Vetiverianines A, B, and C: Sesquiterpenoids from Vetiveria zizanioides Roots

Abstract

Three new sesquiterpenoids-vetiverianines A (1), B (2), and C (3)-and a known eudesmane sesquiterpenoid (4) were isolated from the roots of Vetiveria zizanioides. Vetiverianine A (1) has a unique carbon framework comprising a rigid tricyclic ring system. Vetiverianines B (2) and C (3) are new eremophilane sesquiterpenoids. The structures of sesquiterpenoids 1-3, including the absolute configurations, were determined by NMR spectroscopic, X-ray crystallography, and vibrational circular dichroism data analysis. Vetiverianine C (3) exhibited weak cytotoxic activity against HL-60 cells.

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

“…The AC of vetiverianines 51 , 52 , and 53 , (Figure 12), isolated from the roots of Vetiveria zizanioides , were determined by NMR, X-ray crystallography, and VCD studies as (4 S ,5 S ,6 S ,7 S ,10 S )− 51 , (4 R ,5 S ,7 R )− 52 , and (4 R ,5 S ,7 R ,11 R )− 53 . 41…”

“…40 The AC of vetiverianines 51, 52, and 53, (Figure 12), isolated from the roots of Vetiveria zizanioides, were determined by NMR, X-ray crystallography, and VCD studies as (4S,5S,6S,7S ,10S)−51, (4R,5S,7R)−52, and (4R,5S,7R,11R)−53. 41 The AC of (+)-(7R,8R,10S)-inuloxin A (54) ( Figure 13), isolated from Inula viscosa, and of seiricardine A (55), obtained from Seiridium cardinale, fungi, followed from the combined analysis of their ORD, ECD, and VCD properties and by chemical introduction of a suitable chromophore. Thus, (−)−55 was converted into the p-Br-benzoyl ester (−)-(1S,2R,3 aS,4S,5R,7aS)−56 ( Figure 13).…”

A New Neolignan Glycoside from Vetiveria zizanioides Roots

“…The plant material was obtained from a wholesale firm Akaru Co., Ltd., Fukuoka, Japan. A voucher specimen is deposited in the herbarium of our university (KS-2011-004) [2].…”

“…Previous phytochemical examination of V. zizanioides roots resulted in the isolation of three new sesquiterpenoids, vetiverianines A-C. Vetiverianine A is structurally unique, and has a new carbon skeleton with a rigid tricyclic ring, the absolute configurations of which were determined by X-ray crystallography and vibrational circular dichroism [2]. We conducted a further chemical investigation of the MeOH extract of V. zizanioides root focusing on the phenolic compounds monitored by TLC, and we isolated a new neolignan glycoside (1) and four known compounds (2)(3)(4)(5). In this paper, we report the structural characterization of 1-5 based on spectroscopic analysis, hydrolysis, and X-ray crystallography.…”

Chemical Constituents of the Terrestrial Stems of Ephedra sinica and their PPAR-γ Ligand-Binding Activity

“…The instruments and experimental conditions were the same as those described in a previous paper [18]. All solvents used for extraction and isolation were high grade ( > 99 %) (Fujifilm Wako Pure Chemical).…”