New Limonoids from Hortia oreadica and Unexpected Coumarin from H. superba Using Chromatography over Cleaning Sephadex with Sodium Hypochlorite

Abstract

Abstract:Previous investigations of H. oreadica reported the presence of a wide spectrum of complex limonoids and dihydrocinnamic acids. Our interest in the Rutaceae motivated a reinvestigation of H. oreadica, H. brasiliana and H. superba searching for other secondary metabolites present in substantial amounts for taxonomic analysis. In a continuation of the investigation of the H. oreadica, three new limonoids have now been isolated 9α-hydroxyhortiolide A, 11β-hydroxyhortiolide C and 1(S*)-acetoxy-7(R*)-hydroxy-7-deoxoinchangin. All the isolated compounds from the Hortia species reinforce its position in the Rutaceae. With regard to limonoids the genus produces highly specialized compounds, whose structural variations do not occur in any other member of the Rutaceae, thus, it is evident from limonoid data that Hortia takes an isolated position within the family. In addition, H. superba afforded the unexpected coumarin 5-chloro-8-methoxy-psoralen, which may not be a genuine natural product. Solid-state cross-polarisation/magic-anglespinning 13 C nuclear magnetic resonance, X-Ray fluorescence and Field-emission gun scanning electron microscopy experiments show that the Sephadex LH-20 was modified after treatment with NaOCl, suggesting that when xanthotoxin (8-methoxy-psoralen) was extracted from cleaning of the gel column, chlorination of the aromatic system occurred.

Optimization of ultrasound-assisted extraction of phenolic compounds and flavonoids from Hortia oreadicaleaf

“…Although the presence of alkaloids in species of Rutaceae is expected, this metabolite was not found in the present study. In previous studies with H. oreadica leaf, alkaloids were reported (Severino et al, 2009;Braga et al, 2012;Severino et al, 2014). This divergence may be due to differences in soil composition, seasonality, or individual variations (Gobbo-Neto & Lopes, 2007) since the samples were collected in different regions and at different times of the year.…”

Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids

“…A limonoid named hortiolide D (140) was found in CH 2 Cl 2 and MeOH extracts from the stem of Hortia oreadica [154]. The stem bark of Cedrelopsis gracilis (Ptaeroxylaceae) has yielded pentanortriterpenoid, cedkathryn A (141) [155].…”

“…Thus, 6β-hydroxy-3α,5-cyclo-5α-androstan-17-one (149), and other analogues (150, 151 and 158) were synthesized as steroidal blood pressure-lowering hormones [160,161]. Cyclosteroids (152 and 153), which show an anabolic effect, were synthesized from 19-nor steroids, and would be of great interest for sports medicine as representatives of anabolic steroids [162,163], although other cyclosteroids (154)(155)(156)(157) were synthesized as potential agents with antitumor properties [164][165][166].…”

Chemical composition of essential oils of leaves, flowers and fruits of Hortia oreadica

“…Phytochemical studies of Hortia oreadica led to the identification from dichloromethane extract of taproots: six limonoids , the dihydrocinnamic acid derivatives and three new limonoids (9␣-hydroxyhortiolide A, 11␤-hydroxyhortiolide C and 1(S*)-acetoxy-7(R*)-hydroxy-7-deoxoinchangin) (Severino et al, 2014); and from dichloromethane extract from stems, two limonoids (9,11-dehydro-12␣-hydroxyhortiolide A and 6-hydroxyhortiolide C) . Severino et al (2009) verified antimicrobial activity of the hexane extract of H. oreadica roots and the dictamnine alkaloid isolated of this extract against oral pathogens Enterococcus faecalis (ATCC 4082), Streptococcus salivarius (ATCC 25975), S. mitis (ATCC 49456), S. mutans (ATCC 25275), S. sobrinus (ATCC 33478), S. sanguinis (ATCC 10556) and Lactobacillus casei (ATCC 11578).…”