Light Petroleum Extract Research Articles

RETRACTED: In Vitro Antitumor Activities of Biologically Active Extracts and Isolated Phytochemicals From Rabdosia latifolia C. Y. Wu Et H. W. Li in Addenda

To investigate the antitumor activities, as well as phytochemical constituents of Rabdosia latifolia C. Y. Wu et H. W. Li in Addenda ( R. latifolia) extracts, the light petroleum, dichloromethane, ethyl acetate, n-butanol, and water extracts from R. latifolia were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays on MCF-7, HepG2, A549, Hela, and BGC-823 cells. We further examined cell cycle and apoptosis of the biologically active extracts on MCF-7 cells. The constituents of the biologically active extracts were determined using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC-Triple-TOF/MS) and gas chromatography–mass spectrometric (GC–MS) analysis. MTT assays showed that the dichloromethane extract had an inhibitory effect on MCF-7 and BGC-823 cells and that at 50 µg/mL showed 9.9% ± 1.7% inhibition of MCF-7 cells and 81.7% ± 9.5% of BGC-823 cells, respectively. The data for cell cycle analysis clearly showed a significant block in the S-phase. The dichloromethane extract induced apoptosis of MCF-7 cells, and the cell apoptosis rate showed time and concentration effects. UPLC- Triple-TOF/MS analysis revealed the presence of 16 structurally characterized compounds in the dichloromethane extract, all of which were identified for the first time in this species. Ent-kauranoids, such as henryin (9) and its analogs, were the predominant compounds. Subsequently, GC–MS analysis showed the presence of 20 volatile compounds, including γ-sitostenone, β-amyrone, γ-tocopherol, and dotriacontane. Based on the results of this study and previous literature reports, it is concluded that the ent-kauranoids, such as henryin, were the predominant components of R. latifolia with antitumor activity.

A new indole alkaloid, antioxidant and antibacterial activities of crude extracts from Saccocalyx satureioides

The new acylated indole alkaloid glucoside indole-3-carboxylic acid-(6'-O-caffeoyl)-β-D-glucoside 1 has been isolated from the ethyl acetate (EtOAC) extract of Saccocalyx satureioides Coss. & Dur. (Lamiaceae) together with eight known secondary metabolites 2-9. Two indoles 2 and 3, five methylated flavone aglycones 4-8 and one monoterpene glucoside 9 were reported for the first time in the genus Saccocalyx. The structural elucidation of these compounds was accomplished by spectroscopic methods including 1 D (1H and 13C) and 2 D (COSY, HSQC and HMBC) NMR techniques, and mass spectrometry, and by comparison with literature data. Light petroleum, EtOAc, chloroform and n-butanol (n-BuOH) extracts of S. Satureioides were screened for their antioxidant activity using DPPH radical scavenging and β-carotene bleaching methods. The antibacterial activity of these extracts indicates that n-BuOH and EtOAc extracts possess the strongest activity.

Management of Diabetic Bacterial Foot Infections with Organic Extracts of Liverwort Marchantia debilis from Cameroon

Diabetic bacterial foot infections (DBFIs) are limb-threatening complications in patients with diabetes mellitus, accounting for 50% of diabetes related lower limb amputations in developing countries, representing approximately 20 percent of all diabetes-related hospital admissions with significant healthcare-related costs involved. The widespread problem of bacterial resistance to most commonly used antibiotics places a huge economic burden on the healthcare system, with both increased morbidity and mortality among diabetic patients with foot infections. In this study, the antibacterial activity of organic extracts of the fresh liverwort Marchantia debilis from the North West Region of Cameroon is reported. An exit pool system, where patients presenting with DBFIs consented to be involved in the use of phytomedicines, after long term treatment of ulcers with antibiotics and not yielding significant long term benefit, presented themselves at the Phytobiotechnology Research clinic (PRF). Continuous culture of swabs from foot and toe wounds from 30 infected patients on nutrient agar and MacConkey agars in triplicate as well as Gram stain microscopy, revealed the presence of Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis and Bacillus species. Light petroleum and methanol extracts of the whole bryophyte plants at 100% concentration were tested. In vitro inhibition of the tested bacterial isolates from the diabetic foot ulcers by M debilis was observed only with the light petroleum extract. No inhibition by the extracts was observed for the Pseudomonas aeruginosa isolate. The light petroleum extract of M debilis was formulated into a petroleum oil based cream named BryoCream™. This was administered to 20 of the patients with 90% cure rate in a three week time period. The main nonpolar components were determined by GCMS as lepidozene and β-barbatene, and by NMR as stigmasterol and β-sitosterol. In conclusion, nonpolar extracts from bryophytes from Cameroon could, potentially, be used to treat diabetic bacterial foot infections.

Biological Activity and Chemical Constituents of Essential Oil and Extracts of Murraya microphylla

Murraya microphylla is the most closely related species to M. koenigii (Curry tree). Inspired by the traditional effects of M koenigii, the antioxidant, anti- inflammatory, and cytotoxic activities of the essential oil and extracts of M. microphylla were evaluated for the first time. The light petroleum and chloroform extracts were found to be able to scavenge DPPH free radicals, inhibit linoleic acid peroxidation, and nitric oxide production, as well as to present cytotoxicity to the human cancer cell lines HepG2, Bel7402, Bel7403, and Hela, but the essential oil only showed moderate activities. Chemical analysis of the active extracts by LC-DAD-MS" indicated that carbazole alkaloids were the main constituents. GC-MS analysis of the essential oil resulted in identification of 91 constituents, representing 96.9% of the total oil, with (E)-caryophyllene (18.4%) and terpinen-4-ol (12.6%) as the major constituents. These results demonstrate that M microphylla has similar biological activities, as well as chemical constituents to M. koenigii, and the carbazole alkaloids were disclosed to be the main potential active components. A promising development as a flavor and potential therapeutic agent could thus be predicated for this plant.

In vitro Cancer Cell Growth Inhibition and Antioxidant Activity of Bombax ceiba (Bombacaceae) Flower Extracts

The flowers of Bombax ceiba were investigated for their chemical composition, antioxidant effects and antiproliferative activity against seven human cancer cell lines. The antiproliferative responses of diethyl ether (DE) and light petroleum (PE) extracts were evaluated by sulforhodamine B (SRB) assay against MCF-7, HeLa, COR-L23, C32, A375, ACHN, and LNCaP cells in comparison with a human normal cell line, 142BR. Moreover, extracts were characterized by GC-MS analysis and tested for their antioxidant properties by different in vitro systems, namely DPPH, Fe-chelating activity and beta-carotene bleaching test. Both PE and DE extracts showed the highest antiproliferative activity against human renal adenocarcinoma (ACHN) in a concentration-dependent manner. PE extract showed the highest radical scavenging activity against the DPPH radical, while DE extract was more active in the beta-carotene bleaching test. The presence of beta-sitosterol and some fatty acids may contribute to the bioactivity of B. ceiba flower extracts.

Single Crystal X-ray Diffraction, Spectroscopic and Mass Spectrometric Studies of Furanocoumarin Peucedanin

The structure of peucedanin, isolated from Peucedanum tauricum Bieb. (Apiaceae), has been established using single crystal X-ray diffraction. This furanocoumarin isolated from the light petroleum extract of P. tauricum fruits was characterized by high resolution EI-MS, sATR-FTIR and 2D NMR spectroscopic techniques. The EI-MS showed the typical fragmentation pattern of methoxyfuranocoumarins. Extensive 1D (1H and 13C) as well as 2D NMR data enabled complete assignment of the carbon atoms in the peucedanin molecule. The FTIR data confirms intermolecular hydrogen bonding between peucedanin molecules in polar solvents. Peucedanin crystallises in the R-3 space group from the trigonal system with one molecule in the asymmetric part of the unit cell. The crystal lattice of peucedanin consists of the molecules arranged in separate columns. They are related by two fold screw axes and centres of symmetry. Interestingly, peucedanin columns form two channels per unit cell with a diameter of 7.5angstrom going through the crystal lattice in the Z-direction. These channels are filled with disordered water molecules, which are surrounded by hydrophobic methyl groups and are located exactly at the centres of the channels. The peucedanin molecules are stacked in a single column with the opposite orientation of the neighbouring molecules. These results could be interesting in further application of this molecule, for example in biological tests of its activity.

Chemical Constituents from an Endophyte, Cercosporella sp.

Cercosporella sp., an endophyte, was isolated from Schisandra chinensis Baill., a medicinal plant. Extracts of Cercosporella sp. are nontoxic to human lymphocytic MT-4 cells and exhibited potent anti-HIV activity in an in vitro MTT assay [1]. The selectivity index (SI) value was 5.6. The fungi were cultured in wheat bran culture medium (containing dextrose, monopotassium phosphate, magnesium sulfate) on a rocking bed without light. The cultured fungus was filtered to separate mycelium from fermentation liquor. Mycelia were rinsed to eliminate fermentation liquor before desiccation, and dry mycelia, about 832 g, were extracted twice with 95% ethanol for 1 h by reflux. The solvents were removed under reduced pressure to give a crude extract (120 g). The aqueous suspension of the extract was partitioned successively with light petroleum, EtOAc, and n-BuOH, resulting in light petroleum (56 g), ethyl acetate (13 g), and n-BuOH (12 g) extracts. The ethyl acetate-soluble fraction was concentrated and subjected to 200–300 mesh silica gel column chromatography eluting with a gradient of CHCl3–MeOH (from 0:1 to 1:1 ) to yield thirteen fractions. The subfractions were then purified by successive column chromatography on 300–400 mesh silica gel using light petroleum–EtOAc and CHCl3–MeOH as elution systems, monitored by TLC, which led to the isolation of compounds 1–6. The structures were elucidated by 1H NMR, 13C NMR, HSQC, HMBC, and MS analysis. All these data were in good agreement with the literature data. All compounds were isolated from Cercosporella sp. for the first time. Compounds 1 and 4 exhibited potent anti-HIV activity, and the SI values were respectively 3.22 and 2.53 in the in vitro MTT assay. 5,6,7-Trihydroxyflavone (1) [2], 19 mg; yellow needles; C15H10O5, mp 223–226 C. Mass spectrum (EI, 70 eV), m/z: 270 (M+, 100%), 242 (M – CO), 168, 140, 112, 102, 77, 69. 5,7-Dihydroxy-6-methoxyflavone (2) [3], 28 mg; saffron yellow needles; C16H12O5, mp 231–232 C. PMR spectrum (500 MHz, CD3OD, , ppm, J/Hz): 8.02 (2H, dd, J = 9.0, 2.0, H-2 , H-6 ), 7.57 (3H, m, H-3 , H-4 , H-5 ), 6.76 (1H, s, H-8), 6.28 (1H, s, H-3), 3.93 (3H, s, 6-OCH3). 13C NMR spectrum data (125 MHz, CD3OD, , ppm): 184.0 (C-4), 165.4 (C-7), 159.0 (C-9), 158.3 (C-2), 151.3 (C-5), 133.1 (C-4 ), 132.5 (C-6), 130.3 (C-1 ), 129.3 (C-3 , C-5 ), 127.4 (C-2 , C-6 ), 105.9 (C-10), 105.4 (C-3), 100.4 (C-8), 62.0 (6-OCH3). Mass spectrum (EI, 70 eV), m/z: 284 (M+), 269 (M – 15, 100%), 241, 167, 139, 103, 77, 69. Physcion (3) [4], 38 mg; red needles; C16H12O5, mp 203–205 C. PMR spectrum (600 MHz, CD3OD, , ppm, J/Hz): 12.31 (1H, s, OH), 12.11 (1H, s, OH), 7.63 (1H, dd, J = 1.5, 0.5, H-14), 7.37 (1H, d, J = 2.5, H-10), 7.08 (1H, dd, J = 2.5, 1.0, H-9), 6.69 (1H, d, J = 2.5, H-13), 3.94 (3H, s, H-16), 2.45 (3H, s, H-15). 13C NMR spectrum data (150 MHz, CD3OD, , ppm): 190.8 (C-1), 182.0 (C-2), 162.5 (C-3), 166.6 (C-4), 148.4 (C-5), 165.2 (C-6), 133.2 (C-7), 113.7 (C-8), 124.5 (C-9), 110.3 (C-10), 135.3 (C-11), 108.2 (C-12), 106.8 (C-13), 121.3 (C-14), 22.1 (C-15), 56.1 (C-16). Indole-3-carboxylic Acid (4) [5], 10 mg; flavo-green crystal; C9H7O2N, mp 232–234 C. Mass spectrum (EI, 70 eV), m/z: 161 (M+, 100%), 144 (M – OH), 132 (M – CHO), 116 (M – COOH). 4-Hydroxyphenylacetic Acid (5) [5], 5 mg; colorless needles; C8H8O3, mp 148–150 C. 2-(4 -Hydroxyphenyl)ethanol (6) [5], 60 mg; colorless needles; C8H10O2, mp 89–92 C. Mass spectrum (EI, 70 eV), m/z: 138 (M+), 120 (M – H2O), 107 (M – CH2OH, 100%).

Phytopathogenic Fungal Inhibitors from Celery Seeds

Extract of celery (Apium graveolens L.) seeds was investigated against phytopathogenic fungi. The light petroleum extract showed promising inhibition activities in the tests against Rhizoctonia solani and Fusarium oxysporum f. sp. vasinfecum. Chromatographic separation of the extract gave 19 fractions, one of which, QCZ-4, possessed significant inhibitory rates of 64.6%, 88.4% and 54.7% at a concentration of 100 ppm against R. solani, F. oxysporium f. sp. vasinfecum and Alternaria alternata, respectively. Major components in the active fraction were identified by GC-MS as p-(2-aminoethyl)phenol (39.7%), 3-(3,4-dimethybenzoyl) propionic acid (32.6%) and p-heptylphenol (26.9%).

A New Long-Chain Unsaturated Ester and Other Constituents of Hypericum tomentosum

Three long-chain unsaturated esters (1-3), a fatty acid (4), a fatty ester (5), phytone (6) and a phloroglucinol (hyperfoliatin) (7) were isolated from the light petroleum extract of the endemic species Hypericum tomentosum L. (Clusiaceae). Compound 2, 8,10,13-trimethyltetradecanoic acid (2E)-3-methylhexadec-2-enyl ester, which we named tomentosate, is reported for the first time. The structures of the identified compounds were established on the basis of physical and spectroscopic analysis, and by comparison with literature data.

Antimicrobial Investigation of Linum usitatissimum for the Treatment of Acne

Light petroleum, dichloromethane and methanolic extracts of Linum usitatissimum were investigated using GC/MS. The main components of three sequential extracts were methyl linolenate (11.9-33.9%) and methyl linoleate (3.4-9.1%). Components possessing antimicrobial activity against acne causing bacteria, namely alpha-linolenic acid (7.0 -7.1%), alpha-terpinene (1.7-3.1%), terpinen-4-ol (1.3-4.6%), 4-cymene (1.6-7.1%) and alpha-pinene (1.1%), were found in varying amounts. Antimicrobial screening indicated that the light petroleum extract was more active against aerobic and anaerobic test strains with a MIC value of 1.25 mg/mL and a MBC of 2.5 mg/mL against S. aureus and P. acnes. A MIC of 2.5 mg/mL was observed against S. epidermidis.

An Unusual Bisnor-clerodane Diterpenoid from Polyalthia Simiarum

The stem bark of Polyalthia simiarum has yielded a new bisnor-type clerodane diterpenoid, 2-oxo-14,15-bisnor-3,11E-kolavadien-13-one (1), and three previously known clerodane derivatives, kolavenic acid (2), 16beta-hydroxycleroda-3,13(14)Z-dien-15,16-olide (3), and 16-oxocleroda-3,13(14)E-dien-15-oic acid (4). The structures of these compounds were unambiguously determined by extensive NMR studies as well as by comparison with related compounds. Till now this is the second report of the occurrence of any unusual C-18 clerodane diterpenoid from nature. The crude light petroleum extract and the purified compound 3 demonstrated moderate free radical scavenging activity with IC50 values of 21.5 and 23.5 microg/mL, respectively.

Antimicrobial Compounds from the Endophytic Fungus Fusarium sp. Ppf4 Isolated from the Medicinal Plant Paris polyphylla var. yunnanensis

Two sterols and one fatty acid were obtained by bioassay-guided fractionation from the light petroleum extract of the fungus Fusarium sp. Ppf4 isolated from the rhizomes of Paris polyphylla var. yunnanensis Hand.-Mazz., a medicinal species distributed in the southwest of China. The compounds were elucidated as 5alpha, 8alpha-epidioxyergosta-6, 22-dien-3beta-ol (1), ergosta-8(9), 22-dien-3beta, 5alpha, 6beta, 7alpha-tetraol (2), and butanedioic acid (3), respectively, by means of physical and spectrometric analysis. Both fungal spore germination and micro-dilution-MTT assays were employed to evaluate their antimicrobial activity. Compound 1 was found to be the most bioactive, and compound 3 less active against the test pathogens. This is the first report of the antimicrobial activity of the compounds isolated from the endophytic Fusarium sp. Ppf4 associated with P. polyphylla var. yunnanensis. The results provide promising baseline information for the potential use of the compounds of this endophytic fungus as an antimicrobial agent to control plant and animal diseases.

GC-MS Analysis of the Antioxidant Active Fractions ofMicromeria julianawith Anticholinesterase Activity

The aerial parts of Micromeria juliana (L.) Bentham ex Reichb. were extracted with light petroleum, acetone and methanol, successively. The antioxidant activity of different concentrations of the extracts was evaluated using different antioxidant tests, namely total antioxidant (lipid peroxidation inhibition activity), DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging, ferric reducing power, and metal chelating. Total antioxidant activity was determined using the beta-carotene-linoleic acid assay. Unexpectedly, the light petroleum extract exhibited strong lipid peroxidation inhibition activity. The extract was fractionated on a silica gel column and the antioxidant activity of the fractions was determined by the beta-carotene-linoleic assay at 25 microg/mL concentration. The fractions that exhibited more than 50% inhibition activity were analysed by GC and GC/MS; thus, the structure of fourteen compounds were elucidated. In addition, acetyl- and butyryl-cholinesterase inhibitory activities of the extracts were also determined in vitro. The light petroleum and acetone extracts were found to have mild butyrylcholinesterase inhibitory activity.

Phenolic Profile and Antioxidant Evaluation of Mentha x Piperita L. (Peppermint) Extracts

Seven extracts were prepared from Mentha x piperita (peppermint) leaves in sequence using a Soxhlet apparatus, viz. (40-60 degrees) light petroleum (PE), dichloromethane (CH2Cl2), acetonitrile (ACN), ethyl acetate (EtOAc), methanol (MeOH), n-butanol and water (H2O) extracts. The phenolic and flavonoid content of each extract were estimated using spectrophotometric methods whilst a qualitative-quantitative analysis was made by reverse-phase high performance liquid chromatography coupled with photodiode array detection (HPLC-PDA). Each extract was assessed in a battery of six antioxidant-related assays so as to determine their iron(III) reductive, iron(II) chelating and free radical scavenging abilities. The MeOH-soluble extract contained the greatest content of total phenols and flavonoids based upon the Folin-Ciocalteu and 2-aminoethyl diphenylborate reagent data and HPLC-PDA analysis. Based upon the chromatographic and UV-spectral data, the leaves principally contained the cinnamic acid caffeic acid, the depside rosmarinic acid and flavonoids (flavones and flavanones). Eriocitrin (383.3 +/- 2.2 mg/g extract) and rosmarinic acid (381.2 +/- 1.9 mg/g extract) were the most abundant components identified within the leaves, whilst naringenin-7-O-glucoside (0.8 +/- 0.01 mg/g extract) was the least abundant component identified being found only in the EtOAc-soluble extract. The EtOAc, ACN and H2O-soluble extracts demonstrated the most potent iron(III) reductive and 1,1'-diphenyl-2-picrylhydrayl, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) and hydroxyl free radical scavenging properties; however, the H2O and CH2Cl2-soluble extracts were the most potent extracts in the beta-carotene-linoleic acid bleaching inhibition assay. In terms of iron(II) chelation--an important antioxidant property--the PE, MeOH and H2O extracts demonstrated moderate iron(II) chelating activity.

Antiinflammatory Potential and Fatty Acid Content of Lipophilic Leaf Extracts of Four Staphylea L. Species

Staphylea preparations are used in TCM and have been used by native Americans for a number of indications, such as rheumatism. Based on this knowledge, the anti-inflammatory activity of light petroleum extracts of leaves of Staphylea colchica Stev., S. elegans Zab., S. holocarpa Hemsl. and S. pinnata L. has been determined using in vitro assays for inhibition of cyclooxygenase (COX-1 and COX-2) and leukotriene B4 (LTB4) formation by lipoxygenase (5-LOX). All extracts inhibited COX-1 and COX-2, with S. holocarpa and S. elegans performing best. Inhibition of LTB4 formation was less pronounced. As unsaturated fatty acids are known to inhibit arachidonic acid metabolism in vitro, the fatty acid content was determined of the active extracts and set in correlation with their activity. Unsaturated fatty acids were found to contribute to the observed COX-2 and LTB4 formation inhibitory activity to a different extent.

Anti-inflammatory Activity of Piper Magnibaccum (Piperaceae)

Anti-inflammatory activity of a crude extract of Piper magnibaccum (Piperaceae) and of compounds isolated from it was established using the TPA-induced mouse ear edema model and an in vitro quantitative lipoxygenase inhibition assay. Five compounds were isolated from P. magnibaccum [β-sitosterol, N-isobutyl-(2 E,4 E)-tetradecadienamide, linoleic acid, 13-(4′, 5′-dimethoxytridecanoyl)piperidine, and piperine]. The light petroleum extract of the plant exhibited significant anti-inflammatory activity in both models. N-isobutyl-(2 E,4 E)-tetradecadienamide showed significant activity, with an IE % value of 70.2 + 5.4 in the TPA-induced mouse ear edema model and 87.2 + 0.11 in the in vitro quantitative lipoxygenase inhibition assay.

Isolation and Cytotoxic Activity of Compounds from the Root Tuber of Curcuma Wenyujin

Bioassay-directed separation of the light petroleum and methylene chloride extracts of the root tuber of Curcuma wenyujin Y. H. Chen et C. Ling against five cell lines led to the isolation of one hexane derivative, crotepoxide (1), four sesquiterpenes, 4- epi-curcumenol (2), curcumenol (3), curcumadiol (4), and gweicurculactone (5), and three curcuminoids, curcumin (6), demethoxy-curcumin (7), and bisdemethoxycurcumin (8). Compounds 1–5 have not been found previously in C. wenyujin; compounds 2 and 3 were obtained as an epimeric mixture. The structures of the compounds were established on the basis of NMR spectroscopic data. When tested for cytotoxity against cell lines HL-60, HepG2, K562, KB and MCF-7, compounds 5–8 showed better antitumor activity than the others.

Antibacterial and Antioxidant Cassane Diterpenoids from Caesalpinia benthamiana.

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Antibacterial and antioxidant cassane diterpenoids from Caesalpinia benthamiana

Bioactivity-guided fractionation of the light petroleum extract of Caesalpinia benthamiana (= Mezoneuron benthamianum) root bark has led to the isolation of two cassane diterpenoids, designated as benthaminin 1 and 2. A third compound, a deoxy form of caesaldekarin C (also referred to as methyl vouacapenate) which has previously been isolated from Caesalpinia major, C. bonducella, Vouacapoua americana and V. macropetala, was also isolated, together with β-sitosterol and stigmastenone. The antibacterial and antioxidant activities of these cassane diterpenoids have been assessed using the microdilution assay method and DPPH spectrophotometric and TBA lipid peroxidation assays. Benthaminin 1 was the more active antibacterial compound with MIC values of 47.8 μM for both Staphylococcus aureus and Micrococcus flavus. Benthaminin 2 was the more active antioxidant compound and showed IC 50 values of 42.7 μM and 74.2 μM for the DPPH and TBA assays, respectively. Deoxycaesaldekarin C possessed both antibacterial and antioxidant activities. The presence of methyl ester and methyl functional groups as well as an unsaturated furan ring appears to confer antibacterial activity. On the other hand, the relatively stronger antioxidant activity of benthaminin 2 may be associated with the presence of an exocyclic methylene function.

A New Irregular Diterpenoid of Biogenetic Interest from the Flowers of Magydaris Tomentosa (Desf.) DC. (Apiaceae)

A new irregular acyclic diterpene, magytomol acetate (2), has been isolated from the light petroleum extract of the flowers of Magydaris tomentosa (Desf.) DC. (Apiaceae) and its structure has been elucidated by means of extensive spectroscopic experiments. The new compound can be considered the acetyl derivative of the biogenetic precursor of other irregular diterpenes isolated from other species belonging to the family Apiaceae.