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1 () ().20 ().21 () 21 () 22 () () 23 () 24 ().24 ().25 () 25 ().25 () ()

2 () 43 ()..44 () 45 () 45 () () () 47 () 47 ().47 ().48 () \ CMN CMN CMN CMN CMN CMN CMN SB SB SE

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4 2000 (Leguminosae) (Spatholobus suberectus Dunn.) 2 Spatholobus suberectus Dunn. Millettia nitida var. hirsutissima (Fig. ) 1-5 ABCDE (irsutissimiside ABCD E), -7---D (1, formononetin-7-- -D-glucopyranoside -6 -ethylmalonic acid ester, CMN-21), -7---D- -(1 6) -- -D- 2, formononetin D- apiofuranosyl-(1 6) -- -D-glucopyranoside, CMN-25, α-L- -(1 6) -- -D- (3, genistein-5- methylether-7--α-l-rhamnopyranosyl- (1 6) ---D-glucopyranoside, CMN- 31), D- (4, retusin-7,8---d- diglucopyranoside, CMN-32), -8-C--D- -(1 6)---D- (5, genistein-8-c--d- apiofuranosyl-(1 6) ---D-glucopyranoside, CMN-33) 4

5 ( ) (Fig. ) 12, [1--β-D- -(2S3S4R, 7E)-2-N-(2 - )- -7-, SB-1] SE-3SE-4SE-10SB-2SB-6 FXa 95% ADP 1 ADP 5 Fxa 2 3 SE-13, NMR 2 5

6 English Abstract Studies on the Chemical Constituents and Bioactivities of Spatholobus suberectus and Millettia nitida var. hirsutissima Doctor Candidate: Jun Chneg Supervisors: Prof. YuYing Zhao Prof. YinYe Wang Associate Prof. ong Liang (School of Pharmaceutical Sciences, Peking University) Ji Xue Teng is a traditional Chinese folk medicine which is useful in promoting blood circulation or relieving stasis. It has been used to treat pain or numbness of the wrists, knees or other joints and irregular menstruation. Its crude drug involved about 30 species of plant. owever, Spatholobus suberectus is only legal species in Chinese Pharmacopoeia. Millettia nitida var. hirsutissima was used as Ji Xue Teng in JiangXi province. Spatholobus suberectus and Millettia nitida var. hirsutissima were found effective by platelet aggregation test(pat), plasma recalcification time (PRT), euglobulinlysis test(elt). Their chemical constituents were studied by a series of chromatographic technology. From Millettia nitida var. hirsutissima, 22 compounds were isolated by solvent and chromatography methods and their structures were identified on the basis of chemical methods and spectroscopic evidence. There are 16 flavonoids, 4 sitosterols, 2 triterpenoids among these compounds. 1-5 were new compounds and named as formononetin-7-- -D-glucopyranoside -6 -ethylmalonic acid ester (1,CMN-21, irsutissimiside A), formononetin D- apiofuranosyl- (1 6) -- -D-glucopyranoside(2,CMN-2, irsutissimiside B), genistein-5- methylether-7-α-l-rhamnopyranosyl-(1 6)---D-glucopyranoside (3,CMN- 31, irsutissimiside C), retusin-7,8---d-diglucopyranoside (4,CMN-32, irsutissimiside D), genistein -8-C- -D- apiofuranosyl-(1 6) -- -D-glucopyranoside (5,CMN-33, irsutissimiside E). The known compounds(6-22) were obtained from Millettia nitida var. hirsutissima for the first time(see Fig. ). From Spatholobus suberectus, 17 compounds were isolated and identified. 6

7 Among them, there are 6 flavonoids, 1 phenyl-glucopyranoside and 4 other compounds. Compounds 12 is new compounds and denominated as suberectcerebroside. The known conpounds SE-3 SE-4SE-10SB-2SB-6 were obtained from the plant for the first time. The n-bu extracts from Millettia nitida var. hirsutissima and EtAc extracts from Spatholobus suberectus showed inhibition activity to platelet aggregation induced by ADP in vitro. 5 compounds from Spatholobus suberectus showed inhibition effect to FXa. 2 compounds from Spatholobus suberectus and 3 compounds from Millettia nitida var. hirsutissima showed inhibition on blood vessel smooth muscle contraction in vitro. Keywords: Millettia nitida var. hirsutissima; Spatholobus suberectus; chemical constituentsbioactivities 7

8 C 3 C 2 C C 2 C 6''' 5''' 2''' 1''' 1'' C 3 C 4' 3 1. formononetin-7-- -D-glucopyranoside 2. formononetin-7- --D- apiofuranosyl- -6 -ethylmalonic acid ester (CMN-21) (1 6) ---D-glucopyranoside (CMN-25) C 3 C 3 3. genistein-5- methylether-7--α-l-rhamnopyranosyl 4. retusin-7,8---d- -(1 6) ---D-glucopyranoside CMN- 31) diglucopyranoside (CMN-32) C 3 C 3 5. genistein-8-c--d- apiofuranosyl-(1 6) 6. calycosin (CMN-10) ---D-glucopyranoside (CMN-33) C 3 7. symplocoside (CMN-27) 8. isoliquiritigenin (CMN-15) R C 3 9. formononetin(r=) (CMN-13) 11. genistin (CMN-17) 10. ononin(r=glc) (CMN-14) Fig.The compounds from Millettia nitida var. hirsutissima 8

9 C 3 C 3 C gliricidin (CMN-16) methylretusin (CMN-22) C 3 C 3 C afromosin 7-- -D- 15. lanceolarin (CMN-26) glucopyranoside (CMN-19) C sphaerobioside (CMN-28) 17 stigmasterol D-glucopyranoside (CMN-11a) 19. lupeol (MN-3) 20. 3β-Friedelanol (MN-2) R 21. -sitosterol(r=) (MN-1) 22 stigmasterol 18. daucosterol(r-glc) Fig.The compounds from Millettia nitida var. hirsutissima 9

10 R 7 R 6 R 2 R 4 R 5 1 genistein(se-13) 5isoliquirtigenin(SE-16) 62S,3R- catechin(se-18) (R 4 =R 5 =R 7 =,R 2 =R 6 =) 2cajanin(SE-15) (R 2 =R 4 =R 5 =, R 7 = C 3,R 6 =) 3afrormosin(SE-19) (R 7 =,R 4 = R 6 =C 3, R 2 =R 5 =) C 3 (C 2 ) 24 C C 3 (C 2 ) 19 4formononetin(SE-8a) (R 7 =, R 4 =C 3, R 2 = R 5 = R 6 =) 16. cerotic acidse eicosanol(sb-7) C 7lupeol (SE-1) 8lupenone (SE-20) 9betulinic acid (SE-10) 4' 2' C 2 1' 3' C C 2 (C 2 ) 14 C 3 R 1 C N 2C C 2 3 C (C 2 ) 14 C 3 C 4 9 C sitosterol(r=)( SE-2) 12Suberectcerebroside A (SB-1) 13n-butyl---D- 11 -daucosterol(r=glu)( SE-5) fructopyranoside (SB-2) C 2 C 2 C methoxy-4-(2 -hydroxy ethyl ) - phenol --D-glucopyranoside(SB-6) C 2 C C 2 C C 2 (C 2 ) 21 C 2 C 3 15glycerol--pentacosanoate (SE-4) Fig.The Structures of compounds from Spatholobus suberectus Dunn. 10

11 [1] () 1 2 Table 1-1 Table

12 (1) (2) (3) () 1. 2.

13 13 () Table 1-2 Table

14 () () () () () CTMRI MRA GRE DWI MRI () FDA t-pa 3 14

15 [3-4]

H 2 SO ml ml 1. 0 ml C 4. 0 ml - 30 min 490 nm 0 ~ 100 μg /ml Zhao = VρN 100% 1 m V ml ρ g

H 2 SO ml ml 1. 0 ml C 4. 0 ml - 30 min 490 nm 0 ~ 100 μg /ml Zhao = VρN 100% 1 m V ml ρ g 16 6 2018 11 Chinese Journal of Bioprocess Engineering Vol. 16 No. 6 Nov. 2018 doi 10. 3969 /j. issn. 1672-3678. 2018. 06. 004 1 2 1 1 1. 330200 2. 330006 4 Box-Behnken 1 25 g /ml 121 92 min 2 6. 284%