References
1. DivLon R A.. Smick D (2003). Phuoc he mistiy meets genome analysis, and beyond. Phytochemistry 62, 815-816.1 Sumner L W. Mendes P , Dixon R A. (2003), Plant metabolomics' large-scale phytochemistry in the fiinctional genomics era, Phviochemisirv. 62. 817-836 3. Stobieeki M , Kachlicki P (2005), Metabolomics and metabolite profiling - can w achieve the %oa.P. Ada Pliysiologiae Planianim, 27, 109-116. 4. Roessner U., Luedemann A., Brasi D., Fiehn O.. LinkeT Wiilmilzer L, Femie A R (2001), Metabolic profiling and phenoiyping of genetically and environmentally modified planl si^icms, Planl Cell. 13, 11-29- 5. Roessner U , Wagner C , Kopka J., Trethewey R. N , Willmitzer L. (2000), Simultaneous anal) sis of metabolites in potato tuber by gas chromatography-mass spectrometry, Planl Journal, 23, 131-142. 6. RohdeA, Morreel K, Ralph J. (2004), Molecular phenoiypmg of the pall and pal2 mutants of Arabidopsis thaliana reveals far- reaching consequences on phenylpropanoid, amino acid, and carbohydrate metabolism. Plant Cell, 16, 2749-2771 7.
Graham T (1998), Flavonoid and flavonol glycoside metabolism in Arabidopsis, Planl Physiology and Biochemislry, 36, 165-144 8 Bloor S J., Abrahams S. (2002), The structure of the major anthocyanin \n Arabidopsis thaliana, Phytochemisln.
59, 343-346. 9. Kerhoas L., Aouak D., Cingoz A., Routaboui J M , Lepiniec L , Einhom J. and Birlirakis N (20061 Structural characterization of the major fiavonoid glycosides from Arabidopsis thaliana seeds. Journal of Agncullural and Food Chemistry. 54, 6603-6612, 10. Veit M.. Pauli G. F. (1999), Major fiavonoids from Arabidopsis thaliana leaves Jounuil of Natural Products, 62, 1301-1303. 11. Cheynier V. (2005), Polyphenols in foods are more complex than often thought, American Journal of Clinical S'uiniion. 81, 223S-229S
Journal of Medicinal Materials, 2016, Vol. 21, No. 5 (pp. 304-309)
FLAVONOID AND PHENYLPROPANOID GLYCOSIDES ISOLATED FROM ANODENDRONPANICULATUM(ROXB.) A. DC.
Hoang Thi Nhu Hanh, Ho Viet Due, Tran Thi Thuy Linh, Vo Quoc Hung, Nguyen Thi Hoai * Faculty of Pharmacy, Hue Umversity of Medicine and Pharmacy. Hue University, Vietnam
•Corresponding author: hoai77(ggmail.com (Received September, 09"', 2016)
Summary
Flavonoid and Phenylpropanoid Glycosides Isolated from Anodendron paniculaium (Roxb.) A. DC.
Phytochemical sludy on the aerial parts of Anodendron paniculaium led to Ihc isolation of three compounds, including kaemprerol-3-O-rulinoside (1), rutin (2), and sargentol (3). The chemical struclures of the isolated compounds were elucidated on the basis of spectroscopic analyses
Keywords: Anodendron paniculaium, Kaempferol-3-O-rutinoside. Rutin. Sargentol.
1. Introduction still insufficient [5], [6]. In our effort to discover Anodendron is one of about 200 genera anticancerous herbs, the bioactive screening belonging to Apocynaceae family Up to this time, results showed that the methanolic extract from there are approximately 80 compounds which are aerial parts of this plant possessed potent mostly cardenolide glycosides isolated from only inhibitory activity toward LU-1, KB, Hep-G2, 3 species including A. affme, A. formicinum, and MKN-7, and S W ^ 8 0 cancer cell-lines [7].
A. paniculaium [1]. Among those, A. paniculatum Therefore, this study was conducted to clarify the (Roxb.) A. DC. is known to be distributed in the phytochemistry of this plant. Herein we report the woodland or the scrub of Quang Tri, Thua Thien isolation and the structural elucidation of flavonoid Hue, Khanh Hoa, Dong Nai, Ben Tre, and Kien and phenylpropanoid glycoside compounds isolated Giang province, Vietnam [2]. Its root and latex from the aerial parts of ^ . paniculatum collected in have been used as an emetic, cough suppressant Vietnam.
[3] and snakebite treatment [4] Aside from some 2. Material and methods cardenoltdes including anodendroside-A. -E„ -E,, 2.7. Plant material
-h, and -G reported ,n the literature, the knowledge The aerial parts of ^ . paniculatum (Roxb.) A.
about chemical constituents of A. paniculaium is DC.were collected in Dakrong district, Quang Tri
304 Journal of Medicinal Materials, 2016, VoL 21, No. 5
t province m June, 2016, and were identified by
;= Dr- Nguyen Tlie Cuong, Institute of Ecology and
• Biological Resources. VAST, Vietnam. A , voucher specimen (AV03) was deposited at the i Faculty of Pharmacy, Hue University of
« Medicine and Phannacy, Hue University.
•; 2.2. General experimem procedures _ Thin layer chromatography (TLC) was carried , out on pre-coated silica gel DC-Alufolien 60 ?„<
(Merck) or RP„ F,„ (Merck) plates. Compounds - were detected under UV 254 nm and/or by
; spraying with 10% HjSO. reagent, followed by heating for 1-2 min. Column chromatography was performed using silica gel (240-430 mesh Merck) or YMC RP„ resin (ODS-6O-I4/63' Fujisilisa-Japan) Ion-exchange chromatography was performed by using Diaion HP-20 (Mitsubishi Chem. Co.). Gel-filtration chromatography was conducted by using Sephadex LH-20 (Dowex*
50WX2-100, Sigma-Aldrich).
The ultra violet (UV) spectrum was recorded on Shimadzu U V-1 SOO spectrophotometer.
Infrared (IR) spectroscopy was investigated on IR Prestige-21 spectrophotometer. Electrospray ionization mass spectrometry (ESI-MS) was recorded on Agilent 6310 Ion Trap mass spectrometer. The nuclear magnetic resonance (NMR) spectra including 'H, " C , DEPT, HSQC HMBC, and ' H - ' H COSY were measured on Bruker AMSOO FT-NMR spectrometer using tetramcthylsilane as an intemal standard.
2.3 Exiraction and Isolation
The dried powder of A paniculaium (2.5 ko) was extracted with methanol (MeOH, 3 times, To L each) at room temperature. The combined MeOH solution was concentrated In vacuo to obtain MeOH extract (105 g). This extract was suspended in water and was then partitioned with chloroform (CHCI3) and ethyl acetate (EtOAc) respectively. Then, the combined filtrates were evaporated solvents In vacuo until dryness to yield die CHCI, (AC, 50.7 g), the EtOAc (AE, 10.2 g), and the water (AW, 27.5 g) fractions.
The AW fraction was applied for a Diaion HP-20 column eluted with gradient solvent systems of MeOH-HjO (0:1, 1:3, 1:1, 3:1, Jo,
Journal of Medicmal Materials, 2016, Vol. 21, No. S
viv) to give four fractions, AWI-AW4. The AWI fraction (4.5 g) was subjected to a RP C-18 column eluted widi MeOH-HjO (1:1, v/v) to obtain three subftactions, AWI.1-AW1.3. The AWI.I traction (l.05g)was chromatographed on a silica gel column eluted with CHCb-MeOH- H2O (4:1:0.1, v/v) to give four subtractions, AWI l.l-AWl.1.4. The AWI.1.2 fraction (95 mg) was subjected to a Sephadex LH-20 column using MeOH-H,0 (I: I, v/v) as a mobile phase to yield compound 1 (20.5 mg). The similar procedure was applied to the AWI.1.4 fracdon (117 mg) to obtain compound 2 (38.6 mg).
The AW3 fraction (1.25 g) was chromatographed on a Sephadex LH-20 column using MeOH 100% as an eluent to give three fractions, AW3.I-AW3.3. The AW3.3 fraction (600 mg) was subjected to a silica gel column eluted with CHCIj-MeOH-HjO (3:1:0.1, v/v) to yield five subfractions, AW3.3.I-AW3.3.S. Compound 3 (132 mg) was obtained from fraction AW3.3.3 after being crystallized and washed to purify.
3. Results and discussion
Compound I was obtained as a yellow powder. Its UV (MeOH) spectrum indicated typical absorption maxima at 267 nm and 351 nm of a kaempferol glycoside [8J. The IR spectrum (KBr) suggested the presence of hydroxyl (3410 cm-'), carbonyl (1659 cm'"), aromatic rings (1605, 1566, 1497 cm'), and ether (1180, 1065 cm"') groups The ESI- MS of compound 1 showed basic molecular ion peaks at m/z 617.1 [M-l-Na]*
and 593.1 [M-H]". In combination with "C-NMR and DEPT spectra, molecular formula of 1 was deduced to be C„Hj„0|5 (M - 594.2 g/mol)
The 'H-NMR specmim of compound 1 exhibited signals for a flavone skeleton including two protons ,n mela positions of the A-ring at <!„
OM (s, H-8) and 6.22 (s, H-6), four aromatic protons of the l,4-disubsti.u,ed B-ring at S„ 8.07 ( d , y = 8 5 H 2 , H - 2 7 6 ' ) a n d 4 6 9 0 ( d , / » 8 5 Hz, H-375'). In addition, the signals of two anomeric protons at <!„ 5.14 (d, y - 7 5 Hz H I") 4 54 (s. H-r-) suggested the presence of two sugar UMS with ^- and ,,„„ng„^,,.„„_
Furthermore, the signal of a methyl group at J„
1.15 (d,J= 6.S Hz, H-6'") was also observed.
The '^C-NMR and DEPT spectra of compound 1 indicated the signals of 27 carbons belonging to a methyl, a methylene, sixteen methine groups, and nine quaternary carbons.
\mong those, fifteen carbon signals were -Oiresponded to the flavone skeleton and the ,-(hers were of two hexose moieties. The C- -SMR peaks at Sc 104.7 (C-l"), 75.7 (C-2"), 78.1 (C-3"), 71.4 (C-4"), 77.2 (C-5"), and 68.6 (C-6") revealed the presence of a ^-D-glucopyranosyl moiety. Whereas, the signals at Sc 102.4 (C-l'"), 72.3 (C-2'"), 72.1 (C-3'"), 73.9 (C-4"'), 69.7 (C- 5"'), and 17.9 (C-6"') suggested the other sugar unit was c-L-rhamnopyranosyl [9]. This saccharide moiety was then confirmed to be a-L- rhamnopyranosyl-(l—t6)-^-D-glucopyranoside by analyzing 2D-NMR data which showed the HMBC correlations be^veen H - l ' " (Sn 4.54) and C-6" (<5c 68.6) together with the downfield shift of C-6" signal in comparison with its normal value in a^-D-glucopyranose moiety [10].
The cross-peaks observed in HMBC spectrum between H-6/H-8 and C-7 (^c 165.9)/C-10 (^c 105.6), between H-6 and C-5 (^c 162.9), between H-8 and C-9 (^c 158.5), beUveen H-2'/6' and C-4' {Sc i61.4)/C-2 (Sc 159.4), between H-3'/5' and C - r {^c 122.7); together with COSY correlations between H-2'/H-3' and H-5'/H-6' indicated the aglycone moiety was kaempferol [11] (Figure 1).
In addition, the HMBC correlation between H - l "
(^H 5.14) and C-3 (Sc 135.5) confirmed the location of sugar moiety being at C-3 position of flavone skeleton. Based on the above observations and in comparison with reported data [12], compound 1 was identified as kaempferol-3-O-a- L-rhamnopyranosyl-(l->6)-^-D-glucopyranoside (known as kaempferol-3-O-rutinoside)
Compound 2 was obtained as yellow powder. The UV (MeOH) spectmm of 1 indicated maximum absorption bands at 257 and 357 nm. The IR (KBr) spectroscopy exhibited typical absorption bands of hydroxyl (3418 cm"'), carbonyl (1651 cm"'), aromatic ring (1605, 1504
C27H30O16 (M = 610.2 g/mol) due to the basic m peaks at m/z 633.1 [M+Na]* and 609.1 [M-H]"
observed on ESI-MS spectra, and in combination with ' C-NMR analyses.
In general, the ' H - and '^C-NMR daU of compound 2 (Table 1) were similar to those trf"
compound 1 suggesting the analogous structure of these two compounds. The difference however, was the presence o f a hydroxyl group at C-3' of compound 2. It was confirmed by the strong downfleld shift of the signal corresponding to C-3' and by the upfield shift of signals corresponding to C-2', C-4', and C-6' in NMR data of 2. The presence of three aromatic proton signals belonging to 1,3,4-trisubstituted B- ring at ^H 6.90 (d,J= 8.5 Hz, H-5'), 7.65 (dd,J=
8.5, 2.0 Hz, H-6'), and 7.69 (d, J = 2 0 Hz, H-2') IS consistent with the above suggestion. The complete assignment of all protons and their corresponding carbons as well as the structural confirmation were conducted using 2D-NMR data (Figure 2). From the above evidence, compound 2 was determined to be quercetin-3-0- a-L-rhamnopyranosyl-( i —*6)-^-D- glucopyranoside (known as rutin) [12]
Compound 3 was obtained as a while amorphous powder. The IR spectrum of 3 revealed strong absorption bands corresponding to hydroxyl groups (3387 cm"'), aromatic ring (1597, 1504, 1466 cm"'), ethers and epoxy (1234, 1072 cm'').
Molecular formula of 3 was determined to be C,7H240i by ESI-MS at m/z 325 [M-H-20CH3]' in conjunction with NMR data analysis.
The H-NMR spectrum showed typical signals of two aromatic protons [^H 6.66 (s, H-3/5)], two methoxy groups [3n 3.76 (s, H-7/8)], two oxymethine groups [S„ 4.67 (d, J = 3.5 Hz, H-l') and 3.09 (m, H-2')], one oxymethylene group [Sw 4.20 (dd, 7 = 9.0, 6.5 Hz, H-3'a) and 3.83 (<id,J=
9.0, 3.0 Hz, H-3'b)]. In addition, the signal of one anomeric proton at SH 4.88 (d, J = 7.0 Hz, H-l") corresponding to the presence of one sugar unit with ^-configuration.
Analysis of the '^C NMR, DEPT and HSQC , and ether (1204, 1065 cm"') groups. The spectra of 3 revealed seventeen signals including molecular formula of 1 was deduced to be two methyl, two methylene, nine methine. and
306 Journal of Medicinal Materials, 2016, VoL 21, No. 5
four quaternary carbons. Of which, eleven carbons were assigned to an aglycone, six to one sugar moiety. The '=C-NMR spectrum also showed characteristic signals of methoxy groups at Sc 56.4 (x2, C-7/S), two oxymethine at ic 53.6 (C-2') and 85.1 (C-l'), one oxymethylene at ^c 71.3 (C-3'). The signals of six aromatic carbons [*c 152.6 (x2), 133 8, 137.1 and 104.3 (x2)]
together wilh signals of two equivalent aromatic protons [S„ 6.66 (s, H-3/5)] suggested the presence of one C-l/C-4 symmetric benzene nucleus. Moreover, signals of sugar moiety at ^c 102.7 (C-l"), 74.2 (C-2"), 76.5 (C-3"), 69.9 (C- 4"), 77.2 (C-5"), and 60.9 (C-6") revealed the presence of^-D-glucopyranosyl [10].
The COSY correlations between H-l' (d'„
4.67) and H-2' (i„ 3.09), between H-2' and H-3' {SH 4.20 and 3.83) led to the assignment of the connectivity of C-r/C-2'/C-3', respectively. The HMBC correlations fi-om H3-7 to C-2 and from H3-8 to C-6 confirmed that the position of two methoxy groups were at C-2 and C-6, respectively. In a similar manner, the HMBC correlations between H-3/H-5 and C-l', between H-2' and C^t (<!c 137.1) indicated die 1,2-epoxy- propan-3-ol fragment linked to aromatic ring at C^. Remarkably, the position of sugar moiety at C-l was determined by the correlation from H-l"
to C-l (<5c 133.8). Based on the above analyses, compound 3 was identified to be [4-(l',2'-epoxy- 3'-hydroxypropyl)-2,6-dimethoxyphenyl]-0-/9-D- glucopyranoside (also named sargentol) [13].
3" OHI" , 0
Figure I. Chemical smicture of isolated compounds (1-3)
Journal of Meilicinal Materiab, 2016, Vol. 21, No. S
8 1 94 9 9 10 1' 2' 3-
4' 5' 6' 1"
2"
158 5 105 6
6.40 s 1 ( 9 4 . 9 1 6 42 d (1.5) i i 158.5 1 1 105 6 1227 I - i ! 12J-1 132.4 1 8.07 d (8.5) | 116.1
161.4 116.1 132.4 104 7 75.7 3" 1 78-1 4"
5"
6"
1'"
2'"
3"' 4"' 5'"
6'"
7i 4 77.2 68 6 102.4 72 3 72.1 73.9 69.7 17.9
6 90 d (8.5)
-
6 90 d (8.5) 8.07 d (8.5) 5.14 d (7.5)
3.48' i 3.46
3.29' 3 3 8 ' 3.83 br.d (10.0) 3.41*
4,54 s 3.67 br.s 3 55 dd (9 5, 3 0) 3.33' 3 4 8 ' 1 1 5 d ( 6 5)
117.7 145.8
149.8 1161 123.1 104.7 75 7 i 78.2 71.4 77.2 68.5 102.4 72 2 72.1 73 9 69 7 17.9
- - -
7.69 d (2.0)
-
6 90 d (8.5) 7 65 dd (8,5, 2.0) 5-13 d (7.5) 3 50 3,45"3.30' 3.36 3 83 dd (10.5, 1.5) 3 . 4 1 ' 4.54 br.s 3.66 dd (3.5, 1.5) 3.55 dd {9 5, 3.5) 3.33' 3.48' 1.15 d (6.5)
56.4
- -
85.153.6 71.3
- - -
102 7 74,2 76.5 69.9 77.2 60.9
- - - - - -
3.76 s
- -
4 67 d (3.5) 3.09 m 4.20 dd (9.0, 6 5) 3.83 dd (9,0,3.0)
- - -
4.88 d (7.0) 3.20' 3.20' 3 12"3,04 m 3 , 6 0 d d (12.0. 5.0) 3.41 dd (12.0, 5.5)
- - - - - -
" Measured in CD,OD. * measured in Dh4S0-di, 'overlapped signal In our present study, compounds 1-3 were isolated from Anodendron genus for the first time. The previous researches have proved that kaempferol-3-O-rutinoside (1) possessed peroxyi radical (ROO") scavenging capacity, hepatoprotective activity in mice, and hypotensive effect in rat [14],[15]. Furthermore, rutin (2) is known to possess various bioaetivities such as antioxidant, anti-inflammatory, antidiabetic, antiplatelet, and anti-cancer activities [16]. Moreover, sargentol
xylene-induced ear edema in mice assay [17].
4, Conclusion
Three compounds including kaempferol-3-0- rutinoside (1), rutin (2), and sargentol (3) were isolated from Anodendron paniculaium. To the best of our knowledge, this is the first repoil about phytochemistry of A. paniculatum collected in Vietnam. The structural identification of the isolated compounds was conducted by using the combination (3) showed remarkable iW v/Vo anti-inflammatory spectroscopic data including UV, IR, MS, ID- effect with inhibition of 47.2% and 2 9 . 1 % at the and 2D-NMR, and in comparison' with the dosage of 100 and 50 mg/kg, respectively, using literatures.
References
n ? i " ° n Z , f ' ! . r ' ° " ' " ' ' " " ' ° " "''''• '''"""" ' LonJou, UK: CRC Press T.,10, and Frauds Group, 2012. 2.Tr.
uinn Ly (2007). Flora of Vietnam [in Vielnamose], 5, Science and Tecliuics Publishing House, Hanoi. 3. Vo Van Chi (1)97), D.otionory o/V„inan„se medicinal planl, / » fl.tnam,,,], 2, Medical Publishing House, Hanoi. 4. Forster P. I. (1»3), Hi.
^^oo„ of Anodendron ponionlotum (Apocynaceae) wilh notes on distribution and elhnobolany in Papuasia. K,„ Bullrtu //wl, T-f '-"'"'"••'=»"' ^^ S-«k=l K., Polonia J., ReichsleinT.(1972),Die vemiullichesmiklurder«,odendmsidt AIZZ , * " • ' " " ' * • '• ' ' ° ' " " '•• " 8 " "•• •="- '• ^ . " " " ' " ' • i " T. (1970), Die cardenohde . » t^oZ ITZ ^ ° •' *• °^" "''"••" " " - " ''"• " • ' 2 5 ' - " - '• Nguyen Thi Hod. Trinh mi Dl.p, D.
Th, Thao, Nguyen Khanh Thuy Lmh, Nguyen Bich Hien, Hoan, Tli some medicinal plane of Pal;o aid Van Kieu Peoples in Quang Tr
di^or,r„i.\„.^ I, "" ^" ^"^ ^•' ^^° ^' ' ^ ' " ' ' ' 's'^lation and idemification of phenolic compounds from Cmtm l „ c s , Fl,armaeo,no„Magazine. 7(26), 101-08. 9. Lipkind G. M, Shashko. A. S.. Knirel V. A., Vinogrado.E
), A computer-assisted stmclural analysis of regular polysaccharides on the basis of "C-NMR Dieu Huong (2012), Screening the cylotoxic aclivity of Quang Tri Province, Joumal of Medicinal Materials, 17(2), 95-100.
v., Kochelkov N. K (I?
308 Journal of Medicmal Materials, 2016, Vol. 21, No. S
^ aia. Carbohydrate Research, 175. 59-75. 10. Roslund M. U, Tlhtmen P., Niemitz M., SjSholm R. (2008), Complele assignmenis of the H and '^C chemical shifts and Jun coupling conslants in NMR spectra of D-glucopyranose and all D- gucopyranosyl-D-glucopyninosides, Carbohydrate Research. 343(1), 101-12. 11. Adebayo A H, Tan N H., Akindahunsi ' IA ' ^"^ ^ ' ^^^ ^ ^ (2010), Anticancer and anliradical scavenging aclivity of Ageralum conyzoides L
^ o g ' r r ' ' ' ° " " ' " S ' « ' V Uaearlne. 6(21), 62-66 12. Kim S. Y. Gao J. 1. Lee W C, Ryu K. S., Lee K R, Kim Y. C.
A " ' • " ° ' " ° " " " "'"mollis from lhe leaves ofM,™ alba. Archives of Pharmacol Research, 22(1), 81-85. 13. Damo HI " I rn ^'" ^ ^'' "" '^ '^•' " " "^^ ^' '™°'>' Chemical constinients of lhe stem ot Sargenlodoxa citneala,
• "'''"y^l". 60 (7), 1645-52. 14. Ahmad M., Gitai A. U H., Aftab K., Ahmad V. U (1993), Effects of kacmpfe,ol-3-0-
• niimosioe on rai blood pressure, Phyiollierapy Research. 7(4), 314-16. 15. Wang Y, Tang C, Zhang H. (2015), r „ r T H " " °, »f'••empferol 3-0-™tinoside and kaempferol 3-0-gl„cosidc from Carihamu, llnclorius L. on CCI,- induced oxidative hver injuiy i„ mice, Jonrnal of Food and Drug Analysis. 23 (2), 310-17. 16. Chua L. S. (2013), A review pani-baseo rutin exiraclion methods and ils pharmacological acliviiies. Journal of Elhnopharmacohgy. 150(3), 805-17.
. iang 1, Ma K. L., Ouyang Z., Chen H S. (2012), Chemical conslituenis liom die waler-soluble faction of wild '•'•'S»'t'"'o^acuneaia.Chinese Journal of Nalural Mediclnes.ia.2).\\i-\i.
Journal of Meilicinal Materials, 2016, Vol. 21, No. S (pp. 309 - 314)
CHEMICAL CONSTITUENTS OF CUDRINA TRICUSPIDATA CARR BUR ' ^ ^ THEIR ANTIOXIDANT ACTIVITY
Do Tltanh Tuan , Do Thi Trang', Nguyen Xttan Nltiem; Duong TltiDung-, Pham Hui Yen', Trieu Qay Hung; Duong Thi Hai Yen', Phan Van Kiem', Hoang Le Tuan Anh'"
Institute of Marine Biochemislry. Vietnam Academy ofScience and Technology (VAST) nai Btnh Medical Universily. ll Bon. That Blnh. Vielnam
Facully of Natural Sciences. Hung Vuong University. Viet Tri. Phu Tho. Vietnam
•Corresponding aulhor anh 792002(gyahoo.goni (Received September 19"^, 2016)
Summary
'^'"^"'''»"^»""H''«"'">fC«''™ii«c"SfWoUC.rr.EurandlhtirAnlitoxid.ntAcllvitv k a e S o n T L ' " ' " • " " ' " ' ^ " ' " " H " " , ' ; ' ; * ' ", - ^ « * " > ™ . " " - o , A (.), and Ihree iT.; ol " L " " » = C (2) , r i J ™ ? , -S • * ' " ™ " " " '^'' " ' ' »"'™1«»'i'i" W l»ve been isolated from lhe liavcs of Cudralk,
Keywords: Cudrania irlcuspidaia ,ilsonol A. licoflavone C. aromodendrin. b.cmpferol.7.0.r.D-gl.copyranoside.
1. Introiluction . Irlcuspidaia. Our previous results reported the Cudrania Iricasptdala. a deciduous thoruy isolation of two peptides, aitrantiamide acetate free belonging Moraceae family, is widely and aurantiamide, and two phenolic compounds d, r t a e d ,n Asia, sue as China, Korea, and (E)-;,.coun,aric acid and methanol extrae'of th Vietnam [ 1 2 ] , Recently, C. tricusptdata has C«*™,„ ,n.,„;,/rf„,„ leaves and their cytotoxic been teported to be rich of prenylated xanthones activities [9]. Herein, we report the isolation and and fiavonoids which were displayed promising structure of a megastigmane, wilsonol A (1) and anti-eaneer, anti-inflammation, anti-obesity, and three fiavonoids, licoflavone C (2) kaemofeol 7
cancer in Korea [ 3 , Besides, en.nte inhibitors L!ivities. To r m T e g l i s t T e t ; toward protein tyrosine phosphatase IB [4], report of wilsonol A (1) from the e e n u s r ^ neuraminidase [5, 6), a-glucosidase [7] and 2. Material and J e l d s * """'•
tyrosinase [8] wets also found from C. Plant mai,rl,i. Tt ,
™ ° ' """"111: The leaves of C Irlcuspidaia
Journal ofMeilicmal Materials, 2016, Vol 21 No S "
' • 309
