Gansongon, ein neues Aristolan-Keton ausNardostachys chinensis Batalinund Strukturrevision eines Aristolenols

Abstract

A new instable aristolane type sesquiterpene ketone, gansongone ( 1), was isolated from the fresh underground parts of NARDOSTACHYS CHINESIS Batalin (Valerianaceae), growing in the province Sichuan (China). The structure of 1 was elucidated by spectroscopic and chemical methods. The structure of the corresponding alcohol 2, which was also found in N. CHINENSIS and formerly regarded as 9-aristolene-1alpha-ol ( 5) has to be revised to l(10)-aristolene-9beta-ol ( 2) from results of 2D-NMR-spectroscopy and oxidation to 1. Besides 1 and 2, the following compounds have been identified in the ethanol extract of the fresh plant material of N. CHINENSIS: nardosinone, nardosinondiol, deoxonarchinol A, beta-sitosterol, oleanolic acid, ethyl beta- D-glucopyranoside.

Brominated Metabolites from the Marine Red Alga Laurencia similis

“…The NOE correlations of the two methyl signals H-14 and H-15 with H-6 indicated that H-6 and the two methyls (C-14 and C-15) are on the same face of the ring system. The coupling constant between H-6 and H-7 (J = 9.2 Hz) implied the cis-orientation of H-6 and H-7 [15,16], which was also verified by the NOESY experiment. The small coupling constant for H-1 (J = 2.2 Hz) clearly established the Br functionality at C-1 to be in the α position.…”

“…Since all 15 carbons were sp 3 hybridized as indicated by 13 C NMR and DEPT spectra (Table 1), the 4 degrees of unsaturation indicated the presence of a tetracyclic ring system in 1. The methine signal at δ C = 65.2 and the quaternary carbon signal at δ C = 66.5 were deduced to be those connected to the oxygen atom, and the methine signal resonating at δ C = 57.2 was ascribed to be brominated.…”

“…In the course of our continuing studies on structurally interesting secondary metabolites from the genus Laurencia [5 -11], the species of L. similis was re-investigated, and as a result one new sesquiterpenoid, aristolan-1α-bromo-9β ,10β -epoxide (1), and one new indole alkaloid, 2,5-dibromo-N-methylindole (2), were identified. In addition, six known compounds including aristol-8(9)-en-1-one (3) [5], aristol-9(10)-en-8-one (4) [12], 9β -aristol-1(10)-en-9-ol (5) [13], 2,3,5-tribromo-1-methyl-1H-indole (6) [14], 2,3,5,6-tetrabromo-1H-indole (7) [14], and 3,5,6-tribromo-1H-indole (8) [5], were also isolated and identified. Herein, we report the isolation and structure elucidation of the new compounds.…”

Quality assessment of the essential oils from Nardostachys jatamansi (d. Don) dc and Nardostachys chinensis batal obtained from Kathmandu valley market

“…Similarly, sesquiterpenes such as aristolene, â-maaliene, isonardosione, nardostachin, nardofuran, nardoquaianone (3,(20)(21)(22) have been reported in N. chinensis.…”

Chemical constituents of Chondrophycus papillosus and their cytotoxicity in vitro

“…The structures of compounds 1-9 were determined to be aristolone (1) [3], 1(10)-aristolen-9E-ol (2) [4], 1(10),8-aristoladien-2-one (3) [5,6], aplysistatin (4) [7], 2,3,5,6-tetrabromo-1-methyl-1H-indole (5) [8], 2,3,5,6-tetrabromoindole (6) [9], 3,5,6-tribromo-1H-indole (7) [10], phytol (8) [7,11], and cholesterol (9) [12] on the basis of their 1 H NMR, 13 C NMR, and EI-MS spectral data and by comparison with those previously reported in the literature. Among these metabolites, compounds 1-7 were first isolated from C. papillosus.…”