Complete assignments of ¹H and ¹³C NMR data for two new sesquiterpenes from Cyperus rotundus L.

Abstract

Two new sesquiterpenes, epi-guaidiol A (1) and sugebiol (3), together with four known sesquiterpenes, guaidiol A(2), sugetriol triacetate (4), cyperenoic acid (5), and cyperotundone (6) were isolated from the rhizomes of Cyperus rotundus L. Their structures were identified by MS and NMR experiments, and the complete assignments of (1)H and (13)C NMR data for two new sesquiterpenes were obtained by the aid of two-dimensional (2D) NMR techniques, including HSQC, HMBC, (1)H-(1)HCOSY and nuclear overhauser enhancement spectroscopy(NOESY).

Sesquiterpenes from the Rhizomes of Cyperus rotundus and Their Potential to Inhibit LPS-induced Nitric Oxide Production

“…C-NMR spectra of 1 exhibited strong similarities with those of sugetriol triacetate 10,17 (Tables 1 and 2), which was isolated from the same plant in the previous study.…”

“…The absolute configuration at C-3, C-6 and C-9 was proposed as 3S, 6S, and 9S on the basis of NOESY correlations ( Figure 3) from δ H 5.57 (H-6) to δ H 0.88 (H-12) and δ H 4.66 (H-9) to δ H 0.81 (H-15) and on the basis of sugetriol triacetate of known absolute configuration. 17 Thus, 1 was determined to be sugetriol 6,9-diacetate. Although 1 was synthesized from sugetriol triacetate, 18 it is the first report on the isolation of 1 from natural source, and of its full NMR assignment.…”

Bioactivity-guided isolation of anti-hepatitis B virus active sesquiterpenoids from the traditional Chinese medicine: Rhizomes of Cyperus rotundus

“…The 13 C NMR data (Table 4) were similar with those of the known compound cyperenoic acid (Boonyarathanakornkit et al, 1988), except for the 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 Table 4 13 C NMR data for compounds 1-5 in CDCl 3 (δ in ppm). H-12), indicated the β-orientation at OH-3 and α-orientation at C-15, which was in consistence with the known compounds sugebiol and cyperenoic acid from the same plant (Xu et al, 2009). As a result, compound 4 was determined as 3β-hydroxycyperenoic acid (Fig.…”

“…2). The known compounds 6-37 were identified as cyperenol (6) (Jacobs et al, 1987), cyperenoic acid (7) (Boonyarathanakornkit et al, 1988), cyperotundone (8) (Hikino et al, 1965(Hikino et al, , 1966, sugeonol (9) (Hikino et al, 1968a), scariodione (10) (Hikino et al, 1968a), sugetriol triacetate (11) (Xu et al, 2009), α-cyperone (12) (Naya et al, 1990), (4aS, 7S),-7-hydroxy-1, 4a-dimethyl-7-(prop-1-en-2-yl),-4, 4a, 5, 6, 7, 8-hexahydronaphthalen-2 (3H),-one (13) (Nozaki et al, 1995), (4aS, 7S, 8R),-8-hydroxy-1, 4a-dimethyl-7-(prop-1-en-2-yl), -4, 4a, 5, 6, 7, 8-hexahydronaphtha-len-2 (3H), -one (14) (Nozaki et al, 1995), cyperol (15) (Sun et al, 2000), 1β-hydroxy-α-cyperone (16) (Sanz and Marco, 1990), 10-epieudesm-11-ene-3β, 5α-diol (17) (Huffman et al, 1980), 3β-hydroxyilicic alcohol (11 (13),-eudesmene-3, 4, 12-triol) (18) (Zhang et al, 2007), cyperusol C (19) (Xu et al, 2004), α-corymbolol (20) (Nyasse et al, 1988), 3β, 4α-dihydroxy-7-epieudesm-11 (13), -ene (21) (Ahmed et al, 1998), 2-oxo-α-cyperone (22) (Murai et al, 1982), 7α (H), 10β-eudesm-4-en-3-one-11,12-diol (23) (Hikino et al, 1975), rhombitriol (24) (Rukachaisirikul et al, 2005), 7-epi-teucrenone (25) (Fraga et al, 1995), α-rotunol (26) (Hiking et al, 1971), nootkatone (27) (Gliszczyńska et al, 2011), 12-hydroxynootkatone (28) , oxyphyllol C (29) (Morikawa et al, 2002), 5-hydroxylucinone (30) (Chiu et al, 2001), oplopanone (31) (Carvalho et al, 2003), 10-hydroxyamorph-4-en-3-one (32) (Wu et al, 2007), cyperusol D (33) (Xu et al, 2004), 2-hydroxy-14-calamenenone (34) (Morimoto et al, 2009), 1-isopropyl-2, 7 dimethylnaphthalene (35) (Qin ...…”

New Thomimarine E from Marine Isolate of the Fungus Penicillium thomii

“…Guaiadiol was isolated previously from roots of Curcuma zedoaria [16], from rhizomes of the perennial herbaceous plant Cyperus rotundus [17,18], and from branches and leaves of the bush Turraea pubescens [19]. 4,10,11-Trihydroxyguaiane was isolated first from flowers of Achillea clypeolata [20].…”