Chaparrinone

Evaluating the in Vitro Efficacy of Quassinoids from Eurycoma longifolia and Eurycoma harmandiana against Common Cold Human Coronavirus OC43 and SARS-CoV-2 Using In-Cell Enzyme-Linked Immunosorbent Assay.[Pubmed:36399766]

J Nat Prod. 2022 Dec 23;85(12):2779-2788.

Coronavirus disease-2019 (COVID-19), caused by severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) infection, has become a pandemic and public health crisis. SARS-CoV-2 and the seasonal common cold coronavirus (HCoV-OC43) belong to the beta genus of human coronaviruses (HCoVs). In-cell ELISA assays were performed using HCoV-OC43 and SARS-CoV-2 and evaluated the antiviral activity of herbal plants. Eurycoma longifolia (EL) and Eurycoma harmandiana (EH) roots (antipyretic properties) and their constituent quassinoids, especially Chaparrinone and eurycomalactone, showed potent anti-HCoV-OC43 and SARS-CoV-2 activities, and the low IC(50) values of the mentioned constituents were observed in the range of 0.32-0.51 muM. Eurycomanone and 13beta,21-dihydroeurycomanone may contribute to the antiviral activity of EL, whereas Chaparrinone is the major and active antiviral constituent of EH root. The content of quassinoids, beta-carboline, and canthin-6-one alkaloids and the cytotoxicity profile of EL and EH extracts were varied regarding extraction solvents. The boiled water and 50% EtOH extractions of both plants were less toxic than those with 95% EtOH as the extraction solvent. Our research suggests that quassinoids, which come from EL and EH roots and are anti-coronavirus compounds, are potential treatment candidates for COVID-19 and merit further in vivo investigations.

HPLC-UV-Based Simultaneous Determination of Canthin-6-One Alkaloids, Quassinoids, and Scopoletin: The Active Ingredients in Eurycoma Longifolia Jack and Eurycoma Harmandiana Pierre, and Their Anti-Inflammatory Activities.[Pubmed:33064798]

J AOAC Int. 2021 Jun 12;104(3):802-810.

BACKGROUND: Quassinoids and canthin-6-one alkaloids are bioactive markers of Eurycoma longifolia (EL) and E. harmandiana (EH) and have been commercially utilized to treat inflammation and male infertility. OBJECTIVES: This study aims to reveal the contents of bioactive compounds and compare anti-inflammatory activities of these two species. METHODS: HPLC methods coupled with UV-Vis detection were developed and validated for the simultaneous analysis of the chemical profiles and their contents in EL and EH. The anti-inflammatory activities of both species were investigated using RAW 264.7 cell line. RESULTS: The HPLC methods provided a sensitivity (LOD) of 0.02-0.05 microg/mL for the eight bioactive compounds (canthin-6-one alkaloids, quassinoids, and scopoletin) with high precision (% relative standard deviation (RSD) Chaparrinone: eurycomanone ratio was high in EH, whereas EL had a higher ratio of eurycomanone: Chaparrinone than EH. The contents of total canthin-6-one alkaloids, quassinoids, and scopoletin were 0.01-0.75, 0.19-1.54, and 0.01-0.28 mg/g, respectively, in EL roots and 0.12-1.80, 7.05-9.26, and 0.02 mg/g, respectively, in EH roots. The anti-inflammatory effects of EL and EH extracts varied among the samples due to the variation in their chemical constituents. CONCLUSIONS: In summary, our study indicated that Chaparrinone was the major compound in EH. EH exhibited anti-inflammatory activity to the same extent as EL. HIGHLIGHTS: EH and EL extracts were analyzed using developed HPLC-UV methods, revealing a high concentration of Chaparrinone in EH, and an anti-inflammatory assay indicated that EH had a potency comparable to that of EL.

Anti-Tobacco Mosaic Virus Quassinoids from Ailanthus altissima (Mill.) Swingle.[Pubmed:29953225]

J Agric Food Chem. 2018 Jul 18;66(28):7347-7357.

Quassinoids are bitter constituents characteristic of the family Simaroubaceae. A total of 18 C(20) quassinoids, including nine new quassinoid glycosides, named chuglycosides A-I (1-6 and 8-10), were identified from the samara of Ailanthus altissima (Mill.) Swingle. All of the quassinoids showed potent anti-tobacco mosaic virus (TMV) activity. A preliminary structure-anti-TMV activity relationship of quassinoids was discussed. The effects of three quassinoids, including Chaparrinone (12), glaucarubinone (15), and ailanthone (16), on the accumulation of TMV coat protein (CP) were studied by western blot analysis. Ailanthone (16) was further investigated for its influence on TMV spread in the Nicotiana benthamiana plant.

Cymosanine, a novel C19-quassinoid from Simaba subcymosa.[Pubmed:15715259]

Nat Prod Res. 2005 Feb;19(2):151-5.

Cymosanine (1) and three further known quassinoids, cedronin (2), Chaparrinone (3), and simarolide (4), were isolated from the root bark of Simaba subcymosa. The structures were established by spectroscopic data, mainly 1D, 2D NMR and mass spectra.

Synthetic Studies on Quassinoids: Total Synthesis and Biological Evaluation of (+)-Des-D-chaparrinone.[Pubmed:11672197]

J Org Chem. 1998 Aug 21;63(17):5929-5936.

A total synthesis of des-D-Chaparrinone (2), which lacks the ring D delta-lactone of (-)-Chaparrinone (1) has been developed. The synthesis commences with the known, readily available tricyclic ketone 3 (R = Me). Elaboration of the configuration at C(5) followed by resolution of 6 employing 2(R),3(R)-2,3-butanediol gave rise to 9. Installation of the ring C functionality provided 15 which was transformed into tricyclic diketone 25. Introduction of the ring A functional groups afforded 29, which upon exposure to aluminum trichloride and sodium iodide gave rise directly to (+)-des-D-Chaparrinone (2). Biological studies revealed that (+)-2 was devoid of any solid tumor activity.

Quassinoids from Eurycoma harmandiana.[Pubmed:11454344]

Phytochemistry. 2001 Aug;57(8):1205-8.

Three quassinoids, iandonosides A and B and iandonone, were isolated from the root of Eurycoma harmandiana, along with five known quassinoids, casteloside B, 13 beta, 21-dihydroeurycomanone, Chaparrinone, glaucarubolone and ailanquassin B as well as the coumarin, scopoletin. The structural elucidations were based on analyses of spectroscopic data.

Cytotoxic quassinoids from Simaba cedron.[Pubmed:9644063]

J Nat Prod. 1998 Jun 26;61(6):776-80.

Four new quassinoids, cedronolactones A-D (1-4), together with nine known compounds, simalikalactone D (5), Chaparrinone (6), chaparrin (7), glaucarubolone (8), glaucarubol (9), samaderine Z (10), guanepolide (11), ailanquassin A (12), and polyandrol (13), were isolated from the wood of Simaba cedron. The chemical structures of 1-4 were elucidated on the basis of their chemical and spectral properties. Cedronolactone A (1) was shown to exhibit a significant in vitro cytotoxicity (IC50 0.0074 microg/mL) against P-388 cells.

Antimalarial and cytotoxic potential of four quassinoids from Hannoa chlorantha and Hannoa klaineana, and their structure-activity relationships.[Pubmed:9602388]

Int J Parasitol. 1998 Apr;28(4):635-40.

Hannoa chlorantha and Hannoa klaineana (Simaroubaceae) are used in traditional medicine of Central African countries against fevers and malaria. Four stem bark extracts from H. klaineana and four quassinoids from H. chlorantha were examined in vitro against Plasmodium falciparum NF 54. The extracts displayed good activities, while the quassinoids were highly active, with IC50 values well below 1 microgram ml-1, those of Chaparrinone and 15-desacetylundulatone being much lower than 0.1 microgram ml-1 (0.037 and 0.047 microgram ml-1, respectively). Chaparrinone is five times more active than 14-hydroxyChaparrinone against P. falciparum, indicating that the hydroxyl function at C-14 is unfavourable for antiplasmodial activity. As 14-hydroxyChaparrinone has a seven-times higher cytotoxic activity against P-388 cells than Chaparrinone, the latter compound has the better antiplasmodial therapeutic index. All four quassinoids were evaluated in vivo in a standard 4-day test as well. 15-Desacetylundulatone was proven to be the most active compound, almost totally suppressing the parasitaemias of OF1 mice for at least 7 days, while both Chaparrinone and 14-hydroxyChaparrinone were active for at least 4 days. Quassinoids have ED50 values much lower than 50 mg kg-1 body weight day-1 and none of them caused obvious side effects. The keto function at C-2 in 15-desacetylundulatone is apparently of crucial importance for its high activity. 6-alpha-Tigloyloxyglaucarubol was not active at all. Chaparrinone is considered the most interesting of the investigated quassinoids and its in-vivo antimalarial potential will be examined further.

A new quassinoid from Castela texana.[Pubmed:8984156]

J Nat Prod. 1996 Jan;59(1):73-6.

A new quassinoid, 11-O-trans-p-coumaroyl amarolide (1) was isolated from Castela texana, and the structure was elucidated by spectroscopic analysis. Compound 1 is the first coumaroyl quassinoid derivative to have been isolated from nature. The known compounds amarolide (2), Chaparrinone, chaparrin, glaucarubolone, holacanthone, and 15-O-beta-D-glucopyranosyl glaucarubol were also isolated. All isolated compounds were tested for their cytotoxicity and antiprotozoal activities.

Quantification of insect growth and its use in screening of naturally occurring insect control agents.[Pubmed:24249129]

J Chem Ecol. 1993 Jun;19(6):1109-18.

In studies of the effects of allelochemicals or other factors on the development of different insect species, comparison of growth-inhibiting activities is difficult using the parameters currently employed. We introduce two new parameters, growth index (GI) and relative growth index (RGI), which can unify the quantification of insect development. This quantification can also eliminate the effects of different growth characteristics due to the genetic differences between insect species. By measuring growth-inhibiting effects of two phytochemicals, chaparrin and Chaparrinone, on the tobacco budworm,Heliothis virescens, and the beet armyworm,Spodoptera exigua, bioassay procedures and GI and RGI calculations are demonstrated.

Plant anticancer agents. XXIII. 6 alpha-senecioyloxychaparrin, a new antileukemic quassinoid from Simaba multiflora.[Pubmed:6875576]

J Nat Prod. 1983 Mar-Apr;46(2):218-21.

Fractionation of an aqueous ethanol extract of the wood of Simaba multiflora afforded a new antineoplastic quassinoid, 6 alpha-senecioyloxychaparrin (5), and two known quassinoids 6 alpha-senecioyloxyChaparrinone (1) and Chaparrinone (2). The structure of 5, which displayed activity against the KB and P-388 test systems, was established through the interpretation of spectral data.

Soularubinone, a new antileukemic quassionoid from Soulamea tomentosa.[Pubmed:7264678]

J Nat Prod. 1981 May-Jun;44(3):279-84.

The structure of soularubinone 3, a new antileukemic quassinoid isolated from the leaves of Soulamea tomentosa (Brongn, and Gris), has been established by spectral and chemical methods. It has been shown to be the C-15 beta-hydroxy-isovaleric ester of glaucarubolone. Soularubinone shows significant antineoplastic activity against mouse leukemia P-388 and inhibits cell transformation induced by Rous sarcoma virus. The known quassinoid Chaparrinone I has also been isolated.

Antimalarial activity of quassinoids against chloroquine-resistant Plasmodium falciparum in vitro.[Pubmed:7020445]

Am J Trop Med Hyg. 1981 May;30(3):531-7.

The growth of Plasmodium falciparum in vitro was markedly inhibited by certain quassinoids (the bitter principles from plants of the family Simaroubaceae). The most active compound, simalikalactone D, gave complete inhibition at 0.005 microgram/ml. Glaucarubinone an soularubinone were equally effective at 0.006 microgram/ml, whereas Chaparrinone and simarolide had little effect even at 0.01 microgram/ml. These relative activities are parallel to the antineoplastic activities of these materials.