The structure of handelin — A new diguaianolide fromHandelia trichophylla

Natural disesquiterpenoids

“…The dimeric guaianolide handelin (which also has the trivial names yejuhua lactone and chrysanthelide) was isolated from Handelia trichophylla. 74 On the basis of spectroscopic and chemical characteristics, structure 74 was proposed, 75,76 and this was confirmed by X-ray analyses. 77 The metabolite was also found in Chrysanthemum indicum and C. boreale.…”

Disesquiterpenoid and Sesquiterpenes from the Flos of <i>Chrysanthemum indicum</i>

“…Mass spectra were obtained on a MS Agilent 1100 Series LC/ MSD Trap mass spectrometer (ESI-MS) and an Agilent 6520B Q-TOF spectrometer (HR-ESI-MS), respectively. NMR spectra were recorded on a Bruker AVANCE-III NMR instrument ( 1 H: 500 MHz, 13 C: 125 MHz) with tetramethylsilane (TMS) as internal standard. Silica gel (200-300 mesh, Qingdao Haiyang Chemical Co., Ltd., China), and RP-C 18 (40-63 µm, FuJi, Japan) were used for column chromatography (CC).…”

“…), carbonyl (1754, 1740, 1706 cm A detailed analysis of the 13 C-NMR spectrum of 1 with the help of 1 H-detected heteronuclear single-quantum coherence spectrum (HSQC) techinque revealed the presence of four methyls, seven methylenes (two olefinic), eleven methines (four oxygenated, two olefinic), and ten quaternary carbons (two oxygenated, two olefinic, three ester carbonyl). Deducting the acetyl group, the remaining thirty carbons and the appearance of the NMR signals (Table 1) in pairs suggested 1 to be a sesquiterpene dimer similar to yejuhua lactone, a dimeric guaiane sesquiterpene.…”

“…3) was obtained and analyzed on an X-ray diffractometer with a mirror CuKα (λ= 1.54184 Å) radiation (ω scans, 2θ max =71.94). By anomalous dispersion methods with Flack= 0.02 (14), 15) the absolute configuration of 1 was determined to be 1R, 3R, 5R, 6R, 7R, 8S, 10R, 11R, 1′R, 4′R, 5′S, 6′R, 7′S, and 10′R.…”

Monomeric and Dimeric Cytotoxic Guaianolide-Type Sesquiterpenoids from the Aerial Parts of Chrysanthemum indicum

“…Considering the reported structural type from C. indicum , compound 1 is most likely a guaianolide-type sesquiterpenoid dimer. Analysis of the 1D and 2D NMR spectra showed that compound 1 has the same 2D structure as deacetylhandelin, isolated from Handelia trichophylla . The NOESY correlations of H-7/H-5, H-5/H-1, H-6/H-8, H-8/H 2 -13, H 3 -15′/H-6′, and H-5′/H-7′ suggest that H-1, H-5, H-7, H-5′, and H-7′ could be assigned as α-oriented and H-6, H-8, H 2 -13, H-6′, and H 3 -15′ as β-oriented.…”