Liang Xiong

Chengdu University Of Traditional Chinese Medicine · School of Pharmacy

To explore the sesquiterpenoids in Curcuma longa L. and their activity related to anti-atherosclerosis. The chemical compounds of the rhizomes of C. longa were separated and purified by multiple chromatography techniques. Their structures were established by a variety of spectroscopic experiments. The absolute configurations were determined by comp...

Four novel indane derivatives, anisotindans A-D (1-4), were isolated from the roots of Anisodus tanguticus. Their structures were established using comprehensive spectroscopic analyses, and their absolute configurations were determined by electronic circular dichroism (ECD) calculations and single-crystal X-ray diffraction analyses. Anisotindans C...

In this phytochemical study, a novel arborinane-type triterpenoid glycoside (1) and three known megastigmanes (2–4) were isolated from the dried roots of Cyathula officinalis K.C.Kuan. The structures of these compounds were elucidated using NMR spectroscopy. This is the first report of arborinane-type triterpenoids in the Amaranthaceae family. Amon...

This study investigated the chemical components from the florets of Carthamus tinctorius. Five compounds were isolated from C. tinctorius by column chromatography with silica gel and toyopearl HW-40 F, preparative thin-layer chromatography(TLC), and semi-preparative reverse phased high performance liquid chromatography(RP-HPLC). Their structures we...

Perilla frutescens (L.) Britt. (Labiatae), a medicinal plant, has been widely used for the therapy of multiple diseases since about 1800 years ago. It has been demonstrated that the extracts of P. frutescens exert significant anti-inflammatory effects. In this research, two pairs of 7,7′-cyclolignan enantiomers, possessing a cyclobutane moiety, (+)...

Two new sesquiterpenoids, curcumanes E (1) and F (2), were isolated from the rhizome of Curcuma longa, and their structures and absolute configurations were examined using extensive spectroscopic analyses and ECD calculations. Interestingly, compounds 1 and 2 are diastereoisomers possessing a rare sesquiterpenoid skeleton that has been reported onl...

Pocahemiketone A, a novel sesquiterpenoid possessing a unique spirocyclic skeleton with a hemiketal endoperoxide unit, was isolated from the essential oil of Pogostemon cablin. Its structure was determined by spectroscopic methods and single-crystal X-ray diffraction analyses. Pocahemiketone A exhibits a significant neuroprotective effect against A...

Six pairs of enantiomeric phthalide dimers (1-6) were isolated from the rhizomes of Ligusticum chuanxiong. Their structures and absolute configurations were elucidated by NMR spectroscopy, X-ray diffraction analyses, and electronic circular dichroism calculations. Compounds (+)-1 and (-)-1 are new phthalide dimers, featuring two classes of monomeri...

Macroporous resin chromatography, silica gel column chromatography, preparative thin layer chromatography, and semi-preparative high performance liquid chromatography were performed to isolate two compounds from the acid extract of the lateral roots of Aconitum carmichaelii: a new 9-phenylisoquinoline alkaloid(1) and a known pavine alkaloid(2). The...

Lung cancer continues to be the world’s leading cause of cancer death and the treatment of non-small cell lung cancer (NSCLC) has attracted much attention. The tubers of Bletilla striata are regarded as “an excellent medicine for lung diseases” and as the first choice to treat several lung diseases. In this study, seventeen phenanthrene derivatives...

Ethnopharmacological relevance Curcuma longa L. (Zingiberaceae) is a known blood-activating and stasis-removing traditional Chinese medicine and has relevant pharmacological properties. The rhizomes of C. longa have been used for the treatment of cardiovascular disease (CVD) in China. Previous studies have shown that sesquiterpenoids from C. longa...

Breast cancer ranks as the leading cause of death in lethal malignancies among women worldwide, with a sharp increase of incidence since 2008. Triple negative breast cancer (TNBC) gives rise to the largest proportion in breast cancer-related deaths because of its aggressive growth and rapid metastasis. Hence, searching for promising targets and inn...

Three undescribed isoindoline alkaloids, (+)-(R)-3-butyl-3-ethoxyisoindolin-1-one, (+)-(3S,6S,7R)-3-butyl-6,7-dihydroxy-3-methoxy-4,5,6,7-tetrahydroisoindolin-1-one, and (−)-(3R,6S,7R)-3-butyl-6,7-dihydroxy-3-methoxy-4,5,6,7-tetrahydroisoindolin-1-one, along with nine known phthalides were isolated from a water decoction of the rhizomes of Ligustic...

Two new neolignans and one new lignan (1–3) were obtained from the roots of Paeonia lactiflora. Their structures were unambiguously elucidated based on extensive spectroscopic analysis, single-crystal X-ray crystallography, and the calculated and experimental electronic circular dichroism (ECD) spectra. Compound 1 was a racemic mixture and successf...

Bisabolane-type sesquiterpenoids, a class of monocyclic sesquiterpenoids, are widely distributed in nature and have a variety of biological activities. To provide a reference for the further research and development of these compounds, the phytochemical and biological properties of natural bisabolane-type sesquiterpenoids (356 compounds in total) i...

Purpose: Perilla frutescens (L.) Britt., a traditional edible-medicinal herb in China, has been used to treat cardiovascular and cerebrovascular (cardio-cerebrovascular) diseases for thousands of years. However, knowledge of the mechanisms underlying the effects of essential oil from P. frutescens (EOPF) in the treatment of cardio-cerebrovascular...

Anisotanols A–D (1–4), four new compounds possessing an unprecedented sesquiterpenoid skeleton with a congested tricyclic 6/3/5 ring system, were obtained from Anisodus tanguticus. Their structures were elucidated by comprehensive spectroscopic techniques, and the absolute configurations were confirmed via ECD calculations and single-crystal X-ray...

Twelve tetrahydrofuran lignans (1–12), including six new compounds (1–6), were isolated from the 70% EtOH extract of the fruits of Leonurus japonicus. Spectroscopic analyses and ECD and OR calculations were used to determine their structures. Compounds 5 and 6 were unusual alkaloidal lignans with a butyrolactam unit. Based on the beneficial effects...

Five previously undescribed polyacetylene glucosides, namely, four C10- and one C14-acetylenes, together with three known analogues, were isolated from the florets of Carthamus tinctorius L. The structures of these novel compounds were elucidated to be (5R)-5-acetoxy-8,10,12-tetradecatriyne-1-O-β-D-glucopyranoside, (2Z)-decaene-4,6,8-triyne-1-O-β-D...

Ethnopharmacological relevance Dysmenorrhea is one of the most common gynecological problems among menstruating females. Blood-activating and stasis-resolving herbs (BASRHs) have been employed to be the first choice for treating dysmenorrhea in China. Especially, the essential oils of some BASRHs have been confirmed to play important roles in the t...

Lanostane triterpenoids are thought to be the main underlying preclinical antitumor secondary metabolites of the genus Ganoderma. To further explore the potential cytotoxic triterpenoids from Ganoderma luteomarginatum, the ethyl acetate soluble fraction of 95% ethanolic extract was systematically studied. Twelve previously undescribed lanostane-typ...

Ethnopharmacological relevance Many studies have shown the beneficial effects of aconite water-soluble alkaloid extract (AWA) in experimental models of heart disease, which have been ascribed to the presence of aconine, hypaconine, talatisamine, fuziline, neoline, and songorine. This study evaluated the effects of a chemically characterized AWA by...

Ischemic diseases, such as ischemic heart diseases and ischemic stroke, are the leading cause of death worldwide. Angiogenic therapy is a wide-ranging approach to fighting ischemic diseases. However, compared with anti-angiogenesis therapy for tumors, less attention has been paid to therapeutic angiogenesis. Recently, Traditional Chinese medicine (...

Fuzi, a well-known traditional Chinese medicine developed from the lateral roots of Aconitum carmichaelii Debx., has been widely used for the treatment of heart failure. In order to search for active compounds from Fuzi, a phytochemical study was performed, which resulted in the isolation of 14 aminoalcohol-diterpenoid alkaloids, including one new...

Rhizome Chuanxiong (RCX), the dried rhizomes of Ligusticum striatum DC., is a geoauthentic TCM herb distributed in Sichuan province of China that possesses efficacy in promoting blood circulation, removing blood stasis and alleviating pain. Rhizome Chuanxiong total alkaloids (RCXTAs) are one of the major characteristic constituents of RCX with the...

Stachydrine is a main active component of Leonurus japonicus (Chinese motherwort), which has traditionally been used to promote postpartum recovery and alleviate myocardial and cerebral ischemic injuries due to its pro-angiogenic effect. Our prior study demonstrated that stachydrine increased angiogenesis in zebrafish embryos, but its pro-angiogeni...

Two new amides (1 and 2) and four known analogues (3–6) were isolated from the roots of Anisodus tanguticus (Maxim.) Pascher. Their structures were determined by extensive spectroscopic analyses. The absolute configuration of compound 1 was determined by comparison of the calculated optical rotation (OR) value with the experimental OR value. All kn...

Seven pairs of new enantiomeric sesquiterpenoids, (+)/(–)-phaeocauline A−G [(+)/(–)-1−7], were isolated from the rhizomes of Curcuma phaeocaulis by chiral HPLC separation. Their structures, including absolute configurations, were determined by spectroscopic analyses and ECD data. The isolates were assessed for vasorelaxant, anti-platelet aggregativ...

Triple-negative breast cancer (TNBC) is a subtype of breast cancer that accounts for the largest proportion of breast cancer-related deaths. Thus, it is imperative to search for novel drug candidates with potent anti-TNBC effects. Recent studies suggest that isoliquiritigenin (ISL) can significantly suppress the growth, migration, and invasion of b...

Epithelial-to-mesenchymal transition (EMT) in cancer cells could convert epithelial-like cells to mesenchymal-like cells, resulting in the increased capacity of migration and invasion of cancer cells, and is an essential step in triple negative breast cancer (TNBC) development. Recent reports exert that these EMT-activated TNBC cells are more resis...

Fuzi is a well-known traditional Chinese medicine developed from the lateral roots of Aconitum carmichaelii Debx. It is rich in alkaloids that display a wide variety of bioactivities, and it has a strong cardiotoxicity and neurotoxicity. In order to discriminate the geographical origin and evaluate the quality of this medicine, a method based on hi...

Omphalia lapidescens Schroet. is a medicinal macrofungus in China that has shown good antitumor activity in recent research. To explore the potential cytotoxic compounds from O. lapidescens, the ethyl acetate soluble fraction of a 95% ethanol extract with cytotoxic activity was phytochemically investigated. A new tetranorlanostane triterpenoid (1)...

A pair of new alkaloid enantiomers [(+)- and (−)-1] as well as a pair of known enantiomeric analogues [(+)- and (−)-2] were isolated from the fruiting bodies of Ganoderma luteomarginatum. Their planar structures were determined by extensive spectroscopic analyses. The absolute configurations were established by comparison of the experimental and ca...

The rattans of Spatholobus suberectus Dunn are a traditional Chinese medicine activating blood circulation and removing stasis. They have often been used for the traditional Chinese medicinal treatment of breast cancer in modern China. In this study, four novel isoflavanes (1–3 and 5) and four known analogues (4 and 6–8) were isolated from an ethan...

Leonurus japonicus Houtt. is a traditional medicinal herb with significant effects; dating back more than 1800 years, it is widely used in Asia. In traditional Chinese medicine, it is essential in the treatment of menstrual and delivery disorders caused by blood stasis, such as dysmenorrhea, amenorrhea, and postpartum hemorrhage. In the last three...

A new seco-cadinane sesquiterpenoid (curcumane C, 1) and a pair of new nor-bisabolene enantiomers [(+)- and (-)-curcumane D, 2a and 2b] were isolated from C. longa. Compound 1 possesses an unusual 4,5-seco-cadinane skeleton with a tetrahydrophthalide moiety, while 2a and 2b contain an unusual 15-nor-bisabolene skeleton with a chromone core. All com...

Three new sesquiterpenoids, (+)-(1R,2S,3R,4S,5R,6S,9R)-3,11,12-trihydroxypicrotoxane-2(15)-lactone (1), (-)-(1S,2R,3S,4R,5S,6R,9S,12R)-3,11,13-trihydroxypicrotoxane-2(15)-lactone (2), and (+)-(1R,5R,6S,8R,9R)-8,12-dihydroxy-copacamphan-3-en-2-one (3), together with five known compounds, were isolated from the n-butanol soluble fraction of a 95% EtO...

Ethnopharmacological relevance Migraine is a prevalent, complex, painful, and disabling neurovascular disorder that places an enormous social and economic burden on patients. Rhizome Chuanxiong (RCX), the dried rhizomes of Ligusticum striatum DC., has been widely used in the clinic for the treatment of migraine for centuries in China. Total alkaloi...

Three new triterpenoids (1, 4, and 5), together with 17 known analogues, were isolated from the ethyl acetate soluble portion of the EtOH extract of Leonurus japonicus Houtt. Their structures were determined by spectroscopic analysis. All known triterpenoids were isolated from the genus Leonurus for the first time. Among them, triterpenoids 2–3, 9–...

The Lamiales order presents highly varied genome sizes and highly specialized life strategies. Patchouli, Pogostemon cablin (Blanco) Benth. from the Lamiales, has been widely cultivated in tropical and subtropical areas of Asia owing to high demand for its essential oil. Here, we generated ~681 Gb genomic sequences (~355X coverage) for the patchoul...

Three new neolignans (1−3), including one 2,4′-epoxy-8,5′-neolignan and two 2,4′-epoxy-8,3′-neolignan glycosides, were isolated from the EtOAc-soluble portion of the water decoction of Penthorum chinense Pursh. Their structures and absolute configurations were elucidated by comprehensive analysis of spectroscopic data and electronic circular dichro...

Lanostane triterpenoids are major metabolites of macrofungi from the genus Ganoderma and possess enormous substitution diversity and remarkable biological activities, especially anticancer, antioxidant, and anti-inflammatory effects. The present phytochemical investigation resulted in the isolation of nine undescribed lanostane triterpenoids and fi...

Seven novel guaiane sesquiterpenoids (1–7) and three known seco-guaianes were isolated from the volatile oil of Pogostemon cablin. Their structures including absolute configurations were determined by spectroscopic analyses, a modified Mosher’s method, and X-ray diffraction and ECD data. The results indicated that the ECD Cotton effects arising fro...

Seventeen polyoxygenated Δ²²-ergosteroids (1–17), including two new compounds (1 and 15), were isolated from the ethyl acetate soluble fraction of a 95% ethanol extract of Omphalia lapidescens Schroet. According to the oxidation degree and the oxidation positions of A and B rings, the isolates could be divided into three subtypes: 3,5,6-trioxygenat...

There is growing evidence that motherwort (Leonurus japonicus Houtt.), and Chinese patent medicines derived from motherwort, alleviate postpartum uterine subinvolution, as well as the effects on myocardial and cerebral ischemic injuries. We hypothesized that these beneficial effects of motherwort may be related to angiogenesis. To test this hypothe...

Six sesquiterpenoids including three previously undescribed ones (1–3) were isolated from the essential oil of the aerial parts of Pogostemon cablin. Their structures were determined to be (+)-(1S,4R,6S,7R,10S)-1-hydroxycadinan-12-ene-5-one (1), 11-dehydroxy-cinnamosin A (2), and 1-methoxy-senecrassidiol (3) by extensive spectroscopic analyses. Thi...

Introduction: Bulbus fritillariae cirrhosae (known as Chuān bèi mǔ in China, BFC) contain fritillaria steroidal alkaloids as the bioactive ingredients and are widely used as traditional Chinese medicine for the treatment of cough and phlegm. Due to limited wild resources, the cultivated species are becoming predominantly used in Chinese traditiona...

Two new (1-2) and six known (3-8) nucleoside alkaloids were isolated from the rhizomes of Ligusticum striatum DC. Compounds 1 and 2 (liguadenosines A and B) were unusual N-10 substituted adenosine derivatives. Their structures were elucidated by extensive spectroscopic analyses and ECD calculation. Most of them significantly inhibited the abnormal...

Breast cancer is one of the most frightful causes of death among females worldwide. Accumulating evidence attached the importance of microRNAs negative regulation to tumorigenesis in breast cancer, suggesting novel cancer therapies targeting microRNAs modulation. Recent studies demonstrated that isoliquiritigenin could inhibit breast cancer cells p...

Four new lupane triterpenoid saponins, along with one known lupane and eight hederagenin saponins, were isolated from the EtOH extract of the buds of Lonicera similis Hemsl. The structures of the new compounds were established as 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl 23-hydroxybetulinic acid 28-O-β-D-glucopyranosyl ester (lonisimilioside...

The crude extract and some Chinese patented medicines of Leonurus japonicus Houtt. have been proven to affect the uterine smooth muscle. L. japonicus injection is widely used in obstetric departments in China for treating postpartum hemorrhage caused by uterine inertia. Bioassay-guided isolation of the 95% EtOH extract of L. japonicus yielded four...

Objective To investigate the chemical constituents of the rhizomes of Ligusticum chuanxiong and discuss the significance of first discovery of ginsenosides from the plant. Methods The compounds were isolated and repeatedly purified by column chromatographies such as macroperous resin, Sephadex LH-20, silica gel, and preparative TLC as well as semi-...

Ethnopharmacological relevance: The aerial parts of Pogostemon cablin (Blanco) Benth. for the treatment of cardiodynia have been documented in Mingyi Bielu of late Han Dynasty, in addition to that the Ca(2+) antagonized activities of P. cablin and its critically pharmacological ingredient patchouli alcohol (PA) were reported previously. Aim of th...

Five picrotoxane sesquiterpenoids belonging to the unusual dendrobine-type (1 and 4) and the picrotoxinin-type (2, 3, and 5) were isolated from the stems of Dendrobium nobile Lindl. Their structures were established by spectroscopic analyses and physical properties. Compound 1 was a new dendrobine analogue. Although the planar structure of 2 and 3...

Pocahemiketals A and B (1 and 2), two novel hemiketal sesquiterpenoids with unprecedented skeletons, were isolated from the essential oil of the aerial parts of Pogostemon cablin. In addition to a bicyclo[3.2.1]-carbon core, 1 and 2 possessed a hemiketal α,β-unsaturated-γ-lactone moiety. Their structures were determined by extensive spectroscopic a...

Objective: To study the chemical constituents of Penthorum chinense. Methods: The compounds were isolated and repeatedly purified by column chromatography over macroperous resin, polyamide, silica gel, and Sephadex LH-20, preparative TLC, and preparative RP-HPLC. Their structures were elucidated by physicochemical properties and spectral analyses....

Angelica sinensis contains a large amount of essential oil (angelica oil), which is rich in phthalide derivatives with a lot of bioactivities. In vitro activity screening of angelica oil from the roots of A. sinensis found that it had concentration-dependent effect on glutamate-induced injury in PC12 cells. Further phytochemical investigation on th...

Essential oil is the low polar and volatile components distilled or extracted from Ligusticum chuanxiong, the dry root of perennial herb L. chuanxiong, which has proven to be one of the main biological active ingredients of L. chuanxiong. Studies suggested that essential oil of L. chuanxiong mainly contains phthalide, terpene alcohols and fatty aci...

Breast cancer is a malignant disease to treat among female worldwide due to its high capability to metastasize and mutate. Epithelial-mesenchymal transition is one of the essential processes involved in the metastatic capacity of breast cancer. In the recent time, the studies demonstrate that microRNAs, a kind of small non-coding RNA molecules, cou...

Pogostemon cablin (Blanco) Benth. is an important medicinal plant; however, its molecular biology remains largely unexplored. Here, we report the results of whole transcriptome-wide analyses of P. cablin using next-generation sequencing technology. In the present study, we generated 108,996 unigenes using RNA sequencing data. Among these unigenes,...

Ethnophamacological relevance: Pogostemon cablin is a medicinal herb widely used to treat gastrointestinal diseases in many Asian countries. Pogostone is an important constituent of Pogostemon cablin, and possesses various bioactivitys. In this study, we performed to investigate the anti-colorectal tumor property of Pogostone by inducing aurophagy...

Pogostemon cablin, the natural source of patchouli alcohol, is an important herb in the Lamiaceae family. Here, we present the entire chloroplast genome of P. cablin. This genome, with 38.24% GC content, is 152,460 bp in length. The genome presents a typical quadripartite structure with two inverted repeats (each 25,417 bp in length), separated by...

Pogostemon cablin (Blanco) Benth. (Patchouli) is an important traditional Chinese medicinal plant that has both essential oil value and a broad range of therapeutic effects. Here we report the first de novo assembled 1.15-Gb draft genome sequence for P. cablin from next-generation sequencing technology. Our assembly, with a misassembly rate of <4 b...

Objective: To investigate the antibacterial activity of patchouli alcohol (PA) against 127 bacteria strains, including the common bacteria and drug-resistant bacteria strains both in the in vitro and in vivo tests. Methods: For the in vitro trial, the antibacterial property of PA against 107 Gram-positive and 20 Gram-negative bacteria strains wa...

isolation, structure elucidation and vasorelaxant activity

Five isoliquiritigenin analogues, including a new methylene-bridged bischalcone (1), were isolated from Spatholobus suberectus. Cytotoxicity screening of these isolates and several synthetic derivatives indicated that the introduction, removal, position modification, or glycosylation of hydroxy groups in isoliquiritigenin did not improve the result...

An architecturally complex spiroketal diterpenoid, leonuketal (1), was isolated from the aerial parts of the plant Leonurus japonicus. This compound possessed an unprecedented tetracyclic skeleton that comprised a bridged spiroketal moiety fused with a ketal-γ-lactone unit. The structure and absolute configuration were determined by spectroscopic a...

Two novel spirostanols, (23S,24R,25S)-18-norspirost-1,4,13-triene-21,23,24-triol-3,15-dione (1) and (23S,24S,25S)-spirost-5-ene-1β,3β,21,23,24-pentaol (2), a new natural product (3), and two known analogues (4 and 5) were isolated from the ethyl acetate-soluble portion of the ethanolic extract of Trillium tschonoskii Maxim. Their structures were el...