Three eudesmane sesquiterpene lactones, namely artemivestinolides A-C (1-3), along with three known 11-epimeric lactones (4-6), were isolated from the aerial parts ofArtemisia vestim. Their structures were elucidated on the basis of extensive spectroscopic analyses (IR, HR-ESIMS, 1D NMR and 2D NMR), and the absolute configurations were determined by single-crystal X-ray diffraction (with copper radiation). Furthermore, in an in vitro assay, the three new compounds exhibited a moderate inhibition of the lipopolysaccharide (LPS)-induced nitric: oxide (NO) production in BV-2 microglial cells.
Shuai-Hua TianXing-Yun ChaiKe ZanKe-Wu ZengPeng-Fei Tu
Chemical constituents of the leaves of Artemisia argyi were investigated. By using a variety of chromatographic techniques and spectroscopic methods, six compounds were isolated and identified as follows: clemaphenol A (1), aurantiamide acetate (2), camelliagenin A (3), japonica acid (4), labd-13(E)-ene-8α,15-diol (5), and 313-acetoxy-20-oxo-21-nordammaran-23-oic acid (6). Among these products, compounds 1 and 3-6 were obtained from the genus Artemisia for the first time and compound 2 was firstly reported from the species. Additionally, compound 5 displayed an inhibitory effect against the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglial cells with an IC50 value of 6.68 μM.
A chemical investigation of the aerial parts ofArtemisia vestita Wall. led to the isolation of 12 known sesquiterpenes, including 2 furan-containing sesquiterpenoids and 10 eudesmane sesquiterpene lactones. Their structures were identified as negunfurol (1), schensianol A (2), artemine (3), erivanin (4), 1,5-diepi-artemin (5), acetylartemin (6), naphtho[1,2-b]furan-2(3H)-one, 6-(acetyloxy) decahydro-9a-hydroxy-3,Sa-dimethyl-9-methylene-(3S,3aS,5aS,6S,9aS, ghS) (7), naphtho[1,2-b]furan-2(3H)-one, 6-(acetyloxy)- 3a,4,5,5a,6,7,8,9b-octahydro-8-hydroxy-3,Sa,9-trimethyl- (3S,3aS, SaR,6S, SS,9bS) (8), isoerivanin (9), harrelierin (10), (11S)-1- oxoeudesm-4(14)-eno-13,6a-lactone (11), 1-epi-dehydroisoeranin (12), respectively. All of these compounds were isolated from Artemisia vestita for the first time, and compounds 1 and 2 were isolated from the genus Artemisia for the first time.
Nine lignans were isolated and purified by silica gel, ODS, Sephadex LH-20 column chromatographies, preparative HPLC and recrystallization from the aerial parts ofArtemisia absinthium L., and identified as follows: diayangambin (1), sesartemin (2), epiyangambin (3), (+)arborone (4), (-)syringaresinol (5), epiashchantin (6), caruilignan C (7), 7β-caruilignan C (8), yangambin (9). Compounds 4, 5, 7, 8 were isolated from this plant for the first time.
Fourteen known compounds were isolated from the aerial parts of Artemisia anomala and identified as follows: zhepiresinol (1), (-)-lariciresinol (2), ficusal (3), medioresinol (4), (+)-syringaresinol (5), 1β,2β-epoxy-3β,4α,10α-trihydroxyguaian- 6α,12-olide (6), 5β,10α-dihydroxy-1α/-dehydroleucodin (7), 3α-chloro-8α-acetoxy-4β,10α-dihydroxy-1β,2β-epoxy-5α,7αHguai- 11 (13)-en- 12,6α-olide (8), 13-O-desacetyleudesma-afraglaucolide (9), 1,10-seco-4ξ-hydroxy-muurol-5-ene- 1,10-diketone (10), 1α-hydroxyafraglaucolide(11), aurantiamide (12), indole-3-aldehyde (13), loliolide (14). All these compounds were isolated from this plant for the first time and compounds 1-4, 8, 10, 13 were obtained from genus Artemisia for the first time.