Iridal-type Triterpenoids Research Articles

IRIDAL-TYPE TRITERPENOID DERIVATIVES AND ISOFLAVONOIDS FROM BELAMCANDA CHINENSIS ROOTS

Belamcanda chinensis (L.) DC is a popular ornamental and medicinal plant belonging to the Iridaceae family. Its rhizomes were used in Vietnamese traditional medicine for the treatment of inflammation and respiratory disorders, such as asthma, tonsillitis, coughing, and pharyngitis. In this study, four iridal-type triterpenoid derivatives (1–4) and four isoflavonoids (5–8) have been isolated from the methanol extract of Belamcanda chinensis roots. The structures of the isolated compounds were determined using NMR spectroscopic analysis combined with comparison with the literature and were found to be isoiridogermanal (1), iridobelamal A (2), 16-O-acetylisoiridogermanal (3), 16-O-acetyliridobelamal A (4), irigenin (5), irisflorentin (6), irilin D (7), and tectoridin (8).

Cytotoxic Compounds from Belamcanda chinensis (L.) DC Induced Apoptosis in Triple-Negative Breast Cancer Cells.

Four compounds (1, 5, 7, and 8) were first isolated from the genus Belamcanda Adans. nom. conserv., and six known compounds (2-4, 6, 9, and 10) were isolated from the rhizome of Belamcanda chinensis (L.) DC. Their structures were confirmed by spectroscopic data. Herein, compounds 1-10 were rhapontigenin, trans-resveratrol, 5,7,4'-trihydroxy-6,3',5'-trimethoxy-isoflavone, irisflorentin, 6-hydroxybiochannin A, iridin S, pinoresinol, 31-norsysloartanol, isoiridogermanal, and iristectorene B, respectively. All compounds were evaluated for their antiproliferative effects against five tumor cell lines (BT549, 4T1, MCF7, MDA-MB-231, and MDA-MB-468). Among them, compound 9 (an iridal-type triterpenoid) showed the highest activity against 4T1 and MDA-MB-468 cells. Further studies displayed that compound 9 inhibited cell metastasis, induced cells cycle arrest in the G1 phase, exhibited significant mitochondrial damage in 4T1 and MDA-MB-468 cells including excess reactive oxygen species, decreased mitochondrial membrane potential, and induced 4T1 and MDA-MB-468 cell apoptosis for the first time. In summary, these findings demonstrate that compound 9 exerts promising potential for triple-negative breast cancer treatment and deserves further evaluation.

New iridal-type triterpenoid analogues with 6/5/6-fused carbon skeleton from the rhizomes of Belamcanda chinensis

Five new iridal-type triterpenoid derivatives with 6/5/6 tricyclic ring skeleton (1–5) were obtained from the rhizomes of Belamcanda chinensis. Their structures were determined on the basis of detailed spectroscopic data and ECD calculation. Compounds 1–5 possessed the same 6/5/6-fused carbon skeleton as Belamchinenin A, which further enriched this kind of iridals. In vitro bioassay, compounds 2 and 3 exhibited 51.95 and 54.52% inhibitory activities, respectively, against Fe2+/cysteine-induced liver microsomal lipid peroxidation at a concentration of 10 μM. A putative biogenetic pathway for compounds 1–5 was proposed.

Iridal-Type Triterpenoids Displaying Human Neutrophil Elastase Inhibition and Anti-Inflammatory Effects from Belamcanda chinensis.

The aim of this study is to explore anti-inflammatory phytochemicals from B. chinensis based on the inhibition of pro-inflammatory enzyme, human neutrophil elastase (HNE) and anti-inflammatory activities in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage. Three stereoisomers of iridal-type triterpenoids (1–3) were isolated from the roots of B. chinensis and their stereochemistries were completely identified by NOESY spectra. These compounds were confirmed as reversible noncompetitive inhibitors against HNE with IC50 values of 6.8–27.0 µM. The binding affinity experiment proved that iridal-type triterpenoids had only a single binding site to the HNE enzyme. Among them, isoiridogermanal (1) and iridobelamal A (2) displayed significant anti-inflammatory effects by suppressing the expressions of pro-inflammatory cytokines, such as iNOS, IL-1β, and TNF-α through the NF-κB pathway in LPS-stimulated RAW264.7 cells. This is the first report that iridal-type triterpenoids are considered responsible phytochemicals for anti-inflammatory effects of B. chinensis.

Iridal-Type Triterpenoids with a Cyclopentane Unit from the Rhizomes of Belamcanda chinensis.

Ten new iridal-type triterpenoid derivatives, polycycloiridals K-T (1-10), with a cyclopentane moiety originating from the cyclization of the homofarnesyl side chain were isolated from the rhizomes of Belamcanda chinensis. Their structures were established by spectroscopic data, a single-crystal X-ray diffraction analysis, TDDFT quantum mechanical calculations, and chemical derivatization. Compounds 2 and 10 exhibited 33.4% and 32.9% inhibitory activities, respectively, against PTP1b (protein tyrosine phosphatase) at a concentration of 10 μM. A putative biosynthetic pathway is proposed.

Rearranged iridal-type triterpenoids from Iris tectorum

Three new iridal-type triterpenoids (1–3) featuring a rearranged homofarnesylside chain were isolated from the rhizomes of Iris tectorum. Compounds 2 and 3 were found to be a pair of epimers. Their structures were elucidated on the basis of comprehensive spectroscopic analysis. A possible biosynthetic pathway for them was postulated. Moreover, the mixture of compounds 2 and 3 exhibited moderate neuroprotective activity against serum deprivation-induced PC12 cell death.

Two unprecedented nor-iridal esters from Iris wattii Baker and their bioactivities

Two unprecedented C16nor-iridal esters (1―2), named iriwattin A (1) and iriwattin B (2), along with one known iridal ester and two known iridal-type triterpenoids were isolated from Iris wattii Baker by comprehensive chromatographic methods. The structures of 1―2 were elucidated by interpretation of extensive spectroscopic analyses (1D and 2D NMR, ESI- and HRESI-MS). The two new compounds have interesting nor-iridal skeleton that are previously undescribed, and therefore constitute a new class of C16nor-iridal esters. Furthermore, compounds 1 and 2 were tested for their in vitro inhibitory activities against α-glucosidase and protein tyrosine phosphatase 1B (PTP1B). Compound 1 showed a certain degree of inhibitory effect on the PTP1B enzyme, with 52.0% inhibition.

Two new iridal-type triterpenoids from Iris forrestii

Two new iridal-type triterpenoids, named forrestins A and B (1 and 2), were isolated from Iris forrestii Dykes by comprehensive chromatographic methods. The structures of 1 and 2 were elucidated by interpretation of extensive spectroscopic data including 1D and 2D NMR and HRESIMS.

New iridal-type triterpenoid derivatives with cytotoxic activities from Belamcanda chinensis

Eight new iridal-type triterpenoid derivatives, including two noriridals with ether bridge (1–2); two iridals lactone (3–4), four monocyclic iridals (5–8), together with five known iridals (9–14) were identified from the rhizome of Belamcanda chinensis. Their structures were elucidated on the basis of comprehensive spectroscopic methods and electronic circular dichroism (ECD) calculations. Bioassay results showed that belamcanoxide B (1) exhibited moderated cytotoxic activities against HCT-116 and MCF-7 cell lines with IC50 values of 5.58 and 3.35 μM.

Iridal-type triterpenoids with anti-HBV activity from Iris confusa

Five new iridal-type triterpenoids, named as spirioiridoconfal A-C (1–3), isobelamcandal (4) and 17-hydroxyl-27-ene-iridal (5), along with one known compound (6) were isolated from the whole plant of Iris confusa. Their structures were determined by extensive spectroscopic analyses. Compounds 3 and 6 showed moderate activity against HBV DNA replication in vitro with the IC50 value at 84.6 ± 24.9 (SI = 2.1) and 58.6 ± 6.1 (SI = 12.7) μM relatively.

Iritectol G, a novel iridal-type triterpenoid from Iris tectorum displays anti-epileptic activity in vitro through inhibition of sodium channels

Iritectol G, a novel iridal-type triterpenoid containing an uncommon tetrahydrofuran moiety, was isolated from the rhizomes of Iris tectorum. The structure was elucidated by comprehensive spectroscopic analysis. Iritectol G inhibited spontaneous and 4-aminopyridine-evoked calcium oscillations in primary cultured neocortical neurons with IC50 values of 8.2μM and 12.5μM, respectively. Further electrophysiological study demonstrated that iritectol G preferred to interact with inactivated state of voltage-gated sodium channel with an IC50 value of 7.0μM. These data demonstrated that iritectol G was a novel sodium channel inhibitor.

The unprecedented iridal lactone and adducts of spiroiridal and isoflavonoid from Belamcanda chinensis

Five novel iridal-type triterpenoid derivatives have been isolated from the rhizomes of Belamcanda chinensis, along with five known compounds. Their structures were elucidated by extensive spectroscopic analysis.

Polycycloiridals with a Cyclopentane Ring from Iris tectorum.

Six new iridal-type triterpenoids containing an unprecedented cyclopentane ring, polycycloiridals E-J (1-6), were isolated from a large-scale re-extraction of Iris tectorum. A possible biosynthesis pathway is postulated. The known spirioiridotectal D (7) was also obtained in the current investigation, and its structure was unequivocally defined using X-ray diffraction data. Compound 7 suppressed LPS-activated NO production in the BV2 cell line with an IC50 value of 0.54 μM.

<i>Belamcanda chinensis</i> (l.) Dc: Ethnopharmacology, phytochemistryand pharmacology of an important traditional Chinese medicine

Background: Belamcanda chinensis (L.) DC (Iridaceae), a widely used traditional Chinese medicine known as She Gan (Chinese: 射干), is a flowering perennial herb native to East Asia. For thousands of years in China, the rhizome of Belamcanda chinensis has been used to treat inflammation, oxyhepatitis, mumps, acute mastitis, and asthma, as well as throat disorders such as cough, tonsillitis and pharyngitis. Belamcanda chinensis is now listed in the Pharmacopoeia of the People’s Republic of China. The present paper reviews the advancements in the investigation of botany, ethnopharmacology, phytochemistry, pharmacology and toxicology of Belamcanda chinensis . Materials and Methods: Information on Belamcanda chinensis was collected from scientific journals, books, theses and reports via library and electronic search (PubMed, CNKI, Elsevier, ACS, Google Scholar, Baidu Scholar,Web of Science and Science Direct). Results: A number of chemical compounds have been isolated from Belamcanda chinensis , and the major isolated compounds have been identified as isoflavonoids, flavonoids and iridal-type triterpenoids. Among these active compounds, the effects of tectoridin and tectorigenin have been widely investigated. The primary active components in Belamcanda chinensis possess a wide range of pharmacological activities, including anti-inflammatory, anti-oxidative, anti-tumour, anti-alcohol injury, cardiovascular and oestrogenic activities. Conclusions: As an important traditional Chinese medicine, Belamcanda chinensis has been demonstrated to have marked bioactivity, especially in the respiratory system and as an oestrogenic and hepatoprotective agent. This activity is related to its traditional use and provides opportunities for the development of novel drugs and therapeutic products for various diseases. However, the toxicity of Belamcanda chinensis will require further study, and more attention should be devoted to its better utilization. Keywords: Belamcanda chinensis ; Ethnopharmacology; Phytochemistry; Pharmacology; Toxicology

BELAMCANDA CHINENSIS (L.) DC: ETHNOPHARMACOLOGY, PHYTOCHEMISTRY AND PHARMACOLOGY OF AN IMPORTANT TRADITIONAL CHINESE MEDICINE

Background: Belamcanda chinensis (L.) DC (Iridaceae), a widely used traditional Chinese medicine known as She Gan (Chinese: 射干), is a
 flowering perennial herb native to East Asia. For thousands of years in China, the rhizome of Belamcanda chinensis has been used to treat
 inflammation, oxyhepatitis, mumps, acute mastitis, and asthma, as well as throat disorders such as cough, tonsillitis and pharyngitis. Belamcanda
 chinensis is now listed in the Pharmacopoeia of the People’s Republic of China. The present paper reviews the advancements in the investigation
 of botany, ethnopharmacology, phytochemistry, pharmacology and toxicology of Belamcanda chinensis.
 Materials and Methods: Information on Belamcanda chinensis was collected from scientific journals, books, theses and reports via library and
 electronic search (PubMed, CNKI, Elsevier, ACS, Google Scholar, Baidu Scholar,Web of Science and Science Direct).
 Results: A number of chemical compounds have been isolated from Belamcanda chinensis, and the major isolated compounds have been
 identified as isoflavonoids, flavonoids and iridal-type triterpenoids. Among these active compounds, the effects of tectoridin and tectorigenin
 have been widely investigated. The primary active components in Belamcanda chinensis possess a wide range of pharmacological activities,
 including anti-inflammatory, anti-oxidative, anti-tumour, anti-alcohol injury, cardiovascular and oestrogenic activities.
 Conclusions: As an important traditional Chinese medicine, Belamcanda chinensis has been demonstrated to have marked bioactivity, especially
 in the respiratory system and as an oestrogenic and hepatoprotective agent. This activity is related to its traditional use and provides
 opportunities for the development of novel drugs and therapeutic products for various diseases. However, the toxicity of Belamcanda chinensis
 will require further study, and more attention should be devoted to its better utilization.

Iridal-Type Triterpenoids with Neuroprotective Activities from Iris tectorum

Six novel iridal-type triterpenoids with a previously unreported 3,6-dihydro-2H-pyran moiety, named spirioiridotectals A-F (1-6), were isolated from the ethanol extract of the rhizomes of Iris tectorum. Their structures were elucidated on the basis of extensive spectroscopic analysis. Furthermore, in in vitro bioactivity assays, compounds 1, 2, and 6 exhibited neuroprotective activities against serum-deprivation-induced PC12 cell damage.

Chemical Diversity of Iridal-Type Triterpenes in Iris Delavayi Collected in Yunnan Province of China

From Iris delavayi collected in the northwestern Yunnan Province of China, eight iridal-type triterpenoids were isolated, three of which were new. Both 2(7)Z- and 2(7)E-iridals were isolated in about equal amounts from the sample collected at Laojunshan, while only 2(7)Z-iridals were isolated from samples collected in Shangrila area, indicating the presence of chemical diversity in the species.

ChemInform Abstract: A New Dimeric Iridal Triterpenoid from Belamcanda chinensis with Significant Molluscicide Activity

Abstract[i.e.

Isolation and structure determination of triterpenes from Iris tectorum

Four iridal-type triterpenoids, two of which were new compounds, have been isolated from rhizomes of Iris tectorum Maxim. Their structures were determined by 1D and 2D NMR spectroscopy and ESI-MS spectrometry. The compounds were identified as the iritectols A and B, and the known iridobelamal A and isoiridogermanal. The presence of epoxide and tetrahydrofuran functions are not common in previously isolated iridal-type triterpenoids.

Iridal-type triterpenoids with ichthyotoxic activity from belamcanda chinensis

Ichthyotoxic activity-guided fractionation of the hexane and ether extracts of Belamcanda chinensis (Iridaceae) has resulted in the isolation of eleven iridal-type triterpenoids including six new compounds, 3-O-tetradecanoyl-16-O-acetylisoiridogermanal (4), 3-O-decanoyl-16-O-acetylisoiridogermanal (5), belachinal (7), anhydrobelachinal (9), epianhydrobelachinal (10), and isoanhydrobelachinal (11). Structures of the new iridals were determined by spectral and chemical methods. The absolute configuration of isoiridogermanal (1) at C-16 was determined to be R by the modified Mosher's method. Of these compounds, 16-O-acetylisoiridogermanal (3), 7, and spiroiridal (12) exhibited potent ichthyotoxic activity against killie-fish (Oryzias latipes).