose (27)、1,2,3,6-tetra-O-galloyl-β-D-glucose (28);自n-BuOH層萃取物得到(+)-gallocatechin (18)、(+)-catechin (19)。另外,由山茱萸分離出之化合物中,compound 3、8、12能抑制PEPCK mRNA表現的活性;compound 3、5、9具有抑制β細胞產生NO 的能力;而compound 5、6能抑制β細胞被cytokine毒殺的能力。此外,自野生番石榴葉分離出之化合物,發現compound 13、17、18、19、20、21對glucose uptake有促進作用。其中compound 13、20已有文獻發表,compound 17、18、19、21則為首次發現具有glucose uptake的促進效果。
In this study, bioactive constituents of Fructus corni and Psidium guajava L. were investigated. Fructus corni is one of the component of Liuwei Dihuang Pills, and Psidium guajava L. is often used as an antiglycemic drug. Through a variety of chromatography, totaly 28 compounds were isolated. Twelve compounds which have been isolated from the n-BuOH and n-Hexane layer of 70 % acetone/H2O extract of Fructus corni including quercetin 3-O-β-D-glucuronide (1), quercetin 3-O-β-D-(6″-n-butyl glucuronide) (2), epicatechin 3-O-gallate (3), loganin (4), (7R)-n-butyl morroniside (5), gallic acid (6), caffeic acid (7), caftaric acid monomethyl ester (8), oleanolic acid (9), β-sitosterol (10), cornuside (11), and 2-butoxybutandioic acid (12). Among them, compounds 8, 12 were first isolated from the plant. In addition, sixteen compounds have been isolated from the ethyl acetate and n-BuOH layer of 70 % acetone/H2O extracts of Psidium guajava L. including quercetin (13), quercerin 3-O-β-D-galactopytanoside (14), quercetin 3-O-α-L-arabinofuranoside (15), quercerin 3-O-β-D-xylopyranoside (16), quercetin 3-O-β-D-glucuronide (17), (+)-gallocatechin (18), (+)-catechin (19), gallic acid (20), protocatehuic acid (21), p-coumaric acid (22), ferulic acid (23), strictinin (24), isostrictinin (25), casuarinin (26), 1,2,3,4,6-penta-O-galloyl-β-D-glucose (27), and 1,2,3,6-tetra-O-galloyl-β-D-glucose (28). For Fructus corni, compounds 3、8、12 can inhibit the expression of PEPCK mRNA, compound 3、5、9 can inhibit NO production, and compound 5、6 can inhibit cytokine mediated cell death. On the other hand, compounds 13、17、18、19、20、21 form Psidium guajava L. can enhance glucose uptake in C2C12 cell. It was documental that compouns 13、20 can increase the glucose uptake. It’s the first time to find that compounds 17、18、19、21 can enhance glucose uptake.