Antifungal Clerodane Diterpenes from Macaranga monandra (L) Muell. et Arg. (Euphorbiaceae)

Abstract

Hexane and ethyl acetate phases of the methanol extract of Macaranga monandra showed fungal growth inhibition of Colletotrichum acutatum, C. fragariae and C. gloeosporioides, Fusarium oxysporum, Botrytis cinerea, Phomopsis obscurans, and P. viticola. Bioassay-guided fractionation led to the isolation of two active clerodane-type diterpenes that were elucidated by spectroscopic methods (1D-, 2D-NMR, and MS) as kolavenic acid and 2-oxo-kolavenic acid. A 96-well microbioassay revealed that kolavenic acid and 2-oxo-kolavenic acid produced moderate growth inhibition in Phomopsis viticola and Botrytis cinerea.

Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest,1

“…The NMR spectra of 1 corresponded closely with those of vedelianin (6) 22 and schweinfurthin B (12). 20 In particular, the observation of a "quartet" with J = 3.5 Hz for H-3 was in complete agreement with the "quartet" observed for H-3 of schweinfurthin B with J = 3.…”

Phytochemistry and pharmacology of the genus Macaranga: A review

“…Investigation of the Cameroonian plant, M. monandra for possible antifungal compounds was undertaken by Salah et al (2003). Bioassay-guided fractionation of the hexane and ethyl acetate fractions of the methanol extract led to the isolation of two active clerodane-type diterpenes (146 and 147).…”

“…Bioassay-guided fractionation of the hexane and ethyl acetate fractions of the methanol extract led to the isolation of two active clerodane-type diterpenes (146 and 147). A 96-well microbioassay revealed that kolavenic acid (146) and 2-oxo-kolavenic acid (147) produced moderate growth inhibition in Phomopsis viticola and Botrytis cinerea (Salah et al, 2003). Compound 146 was slightly more active against P. viticola and showed 50% growth inhibition at 30 µM, whereas 147 showed 46% growth inhibition.…”

“…A phytochemical review of literatures indicates the genus Macaranga to be a rich source of the isoprenylated, geranylated and farnesylated flavonoids (Schutz et al, 1995;Jang et al, 2002;Phormmart et al, 2005;Kawakami et al, 2008;Thanh et al, 2012) and stilbenes (Beutler et al, 1998;Yoder et al, 2007;Thanh et al, 2012). Furthermore, more classes of secondary metabolites like terpenes (Salah et al, 2003;Jang et al, 2004;Phormmart et al, 2005;Kawakami et al, 2008), tannins (Lin et al, 1990;Gunawan-Puteri and Kawabata, 2010;Ngoumfo et al, 2008), coumarins (Sutthivaiyakit et al, 2002;Darmawan et al, 2012) and other types of compounds (Ramaiah et al, 1979;Ngoumfo et al, 2008;Matsunami et al, 2009;Zakaria et al, 2010) are known to be isolated from different species of the genus Macaranga. Flavonoids and stilbenes are regarded as the major constituents and are most likely responsible for most of the activities found in the plants of this genus.…”

“…An increasing number of phytochemical studies are being carried out on plants belonging to the genus Macaranga due to their various traditional uses. Thus, the isolated natural products from this genus have been reported to display interesting biological activities including antitumor (Kaaden et al, 2001;Yoder et al, 2007;Zakaria et al, 2012), antioxidant (Sutthivaiyakit et al, 2002;Phormmart et al, 2005;Matsunami et al, 2009), antimicrobial (Salah et al, 2003;Lim et al, 2009) and anti-inflammatory (Jang, et al, 2002). This is a resourceful area of research as many species of Macaranga are used in traditional medicine as well as exhibits various pharmacological properties while their chemistry indicates varied chemical structures.…”