Two new sesquiterpene dimers isolated from the roots of Saussurea lappa (Yunmuxiang).

Two new sesquiterpene dimers, lappadimers A and B, were isolated from the roots of Saussurea lappa (Yunmuxiang). Their structures were established on the basis of spectroscopic methods. They were found to have potential anti-inflammatory activity at 10 µM and could reduce LPS-induced NO levels in murine macrophage, with inhibitory rates of 67% and 47%, respectively.

[Advances in studies on structure and pharmacological activities of natural tirucallane-type triterpenoids].

The tirucallane-type triterpenoids, composed of six isoprene units, belong to a group of tetracyclic triterpenoids. Although the naturally-derived tirucallane-type triterpenoids were found in a small amount, the kind of compounds showed various structures, which consist of apo-type, linear said-chain-type and cyclolike said-chain-type and broad bioactivities, such as cytotoxicity, anti-inflammation, antioxidation and anti-plasmin, etc. This paper summarized origins, structures and bioactivities of tirucallane-type triterpenoids in recent ten years. The future research and exploration of tirucallane-type triterpenoids were discussed and prospected.

[Reviews on natural monocyclic sesquiterpenoids and their bioactivities].

Sesquiterpenes are a class of terpenoids composed of three isoprene units( 15 carbons). Sesquiterpenoids possess a variety of different structures,including acyclic sesquiterpenes,monocyclic sesquiterpenoids,bicyclic sesquiterpenoids,tricyclic sesquiterpenoids,tetracyclic sesquiterpenoids and macrocyclic sesquiterpenoids. Among them,a large number of monocyclic sesquiterpenoids were isolated and display extensive bioactivities,such as cytotoxic,antioxidant,anti-inflammatory,antibacterial and other activities. In this review,we summarized the progress about the phytochemistry and biological activities of monocyclic sesquiterpenoids( a total of161 compounds) reported from 2014 to 2018( 5 years),including megastigmanes,monocyclofarnesol-type,bisabolane-type,germacrane-type,and other types of monocyclic sesquiterpenoids. Furthermore,several future research perspectives and development of sesquiterpenoids as potential therapeutic agents were discussed as well.

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.

[Reviews on natural naphthoquinones and their bioactivities].

The naphthaquinones are widely distributed in plants. They are usually in higher plants, but a few of them were also found in microorganisms. There is a lot of research showing that they had multiple pharmaco-activities such as cytotoxic, antioxidant, anti-inflammatory and antibacterial activities, etc. In recent years, they have attracted extensive attention at home and abroad especially in terms of the anti-tumor activity. For further research, 69 new natural naphthoquinones reported in the last five years (2013-2017) were reviewed. They were divided into five major types: simple 1,4-naphthoquinones, furan and pyran naphthoquinones, 1,2-naphthoquinones, naphthohydroquinones and naphthoquinone polymers, which showed cytotoxic, antioxidative, anti-inflammatory and antibacterial biological activities, et al. The research of these compounds in the future was also proposed.

A Chemical Investigation of the Leaves of Morus alba L.

The leaves of Morus alba L. are an important herbal medicine in Asia. The systematic isolation of the metabolites of the leaves of Morus alba L. was achieved using a combination of liquid chromatography techniques. The structures were elucidated by spectroscopic data analysis and the absolute configuration was determined based on electronic circular dichroism (ECD) spectroscopic data and hydrolysis experiments. Their biological activity was evaluated using different biological assays, such as the assessment of their capacity to inhibit the aldose reductase enzyme; the determination of their cytotoxic activity and the evaluation of their neuroprotective effects against the deprivation of serum or against the presence of nicouline. Chemical investigation of the leaves of Morus alba L. resulted in four new structures 1⁻4 and a known molecule 5. Compounds 2 and 5 inhibited aldose reductase with IC50 values of 4.33 µM and 6.0 µM compared with the potent AR inhibitor epalrestat (IC50 1.88 × 10−3 µM). Pretreatment with compound 3 decreased PC12 cell apoptosis subsequent serum deprivation condition and pretreatment with compound 5 decreased nicouline-induced PC12 cell apoptosis as compared with control cells (p < 0.001).

[Constituents isolated from n-butanol extract of leaves of Moringa oleifera].

Seventeen compounds were isolated from n-butanol extract of the leaves of Moringa oleifera, using column chromatography over macroporous resin HP-20,Sephadex LH-20, and ODS. Their structures were identified as two carboline,tangutorid E(1) and tangutorid F(2); three phenolic glycosides,niazirin(3)，benzaldehyde 4-O-α-L-rhamnopyranoside(4) and 4-O-ß-D-glucopyranosidebenzoic acid(5); four chlorogenic acid and derivatives,4-caffeoylquinic acid(6),methyl 4-caffeoylquinate(7),caffeoylquinic acid(8) and methyl caffeoylquinate(9); two nucleosids,uridine(10) and adenosine(11); one flavone,quercetin 3-O-ß-D-glucopyranoside(12); five other types of compounds,phthalimidineacetic acid(13),3-pyridinecarboxamide(14),3,4-dihydroxy-benzoic acid(15),5-hydroxymethyl-2-furancarboxylic acid(16) and 5-hydroxymethyl-2-furaldehyde(17) by the spectral data of ¹H, ¹³C-NMR and MS. Among them,compounds 1-2,7,9-10,16 and 17 were isolated from M. oleifera for the first time.

[Anti-tumor target prediction and activity verification of Ganoderma lucidum triterpenoids].

It has reported that Ganoderma lucidum triterpenoids had anti-tumor activity. However, the anti-tumor target is still unclear. The present study was designed to investigate the anti-tumor activity of G. lucidum triterpenoids on different tumor cells, and predict their potential targets by virtual screening. In this experiment, molecular docking was used to simulate the interactions of 26 triterpenoids isolated from G. lucidum and 11 target proteins by LibDock module of Discovery Studio2016 software, then the anti-tumor targets of triterpenoids were predicted. In addition, the in vitro anti-tumor effects of triterpenoids were evaluated by MTT assay by determining the inhibition of proliferation in 5 tumor cell lines. The docking results showed that the poses were greater than five, and Libdock Scores higher than 100, which can be used to determine whether compounds were activity. Eight triterpenoids might have anti-tumor activity as a result of good docking, five of which had multiple targets. MTT experiments demonstrated that the ganoderic acid Y had a certain inhibitory activity on lung cancer cell H460, with IC50 of 22.4 µmol•L ⁻¹, followed by 7-oxo-ganoderic acid Z2, with IC50 of 43.1 µmol•L ⁻¹. However, the other triterpenoids had no anti-tumor activity in the detected tumor cell lines. Taking together, molecular docking approach established here can be used for preliminary screening of anti-tumor activity of G.lucidum ingredients. Through this screening method, combined with the MTT assay, we can conclude that ganoderic acid Y had antitumor activity, especially anti-lung cancer, and 7-oxo-ganoderic acid Z2 as well as ganoderon B, to a certain extent, had anti-tumor activity. These findings can provide basis for the development of anti-tumor drugs. However, the anti-tumor mechanisms need to be further studied.

Aristolochic acid derivatives from the rhizome of Arisolochia championii.

Four new aristolochic acid derivatives aristchamic A (1), aristchamic B (2), aristochamic C (3a), aristchamic D (3b) and one new aristolactam aristolactam-CV (4), together with 10 known compounds (5-14), were isolated from the rhizomes of Aristolochia championii. Their structures were assigned by detailed analysis of MS and NMR spectroscopic data. All of the isolated compounds were evaluated for their cytotoxic activities against HCT-116, HepG2, BGC-823, NCI-H1650, and A2780 cell. Compound 1 exhibited significant cytotoxic activity against HCT-116, HepG2, BGC-823, and NCI-H1650, with IC50 values of 0.50, 7.37, 2.66, and 0.75µM, respectively.

Three new triterpenoids from Ganoderma theaecolum.

Three new triterpenoids (1-3), together with four known triterpenoids (4-7), were isolated from the fruiting bodies of Ganoderma theaecolum. Their structures were elucidated on the basis of their spectroscopic data and chemical evidence. Compounds 4 and 6 exhibited antitumor activities against H460 cells with IC50 values of 22.4 and 43.1 µM, respectively. And the cytotoxic activities of compounds 4 and 5 against MDA-MB-231 cancer cell lines were assayed with IC50 values of 49.1 and 75.8 µM, respectively.

Apocynin derivatives from Iris tectorum.

Phytochemical investigation of the rhizomes of Iris tectorum resulted in the isolation and characterization of three new apocynin derivatives, apocynin-4-O-ß-D-(6'-O-syringyl)glucopyranoside (1), scrophenoside C-7-ethyl ether (2, 3), together with a new naturally occurring compound but known by synthesis, apocynin-4-O-ß-D-xylopyranoside (4), and five known ones (5-9). Their structures were elucidated on the basis of spectroscopic data interpretation.

Four new compounds from the rhizome of Aristolochia championii.

Three new flavonoid glycosides (1-3) and one new aristololactam N-glycoside (4) were isolated from the rhizome of Aristolochia championii. The structures of compounds 1-4 were elucidated on the basis of their spectroscopic data and chemical evidence (UV, IR, HR-ESI-MS, 1D and 2D NMR). Their structures were determined as 8-(5-formyl-2-furanmethyl)-isorhamentin 3-O-robinobioside (1), 8-(5-methyl-2-furanoyl)-isorhamentin 3-O-robinobioside (2), 8-formylisorhamentin 3-O-robinobioside (3), and N-ß-D-glucopyranosylaristololactam V (4), respectively.

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.

Aromatic glycosides from the whole plants of Iris japonica.

Phytochemical investigation on the whole plants of Iris japonica led to the isolation of four new aromatic glycosides. Their structures including the absolute configurations were determined by spectroscopic and chemical methods as (-)-4-hydroxy-3-methoxy acetophenone 4-O-ß-d-{6-O-[4-O-(7R,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (1), (-)-4-hydroxy-3-methoxy acetophenone 4-O-ß-d-{6-O-[4-O-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (2), (-)-4-hydroxy-3-methoxy acetophenone 4-O-ß-d-{6-O-[4-O-(7R,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (3), (-)-4-hydroxy-3-methoxy acetophenone 4-O-ß-d-{6-O-[4-O-(7S,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (4), respectively.

Nine new compounds from the whole plants of Rehmannia chingii.

Nine new compounds, together with 16 known analogs, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of their spectroscopic data and chemical evidence. In addition, the new compounds were tested for their hepatoprotective activities against APAP-induced HepG2 cell damage and their ability to inhibit LPS-induced nitric oxide production in the murine microglia BV2 cell line. Compounds 2 and 5 exhibited pronounced hepatoprotective activities against APAP-induced HepG2 cell damage at a concentration of 10 µM, and compounds 4 and 9 showed moderate inhibitory activity against microglial inflammation factor with IC50 values of 3.51 and 7.11 µM, respectively.

Bioactive Iridoid Glycosides from the Whole Plants of Rehmannia chingii.

Nine new iridoid glycosides, rehmachingiiosides A-I (1-9), together with 16 known analogues, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of spectroscopic data analysis and from chemical evidence. Furthermore, in two vitro assays, compounds 5 and 10 showed an inhibitory effect on LPS-induced NO production with IC50 values of 2.5 and 7.3 µM, and compounds 4, 6, and 10-12 (when evaluated at 10 µM) exhibited evidence of hepatoprotective effects against APAP-induced HepG2 cell damage.

Lignans from the rhizomes of Iris tectorum.

Chemical examination of the ethanol extract of rhizomes of Iris tectorum led to the isolation and characterization of three new lignans, (7R,7'R,8S,8'S)-5'-methoxy-neo-olivil (1a), (7S,7'S,8R,8'R) -5'-methoxy-neo-olivil (1b), (7S,7'R,8S,8'S)-neo-olivil (2a), (7R,7'S,8R,8'R)-neo-olivil (2b), (7R,7'R,8S,8'S,7''S,8''S)-threo-neo-olivil-4'-O-8-guaiacylglycerol ether (3), together with six known ones (4-9). Among them, compounds 1 and 2 were found to be racemic mixtures, respectively, which were verified by chiral HPLC analysis, compound 3 was a new sesquineolignan. The structures were elucidated on the basis of extensive spectroscopic analysis. To our knowledge, this is the first report of lignan constituents isolated from I. tectorum. All compounds were evaluated for their cytotoxicity against five human tumor cell lines and none of them displayed significant toxicity in tested cell lines at a concentration of 10 µM.

[Triterpenoids from Ganoderma theaecolum].

Fifteenlanostane triterpenoids were isolated from the ethanol extract of Ganoderma theaecolum by means of preparative HPLC,column chromatography over silica gel,ODS and were identified as lucidone C(1),lucidone D(2),7-oxo-ganoderic acid Z2(3),7-oxo-ganoderic acid Z(4),ganoderenicacid H(5),ganoderenic acid B(6),3ß,7ß-dihydroyl-11,15,23-trioxo-lanost-8,16-dien-26-oic acid(7),3ß,7ß-dihydroyl-11,15,23-trioxo-lanost-8,16-dien-26-oic acid methyl ester(8),ganolucidic acid B(9),ganolucidate F(10),methyl ganoderate C2(11),ganoderic acid ζ(12),ganoderic acid AP3(13),methyl ganoderate B(14),and ganoderol B(15). Compounds 1-15 were isolated from this specie for the first time.

[Research on certified reference material of emodin in rhubarb and its alcohol extract, water extract].

The certified reference materials (CRMs) of emodin in rhubarb and its alcohol extract, water extract were developed by using quantity transfer technology from single chemical composition to the complex systems. The CRM of emodin was used for quantity transfer, and high performance liquid chromatography (HPLC) method was used to determine the contents of emodin in different matrix composition. By establishing mathematical model and calculating the parts of uncertainty, the uncertainty values were finally gotten. CRMs of emodin in rhubarb, alcohol extract and water extract were accomplished. The content values of emodin were 0.40% ±0.03%, 1.15%±0.18%, 0.16%±0.08% (k=2,P=0.95), respectively. The established method for quantity transfer has successfully solved the technical problems that the value of active ingredient of traditional Chinese medicine can't be traced to SI units. The series of CRMs are assigned as grade primary reference materials, which are useful for quality control of the emodin content, also provide the accurate and reliable CRM, materials standard and standard methods.

[Chemical constituents from Morus notabilis and their cytotoxic effect].

Une new flavonoids named as notabilisin K (1), together with four known compounds, morusin (2), mulberrofuran A (3), neocyclomorusin (4) and mornigrol F (5) are separated from 95% ethanol extracts of the twigs of Morus notabilis. Compounds 2-5 are separated from this plant for the first time. Notabilisin I, notabilisin J exhibits certain effect against cells of HCT-116, HepG2 and A2780 with IC50 values ranging from 1.47 µmol x L(-1) to 5.46 µmol x L(-1). Morusin exhibits strong effect against five kinds of human cancer cells (BGC823, A2780, HCT-116, HepG2 and NCI-H1650) with IC50 values ranging from 0.74 µmol x L(-1) to 1.58 µmol x L(-1).