Cytotoxic Germacrane-Type Sesquiterpenes, Pimarane-Type Diterpenes, and a Naphthalene Derivative from Wollastonia biflora

Abstract

Phytochemical investigation of the whole plants of Wollastonia biflora led to the isolation and identification of three new germacrane-type sesquiterpenes (1-3), two new pimarane-type diterpenes (4, 5), and a new naphthalene glycoside (6), along with 11 known compounds. Their structures were characterized on the basis of spectroscopic analyses and chemical methods. Compounds 1, 2, and 3 showed significant cytotoxic activity against the growth of hepatocellular carcinoma BEL-7402 cells in vitro.

Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity

“…This plant is widely spread in South Asia and Oceania and used in folk Chinese medicine for the treatment of rheumatism, bone aches, sore galls, and injuries. 52 46 and 47 appeared to be the 3-O-β-glucosides of darutigenol and kirenol, the first one being the product obtained from enzymatic hydrolysis darutoside, a glucoside isolated from Siegesbechia orientalis, a Madagascan plant. 53 Kirenol is a metabolite of Siegesbechia pubescens Makino, a plant used in Japanese folk medicine.…”

Tedanol: A potent anti-inflammatory ent-pimarane diterpene from the Caribbean Sponge Tedania ignis

“…Derivatization of 0.6 mg of tedanol with Ac 2 O in Py gave the monoacetyl derivative 2, which showed a remarkable downfield shift of H-7 from d 3.02 in the natural compound 1 to d 4.39 in the acetate 2, thus demonstrating that the hydroxyl function is located at position 7. The two bromine atoms present in the molecular formula were located at C-3 (d 69.6) and C-15 (d 61.8), because the chemical shift of these carbon atoms were about 15 ppm lower than those observed in pimaranes oxygenated at these positions, 9 while are close to those observed in a 3,15-dibromoisopimarane from Laurencia perforata. 13 Finally, the sulfate group was located at the remaining position 16, thus completing the planar structure of compound 1.…”

Morinlongosides A–C, Two New Naphthalene Glycoside and a New Iridoid Glycoside from the Roots of <i>Morinda longissima</i>

“…11,13) Furthermore, the strong cross-peaks between anomeric protons at δ H 4.68 (H-1′) and δ C 148.2 (C-1), δ H 4.88 (H-1″) and δ C 148.5 (C-4) in the heteronuclear multiple bond connectivity (HMBC) spectrum suggested that two sugar moieties are located at C-1 and C-4 of the naphthalenyl ring. C-NMR of compound 1 were similar to those of 2-carbomethoxy-3-prenyl-1,4-naphthohydroquinone 1,4-di-O-β-D-glucopyranoside, 14) except for the presence of a methylene hydroxyl group located at C-13 ( Fig.…”