Rudi Hendra 1, Paul A. Keller 1* Telephone: Fax:
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1 Supporting Information for Phytochemical Studies on Two Australian Anigozanthos Plant Species Rudi Hendra 1, Paul A. Keller 1* 1 School of Chemistry, University of Wollongong, NSW 2522, Australia Telephone: Fax: keller@uow.edu.au S1
2 Table of Contents General Procedures... 4 Figure S1. HPLC profile of polar extracts from A. flavidus (a) and A. pulcherrimus (b) flowers... 5 Table S1. NMR spectroscopic data for compound Figure S2. 1 H-NMR spectrum of compound 1 (in methanol-d 4 )... 7 Figure S3. UV-Vis spectroscopy of compound Table S2. NMR spectroscopic data for compound Figure S4. 1 H-NMR spectrum of compound 2 (in methanol-d 4 )... 9 Figure S5. UV-Vis spectroscopy of compound Table S3. NMR spectroscopic data for compound Figure S6. 1 H-NMR spectrum of compound 4 (in methanol-d 4 ) Figure S7. UV-Vis spectroscopy of compound Table S4. NMR spectroscopic data for compound Figure S8. 1 H-NMR spectrum of compound 5 (in methanol-d 4 ) Figure S9. UV-Vis spectroscopy of compound Table S5. NMR spectroscopic data for compound Figure S10. 1 H-NMR spectrum of compound 6 (in methanol-d 4 ) Figure S11. UV-Vis spectroscopy of compound Table S6. NMR spectroscopic data for compound Figure S12. 1 H-NMR spectrum of compound 7 (in methanol-d 4 ) Figure S13. UV-Vis spectroscopy of compound Table S7. NMR spectroscopic data for compound Figure S14. 1 H-NMR spectrum of compound 8 (in methanol-d 4 ) Figure S15. UV-Vis spectroscopy of compound Table S8. NMR spectroscopic data for compound Figure S16. 1 H-NMR spectrum of compound 9 (in methanol-d 4 ) Figure S17. UV-Vis spectroscopy of compound Table S9. NMR spectroscopic data for compound Figure S18. 1 H-NMR spectrum of compound 10 (in methanol-d 4 ) Figure S19. UV-Vis spectroscopy of compound Table S10. NMR spectroscopic data for compound Figure S20. 1 H-NMR spectrum of compound 11 (in methanol-d 4 ) Figure S21. UV-Vis spectroscopy of compound S2
3 Table S11. NMR spectroscopic data for compound Figure S22. 1 H-NMR spectrum of compound 13 (in methanol-d 4 ) Figure S22. UV-Vis spectroscopy of compound Characterisation of New Compounds Figure S23. LRESIMS from compound Figure S24. HRESIMS from compound Figure S25. UV-Vis spectroscopy of compound Figure S C-NMR spectrum of compound 3 (in methanol-d 4 ) Figure S28. HSQC spectrum of compound 3 (in methanol-d 4 ) Figure S29. COSY spectrum of compound 3 (in methanol-d 4 ) Figure S30. HMBC spectrum of compound 3 (in methanol-d 4 ) Figure S31. HMBC spectrum of compound 3 (in methanol-d 4 ) (zoom) Figure S32. LRESIMS from compound Figure S33. HRESIMS from compound Figure S34. UV-Vis spectroscopy of compound Figure S35. RP-HPLC profile from acid hydrolysis of 12 compared to authentic standard Figure S36. 1 H-NMR spectrum of compound 12 (in methanol-d 4 ) Figure S C-NMR spectrum of compound 12 (in methanol-d 4 ) Figure S38. HSQC spectrum of compound 12 (in methanol-d 4 ) Figure S39. COSY spectrum of compound 12 (in methanol-d 4 ) Figure S40. NOESY spectrum of compound 12 (in methanol-d 4 ) Figure S41. HMBC spectrum of compound 12 (in methanol-d 4 ) Figure S42. GCMS Spectrum of Anigozanthos sp Table S12. GCMS Data of Anigozanthos sp Table S13. Antibacterial Activity of methanol extracts and pure compounds obtained from A. rufus and A. pulcherrimus Figure S43. Colour solutions from compound 1 13 in methanol References S3
4 General Procedures Optical Rotations for compound 3 and 12 was measured a 25 o C in methanol with a path length of 1.0 dm on a Jasco P-2000 Digital Polarimeter (l = 589 nm). Proton ( 1 H) and carbon ( 13 C) nuclear magnetic resonance (NMR) spectra were recorded at 500 and MHz respectively on a Varian Unity Inova-500 MHz spectrometer, controlled by Varian VNMR software (version 6.1 revision C). NMR spectra were acquired in CD 3 OD with chemical shifts (δ) reported in parts per million (ppm) relative to CD 3 OD ( 1 H: δ = 3.31 ppm; 13 C: δ= 49.2 ppm). Coupling constants (J) are reported in Hertz (Hz). J values listed in 1 H NMR spectral data refer to coupling between hydrogen nuclei. Electrospray (ES) mass spectra were obtained on a LCMS-2010 EV (Shimadzu). Samples were injected as a solution in methanol HPLC grade. High Resolution (HR) ES mass spectrometry (MS) was performed on a Micromass QTOF2 Ultima Spectrometer. The HPLC profiles from both species were obtained using a Waters (Waters 1525 pump, Waters 2487 detector, controlled by Breeze software v3.30) with a Symmetry C 18 column (5 µm, 4.9 x 150 mm) with a Wakosil C 18 RS column (5 µm, 4.6 x 250 mm). All compounds were isolated by preparative HPLC using a Waters prep-lc system (LC-600 controller, 2489 detector, LC150 Pump, PD1 degasser) with a Waters reverse-phase OBD Sunfire TM C 18 column (5 µm, 19 x 150 mm) protected with a Waters Sunfire TM C 18 guard column (5 µm, 19 x 10 mm). To determine of sugar moiety from compound 12, a RP-HPLC (Shimadzu HPLC) system, coupled with an automatic sampler (Shimadzu SIL-10A XL) and a Sedere Sedex 60 LT Evaporative Light Scattering Detector (ELSD) with Prevail Carbohydrates ES column (250 x 4.6 i.d.; Alltech). All analytical HPLC samples were filtered through a Whatman syringe filter PTFE 0.45 µm, 4 mm and preparative HPLC samples were filtered through a Bonnet syringe filter 0.45 µm, 30 mm. A Büchi Rotary Evaporator (R-114/200) with a high vacuum pump was used for evaporation of solvents under reduced pressure at 40 ºC. S4
5 Figure S1. HPLC profile of polar extracts from A. flavidus (a) and A. pulcherrimus (b) flowers. AU A 1 2 λ: 254 nm Minutes B λ: 254 nm AU Minutes S5
6 Table S1. NMR spectroscopic data for compound 1 Cyanidin-3-rutinoside, red solid. UVmax (Me) (nm): 280 (7451); 519 (8905). ESIMS m/z: 595 [M+1] +. HRESIMS calculated for C 27 H 31 O 15 [M+H] + : , found Position 0.1% TFA-d in Methanol-d % TFA-d in Methanol-d 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , s , s , s , s , s , s a a ' ' 8.00, s , s ' ' ' 7.00, d (8.7) , d (8.5) ' 8.22, d (8.3) , d (9.0) β-d-glucopyranose d, (8.3) , d (8.0) dd, (8.4, 8.0) , m dd, (8.4, 8.0) , m , m , m dd, (8.4, 8.0) , m d, (11.0) , m , dd (11.0, 2.0) , m 66.9 α-l-rhamnopyranose (s) d, (8.0) , m , m , m , m , m , m m , m s d, (6.0) 16.9 S6
7 Figure S2. 1 H-NMR spectrum of compound 1 (in methanol-d 4 ) HO 6 8 O 4 5' 1' 1'' O O HO 3'' 6'' O1''' O HO Figure S3. UV-Vis spectroscopy of compound 1 AU S7
8 Table S2. NMR spectroscopic data for compound 2 Quercetin-3-rutinoside. Yellow solid. ESIMS m/z: 633 [M+Na] +, 609 [M+H] -. Position Methanol-d 4 2 Methanol-d 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , s , d (2.0) , s , d (2.0) a a ' ' 7.67, s , d (2.1) ' ' ' 6.88, d (8.4) , d (8.5) ' 7.62, d (8.5) , dd (2.1, 8.5) β-d-glucopyranose , d (7.5) , d (7.7) , dd (8.4, 8.0) , dd (7.7, 8.9) , dd (8.4, 8.0) , t (8.9) , m , t (8.9) , dd (8.4, 8.0) , ddd (1.2, 5.7, 8.6) , d (15.0) , m , dd (6.1, 11.0) 3.38, dd (6.1, 11.0) 68.5 α-l-rhamnopyranose , (s) , d (1.5) , m , dd (1.5, 3.4) , m , dd (3.4, 9.6) , m , t (9.6) , m , dq (6.2, 9.6) , d (6.2) , d (6.1) 17.8 S8
9 Figure S4. 1 H-NMR spectrum of compound 2 (in methanol-d 4 ) Figure S5. UV-Vis spectroscopy of compound 2 S9
10 Table S3. NMR spectroscopic data for compound 4 Cyanidin-3-O-(6-O-p-coumaryl-O-β-D-glucopyranoside, red solid. UVmax (Me) (nm): 282 (8302); 313 (7052); 523 (6981). ESIMS m/z: 595 [M+1] +. HRESIMS calculated for C 30 H 27 O 13 [M+H] + : , found Position 0.1% TFA-d in Methanol-d % TFA-d in Methanol-d 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , s , s , s , d (1.8) , s , d (1.8) a a ' ' 8.00, d (2.2) , d (1.8) ' ' ' 7.01, d (8.7) , d (8.7) ' 8.24, dd (8.7, 2.2) , dd (1.8, 8.7) β-d-glucopyranose , d (7.5) , d (7.1) , dd (7.5, 9.0) , dd (7.1, 8.5) , dd (9.0, 9.5) , dd (8.5, 2.7) , dd (9.5, 8.0) , d (2.7) , ddd (8.0, 6.5, 1.2) , ddd (8.0, 6.5, 1.2) , dd (1.2, 11.5), , dd (8.0, 12.0) , dd (6.5, 11.0) 4.24, d (12.0) p- Coumaryl , d (8.2) , d (1.6) , d (8.2) , dd (1.6, 8.0) , d (8.2) , d (8.0) , d (8.2) α 6.22, d (16.0) , d (15.9) β 7.44, d (16.0) , d (15.9) carbonyl S10
11 Figure S6. 1 H-NMR spectrum of compound 4 (in methanol-d 4 ) HO O O HO 1'' O 3'' 6'' O O Figure S7. UV-Vis spectroscopy of compound 4 AU nm S11
12 Table S4. NMR spectroscopic data for compound 5 Kaempferol, yellow solid. UVmax (Me) (nm): 228 (13855); 267 (11997); 366 (10424). ESIMS m/z: 310 [M+Na] + Position Methanol-d 4 Methanol-d 2 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , d (2.0) , d (2.0) , d (2.0) , d (2.0) a a ' ' 8.08, d (8.6) , d (8.6) ' 6.90, d (8.6) , d (8.6) ' ' 6.90, d (8.6) , d (8.6) ' 8.08, d (8.6) , d (8.6) S12
13 Figure S8. 1 H-NMR spectrum of compound 5 (in methanol-d 4 ) Figure S9. UV-Vis spectroscopy of compound 5 S13
14 Table S5. NMR spectroscopic data for compound 6 Kaempferol-3-rutinoside, yellow solid. UVmax (Me) (nm): 225 (12018); 268 (10675); 350 (9870). ESIMS, m/z:595 [M+1] +. HRESIMS: calculated for C 27 H 30 O 15 Na [M+Na] + : , found Position CD 3 OD CD 3 OD 2 δ H (J in Hz) δ C δ H (J in Hz) δ C , d (2.1) , d (2.1) , d (2.1) , d (2.1) a a ' ' 8.06, d (8.4) ,, d (8.5) ' 6.89, d (8.5) , d (8.5) ' ' 6.89, d (8.5) , d (8.5) ' 8.06, d (8.4) , d (8.5) β-d-glucopyranose , d (7.0) , d (7.0) , dd (7.0, 8.5) , dd (7.7, 8.9) , dd (8.5, 9.0) , t (8.9) , dd (9.0, 8.5) , t (8.9) , ddd (8.5, 6.5, 1.5) , ddd (1.2, 6.1, 8.9) , dd (1.5, 10.5) 3.37, dd (10.5, 6.5) , dd (1.2, 11.0) 3.37, dd (6.1, 11.0) 68.5 α-l-rhamnopyranose , d (2.0) , d (1.5) , dd (2.0, 3.0) , dd (1.5, 3.5) , dd (3.0, 9.0) , dd (3.5, 9.6) , dd (9.0, 9.5) , t (9.6) , dd (9.5, 6.5) , dd (6.2, 9.6) , d (6.5) , d (6.2) 17.9 S14
15 Figure S10. 1 H-NMR spectrum of compound 6 (in methanol-d 4 ) HO O O O HO 1'' O 3'' 6'' O 1''' O HO Series1 Figure S11. UV-Vis spectroscopy of compound 6 S15
16 Table S6. NMR spectroscopic data for compound 7 Apigenin-7-O-β-D-glucopyranoside, light yellow solid. ESIMS m/z: 469 [M+Na] +. Position Methanol-d 4 4,5 Methanol-d 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , s , s , d (2.1) , d (2.0) , d (2.2) , d (2.0) a a ' ' 7.86, d (8.5) , d (9.0) ' , d (9.0) ' ' , d (9.0) ' 7.86, d (8.5) , d (9.0) '' 5.14, d (7.0) , d (7.0) '' , m , m '' , m , m '' 3.64, dd (10.6, , m ) 5'' 4.11, d (9.6) , m '' S16
17 Figure S12. 1 H-NMR spectrum of compound 7 (in methanol-d 4 ) Figure S13. UV-Vis spectroscopy of compound 7 S17
18 Table S7. NMR spectroscopic data for compound 8 Kaempferol-3-O-(6-O-p-coumaryl)-O-β-D-glucopyranoside. Yellow solid, ESIMS m/z: 593 [M-H] -, 617 [M+Na] + ; Position Methanol-d 4 6 Methanol-d 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , s , d (2.0) , s , d (2.4) a a ' ' 8.06, d (8.5) , d (8.4) ' 6.89, d (8.5) , d (8.4) ' ' 6.89, d (8.5) , d (8.4) ' 8.06, d (8.5) , d (8.4) β-d-glucopyranose , d (6.7) d, (7.60) , dd (7.0, 8.9) , m , dd (9.0, 9.5) , m , dd (9.0, 8.0) , m , ddd (8.9, 6.5, , m ) , dd (11.5, 6.8) , dd (11.5, 6.8) , dd (11.9, 2.2) 4.30, dd (11.9, 2.2) p- Coumaryl , d (8.2) , d (1.6) , d (8.2) , dd (1.6, 8.0) , d (8.2) , d (8.0) , d (8.2) α 6.22, d (16.0) , d (15.9) , d (8.1) , d (8.4) (C=O) S18
19 Figure S14. 1 H-NMR spectrum of compound 8 (in methanol-d 4 ) Figure S15. UV-Vis spectroscopy of compound 8 S19
20 Table S8. NMR spectroscopic data for compound 9 Quercetin-3-O-(6-O-p-coumaryl)-O-β-D-glucopyranoside. Yellow solid, ESIMS m/z: 609 [M-H] -, 633 [M+Na] + ; Position Methanol-d 4 6 Methanol-d 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , s , d (2.0) , s , d (2.4) a a ' ' 6.80, d (8.1) , d (2.4) ' ' ' 6.81, d (2.4) , d (8.4) ' 7.99, d (8.3) , dd (8.4, 2.4) β-d-glucopyranose , d (6.7) , d (7.60) , dd (7.0, 8.9) , m , dd (9.0, 9.5) , m , dd (9.0, 8.0) , m , ddd (8.9, 6.5, 1.5) , m , dd (11.5, 6.8) , dd (11.5, 6.8) , dd (11.9, 2.2) 4.30, dd (11.9, 2.2) p-coumaryl , d (15.9) , d (16.0) , d (15.8) , d (16.0) , d (8.1) , d (8.4) , d (8.3) , d (8.8) , d (8.3) , d (8.8) , d (8.1) , d (8.4) (C=O) S20
21 Figure S16. 1 H-NMR spectrum of compound 9 (in methanol-d 4 ) Figure S17. UV-Vis spectroscopy of compound 9 S21
22 Table S9. NMR spectroscopic data for compound 10 Quercetin 3-O-β-D-glucopyranoside. Yellow solid. UVmax (Me) (nm): 228 (13855); 259 (13084); 359 (11830). ESIMS m/z: 465 [M+1 ]+ Position Methanol-d 4 2 Methanol-d 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , d (2.1) , d (2.1) , d (2.1) , d, (2.1) a a ' ' 7.84, d (2.2) , d (2.1) ' ' ' 6.87, d (8.6) , d (8.5) ' 7.59, dd (8.5, 2.3) , dd (8.5, 2.2) β-d-glucopyranose 1'' 5.16, d (7.5) , d (7.0) '' 3.47, dd (7.5, 9.0) , dd (7.5, 9.0) '' 3.42, dd (9.0, 9.5) , dd (9.0, 9.5) '' 3.34, dd (9.0, 8.5) , dd (9.0, 8.5) '' 3.25, ddd (8.5, 1.5, 6.5) , ddd (8.5, 1.5, '' 3.71, dd (1.5, 11.0) 3.58, dd (11.0, 6.5) 6.5) , dd (1.5, 11.0) 3.52, dd (11.0, 6.5) 68.6 S22
23 Figure S18. 1 H-NMR spectrum of compound 10 (in methanol-d 4 ) HO O O O HO 1'' O 3'' 6'' Figure S19. UV-Vis spectroscopy of compound 9 S23
24 Table S10. NMR spectroscopic data for compound 11 Luteolin 7-O-β-D-glucopyranoside, Yellow solid. ESIMS m/z: 449 [M+1] Position Methanol-d 4 2 Methanol-d 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , s , s , s , s , s , s a a ' ' 7.84, d (2.2) , d (2.1) ' ' ' 6.87, d (8.6) , d (8.5) ' 7.59, dd (8.5, 2.3) , dd (8.5, 2.2) β-d-glucopyranose 1'' 5.14, d (6.5) , d (7.0) '' 3.47, dd (7.5, 9.0) , dd (7.5, 9.0) '' 3.42, dd (9.0, 9.5) , dd (9.0, 9.5) '' 3.34, dd (9.0, 8.5) , dd (9.0, 8.5) '' 3.25, ddd (8.5, 1.5, 6.5) , ddd (8.5, 1.5, '' 3.71, dd (1.5, 11.0) 3.58, dd (11.0, 6.5) 6.5) , dd (1.5, 11.0) 3.52, dd (11.0, 6.5) 68.6 S24
25 Figure S20. 1 H-NMR spectrum of compound 11 (in methanol-d 4 ) Figure S21. UV-Vis spectroscopy of compound 11 S25
26 Table S11. NMR spectroscopic data for compound 13 Dihydroquercetin, A pale yellow solid. ESIMS m/z 305 [M-H] + Position Methanol-d 4 7 Methanol-d 4 δ H (J in Hz) δ C δ H (J in Hz) δ C , d (11.5) , d (11.5) , d (11.5) , d (11.5) , d (2.1) , s , d (2.1) , s a a ' ' 6.97, d (2.1) , d (2.1) ' ' ' 6.81, d (8.1) , d (8.1) ' 6.85, dd (8.1, 2.1) , dd (8.1, 2.1) S26
27 Figure S22. 1 H-NMR spectrum of compound 13 (in methanol-d 4 ) Figure S22. UV-Vis spectroscopy of compound 13 S27
28 Characterisation of New Compounds Figure S23. LRESIMS from compound 3 S28
29 Figure S24. HRESIMS from compound 3 S29
30 Figure S25. UV-Vis spectroscopy of compound 3 Figure S26. 1 H-NMR spectrum of compound 3 (in methanol-d 4 ) HO 4" 1" 3' 2' HO O O O 6 HO O 4 2 NH 2 S30
31 Figure S C-NMR spectrum of compound 3 (in methanol-d 4 ) HO 4" 1" 3' 2' HO O O O 6 HO O 4 2 NH 2 2''/6'' 3''/5'' 7 1' 4'' 1 3' 1'' 2' S31
32 Figure S28. HSQC spectrum of compound 3 (in methanol-d 4 ) HO 4" 1" 3' 2' HO O O O 6 HO O 4 2 NH 2 S32
33 Figure S29. COSY spectrum of compound 3 (in methanol-d 4 ) HO 4" 1" 3' 2' HO O O O 6 HO O 4 2 NH 2 S33
34 Figure S30. HMBC spectrum of compound 3 (in methanol-d 4 ) HO 4" 1" 3' 2' HO O O O 6 HO O 4 2 NH 2 S34
35 Figure S31. HMBC spectrum of compound 3 (in methanol-d 4 ) (zoom) S35
36 Figure S32. LRESIMS from compound 12 Figure S33. HRESIMS from compound 12 S36
37 Figure S34. UV-Vis spectroscopy of compound 12. S37
38 B. Acid hydrolysis of 12 Figure S35. RP-HPLC profile from acid hydrolysis of 12 compared to authentic standard. RH-HPLC coupled with Evaporative Light Scattering Detector (ELSD) and separation was achieved using isocratic flow on a Prevail Carbohydrates ES Column. S38
39 Figure S36. 1 H-NMR spectrum of compound 12 (in methanol-d 4 ) S39
40 Figure S C-NMR spectrum of compound 12 (in methanol-d 4 ) S40
41 Figure S38. HSQC spectrum of compound 12 (in methanol-d 4 ) 2'';3'';5'' 6'' α2 3'''/5''' 1'' 4 6' 4'' 2'''/6''' 3/5 β2 β1 2/6 α1 S41
42 Figure S39. COSY spectrum of compound 12 (in methanol-d 4 ) S42
43 Figure S40. NOESY spectrum of compound 12 (in methanol-d 4 ) O HO O 2' 2 4' A 1'' O O 5' 6' O 4'' B 5 6"' 5"' 1"' C 3"' S43
44 Figure S41. HMBC spectrum of compound 12 (in methanol-d 4 ) S44
45 Figure S42. GCMS Spectrum of Anigozanthos sp. Table S12. GCMS Data of Anigozanthos sp. NO. RT (min) Compound name ,8-Dimethyldecane Mercapto-2-pyridinone (R)-4-Iodo-1,2-epoxybutane Neophytadiene Methylpalmitate (S)-4-Iodo-1,2-epoxybutane ,4-Bis(methoxymethyl)benzene S45
46 Table S13. Antibacterial Activity of methanol extracts and pure compounds obtained from A. rufus and A. pulcherrimus, showing percentage of inhibition (%) Compound Microorganism SA EC KP PA AB CA CN ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND Me extract of ND ND A. rufus Me extract A. pulcherrimus ND ND Staphylococcus aureus ATCC (MRSA), Eschericia coli ATCC (FDA control strain), Klebsiella penumoniae ATCC (MDA), Pseudomonas aeruginosa ATCC 27853, Acinetobacter baumannii ATCC 19606, Candida albicans ATCC 90028, Cryptococcus neoformans ATCC ND: not inhibition detected. S46
47 Figure S43. Colour solutions from compound 1 13 in methanol. Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6 Compound 7 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12 Compound 13 S47
48 References (1) Du, Q.; Zheng, J.; Xu, Y., J. Food Comp. Anal. 2008, 21, (2) Kazuma, K.; Noda, N.; Suzuki, M., Phytochemistry 2003, 62, (3) Qiu, F.; Luo, J.; Yao, S.; Ma, L.; Kong, L., J. Sep. Sci. 2009, 32, (4) Vanhoenacker, G.; Van Rompaey, P.; De Keukeleire, D.; Sandra, P., Nat. Prod. Lett. 2002, 16, (5) Han, X. H.; Hong, S. S.; Hwang, J. S.; Lee, M. K.; Hwang, B. Y.; Ro, J. S., Arch. Pharm. Res.2007, 30, (6) Ren, X.; Shen, L.-l.; Muraoka, O.; Cheng, M., J. Carbohydr. Chem. 2011, 30, , Lavault, M.; Richomme, P., Chem. Nat. Compd. 2004, 40, (7) Kiehlmann, E.; Szczepina, M. G., Cent. Eur. J. Chem. 2011, 9, S48
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