Mono- and Di-sesquiterpenoids from Chloranthus spicatus

Abstract

Three new dimeric sesquiterpenoids, chloramultilides B-D ( 1- 3), along with 10 known sesquiterpenoids, were isolated from the whole plant of Chloranthus spicatus. Their structures were established by physical data (1D and 2D NMR, MS). The structure and absolute configuration of 1 was confirmed by X-ray crystallography. Compound 1 exhibited moderate in vitro antifungal activity.

Chemotaxonomic significance of sesquiterpenes and amide derivatives from Chloranthus angustifolius Oliv.

“…chloramultilide C) (6) (Li et al, 2008;Xu et al, 2007), shizukaol B (7) (Kawabata and Mizutani, 1992), N-p-trans-coumaroyltyramine (8) (Treeratanapiboon et al, 2011), N-p-trans-feruloyltyramine (9) (Fukuda et al, 1983), cannabisin G (10) (Sakakibara et al, 1995), thoreliamide A (11) (Ge et al, 2008), cannabisin F (12) (Sakakibara et al, 1995), aurantiamide acetate (13) (Banerji and Ray, 1981) (Fig. 1), by comparison of the spectral data ( 1 H NMR, 13 C NMR and ESI-MS data) with those reported in the literature.…”

Sesquiterpenes and Dimers Thereof from Chloranthus fortunei

“…Four of them were new compounds, including one new sesquiterpene dimer, i.e., shizukaol P (1), one new dimeric sesquiterpene glycoside, i.e., 9-O-b-glucopyranosylcycloshizukaol A (2), and two new sesquiterpenes, i.e., shizukanolides G and H (3 and 4, resp.). The other eight known compounds were identified as shizukaol F (5) [18], yinxiancaol (6) [14], chloramultilide B (7) [22], cycloshizukaol A (8) [17], chloranthalactone C (9) [4][9], shizukanolide C (10) [4], shizukanolide F (11) [7], and chloranoside A (12) [10]. Their structures and relative configurations were elucidated on the basis of their spectroscopic data and by comparing with the related compounds reported in the literature.…”

“…Comparison of the NMR and MS data with literature values showed that the known compounds were shizukaol F (5) [18], yinxiancaol (6) [14], chloramultilide B (7) [22], cycloshizukaol A (8) [17], chloranthalactone C (9) [4] [9], shizukanolide C (10) [4], shizukanolide F (11) [7], and chloranoside A (12) Extraction and Isolation. The aerial part of C. fortunei (2 kg) was extracted with 95% EtOH at r.t.…”

Terpenoids from Chloranthus elatior

“…Recent phytochemical investigation on this species reported 18 compounds including nine sesquiterpenoids and four diterpenoids. 8 In the course of our group searching for new sesquiterpenoids from Chloranthus species, two new eudesmane-type sesquiterpenoid lactones, named chlorelactone A (1) and chlorelactone B (2), and one new labdane-type diterpenoid, named elatiorlabdane (3), along with seven known sesquiterpenoids, spathulenol (4), 14 4α-hydroxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide (5), 6 4α-hydroxy-5α,8α(H)-eudesm-7(11)-en-8,12-olide (6), 6 neolitacumone B (7), 15 chlorantholide D (8), 8 4α,8β-dihydroxy-5α(H)-eudesm-7(11)-en-8,12-olide (9), 6 chloranthalic acid (10), 16 and one disesquiterpenoid, chloramultilide C (11) 17 were isolated from the whole plants of C. elatior. Herein, we report the isolation and structural elucidation of these compounds.…”