,Sesquiterpene glycosides from the roots of Codonopsis pilosula

• 作 者: Yueping Jiang Yufeng Liu Qinglan Guo Chengbo Xu Chenggen Zhu Jiangong Shi
• 机 构: State Key Laboratory of Bioactive Substance and Function of Natural Medicines,Institute of Materia M
• 出 处: Acta Pharmaceutica Sinica B
• 发表日期: 2016年01期
• 关键词: Codonopsis pilosula Campanulaceae Sesquiterpene glycoside Codonopsesquilosides A

Three new sesquiterpene glycosides,named codonopsesquilosides A C(1 3),were isolated from an aqueous extract of the dried roots of Codonopsis pilosula.Their structures including absolute configurations were determined by spectroscopic and chemical methods.These glycosides are categorized as C_(15) carotenoid(1),gymnomitrane(2),and eudesmane(3)types of sesquiterpenoids,respectively.Compound 1 is the first diglycoside of C_(15) carotenoids to be reported.Compound 2 represents the second reported example of gymnomitrane-type sesquiterpenoids from higher plants.The absolute configurations were supported by comparison of the experimental circular dichroism(CD)spectra with the calculated electronic CD(ECD)spectra of 13,their aglycones,and model compounds based on quantummechanical time-dependent density functional theory.The influences of the glycosyls on the calculated ECD spectra of the glycosidic sesquiterpenoids,as well as some nomenclature and descriptive problems with gymnomitrane-type sesquiterpenoids are discussed.

Three new sesquiterpene glycosides, named codonopsesquilosides AC (1 3), were isolated from an aqueous extract of the dried roots of Codonopsis pilosula.Their structures including absolute configurations were determined by spectroscopic and chemical methods. These glycosides are categorized as C_ (15) carotenoid (1), gymnomitrane (2), and eudesmane (3) types of sesquiterpenoids, respectively. Compound 1 is the first diglycoside of C_ (15) carotenoids to be reported. Compound 2 represents the second reported example of gymnomitrane-type sesquiterpenoids from higher plants. The absolute configurations were supported by comparison of the experimental circular dichroism (CD) spectra with the calculated electronic CD (ECD) spectra of 13, their aglycones, and model compounds based on quantum mechanic time-dependent density functional theory. These influences of the glycosyls on the calculated ECD spectra of the glycosidic sesquiterpenoids, as well as some nomenclature and descriptive problems with gymnomitrane-type sesquiterpenoids are discussed.