New Guaiane Sesquiterpenes and Furanocoumarins fromNotopterygium incisum

Abstract

In addition to twenty-nine known compounds, two new guaiane sesquiterpenes and two new furanocoumarins were isolated from the chloroform extract of the rhizomes of Notopterygium incisum. The new structures were elucidated by means of spectroscopic methods including 2 D NMR techniques and mass spectrometry to be 8β-acetoxy-4α,6α-dihydroxy-1α,5α(H)-guai-9-ene (incisumdiol A, 1), 4α,6α-dihydroxy-1α,5α(H)-guai-9-ene (incisumdiol B, 2), 5-[(2E,5Z)-7-hydroxy- 3,7-dimethyl-2,5-octadienoxy]psoralene (3) and 5-[(2,5)-epoxy-3-hydroxy-3,7-dimethyl-6-octenoxy]psoralene (4).

Glycosides from the Methanol Extract ofNotopterygium incisum

“…Similar to 5b, the carbon chemical shift (δ 62.6) [15] of C-6′ in 9 was shifted downfield to δ 68. 3 In agreement with our previous findings (especially coumarins and sesquiterpenoids) from the chloroform extract [7], six coumarin glucosides (5, 9-13) and three sesquiterpenoid glucosides (4,7,8) were isolated from the methanol extract in this study. In the case of compounds 1, 2, 5, 9, and 10, we extensively proved the sugar moiety to be β-D-glucopyranoside (Supporting Information).…”

“…Chemically, only a few polar constituents (coumarin glycosides, amino acids, chlorogenic acid, ferulic acid, and daucosterol) were previously characterized from this herb medicine [2][3][4][5][6]. In an earlier work on the chloroform extract of the rhizomes of N. incisum, a number of lipophilic constituents (including antiproliferative furocoumarins) have been identified [7]. After being exhaustively extracted with chloroform, the rhizomes were further extracted with methanol.…”

“…The methanol extract was found to show a preliminary cytotoxic effect against the human MCF-7 breast cancer cell line. During a reinvestigation of polar constituents from this plant and in a continuation of our ongoing project towards the discovery of novel antitumor agents from natural products [8], seventeen (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) different types of glycosides and a polar sesquiterpene hedytriol (18) [9] (l " Fig. 1) were obtained from the methanol extract.…”

“…For general experimental procedure, collection, and identification of the plant material, see a preceding paper[7]. For extraction and isolation of compounds 1-18 from the methanol extract of the rhizomes of N. incisum, see Supporting Information.…”

Coumarins from Seseli hartvigii

“…The position of the hydroxyl moiety is determined at C-7" by acetylated experiment. the position of C-2" and C-3" was determined to be E configuration by comparing the chemical shift of H-2'' with a similar type of compound, 5-[(2"E,5"Z)-7"hydroxy-3",7"-dimethyl-2",5"-octadienoxy]psoralen [6].…”