Monoterpene Lactones from the Seeds of Nephelium lappaceum

Ragasa, Consolacion Y.; Luna, Roderick D. De; Cruz, Wilfredo C.; Rideout, John A.

doi:10.1021/np0580053

Cited by 27 publications

(17 citation statements)

References 7 publications

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“…), and mamoncillo (Melicoccus bijugatus Jacq.). As a multifunctional medicinal plant, the roots show anti-fever effects [2], the bark is an astringent [2], the leaves are used as poultices [2], the pericarp can reduce the mortality of infections caused by herpes simplex virus type 1 [3], and the pulp can be used for the treatment of severe dysentery and type 2 diabetes mellitus [4], although it has been reported that it could cause anaphylaxis [5].…”

Section: Introductionmentioning

confidence: 99%

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A Trypsin Inhibitor from Rambutan Seeds with Antitumor, Anti-HIV-1 Reverse Transcriptase, and Nitric Oxide-Inducing Properties

Fang

2015

Appl Biochem Biotechnol

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Nephelium lappaceum L., commonly known as "rambutan," is a typical tropical tree and is well known for its juicy and sweet fruit which has an exotic flavor. Chemical studies on rambutan have led to the identification of various components such as monoterpene lactones and volatile compounds. Here, a 22.5-kDa trypsin inhibitor (N . lappaceum trypsin inhibitor (NLTI)) was isolated from fresh rambutan seeds using liquid chromatographical techniques. NLTI reduced the proteolytic activities of both trypsin and α-chymotrypsin. Dithiothreitol reduced the trypsin inhibitory activity of NLTI at a concentration of 1 mM, indicating that an intact disulfide bond is essential to the activity. NLTI inhibited HIV-1 reverse transcriptase with an IC50 of 0.73 μM. In addition, NLTI manifested a time- and dose-dependent inhibitory effect on growth in many tumor cells. NLTI is one of the few trypsin inhibitors with nitric oxide-inducing activity and may find application in tumor therapy.

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Section: Introductionmentioning

confidence: 99%

“…A limited number of studies have been performed on bioactivity of the seeds [2]. For example, the insecticidal activity of the rambutan seeds was associated with type II cyanolipid components [6].…”

Section: Introductionmentioning

confidence: 99%

A Trypsin Inhibitor from Rambutan Seeds with Antitumor, Anti-HIV-1 Reverse Transcriptase, and Nitric Oxide-Inducing Properties

Fang

2015

Appl Biochem Biotechnol

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“…Native to Southeast Asia, rambutan is cultivated for its fruit and sold commercially [1,2]. It is consumed fresh, canned, or processed, and appreciated for its refreshing flavor and exotic appearance [3].…”

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“…It is consumed fresh, canned, or processed, and appreciated for its refreshing flavor and exotic appearance [3]. The seeds are bitter and narcotic, with the roots used for treating fevers, the leaves as poultices, and the bark as an astringent [2]. The rind of rambutan, which is normally discarded, was found to contain extremely high antioxidant and antibacterial activities, and several potential antioxidant activities, including reducing power, E-carotene bleaching, linoleic peroxidation, and free radical scavenging activity, were also exhibited [4,5].…”

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A new hederagenin glycoside from Nephelium lappaceum

Liang

Jiang

et al. 2012

Chem Nat Compd

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“…aurantiacus that differed primarily by the presence of sterol acetates. Cholesterol acetate was isolated previously from green algae [14] and mutant yeast cells [15]; sitosterol acetate (24R-ethylcholest-5-en-3E-ol), from higher plants [16][17][18]. The remaining components found in the sterolacetate fractions should probably be considered to be new natural compounds.…”

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confidence: 99%

Metabolites of the marine sponge Suberites cf. aurantiacus

et al. 2010

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Fractions of free sterols and sterol esters were observed in the ethylacetate extract of the marine sponge Suberites cf. aurantiacus and their compositions were determined. It was found that cholesterol was the predominant component in all sterol forms. The esters had a high content of unsaturated long-chain fatty acids (C 24 -C 26 ). Sterol acetates have not been previously observed in marine invertebrates.Sponges of the genus Suberites contain various hemolytic toxins, proteins, suberitane sesterterpenes, and other natural compounds [1][2][3][4][5][6]. However, the lipid composition of these sponges is poorly studied. At present sterols and fatty acids of several Suberites species have been studied [7][8][9][10][11][12][13]. Herein we report results from a study of the principal sterol and fatty-acid components from the EtOAc extract of the Caribbean sponge Suberites cf. aurantiacus.The same set of secondary metabolites was observed during preliminary comparison by TLC of the EtOH and EtOAc extracts of S. cf. aurantiacus. Both extracts showed three spots with R f 0.48, 0.88, and 0.95 (hexane:EtOAc, 3:1). Further studies used the EtOAc extract because it contained greater amounts of these metabolites. It was separated by normal column chromatography over silica gel. The resulting fractions were homogeneous according to TLC. PMR analysis revealed complicated mixtures of ' 5 sterols (characteristic resonances at G 0.68, s, CH 3 -18 and 1.]. The sterol compositions of these fractions were analyzed further using GC and GC-MS of the sterol acetates. Fatty acids were identified by these same methods using the corresponding methyl esters and pyrrolidide derivatives.The extract of S. cf. aurantiacus contained mainly ' 5 sterols and their derivatives. Fractions of sterols, sterylacetates, and sterol esters of fatty acids had compositions similar to that of the sterols (Table 1). The predominant component in all sterol compounds was cholesterol (cholest-5-en-3E-ol, 42.4-44.6%). Cholestanol (5D-cholestan-3E-ol) occurred in the fractions in insignificant (1.0-2.5%) amounts. Cholestanol was observed as the predominant component in sterol fractions of previously studied sponges S. domuncula [7,8], S. japonicus [9], and the Mediterrean S. carnosus [10]. However, S. carnosus collected in the Indian Ocean [11] contained ergosterol derivatives. The sponge S. vestigium produced ' 5 sterols, similar to the sponge studied by us, in addition to ' 7 steroidal alcohols, in contrast with it [12]. At least 30 fatty-acid sterol esters were found in S. cf. aurantiacus: 1) Pacific Institute of Bioorganic Chemistry, FEB RAS, 690022, Vladivostok, Russia, fax 7 (4232) 31 40 50, Fatty acid % Fatty acid % Fatty acid % 14:0 4,8,12-Me 3 -13:0 15:0 16:1' 9 16:0 i-17:0 (15-Me-16:0) 17:0 18:1 ' 9 18:1 ' 11 18:0 1.0 2.4 0.2 0.1 3.8 0.2 0.8 0.2 2.0 1.1

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Monoterpene Lactones from the Seeds of Nephelium lappaceum

Cited by 27 publications

References 7 publications

A Trypsin Inhibitor from Rambutan Seeds with Antitumor, Anti-HIV-1 Reverse Transcriptase, and Nitric Oxide-Inducing Properties

A Trypsin Inhibitor from Rambutan Seeds with Antitumor, Anti-HIV-1 Reverse Transcriptase, and Nitric Oxide-Inducing Properties

A new hederagenin glycoside from Nephelium lappaceum

Metabolites of the marine sponge Suberites cf. aurantiacus

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