Salaprinol and ponkoranol with thiosugar sulfonium sulfate structure from Salacia prinoides and α-glucosidase inhibitory activity of ponkoranol and kotalanol desulfate

被引:76
作者
Yoshikawa, Masayuki [1 ]
Xu, Fengming [1 ]
Nakamura, Seikou [1 ]
Wang, Tao [1 ]
Matsuda, Hisashi [1 ]
Tanabe, Genzoh [2 ]
Muraoka, Osamu [2 ]
机构
[1] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan
[2] Kinki Univ, Sch Pharm, Osaka 5778502, Japan
关键词
Salacia prinoides; Indian traditional medicine; inhibitory activity against alpha-glucosidase; thiosugar sulfonium sulfate;
D O I
10.3987/COM-07-11315
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The methanolic extract from the roots and stems of Indian Salacia prinoides and its water-eluted fraction of Diaion HP-20 column were found to exhibit inhibitory activities against cc-glucosidase. From the water-eluted fraction, two new unique constituents with thiosugar sulfonium sulfate, salaprinol (1) and porkoranol (2), were isolated together with 10 known constituents including salacinol and kotalanol. The structures of 1 and 2 were elucidated on the basis of chemical and physicochemical evidence. Furthermore, ponkoranol (2) and kotalanol desulfate (14) were found to show potent inhibitory activities against alpha-glucosidase.
引用
收藏
页码:1397 / 1405
页数:9
相关论文
共 21 条
[1]  
Kishi A, 2003, CHEM PHARM BULL, V51, P1051, DOI 10.1248/cpb.51.1051
[2]  
Matsuda H., 2005, Journal of Traditional Medicines, V22, P145
[3]  
Matsuda H, 1999, CHEM PHARM BULL, V47, P1725, DOI 10.1248/cpb.47.1725
[4]   Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis [J].
Morikawa, T ;
Kishi, A ;
Pongpiriyadacha, Y ;
Matsuda, H ;
Yoshikawa, M .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (09) :1191-1196
[5]   Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity [J].
Muraoka, O ;
Yoshikai, K ;
Takahashi, H ;
Minematsu, T ;
Lu, GX ;
Tanabe, G ;
Wang, T ;
Matsuda, H ;
Yoshikawa, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (02) :500-509
[6]   Synthesis of a nitrogen analogue of salacinol and its α-glucosidase inhibitory activity [J].
Muraoka, O ;
Ying, S ;
Yoshikai, K ;
Matsuura, Y ;
Yamada, E ;
Minematsu, T ;
Tanabe, G ;
Matsuda, H ;
Yoshikawa, M .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (11) :1503-1505
[7]  
Nakamura S, 2008, HETEROCYCLES, V75, P131
[8]   Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity [J].
Tanabe, Genzoh ;
Yoshikai, Kazuya ;
Hatanaka, Takanori ;
Yamamoto, Mizuho ;
Shao, Ying ;
Minematsu, Toshie ;
Muraoka, Osamu ;
Wang, Tao ;
Matsuda, Hisashi ;
Yoshikawa, Masayuki .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (11) :3926-3937
[9]   Floratheasaponins A-C, acylated oleanane-type triterpene oligoglycosides with anti-hyperlipidemic activities from flowers of the tea plant (Camellia sinensis) [J].
Yoshikawa, M ;
Morikawa, T ;
Yamamoto, K ;
Kato, Y ;
Nagatomo, A ;
Matsuda, H .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (09) :1360-1365
[10]   Hepatoprotective and antioxidative properties of Salacia reticulata:: Preventive effects of phenolic constituents on CCl4-induced liver injury in mice [J].
Yoshikawa, M ;
Ninomiya, K ;
Shimoda, H ;
Nishida, N ;
Matsuda, H .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2002, 25 (01) :72-76