Triterpenoids isolated from Machaerium incorruptibile

Alves, Herbert M.; Arndt, Victor Heinrich; Ollis, W. D.; Eyton, W.B.; Gottlieb, Otto R.; Magalhães, Mauro Taveira

doi:10.1016/s0031-9422(00)86130-0

Cited by 28 publications

(15 citation statements)

References 13 publications

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“…The crude extract was submitted to CC (silica gel, gradient CHCl 3 /MeOH). The fraction (13 g) eluted with CHCl 3 /MeOH 98 : 2 was further purified by CC (silica gel; petroleum ether/ (6), CH 2 (4) HÀC (6) 76.9(CH ) 4.18 (dd, J 8.0, 3.5) CH 2 (5) CH 2 (4), Me(10) C (7) 169.5(C ) CH 2 (5) CH 2 (8) 42.3(CH 2 ) 3.12 (m) Me(9) Me (9) 12.0( Me) 1 (7), 438 (7) Methanolysis of 1. Compound 1 (7 mg) was refluxed with 0.9m HCl (2 ml) in 80% aq.…”

Section: Experimental Partmentioning

confidence: 99%

Neoengleromycin, a Novel Compound from Engleromyces goetzii

Liu

Tan

Dong

et al. 2002

HCA

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A novel N-containing compound, neoengleromycin (1) was isolated from the fruiting bodies of the ascomycete Engleromyces goetzii together with two known cytochalasins: cytochalasin D (2) and 19,20-epoxycytochalasin D (3). Structures were established by spectroscopic (including 2D-NMR) and chemical means. Neoengleromycin (1) possesses the rare structure of an N-substituted hydroxamic acid and represents a new type of natural products.Introduction. ± The fungus Engleromyces goetzii belongs to the Hypocreaceae and grows on the bamboo of high mountains. It has been used as a folk remedy against infection and cancer diseases in the area around Tibet of China including Yunnan and Sichuan Provinces [1]. Little attention has been paid to the chemical constituents of this inedible fungus. As one part of our search for bioactive metabolites of the higher fungi in Yunnan Province [2 ± 7], the chemical constituents of E. goetzii collected at Lijiang of Yunnan were investigated. One new compound named neoengleromycin (1) was isolated from the fungus E. goetzii, together with two known cytochalasins, cytochalasin D (2) and 19,20-epoxycytochalasin D (3). This report deals with the characterization and structure elucidation of these three compounds.

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Section: Experimental Partmentioning

confidence: 99%

Neoengleromycin, a Novel Compound from Engleromyces goetzii

Liu

Tan

Dong

et al. 2002

HCA

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“…Machaerium is one of the largest tropical arboreal genera of Papilionoideae, with approximately 160 known taxa and popularly known as "jacarandás" (Plant, 2020;Bastos, 1987;Polido and Sartori, 2011). According to the literature, this genus is recognized by the occurrence of different class of natural products such as triterpenes, proanthocyanidins, cinnamylphenols, alkaloids, benzoquinones, steroids and the incisive presence of flavonoids (Ignoato et al, 2013;Kurosawa et al, 1978a, b;Ollis et al, 1978Ollis et al, , 1968Alves et al, 1966;Bento et al, 2018;Gregson et al, 1968;elSohly et al, 1999;Seo et al, 2001;Adrian et al, 2007;Santos et al, 2009;Oliveira et al, 1968;Braga et al, 1968). Based on previous studies involving the allelopathic activity of isovitexin and Machaerium eriocarpum leaf extract, associated with the absence of phytochemical studies of branch extract of this species, in this work the triterpene lupeol was isolated and its quantification was performed by HPLC-APCI-MS/MS and their allelopathic action.…”

Section: Introductionmentioning

confidence: 99%

The lupeol content in Machaerium species by HPLC-APCI-MS/MS and the allelopathic action

Tahira¹,

Tino²,

Bento³

et al. 2021

J. Hortic. For.

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The use of extracts from plants and/or allelopathic compounds from natural products can minimize the use of pesticides in agriculture. This is a chemical study of Machaerium eriocarpum branch extract and the evaluation of the allelopathic potential of Machaerium hirtum (Vell.) Stellfed and M. eriocarpum Benth (Fabaceae) leaves and branches extracts. The triterpene lupeol was isolated from the hydroethanolic extract of M. eriocarpum branches. The quantification of this compound in all extracts was performed by HPLC-APCI-MS/MS and the highest amount of lupeol was observed in the leaves extract of M. eriocarpum. Allelopathy tests were carried out against seeds of Sorghum bicolor L. (sorghum), evaluating the final percentage of germination, germination speed index (GSI), root growth and number of lateral roots. The leaves extracts of both species were effective in the inhibition of the root growth as well as of the lateral roots. The branches extract of M. hirtum showed inhibitory effect in the root growth and lateral roots only in 50 and 100 mg.L -1 doses. The lupeol showed mainly a strong inhibition of seed germination, root growth and lateral root appearance at 100 μM. This study showed the potentiality of Machaerium extracts and lupeol as bioherbicides.

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“…5' since 1921. These natural products are found in basil, coriander, lemon peels and other various essential oils, such as Aniba rosaedorata Ducke, 1 Cryptocaria aschersoniana Mez., 2 Lilium makinoi Bokz. or L. auratum Lindl.…”

Section: Introductionmentioning

confidence: 99%