Phloroglucinol Benzophenones and Xanthones from the Leaves of Garcinia cowa and Their Nitric Oxide Production and α-Glucosidase Inhibitory Activities

被引:27
作者
Raksat, Achara [1 ,2 ]
Phukhatmuen, Piyaporn [1 ,2 ]
Yang, Jianxiong [5 ]
Maneerat, Wisanu [1 ,2 ]
Charoensup, Rawiwan [3 ,4 ]
Andersen, Raymond J. [5 ,6 ]
Wang, Yan A. [5 ]
Pyne, Stephen G. [7 ]
Laphookhieo, Surat [1 ,2 ]
机构
[1] Mae Fah Luang Univ, Ctr Chem Innovat Sustainabil CIS, Chiang Rai 57100, Thailand
[2] Mae Fah Luang Univ, Sch Sci, Chiang Rai 57100, Thailand
[3] Mae Fah Luang Univ, Ctr Excellence Med Plants & Thai Tradit Med, Chiang Rai 57100, Thailand
[4] Mae Fah Luang Univ, Sch Integrat Med, Chiang Rai 57100, Thailand
[5] Univ British Columbia, Dept Chem, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada
[6] Univ British Columbia, Dept Earth Ocean & Atmospher Sci, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada
[7] Univ Wollongong, Sch Chem & Mol Biosci, Wollongong, NSW 2522, Australia
来源
JOURNAL OF NATURAL PRODUCTS | 2020年 / 83卷 / 01期
关键词
BIOACTIVE PRENYLATED XANTHONES; TETRAOXYGENATED XANTHONES; DERIVATIVES; FRUITS;
D O I
10.1021/acs.jnatprod.9b00849
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Five new compounds-two phloroglucinol benzophenones, garciniacowones F (1) and G (2), and three xanthones, garciniacowones H (3), I (4), and J (5)-together with seven known xanthones (6-12) were isolated from the fresh leaves of Garcinia cowa. Their structures were elucidated by detailed analysis of NMR and MS data. Compounds 1 and 2 are phloroglucinol benzophenones containing a polyprenylated bicyclo[3.3.1]nonane ring system, while compounds 3-5 are rare xanthones having farnesyl (3 and 5) and geranylgeranyl (5) units at C-8. Compounds 1, 3, 4, 7, 8, and 10 exhibited inhibitory effects on NO production in LPS-induced RAW264.7 macrophage cells with IC50 values ranging from 5.4 to 18.6 mu M. Compounds 4 and 8 had alpha-glucosidase inhibitory activities with IC50 values of 15.4 and 11.4 mu M, respectively, which were more potent than that of the acarbose control.
引用
收藏
页码:164 / 168
页数:5
相关论文
共 26 条
[1]   A XANTHONE FROM PERICARPS OF GARCINIA-MANGOSTANA [J].
ASAI, F ;
TOSA, H ;
TANAKA, T ;
IINUMA, M .
PHYTOCHEMISTRY, 1995, 39 (04) :943-944
[2]   Antibacterial tetraoxygenated xanthones from the immature fruits of Garcinia cowa [J].
Auranwiwat, Chiramet ;
Trisuwan, Kongkiat ;
Saiai, Aroonchai ;
Pyne, Stephen G. ;
Ritthiwigrom, Thunwadee .
FITOTERAPIA, 2014, 98 :179-183
[3]   TRITERPENOIDS, TOCOTRIENOLS AND XANTHONES FROM THE BARK OF CRATOXYLUM-COCHINCHINENSE [J].
BENNETT, GJ ;
HARRISON, LJ ;
SIA, GL ;
SIM, KY .
PHYTOCHEMISTRY, 1993, 32 (05) :1245-1251
[4]   Bioactive prenylated xanthones and anthraquinones from Cratoxylum formosum ssp pruniflorum [J].
Boonnak, Nawong ;
Karalai, Chatchanok ;
Chantrapromma, Suchada ;
Ponglimanont, Chanita ;
Fun, Hoong-Kun ;
Kanjana-Opas, Akkharawit ;
Laphookhieo, Surat .
TETRAHEDRON, 2006, 62 (37) :8850-8859
[5]   Cytotoxic farnesyl glycosides from Pittosporum pancheri [J].
Eparvier, Veronique ;
Thoison, Odile ;
Bousserouel, Hadjira ;
Gueritte, Francoise ;
Sevenet, Thierry ;
Litaudon, Marc .
PHYTOCHEMISTRY, 2007, 68 (05) :604-608
[6]   Kaennacowanols A-C, three new xanthones and their cytotoxicity from the roots of Garcinia cowa [J].
Kaennakam, Sutin ;
Siripong, Pongpun ;
Tip-pyang, Santi .
FITOTERAPIA, 2015, 102 :171-176
[7]  
Kumar Sunil, 2011, Pharmacogn Rev, V5, P19, DOI 10.4103/0973-7847.79096
[8]  
Lim T. K., 2012, EDIBLE MED NONMEDICI, V2, P1100
[9]   Regulation of nitric oxide production in health and disease [J].
Luiking, Yvette C. ;
Engelen, Marielle P. K. J. ;
Deutz, Nicolaas E. P. .
CURRENT OPINION IN CLINICAL NUTRITION AND METABOLIC CARE, 2010, 13 (01) :97-104
[10]   Xanthones from Garcinia cowa Roxb. latex [J].
Mahabusarakain, W ;
Chairerk, P ;
Taylor, WC .
PHYTOCHEMISTRY, 2005, 66 (10) :1148-1153