A New ent-Clerodane Diterpene from the Aerial Parts of Baccharis gaudichaudiana.

Abstract

A new ent-clerodane diterpene, named bacchariol (1) was isolated from the aerial parts of Baccharis gaudichaudiana DC. (Compositae), together with known ent-clerodane diterpenes (2, 3), eight known flavonoids (4-11) and 3,5-dicaffeoylquinic acid (12). Their structures were determined by spectroscopic analyses. Flavonoids (7, 8, 11) and 12 showed moderate scavenging activities toward 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals.

Baccharis (Compositae): a review update

“…From B. gaudichaudiana, new clerodane diterpenoids, gaudichanolides A and B ( Figure 3), and a new ent-clerodane diterpene named bacchariol ( Figure 4) were isolated. 17,18 Guo et al 19 Reports on clerodane diterpene components of other species of the Baccharis genus have also been found in the literature. Two clerodane-type diterpene glycoside esters, together with the known diterpene marrubiagenine, were isolated from the aerial parts of Baccharis sagittalis (Less), 20 while the acetone extract of Baccharis flabellata Hook.…”

On‐Line Activity Screening for Radical Scavengers from Baccharis chilco

“…500 species. To date, more than 100 species of Baccharis have been chemically investigated, and some new natural products have been reported, such as the diterpenoids isolated from B. gaudichaudiana [6] and B. flabellata [18]. Some endemic species occur in the West Indies.…”

Clerodane Diterpenoids and Flavonoids with NGF-Potentiating Activity from the Aerial Parts of Baccharis gaudichaudiana

“…Previous phytochemical investigations on the species resulted in the isolation of labdane-type diterpene glycosides, 1,2) clerodane diterpenes. 3,4) In the course of our search for new natural products with nerve growth factor (NGF)-potentiating activity from medicinal plants, we studied the chemical constituents of methanol extract of the aerial parts of B. gaudichaudiana, which showed moderate NGF-potentiating activity.…”

“…Previous phytochemical investigations on the species resulted in the isolation of labdane-type diterpene glycosides, 1,2) clerodane diterpenes. 3,4) In the course of our search for new natural products with nerve growth factor (NGF)-potentiating activity from medicinal plants, we studied the chemical constituents of methanol extract of the aerial parts of B. gaudichaudiana, which showed moderate NGF-potentiating activity.5) The extract was repeatedly subjected to silica gel column chromatography followed by reversed-phase HPLC on an ODS column to yield a new clerodane diterpene, 15-hydroxy-16-acetoxy-ent-clerod-3-en-18-oic acid (1), three known clerodane diterpenes, 15,16-epoxy-7a,18-dihydroxy-15-methoxy-ent-clerod-3-ene (2), 6) 13,14-dihydro-marrubiagenine (3), 7) gaudichanolide A (4), 4) and three known flavones, 5,7,4Ј-trihydroxyflavone (5), 8) 5,7,3Ј,4Ј-tetrahydroxyflavone (6), 8) 5-methoxy-7,4Ј-dihydroxyflavone (7).8)The known compounds were identified by comparing their spectroscopic data with those reported in the literature. Herein, we report the isolation and structural elucidation of the new clerodane diterpene and the biological activities of the isolated compounds as enhancers of NGF action.…”

“…These assignments were consistent with the configurations of H-10, H 3 -17, H 3 -19, and H 3 -20 of clerodane-type diterpenes reported in the literature. 3,6,9) However, the stereochemistry of C-13 could not be deduced spectroscopically. Thus compound 1 was elucidated as the new clerodane diterpene, 15-hydroxy-16-acetoxy-entcleroda-3-en-18-oic acid.…”