A new 3,4-seco-isopimarane and three new isopimarane diterpenoids from Kaempferia champasakensis collected from Vietnam and their cytotoxic activities

被引:2
作者
Do, Kiep Minh [1 ]
Hoshino, Shotaro [2 ]
Kodama, Takeshi [1 ]
Nguyen, Hien Minh [3 ]
Van Le, Son [4 ]
Ikumi, Naotaka [5 ]
Onaka, Hiroyasu [2 ]
Morita, Hiroyuki [1 ]
机构
[1] Univ Toyama, Inst Nat Med, 2630 Sugitani, Toyama 9300194, Japan
[2] Gakushuin Univ, Fac Sci, 1-5-1 Mejiro Toshima Ku, Tokyo 1718588, Japan
[3] Ton Duc Thang Univ, Fac Pharm, Ho Chi Minh City 700000, Vietnam
[4] Thuong Uyen Co Ltd, 116A Mac Dinh Chi Ward 4, Vung Tau 78000, Vietnam
[5] Japan Prevent Med Lab Co Ltd, 3-6-36 Toyoda Suruga Ku, Shizuoka 4228027, Japan
关键词
Kaempferia champasakensis; 3,4-seco-isopimarane diterpenoid; Isopimarane; Kaempferiols A-D; Cytotoxicity; ZINGIBERACEAE;
D O I
10.1007/s11418-024-01789-z
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A phytochemical investigation of Kaempferia champasakensis rhizomes led to the isolation of a new 3,4-seco-isopimarane diterpene, kaempferiol A (1), and three new isopimarane diterpenes, kaempferiols B-D (2-4), together with six known isopimarane diterpenes (5-10). The structures of 1-4 were elucidated by extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, and 1D and 2D NMR. The absolute configurations of 1, 3, and 4 were determined by ECD calculations, while that of 2 was established using the modified Mosher method. All isolated compounds were tested for cytotoxicity against three human cancer cell lines, lung cancer (A549), cervical cancer (HeLa), and breast cancer (MCF-7). Among them, 6 and 7 showed moderate cytotoxic activities against the three tested cell lines, with IC50 values ranging from 38.04 to 27.77 mu M, respectively.
引用
收藏
页码:537 / 546
页数:10
相关论文
共 27 条
[1]   STRUCTURE OF VIRESCENOSIDE C, NEW METABOLITE OF OOSPORA-VIRESCENS (LINK) WALLR [J].
CAGNOLIB.N ;
CECCHERELLI, P ;
MARIANI, R ;
POLONSKY, J ;
BASKEVITCH, Z .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1970, 15 (02) :356-+
[2]   Inhibitory constituents against cyclooxygenases from Aralia cordata thunb [J].
Dang, NH ;
Zhang, XF ;
Zheng, MS ;
Son, KH ;
Chang, HW ;
Kim, HP ;
Bae, K ;
Kang, SS .
ARCHIVES OF PHARMACAL RESEARCH, 2005, 28 (01) :28-33
[3]  
de Pascual TJ., 1980, PHYTOCHEMISTRY, V19
[4]   Seco- and isopimarane diterpenoids from Kaempferia marginata rhizomes and their NO inhibition activities [J].
Do, Kiep Minh ;
Kodama, Takeshi ;
Nguyen, Hien Minh ;
Ikumi, Naoki ;
Soeda, Chigusa ;
Shiokawa, Ken-ichi ;
Morita, Hiroyuki .
PHYTOCHEMISTRY, 2023, 205
[5]   Marginols A-H, unprecedented pimarane diterpenoids from Kaempferia marginata and their NO inhibitory activities [J].
Do, Kiep Minh ;
Kodama, Takeshi ;
Shin, Min-Kyoung ;
Lien Huong Ton Nu ;
Hien Minh Nguyen ;
Son Van Dang ;
Shiokawa, Ken-ichi ;
Hayakawa, Yoshihiro ;
Morita, Hiroyuki .
PHYTOCHEMISTRY, 2022, 196
[6]   Recent Advances in Kaempferia Phytochemistry and Biological Activity: A Comprehensive Review [J].
Elshamy, Abdelsamed I. ;
Mohamed, Tarik A. ;
Essa, Ahmed F. ;
Abd-El Gawad, Ahmed M. ;
Alqahtani, Ali S. ;
Shahat, Abdelaaty A. ;
Yoneyama, Tatsuro ;
Farrag, Abdel Razik H. ;
Noji, Masaaki ;
El-Seedi, Hesham R. ;
Umeyama, Akemi ;
Pare, Paul W. ;
Hegazy, Mohamed-Elamir F. .
NUTRIENTS, 2019, 11 (10)
[7]   THE PIMARANE-TYPE DITERPENOIDS OF SALVIA-MICROPHYLLA VAR NEUREPIA [J].
ESQUIVEL, B ;
MARTINEZ, ND ;
CARDENAS, J ;
RAMAMOORTHY, TP ;
RODRIGUEZHAHN, L .
PLANTA MEDICA, 1989, (01) :62-63
[8]   Chemical Composition of the Volatile Oil from the Leaves of Kaempferia champasakensis Picheans. & Koonterm. (Zingiberaceae) [J].
Hieu, Tran Trung ;
Duc, Dau Xuan ;
Hieu, Nguyen Ngoc ;
Danh, Nguyen Duc ;
Tuan, Nguyen Hoang ;
Van Trung, Hoang ;
Thang, Tran Dinh ;
Giang, Le Duc .
JOURNAL OF ESSENTIAL OIL BEARING PLANTS, 2023, 26 (01) :108-114
[9]  
Van HT, 2021, RES J BIOTECHNOL, V16, P105
[10]   In Vitro Antimicrobial Activity of Isopimarane-Type Diterpenoids [J].
Isca, Vera M. S. ;
Andrade, Joana ;
Fernandes, Ana Sofia ;
Paixao, Paulo ;
Uriel, Clara ;
Gomez, Ana Maria ;
Duarte, Noelia ;
Rijo, Patricia .
MOLECULES, 2020, 25 (18)