Cytotoxic and anti-inflammatory effects of lignans and diterpenes from Cupressus macrocarpa

Cupressus macrocarpa is a windbreak tree and is reported to have various cytotoxic effects. A natural product study on the leaves of C. macrocarpa has yielded ten secondary metabolites, including three new diterpenoids (1–3), four known diterpenoids (4–7), and three known lignans (8–10). The structures of all isolated compounds were elucidated via the interpretation of spectroscopic methods, especially 2D NMR and mass analyses. In the cytotoxic assays, compounds 1–3 and 7–10 showed inhibition effect against HepG2, MDA-MB-231, and A549 cells with IC₅₀ values ranging from 0.004 to 19.9 μg/mL. Moreover, the anti-inflammatory assays revealed that (−)-matairesinol (8) had significant inhibitory activities on superoxide anion generation (IC₅₀ = 2.7 ± 0.3 μM) and elastase release (IC₅₀ = 6.6 ± 0.7 μM).     

Aspernolides F and G,new butyrolactones from the endophytic fungus Aspergillus terreus

Two new butyrolactones: aspernolides F (6) and G (7), together with three stigmasterol derivatives: (22E,24R)-stigmasta-5,7,22-trien-3-β-ol (1), stigmast-4-ene-3-one (2), and stigmasta-4,6,8(14), 22-tetraen-3-one (3), two meroterpenoids: terretonin A (4) and terretonin (5), and a butyrolactone derivative: butyrolactone VI (8) have been isolated from the endophytic fungus Aspergillus terreus isolated from the roots of Carthamus lanatus (Asteraceae). Their structures were determined by spectroscopic means (1D, 2D NMR, and HRESIMS), as well as optical rotation measurement and comparison with literature data. The isolated compounds were evaluated for their anti-microbial, anti-malarial, anti-leishmanial, and cytotoxic activities. Compound 1 displayed a potent activity against MRSA and C. neoformans with IC₅₀ values of 0.96 μg/mL and 4.38 μg/mL, respectively compared to ciprofloxacin (IC₅₀ 0.07 μg/mL) and amphotericin B (IC₅₀ 0.34 μg/mL), respectively. While, 6 showed good activity against C. neoformans (IC₅₀ 5.19 μg/mL) and mild activity against MRSA (IC₅₀ 6.39 μg/mL). Moreover, 1 and 2 exhibited very good anti-leishmanial activity towards L. donovani with IC₅₀ values of 4.61 and 6.31 μg/mL, respectively and IC₉₀ values of 6.02 and 16.71 μg/mL, respectively.     

Chemical constituents of Mussaenda erythrophylla Schumach. & Thonn. (Rubiaceae) and their chemophenetic significance

The chemical investigation of the CH₂Cl₂/MeOH (1:1) extract from the aerial part of Mussaenda erythrophylla Schumach. & Thonn. (Rubiaceae) resulted in the isolation of sixteen known compounds (1–16) distributed in coumarins, flavonoid glucosides, quinic acid derivatives, triterpenoids, monoglycerid, steroids, tetraterpenoid and polyol. The structures of the compounds were determined by spectrometric and spectroscopic analysis including MS and NMR data followed by their comparison with reported ones in the literature. The chemophenetic significance of the isolated compounds was discussed. The crude extract and some of the isolated compounds were assessed in vitro for their antileishmanial, cytotoxic and antiplasmodial activities. The crude extract of M. erythrophylla showed moderate antileishmanial activity (IC₅₀ = 61.6 μg/mL) while the hexane soluble fraction showed good antileishmanial activity (IC₅₀ = 31.06 μg/mL) compared to the reference drug amphotericin B (IC₅₀ = 0.11 μM). Compounds 11 and 9 also exhibited potent antileishmanial activity (IC₅₀ = 53.7–52.0 μM). The crude extract as well as the ethyl acetate soluble fraction also exhibited good antiplasmodial activity (IC₅₀ = 7.43 ± 0.00 μg/mL and 14.49 ± 2.96 μg/mL respectively), while compounds 11, 15 and 16 showed weak activity with IC₅₀ > 20 μM compared to the reference drug artemisinin (IC₅₀ = 0.014 ± 0.001 μM).     

Two polymethoxylated flavonoids with antioxidant activities and a rearranged clerodane diterpenoid from the leaf exudates of Microglossa pyrifolia

Three novel compounds; two polymethoxylated flavonoids, 5,7,4′-trihydroxy-3,8,3′,5′-tetramethoxyflavone (1), 5,7,3′-trihydroxy-3,8,4′,5′-trimethoxyflavone (2), and a clerodane diterpenoid; 8-acetoxyisochiliolide lactone (3) were characterized from the leaf exudates of Microglossa pyrifolia. In addition, three known polymethoxylated flavonoids including; 5,7,4′-trihydroxy-3,8,3′-trimethoxyflavone (4), 5,3′4′-trihydroxy-3,7,8-trimethoxyflavone (5), 5,3′4′-trihydroxy-7-methoxyflavanone (6) and a clerodane diterpenoid; 7,8-epoxyisocholiolide lactone (7) were identified. Their structures were determined on the basis of spectroscopic evidence. All the compounds did not exhibit antiplasmodial and antimicrobial activities at 47.6 μg/mL and were not cytotoxic at 5 μg/mL. Compound 6 exhibited modest antileishmanial activity with IC₅₀ value of 13.13 μg/mL with 5 and 7 showing activities with IC₅₀ values of 31.13 and 38.00 μg/mL, respectively, therefore inactive. The flavonoids (quercetin derivatives, 4 and 5) showed similar antioxidant activities, using 2,2-diphenylpicrylhydrazyl (DPPH) assay, with IC₅₀ values of 6.2 ± 0.3 μg/mL for 4 (17.3 μM) and 5 (17.8 μM) respectively. These activities were comparable to that of the standard quercetin (IC₅₀ value of 6.0 ± 0.2 μg/mL (19.9 μM)), irrespective of methylation of the characteristic hydroxyl groups expected to be responsible for activity and additional substitution at C-8 in ring A of the flavonoid ring. These studies revealed that the presence of an hydroxyl group at C-4′ positions and oxygenation at C-3 in flavone skeleton, appears to be necessary for good antioxidant activities as encountered in compounds 1, 4 and 5. Substantial reduction in antioxidant activity was shown by methoxylation of the 4′-OH as observed in compound 2 with an IC₅₀ value of 8.79 ± 0.3 μg/mL (24.4 μM).     

Alkaloids from the roots of Stemona javanica (Kunth) Engl. (Stemonaceae) and their anti-malarial,acetylcholinesterase inhibitory and cytotoxic activities

Two new protostemonine-type alkaloids, javastemonine A and B (3 and 4) have been isolated from the root extracts of Stemona javanica together with four known Stemona alkaloids, 13-demethoxy-11(S*),12(R*)-dihydroprotostemonine (1), isoprotostemonine (2), protostemonine and isomaistemonine. The structures and relative configurations of the new alkaloids were determined by spectroscopic analysis. The alkaloids 1 and 2 and protostemonine showed moderated antiplasmodial activities against the Plasmodium falciparum strains, TM4 (IC₅₀ values of 17.7 ± 3.7, 16.8 ± 5.4, 16.0 ± 4.2 μg/mL, respectively) and K1 (IC₅₀ values of 16.8 ± 3.1, 14.1 ± 3.7, 11.9 ± 3.3 μg/mL, respectively). These compounds showed no significant cytotoxicities against KB or Vero cells or acetylcholinesterase inhibitory activities.     

Novel phenolic and diterpenoid compounds isolated from the fruit spikes of Prunella vulgaris L. and their anti-inflammatory activities

Two novel phenolic compounds, prunellanate A (1) and prunellanate B (2), together with a diterpenoid compound, prunelladiterpenol A (3), were successfully isolated from the fruit spikes of Prunella vulgaris L. (Figure 1). Their structures were determined after extensive spectroscopic analyses including IR NMR, HR-ESI-MS empirical electronic circular dichroism (ECD), and X-ray diffraction. The biological activities of these new compounds on NO production in LPS (Lipopolysaccharide)-simulated RAW264.7 cells were evaluated. Compounds 1 and 3 showed significant anti-inflammatory activities revealing IC₅₀ values of 6.77 and 8.61 μM, respectively (aminoguanidine as positive control, IC₅₀ 20.33 ± 1.08 μM).     

Cytotoxic terpenoids from the stem bark of Taxus wallichiana

Chemical study of the stem bark of Taxus wallichiana Zucc. afforded the isolation of two new cyclopenta[b]naphthalene terpenoids, wallichianones A (1) and B (2) and 13 taxane diterpenoids, baccatin III (3), 10-deacetylbaccatin III (4), baccatin IV (5), 1-dehydroxybaccatin IV (6), 1-deoxybaccatin VI (7), taxol (8), 10-deacetyltaxol (9), 7-epi-10-deacetyltaxol (10), taxol-7-xyloside (11), 7-xylosyl-10-deacetyltaxol C (12), cephalomannine (13), 10-deacetylcaphalomannine (14), and 7-epi-10-deacetylcephalomannine (15). Their structures were identified by comprehensive analyses of the spectroscopic methods, including NMR and mass spectra. The absolute configurations of 1 and 2 were clarified by time-dependent density functional theory (TD-DFT) electronic circular dichroism (ECD) spectroscopic analyses. Compounds 3 and 7–15 showed cytotoxicity against all five human cancer cell lines, including lung (SK-LU-1), liver (HepG2), breast (MCF7), skin (SK-Mel-2), and prostate (LNCaP), with IC₅₀ values ranging from 1.4 ± 0.2 to 88.1 ± 5.8 μM. Compounds 9–11, 14, and 15 were additionally cytotoxic against human embryonic kidney (HEK-293A) cell line (IC₅₀ = 14.5 ± 1.0–48.4 ± 1.0 μM), however, 13 was noncytotoxic toward this cell line. The positive control, ellipticine showed cytotoxicity against all the cell lines, with IC₅₀ values in a range of 1.5 ± 0.1–2.0 ± 0.3 μM. Preliminary analysis of the structural and cytotoxicity relationship of compounds 3–15 suggested that the phenylalanine substituent at C-13 may contribute an important role for the cytotoxicity of the taxane diterpenoids.     

A new isoflavonol and other constituents from Cameroonian propolis and evaluation of their anti-inflammatory,antifungal and antioxidant potential

Propolis is rich in diverse bioactive compounds. Propolis samples were collected from three localities of Cameroon and used in the study. Column chromatography separation of propolis MeOH:DCM (50:50) extracts yielded a new isoflavonol, 2-hydroxy-8-prenylbiochanin A (1) alongside 2′,3′-dihydroxypropyltetraeicosanoate (2) and triacontyl p-coumarate (3) isolated from propolis for first time together with seven compounds: β-amyrine (4), oleanolic acid (5), β-amyrine acetate (6), lupeol (7), betulinic acid (8), lupeol acetate (9) and lupenone (10). These compounds were tested for their inhibitory effect on oxidative burst where intracellular reactive oxygen species (ROS) were produced from zymosan stimulated human whole blood phagocytes and on production of nitric oxide (NO) from lipopolysaccharide (LPS) stimulated J774.2 mouse macrophages. The cytotoxicity of these compounds was evaluated on NIH-3 T3 normal mouse fibroblast cells, antiradical potential on 2,2-diphenyl-1-picrylhydrazylhydrazyl (DPPH·) as well as their anti-yeast potential on four selected candida species. Compound 1 showed higher NO inhibition (IC₅₀ = 23.3 ± 0.3 µg/mL) than standard compound L-NMMA (IC₅₀ = 24.2 ± 0.8 µg/mL). Higher ROS inhibition was shown by compounds 6 (IC₅₀ = 4.3 ± 0.3 µg/mL) and 9 (IC₅₀ = 1.1 ± 0.1 µg/mL) than Ibuprofen (IC₅₀ = 11.2 ± 1.9 µg/mL). Furthermore, compound 1 displayed moderate level of cytotoxicity on NIH-3 T3 cells, with IC₅₀ = 5.8 ± 0.3 µg/mL compared to the cyclohexamide IC₅₀ = 0.13 ± 0.02 µg/mL. Compound 3 showed lower antifungal activity on Candida krusei and Candida glabrata, MIC of 125 μg/mL on each strain compared to 50 μg/mL for fuconazole. The extracts showed low antifungal activities ranging from 250 to 500 μg/mL on C. albicans, C. krusei and C. glabrata and the values of MIC on Candida parapsilosis were 500 μg/mL and above. DPPH* scavenging activity was exhibited by compounds 1 (IC₅₀ = 15.653 ± 0.335 μg/mL) and 3 (IC₅₀ = 89.077 ± 24.875 μg/mL) compared to Vitamin C (IC₅₀ = 3.343 ± 0.271 μg/mL) while extracts showed moderate antiradical activities with IC₅₀ values ranging from 309.31 ± 2.465 to 635.52 ± 11.05 µg/mL. These results indicate that compounds 1, 6 and 9 are potent anti-inflammatory drug candidates while 1 and 3 could be potent antioxidant drugs.     

Constituents of Nelumbo nucifera leaves and their antimalarial and antifungal activity

From the leaves of Nelumbo nucifera (an aquatic plant), one new compound, 24(R)-ethylcholest-6-ene-5α-ol-3-O-β-d-glucopyranoside (1), along with 11 known metabolites (2–12), were isolated and identified by spectroscopic methods including 1D- and 2D NMR. Antifungal activity for (R)-roemerine (3) (IC₅₀/MIC = 4.5/10 μg/mL against Candida albicans) and antimalarial activity for (R)-roemerine (3) and N-methylasimilobine (5) (IC₅₀ = 0.2 and 4.8 μg/mL for the D6 clone, respectively, and 0.4 and 4.8 μg/mL for the W2 clone, respectively) was observed. None of the compounds were cytotoxic to Vero cells up to a concentration of 23.8 μg/mL. NMR data for 10-eicosanol (7) and 7,11,15-trimethyl-2-hexadecanone (10) are presented for the first time. An analysis of the structure–activity relationship shows that the substituents in position C-1 and C-2 of aporphine alkaloids are crucial for the antimalarial activity.     

Three new 2-(2-phenylethyl)chromones from ‘Chong-lou’ agarwood of Aquilaria sinensis

Three new 2-(2-phenylethyl)chromones (1, 2 and 3), together with four known analogues 4~7 were isolated from ‘Chong-lou’ agarwood originating from Aquilaria sinensis for the first time. Their new structures were elucidated on the basis of spectroscopic techniques (UV, IR, MS, 1D and 2D NMR), as well as by comparison with the literature data. Compounds 6 and 7 exhibited significant cytotoxicity against human cancer cell line K562 with IC₅₀ values of 19.79 ± 0.03 and 21.39 ± 0.05 μM, respectively.     

Bioactive 2-pyrone metabolites from an endophytic Phomopsis asparagi SWUKJ5.2020 of Kadsura angustifolia

Five new 2-pyrone metabolites, phomaspyrones A–E (1–5) along with three known compounds, macommelin-8,9-diol (6), macommelin-9-ol (7), and macommelin (8), were isolated from the culture broth of an endophytic fungus Phomopsis asparagi SWUKJ5.2020 of medicinal plant Kadsura angustifolia by sequentially purification over silica gel, Sephadex LH-20 column chromatography and preparative HPLC. Their structures were elucidated on the basis of spectroscopic analysis, including two-dimensional (2D) NMR and HRMS (ESI-TOF) data. Among them, compounds 3–5 exhibited notable cytotoxicity against HL-60 and K562 cells with IC₅₀ values of below 10 μg/mL better than those of the other isolated metabolites (IC₅₀ = 10.6–26.6 μg/mL). The results showed that the keto or hemiketal functionality might play an important role in cytotoxic activity of this class of compounds.     

Pancreatic lipase inhibitory and antioxidative constituents from the aerial parts of Paeonia lactiflora Pall. (Ranunculaceae)

To date, there have been reports mostly about research results of the peony root in comparison to the aerial parts. According to our study, the aerial parts of P.lactiflora showed superior anti-oxidative and pancreatic lipase inhibitory activities than its root. Especially, the water extract and the ethyl acetate fraction of the ethanol extract exhibited potent pancreatic lipase inhibitory activity by 53.11 ± 1.22% and 46.16 ± 1.55% at the same dose of orlistat (62.5 ± 1.27%). The ethanol extract exhibited the best anti-oxidative activity with IC₅₀ of 17.08 ± 0.9 μg/mL, and the ethyl acetate fraction 19.75 ± 0.02 μg/mL, respectively, comparing to the positive control rutin (IC₅₀, 22.66 ± 0.29 μg/mL). From the anti-oxidative and pancreatic lipase inhibitory active fractions three new compounds, monplacphloroside (1), monplachydroxyquinoside (2) and herbacetin-7-O-β-d-sophoroside (3) were isolated along with 19 (4-22) known ones.Compounds, PGG (14), 1-O-methyl-2,3,4,6-tetra-O-galloyl-β-d-glucopyranose (17) and ethylgallate (9) were found to be the strongest antioxidants and pancreatic lipase inhibitors. Monoterpenes, albiflorin R₂ (19) and albiflorin (20) were determined for the first time as strong pancreatic lipase inhibitors. The presence of the esterified galloyl moiety, with its increasing numbers or the β-lactone cycle within the molecular structure plays an essential role for the enhancement of the pancreatic lipase enzyme inhibitory activity.     

New metabolites (±)-bacillipyrrole A and bacillipyrazine A from the Mariana Trench-associated bacterium Bacillus subtilis SY2101

The new (±)-bacillipyrrole A (1) and bacillipyrazine A (2), together with seven known compounds, were isolated from a culture of the Mariana Trench sediment-derived bacterium Bacillus subtilis SY2101 in rice medium. Structures of the new compounds were elucidated by their HRESIMS data and NMR spectroscopic analyses. The known compound 3,5,6-trimethylpyrazine-2-methyl acetate (4) showed antiproliferative activity against human glioma U87MG cells with an IC₅₀ value of 22.6 ± 2.8 μM.     

Cytotoxic and antimalarial constituents from aerial parts of Sphaeranthus indicus

Two new eudesmanolide type sesquiterpenes, indicusalactone (1) and (⿿)⿿-⿿oxyfrullanolide (2), along with twelve known compounds (3⿿14), were isolated from the aerial parts of Sphaeranthus indicus. The structures of these compounds were established on the basis of their 1D and 2D NMR spectroscopic data. Compounds 1⿿4 and 12⿿14 showed antimalarial activity against Plasmodium falciparum with IC₅₀ values ranging from 2.32 to 6.47μg/mL. In addition, compounds 2⿿5 showed cytotoxicity against cancer cell lines, KB, NCI-H187 and MCF-7 with IC₅₀ values within the range 1.23⿿46.19 μg/mL.     

Dihydrochalcone glucosides and antioxidant activity from the roots of Anneslea fragrans var. lanceolata

Bioassay-guided fractionation of the roots of Anneslea fragrans var. lanceolata led to the isolation of four dihydrochalcone glucosides, davidigenin-2′-O-(6″-O-4″′-hydroxybenzoyl)-β-glucoside (1), davidigenin-2′-O-(2″-O-4″′-hydroxybenzoyl)-β-glucoside (2), davidigenin-2′-O-(3″-O-4″′-hydroxybenzoyl)-β-glucoside (3), and davidigenin-2′-O-(6″-O-syringoyl)-β-glucoside (4), and 13 known compounds. The structures were identified by means of spectroscopic analysis. Davidigenin-2′-O-(6″-O-syringoyl)-β-glucoside (4), 1-O-3,4-dimethoxy-5-hydroxyphenyl-6-O-(3,5-di-O-methylgalloyl)-β-glucopyranoside (5), lyoniresinol (10), and syringic acid (13) showed ABTS [2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)] cation radical scavenging activity, with SC₅₀ values of 52.6 ± 5.5, 26.0 ± 0.7, 6.0 ± 0.2, and 27.5 ± 0.6 μg/mL in 20 min, respectively. Lyoniresinol (10), isofraxidin (12), and syringic acid (13) also showed DPPH [1,1-diphenyl-2-picrylhydrazyl] radical scavenging activity, with SC₅₀ values of 8.4 ± 1.8, 51.6 ± 2.2, and 4.3 ± 0.7 μg/mL in 30 min, respectively.     

Bioactivity-guided isolation of cytotoxic constituents from stem–bark of Premna tomentosa

A bioassay-guided fractionation and chemical investigation of the stem bark of Premna tomentosa resulted in the isolation and characterization of four new icetexane diterpenes (1–4), along with the known compounds coniferaldehyde (5), syringaldehyde (6), lupeol (7), betulin (8), and 2-(4-methoxyphenyl)-2-butanone (9). Their structures were established on the basis of extensive spectroscopic (IR, MS, 2D NMR) data analysis and by comparison with the spectroscopic data reported in the literature. The new compounds exhibited diverse functionalities on a common icetexane diterpene skeleton. In addition, cytotoxic activities of the icetexanes (1–3) were evaluated by determining their inhibitory effects on the human cancer cell lines (MCF-7, HT-29, Hep-G2, A-431, and A-549). Compounds 1 and 3 showed selective inhibitory activity against MCF-7 (15.96 μg/mL and 15.84 μg/mL) and HT-29 cell lines (16.21 μg/mL and 14.57 μg/mL), respectively.     

Two new 1,4-naphthoquinone derivatives from Impatiens balsamina L. flowers

Two new 1,4-naphthoquinone derivatives, balsaminone D (1), balsaminone E (2) along with two known compounds (3 and 4) were discovered from Impatiens balsamina L. flowers. Their structures were identified with spectroscopic methods including HR–EI–MS, 1D and 2D NMR, as well as the absolute configuration was determined by ECD calculation. In addition, new compounds 1 and 2 with IC₅₀ value of 30.54 and 40.67 μg/mL exhibited better activities against activated t-HSC/Cl-6 cells than positive control Silymarin and Fufang Biejia Ruangan Pian, of which the IC₅₀ value were 202.34 and 231.56 μg/mL, respectively.     

Two new flavonols from flowers of Getonia floribunda Roxb.

Phytochemical investigation of the EtOAc and MeOH extracts from flowers of Getonia floribunda Roxb., a Thai herbal medicine, resulted in the isolation of two new flavonols, 4′-hydroxy-6,7,8,3′-tetramethoxyflavonol (1) and 4′-hydroxy-6,7,8-trimethoxyflavonol (2), along with a known pachypodol (3). Their structures were elucidated by spectroscopic methods including UV, IR, 1D and 2D NMR techniques and MS analysis. Compound 1 showed cytotoxicity against the oral cavity cancer (KB) cell line with an IC₅₀ value of 8.99 ± 2.00 μg/ml.     

Screening for tyrosinase inhibitors from actinomycetes; identification of trichostatin derivatives from Streptomyces sp. CA-129531 and scale up production in bioreactor

In the course of a primary screening of 614 microbial actinomycete extracts for the discovery of tyrosinase inhibitors, the EtOAc extract of the fermentation broth of the strain Streptomyces sp. CA-129531 isolated from a Martinique sample, exhibited in cell free and cell-based assays the most promising activity (IC₅₀ value of 63 μg/mL). Scaled-up production in a bioreactor led to the isolation of one new trichostatic acid analogue, namely trichostatic acid B (1), along with six known trichostatin derivatives (2–7), four diketopiperazines (8–11), two butyrolactones (12–13) and one hydroxamic acid siderophore (14). Among them, trichostatin A (4) showed a Ki value of 6.1 μM and six times stronger anti-tyrosinase activity (IC₅₀ 2.18 μΜ) than kojic acid (IC₅₀ 14.07 μΜ) used as a positive control. Deoxytrichostatin A (6) displayed also strong inhibitory activity against tyrosinase (IC₅₀ 19.18 μΜ). Trichostatin A production in bioreactor started together with the exponential phase of growth (day 4) and the maximum concentration was reached at day 9 (2.67 ± 0.13 μg/mL). Despite the cytotoxicity of some individual components, the EtOAc extract showed no cytotoxic effect on HepG2, A2058, A549, MCF-7 and MIA PaCa-2 cell lines, (IC₅₀ >2.84 mg/mL) and against BG fibroblasts at the concentrations where the whitening effect was exerted, reassuring its safety and great tyrosinase inhibitory potential.     

New nemadectin congeners with acaricidal and nematocidal activity from Streptomyces microflavus neau3 Y-3

Two nemadectin congeners 1 and 2 were isolated from the fermentation broth of a mutant strain (Y-3) of Streptomyces microflavus neau3. Their structures were determined on the basis of extensive spectroscopic analysis and comparison with data from the literature. Compound 2 possessed a 5-membered ring lactone that is unprecedented among known milbemycins and avermectins. Both compounds 1 and 2 exhibited potent acaricidal activity and nematocidal activity. Especially, compound 2 demonstrated impressive acaricidal activity against adult mites with an IC₅₀ of 2.3 ± 0.9 μg/mL and mite eggs with an IC₅₀ of 17.5 ± 2.1 μg/mL and nematocidal activity against Caenorhabditis elegans with an IC₅₀ of 0.7 ± 0.2 μg/mL, which are higher than those of nemadectin and the known commercial acaricide and nematocide milbemycin A3/A4.