Synthesis of isoacteoside, a dihydroxyphenylethyl glycoside

Journal of Wood Science

Volumn 48, Issue 6, 2002, Pages 512-515

  Kawada, Toshinari ^a   Asano, Ryuji ^a   Makino, Kozo ^a,b   Sakuno, Tomoyasu ^a  

^a TOTTORI UNIVERSITY   (Japan)

^b E Hiroshima Pref Indust Res I   (Japan)

Author keywords

Caffeic acid sugar ester; Carbohydrates; Dihydroxyphenylethyl glycoside; Phenylpropanoid glycoside; Wood extractives

Indexed keywords

HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

CATALYTIC TRANSFERS;

ORGANIC COMPOUNDS;

HYDROGENATION; NUCLEAR MAGNETIC RESONANCE; ORGANIC COMPOUNDS; PAULOWNIA; SYNTHESIS;

PAULOWNIA; PAULOWNIA TOMENTOSA;

EID: 0142134906     PISSN: 14350211     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00766648     Document Type: Article

References (16)

1. Jiménez C, Riguera R (1994) Phenylethanoid glycosides in plants: structure and biological activity. Nat Prod Rep 11:591-606
2. Cometa F, Tomassini L, Nicoletti M (1993) Phenylpropanoid glycosides: distribution and pharmacological activity. Fitoterapia 64:195-217
3. Mølgaard P, Ravn H (1988) Evolutionary aspects of caffeoyl ester distribution in dicotyledons. Phytochemistry 27:2411-2421
4. Xiong Q, Hase K, Tezuka Y, Tani T, Namba T, Kodata S (1997) Hepatoprotective activity of phenylethanoids from Cistanche deserticola. Planta Med 64:120-125
5. Kawada T, Asano R, Hayashida S, Sakuno T (1999) Total synthesis of the phenylpropanoid glycoside, acteoside. J Org Chem 64:9268-9271
6. Kawada T, Asano R, Makino K, Sakuno T (2000) Synthesis of conandroside: a dihydroxyphenylethyl glycoside from Conandron ramaidioides. Eur J Org Chem 2000:2723-2727
7. Pettit GR, Numata A, Takemura T, Ode RH, Narula AS, Schmidt JM, Cragg GM, Pase CP (1990) Antineoplastic agents, 107: isolation of acteoside and isoacteoside from Castilleja linariaefolia. J Nat Prod 53:456-458
8. Scarpati ML, Monache FD (1963) Isolamento dal verbascum sinuatum di due nuovi glucosidi: il verbascoside e l'isoverbascoside. Ann Chem 53:356-367
9. Miyase T, Koizumi A, Ueno A, Noro T, Kuroyanagi M, Fukushima S, Akiyama Y, Takemoto T (1982) Studies on the acyl glycosides form Leucosceptrum japonicum (MIQ.) Kitamura et Murata. Chem Pharm Bull (Tokyo) 30:2732-2737
10. Schilling G, Hügel M, Mayer W (1982) Verbascoside und Isoverbascoside aus Paulownia tomentosa Steud. Z Naturforsch 37b:1633-1635
11. Sasaki H, Nishimura H, Morota T, Chin M (Chen Z), Mitsuhashi H, Komatsu Y, Maruyama H, Tu G, He W, Xiong Y (1989) Immunosuppressive principles of Rehmannia glutinosa var. hueichingensis. Planta Med 55:458-562
12. Ota M, Azuma T, Onodera S, Taneda K (1993) The chemistry of color changes in kiri wood (Paulownia tomentosa Steud.) III. A new caffeic acid sugar from kiri wood. Mokuzai Gakkaishi 39:479-485
13. Duynstee HI, de Koning MC, Ovaa H, van der Marel GA, van Boom JH (1999) Synthesis of verbascoside: a dehydroxyphenylethyl glycoside with diverse bioactivity. Eur J Org Chem 1999:2623-2632
14. Zhang SQ, Li ZJ, Wand AB, Cai MS, Feng R (1998) Synthesis of a phenylpropanoid glycoside, osmanthuside B6. Carbohydr Res 308:281-285
15. Ota M, Takahashi K, Kofujita H (1998) Role of caffeic glucoside esters in defense-repair processing of trees. II. Synthesis of 2-(3,4-dihydroxyphenyl)- ethyl 3-O-α-L-rhammopyranosyl-β-D-glucopyranoside. J Wood Sci 44:320-326
16. Felix AM, Heimer EP, Lambros TJ, Taougraki C, Meinenhofer J (1978) Rapid removal of protecting groups from peptides by catalytic transfer hydrogenation with 1,4-cyclohexadiene. J Org Chem 21:4194-4196