Spirostanol glycosides with hemostatic and antimicrobial activities from Trillium kamtschaticum.
Ten spirostanol glycosides, trillikamtosides A-J, together with eleven known analogues, were isolated from the hemostatic fraction of the 75% aqueous EtOH extract of the whole herbs of Trillium kamtschaticum. Their structures were established by extensive spectroscopic data analysis and chemical methods. The aglycones of three of these compounds had unique 3β,17α-dihydroxy-spirostanes featuring a double bond between C-4 and C-5, while two others represent a rare class of spirostanol glycosides which possess a 5(6 → 7) abeo-steroidal aglycone. All the compounds were evaluated for their hemostatic and antimicrobial activities. Three of the spirostanol glycosides exhibited induced-platelet aggregation at a concentration of 300 μg/mL with maximal induced-platelet aggregation rates of 72%, 71%, and 62% in rabbits, respectively, and their EC50values were 492.7, 203.3, and 109.8 μM. Five of the spirostanol glycosides showed an anti-Candida albicans effect with MIC values of 21.1, 10.6, 8.8, 21.6, and 11.0 μM, respectively.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; University of Chinese Academy of Sciences, Beijing 100039, China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, China.
Yu
Y
Chen
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, China.
Wei
W
Ni
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, China.
Huan
H
Yan
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, China.
Xu-Jie
XJ
Qin
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.
Afsar
A
Khan
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; University of Chinese Academy of Sciences, Beijing 100039, China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, China.
Hui
H
Liu
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; University of Chinese Academy of Sciences, Beijing 100039, China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, China.
Tong
T
Shu
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, China.
Ling-Yu
LY
Jin
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, China. Electronic address: haiyangliu@mail.kib.ac.cn.
Hai-Yang
HY
Liu
D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006490:Hemostatics / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010974:Platelet Aggregation / Q000187:drug effects; D013150:Spirostans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D031446:Trillium / Q000737:chemistry*
D000890:Anti-Infective Agents; D006027:Glycosides; D006490:Hemostatics; D013150:Spirostans
Antimicrobial activity; Hemostatic activity; Spirostanol glycosides; Trilliaceae; Trillium kamtschaticum