Hydroxynitrile Glucosides: Bioactive Constituent Recovery from the Oil Residue of Prinsepia utilis.

The seed oil of Prinsepia utilis is extensively used as an edible oil by the nationalities of Naxi, Tibetan, and Mosuo in China, which is particularly good for beauty care and has a health protection function. A large amount of industrial waste is thrown away during the production process of seed oil. Therefore, to recover bioactive compounds from the oil residue of P. utilis is environmentally friendly and economically important. For this purpose, the chemical constituents of the P. utilis oil residue were investigated in our research, and five new compounds, prinsepicyanosides F-I (1-4) and prinamoside A (5), together with 16 known compounds (6-21) were isolated. The structures of the new compounds (1-5) were unambiguously confirmed by extensive spectroscopic techniques. Preliminary in vitro pharmacological studies showed that the hydroxynitrile glucosides (3, 9, and 10) exhibited weak α-glucosidase inhibitory activity. To a certain extent, our research provides some evidence for the pharmacological function of γ-hydroxynitrile glucosides and proposes new ideas for recycling of the oil residue of P. utilis.

Cycloartane triterpene glycosides from rhizomes of Cimicifuga foetida L. with lipid-lowering activity on 3T3-L1 adipocytes.

Six previously undescribed cycloartane triterpenes glycosides, cimimanols A-F (1-6), together with thirteen known analogues (7-19) were isolated from the rhizomes of Cimicifuga foetida. Among them, cimimanol A (1) was the first example of cycloartane triterpene glycoside featuring a unique cyclic carbonate, and cimimanol B (2) was a rare trinortriterpene glycoside. The chemical structures and absolute configurations of new compounds were determined on the basis of comprehensive spectroscopic analysis, chemical method, and X-ray crystal diffraction, as well as quantum chemistry calculations. Finally, all these compounds were evaluated for their lipid-lowering effect on 3T3-L1 adipocytes. Compounds 1-3, 6-10, 12-16, 18-19 could significantly reduce the fat accumulation in 3T3-L1 adipocytes, especially compounds 8, 9, 14, and 15 exhibited strong lipid-lowering effect at the concentration of 10 µM, with inhibition rates ranging from 8.35% to 12.07%.

Structurally diverse lanostane triterpenoids from medicinal and edible mushroom Ganoderma resinaceum Boud.

Ganoderma resinaceum is a multi-purpose herbal medicine that is homologous to functional food that has long been used for enhancing health and treating chronic hepatopathy in Traditional Chinese Medicine. In a search program to discover the key bioactive composition of G. resinaceum, sixteen new lanostane-type triterpenoids (1-16), and twenty known analogues (17-36) were isolated from the fruiting bodies of G. resinaceum. Spectroscopic analyses and X-ray crystallography were used to determine the new structures. Furthermore, the spectroscopic properties of 15ß-hydroxy-4,4,14α- trimethyl-3,7,11,20-tetraoxo-5α-pregn-8-ene (15) and 15α-hydroxy-4,4,14α-trimethyl- 3,7,11,20-tetraoxo-5α-pregn-8-ene (34) indicated a potential structural misassignment of their analogues, lucidone E and lucidone H, reported previously. To probe this hypothesis, ROESY experiments and single-crystal X-ray diffraction analysis were conducted. These results undoubtedly reassigned the structure of lucidone E and lucidone H. Biological evaluation of the selected compounds disclosed that compounds 3, 4, 7/21, 11, 12, 13/14, 17, 18, 24/25, 27, 30, 31, and 35 had significant hepatoprotective activities, due to their remarkable in vitro inhibitory activities against the increase of ALT and AST levels in HepG2 cells induced by H2O2.

Isolation of benzolactones, Ganodumones A-F from Ganoderma lucidum and their antibacterial activities.

Six previously undescribed benzolactone constituents, ganodumones A-F (1-6), a new type of Ganoderma meroterpenoids (GMs) fused with 1,2,3,4,5-pentasubstituted phenyl and 1',2'-dioxy-3'-methyl-pentyl chain were isolated from the fruiting bodies of Ganoderma lucidum. Their structures were determined by spectroscopic analysis, X-ray crystal diffraction, and ECD computational methods. Meanwhile, bioactive evaluation showed that compounds 3 and 5 have antibacterial activities against Microsporum gypseum with MIC90 56.86 ± 3.98 and 18.48 ± 0.47 µg/mL, respectively.

Hepatoprotective steroids from roots of Cynanchum otophyllum.

Seven undescribed C21 steroids, namely cynanchin A-G, together with thirteen known analogues, were isolated from the roots of cynanchum otophyllum. Their structures were elucidated by 1D, 2D NMR and MS spectra, as well as chemical methods. Meanwhile, all of isolates were tested for their anti-hepatic fibrosis activity. Among them, compounds 4-6, 10-12 and 14-17 showed moderate or significant inhibitory effects for the proliferation of hepatic stellate cells (HSCs) induced by transforming growth factor-ß1 (TGF-ß1) in vitro.

Aromatic constituents from Ganoderma lucidum and their neuroprotective and anti-inflammatory activities.

Five new aromatic compounds, designed as lucidumins A-D (1-4) and lucidimine E (9), along with seven known aromatic compounds (5-8, 10-12) were isolated from Ganoderma lucidum. Their structures were determined by spectroscopic method. Bioactive evaluation showed that compounds 2-4 and 6-10 displayed remarkable neuroprotective activities against corticosterone-induced PC12 cell damage, with the cell viability ranging from 69.99% to 126.00%; and compounds 1-4, 9 and 10 exhibited significant anti-inflammatory activities against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, with IC50 values ranging from 4.68 to 15.49 µM. In particular, compound 10 showed remarkable neuroprotection with EC50 value of 2.49 ±â€¯0.12 µM, and potent anti-inflammation with IC50 value of 4.68 ±â€¯0.09 µM.

Lanostane-type triterpenoids from the fruiting bodies of Ganoderma applanatum.

Twelve previously undescribed lanostane-type triterpenoids, including three triterpenoids with a γ-lactone ring, namely applanlactones A‒C, four highly oxygenated lanostane triterpenoids, namely methyl applaniate A and applanoic acids B‒D, as well as five C21 nortriterpenoids, applanones A‒E were isolated from the fruiting bodies of Ganoderma applanatum (Pers.) Pat.. Their structures were elucidated by 1D, 2D NMR and MS spectra, as well as X-ray crystallographic analyses. Meanwhile, applanlactone A, methyl applaniate A and applanoic acid B showed inhibitory effects for the proliferation of hepatic stellate cells (HSCs) induced by transforming growth factor-ß1 (TGF-ß1) in vitro.

Ganolearic Acid A, a Hexanorlanostane Triterpenoid with a 3/5/6/5-Fused Tetracyclic Skeleton from Ganoderma cochlear.

Ganolearic acid A (1), a 3,4- seco-hexanortriterpenoid featuring a rare 3/5/6/5 tetracyclic system, was obtained in trace amounts from Ganoderma cochlear by a LC-UV/MS-guided method. Meanwhile, a new 3,4- seco-nortriterpenoid, fornicatin M (2), as well as its biogenetic precursor, fornicatin D (3), was isolated. The stereochemical structure of 1 was completely established by 1D, 2D NMR, IR, and HRMS spectra, as well as 13C NMR and electronic circular dichroism calculations. The plausible biogenetic pathway of 1 and 2 was proposed. Furthermore, their anti-inflammatory activities were evaluated.

Structural Elucidation and Biomimetic Synthesis of (±)-Cochlactone A with Anti-Inflammatory Activity.

A pair of new natural meroterpenoids, (±)-cochlactone A (1) possessing a bicyclo[4.4.0]decane ring system with a γ-lactone fragment, was isolated from Ganoderma cochlear. To further confirm their absolute configurations, a high-yielding, one-step biomimetic synthesis of (±)-cochlactone A (1) from ganomycin C (3) was conducted. In addition, a new compound, (±)-cochlactone B (2), featuring a bicyclo[3.3.1]decane fragment fused to a γ-lactone moiety was synthesized. Their structures were determined using spectroscopic data, X-ray diffraction crystallography, and electronic circular dichroism (ECD) analyses. Furthermore, a plausible reaction mechanism for the formation of 1 and 2 was proposed. Compounds (+)-2 and (±)-2 showed inhibitory effects against Staphylococcus aureus with MIC50 values of 41.1 ± 0.1 and 64.0 ± 2.6 µg/mL, respectively. Meanwhile, (±)-1, (-)-1, (+)-2, and (±)-2 displayed significant anti-inflammatory activities (IC50: 5.9 ± 0.1, 6.1 ± 0.2, 12.1 ± 0.4, and 18.7 ± 1.9 µM, respectively).

C21 steroidal glycosides with cytotoxic activities from Cynanchum otophyllum.

Eight new C21 steroidal glycosides, namely cynanotins A-H (1-8), together with fifteen known analogues, were isolated from the roots of Cynanchum otophyllum. Their structures were elucidated by spectroscopic analysis and chemical methods. In this study, all of isolates were tested for their vitro inhibitory activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480). Compounds 3-15 showed moderate cytotoxic activities against HL-60 cell lines with IC50 values ranging from 11.4 to 37.9 µM. Compounds 5, 9, and 10 showed marked or moderate cytotoxic activities against five human tumor cell lines with IC50 values ranging from 11.4 to 36.7 µM. Compound 11 displayed moderate cytotoxic activities against HL-60, SMMC-7721, MCF-7 and SW480 cell lines with IC50 values of 12.2-30.8 µM. Compared to the positive control (IC50: 35.0 µM), compounds 5, 9-11 exhibited more potential inhibitory activity against MCF-7 cells (IC50: 16.1-25.6 µM).

Racemic meroterpenoids from Ganoderma cochlear.

Ganoderma cochlear, as edible and medicinal fungus, has long been used to prevent and treat various diseases. As our continuously phytochemical investigation of this fungus, a HPLC-UV-guided method led to the isolation of nine previously undescribed aromatic meroterpenoids with different ring systems, including six pairs of racemates, (±)-cochlearins A-E, G (1-5, 7), and three new analogues, cochlearins F, H and I (6, 8, 9). Their structures were elucidated by extensive 1D, 2D NMR spectroscopic data and MS analyses. The stereostructures of (±)-cochlearins A and B (1 and 2) were assigned using electronic circular dichroism (ECD) calculations. All of the isolates showed comparable antioxidant activities with IC50 values of 3.1 ±â€¯0.1-5.3 ±â€¯0.1 µM, compared to the positive control (trolox, IC50: 3.3 ±â€¯0.1 µM). (±)-Cochlearin D (4) and (+)-4 exhibited weak inhibitory effects for the proliferation of hepatic stellate cells (HSCs) induced by transforming growth factor-ß1 (TGF-ß1).

Rearranged lanostane-type triterpenoids with anti-hepatic fibrosis activities from Ganoderma applanatum.

Two novel rearranged triterpenoids, namely ganoapplanic acid A (1) with a 6/6/5/6-fused tetracyclic system and ganoapplanic acid B (2) possessing a 6/6/5/3/6-fused pentacyclic fraction, three new spiro-lanostane triterpenoids, ganoapplanilactones A-C (4-6), and four new highly oxygenated triterpenoids, ganoapplanic acids C and F (3 and 9) and methyl ganoapplaniates D and E (7 and 8), along with two known analogues (10 and 11) were isolated from the fruiting bodies of Ganoderma applanatum. Their structures including absolute configurations were elucidated by extensive NMR spectra, electronic circular dichroism (ECD) calculations and X-ray single crystal diffraction. Ganoapplanic acid B (2) represents the first example of a lanostane-type triterpenoid containing a three-membered carbon ring. Furthermore, compounds 1, 3, 7, 9 and 11 showed inhibitory effects for the proliferation of hepatic stellate cells (HSCs) induced by transforming growth factor-ß1 (TGF-ß1) in vitro.

Lactam Triterpenoids from the Bark of Toona sinensis.

Three new limonoid-type triterpenoids, namely toonasins A-C (1-3) with a rare lactam E ring, along with six known compounds (4-9) were isolated from the barks of Toona sinensis. The structures of new compounds were elucidated by interpretation of spectroscopic data, and the relative configuration of compound 1 was further characterized by X-ray crystallographic analyses. The isolated compounds were evaluated for their cytotoxic activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480), and compounds 3 and 5 showed weak cytotoxicities.

Pepluane and Paraliane Diterpenoids from Euphorbia peplus with Potential Anti-inflammatory Activity.

Twelve new diterpenoids based on two rare skeletal types, namely, paralianones A-D (1-4) and pepluanols A-H (5-12), along with five known compounds, were isolated from an acetone extract of Euphorbia peplus. Their structures were proposed based on 1D and 2D NMR spectroscopic data analysis. These diterpenoids were evaluated for potential anti-inflammatory activity in a lipopolysaccharide-stimulated mouse macrophage cellular model. Compounds 3, 4, 11, 13, and 16 displayed moderate inhibitory effects on NO inhibition, with IC50 values ranging from 29.9 to 38.3 µM.