Constituents of Alphitonia Species. III. Alphitexolide, a New Triterpene, and Other Extractives

Abstract

The extractives of the barks and leaves of Alphitonia excelsa, A. petriei, and A. whitei, and of the wood, bark, and leaves of A. macrocarpa have been examined. Ceanothic, betulinic, and alphitolic acids were isolated from all species, but A. macrocarpa was exceptional in that its wood contained no benzylhydroxycoumarone derivative, characteristic of the other species, and its leaves gave a small yield of the alkaloid, adouetine X. From the bark of A. excelsa a new triterpene, alphitexolide, was isolated in very small amount. By spectroscopic methods and a partial synthesis its structure was established as(1).

Triterpenoids from the leaves of Alphitonia xerocarpus Baill and their biological activity

“…This genus is composed of approximately 20 species growing in tropical regions of Southeast Asia, Oceania and Polynesia (Correa et al, 2010, Richardson et al, 2000. A range of phenolic compounds has already been identified from various Alphitonia species (Branch et al, 1972, Guise et al, 1962, Jou et al, 2004. More precisely, flavonoids have been identified in the leaves (Lin et al, 1995) and fruit (Muhammad et al, 2015) of A. neocaledonica.…”

Anti-Inflammatory Chemical Profiling of the Australian Rainforest Tree Alphitonia petriei (Rhamnaceae)

“…The cell line was maintained in 5% CO 2 at 37 °C, with media being replaced every 3–4 days. Once cells had grown to confluence in the culture flask, they were removed using a rubber policeman, as opposed to using trypsin, which can remove membrane-bound receptors [16]. The cell suspension was concentrated by centrifugation for 3 min at 900 rpm and re-suspended in a small volume of fresh DMEM (with 1% antibiotics and 5% FBS); cell densities were estimated using a Neubauer counting chamber.…”

“…Alphitonia petriei (Braid and C.T.White (family RHAMNACEAE)) is a common rainforest tree in eastern Australia occurring from northern New South Wales to the Torres Strait Islands in Queensland. Previous phytochemical studies of this genus have yielded ceanothic, betulinic, and alphitolic acids, and the novel triterpene, aphitexolide from the bark of A. excelsa [16]. More recently, the chloroform extract of the bark of Alphitonia petriei (collected from Paluma Range in north Queensland) led to the discovery of 2-ketobetulinic acid and betulinic acid, both of which showed antibacterial activity against Bacillus subtilis [17].…”

Isolation of Flavonoids and Triterpenoids from the Fruits of Alphitonia Neocaledonica and Evaluation of their Anti‐oxidant, Anti‐tyrosinase and Cytotoxic Activities

“…More precisely, three isorhamnetin‐derived flavonoids have been identified in the leaves of A. neocaledonica (Lin et al ., ). Pentacyclic triterpenoids, including ceanothic acid, betulin, betulinic acid, alphitolic acid with in vitro cytotoxicity, anti‐inflammatory and anti‐microbial activities (Dzubak et al ., ), have also been detected in several Alphitonia species (Branch et al ., ; Jou et al ., ; Setzer et al ., ).…”

“…A range of phenolic compounds has previously been identified in various Alphitonia species (Guise et al ., ; Branch et al ., ; Jou et al ., ). More precisely, three isorhamnetin‐derived flavonoids have been identified in the leaves of A. neocaledonica (Lin et al ., ).…”