Untiring Researches for Alternative Resources of Rhizoma Paridis.

Rhizoma Paridis (RP, ), a traditional Chinese medicine, is the rhizoma of Paris polyphylla var. yunnanensis (PPY) or P. polyphylla var. chinensis which are widely used as important raw materials for several Chinese patent drugs. However, the wild resources of these herbs have become less and less due to their slow-growing characteristics and previously excessive excavation. This review covers untiring investigations on alternative resources of RP by our research group over the past decades, including non-medicinal parts of PPY as well as other plants of Liliaceae and Liliflorae families. The arial parts of PPY and the whole plants of Trillium kamtschaticum might be alternative resources for RP based on the fact that they shared the same or similar saponins and bioactivities.

Seeing the light: Shifting from wild rhizomes to extraction of active ingredients from above-ground parts of Paris polyphylla var. yunnanensis.

ETHNOPHARMACOLOGICAL RELEVANCE: The dried rhizomes of Paris polyphylla var. yunnanensis are widely used in traditional Chinese medicine (TCM) as hemostatic, antitumor, and antimicrobial agents. More than 70 Chinese patent medicines are based on P. polyphylla var. yunnanensis rhizomes. Steroidal saponins are considered as the main active ingredients of these rhizomes. However, wild populations of P. polyphylla var. yunnanensis are greatly threatened due to the illegal wild harvest and over-utilization of the rhizomes. In contrast, the renewable above-ground parts (leaves and stems) of P. polyphylla var. yunnanensis are usually thrown away as waste material, whether from wild or cultivated material. AIM OF THE STUDY: The aim of this study was to use HPLC analyses of chemical constituents and bioactive assays to assess whether the above-ground parts could be an alternative source of active ingredients to the rhizomes of P. polyphylla var. yunnanensis. MATERIALS AND METHODS: The saponin components of the rhizomes and above-ground parts of P. polyphylla var. yunnanensis were analyzed by HPLC-UV. The total saponins extracted from the rhizomes and above-ground parts of P. polyphylla var. yunnanensis were evaluated for their hemostatic, cytotoxic, and antimicrobial activities by using the rabbit blood in vitro based on turbidimetric method, MTT assay method, and a dilution antimicrobial susceptibility test method, respectively. RESULTS: Four bioactive spirostanol saponins (paris saponins I, II, VI, and VII) were detected in the total saponins from the rhizomes and above-ground parts of P. polyphylla var. yunnanensis, which indicated they should have similar pharmacological properties. The bioactive assays revealed that both the parts of P. polyphylla var. yunnanensis exhibited the same hemostatic, cytotoxic, and antimicrobial effects. CONCLUSION: Our results revealed that based on saponin content in the above-ground parts of P. polyphylla var. yunnanensis and the requirements stipulated in 2015 of Chinese Pharmacopoeia, the above-ground parts (especially its leaves) can be an alternative and more sustainable source of active ingredients compared to the rhizomes.

Steroidal saponins from stems and leaves of Paris polyphylla var. yunnanensis.

Phytochemical investigation of the stems and leaves of Paris polyphylla var. yunnanensis led to isolation of 12 steroidal saponins, chonglouosides SL-9-SL-20, which had not been described previously, along with 13 known compounds. Their structures were established on the basis of extensive spectroscopic analysis and chemical methods. Four of the twelve steroidal saponins possessed three steroidal aglycones which have not been reported in nature. Steroidal saponins were also evaluated for their cytotoxicities against two human cancer cell lines (HepG2 and HEK293) and anti-HCV effects. One known steroidal saponin was the most cytotoxic compound overall with IC50 values of 2.9 ± 0.5 µM and 5.0 ± 0.6 µM against HepG2 and HEK293 cell lines, respectively, while none showed anti-HCV activity at a concentration of 20 µM.

Plantagiolides K-N, three new withanolides and one withanolide glucoside from Tacca plantaginea.

Phytochemical investigation of the whole plants of Tacca plantaginea led to the isolation of 3 new withanolides and one new withanolide glucoside, named plantagiolides K-N (1-4), together with one known withanolide, 4 known withanolide glucosides, and 2 known taccalonolides. Their structures were elucidated by extensive spectroscopic analysis. Compound 4 is the first withanolide glycoside which the sugar moiety is attached at C-7. The effects of the some of isolates on TNFα-induced NF-κB transcriptional activity and cytotoxicity were evaluated.

New 23-spirocholestane derivatives from Ypsilandra thibetica.

Three new unusual 23-spirocholestane derivatives, ypsilanogenin (1), ypsilanogenin 3-O-ß-D-glucopyranoside (2), and 4'-acetylypsilanogenin 3-O-ß-D-glucopyranoside (3), were isolated from the whole plants of Ypsilandra thibetica. The structures of compounds 1-3 were deduced by spectroscopic and chemical methods, and the structure of 1 was further confirmed by a single-crystal diffraction analysis. All isolates were evaluated for their inhibitory activities against HIV-1.

C(22)-steroidal lactone glycosides from stems and leaves of Paris polyphylla var. yunnanensis.

Further phytochemical investigation on the stems and leaves of Paris polyphylla var. yunnanensis has led to the isolation of three C(22)-steroidal lactone glycosides. Two of these are new compounds, designated as chonglouoside SL-7 (1) and chonglouoside SL-8 (2). Their structures were elucidated on the basis of extensive spectroscopic analysis, as well as comparison with the reported spectroscopic data. This is the first report of C(22)-steroidal lactone glycosides isolated from the Paris genus. Compounds 1 and 3 showed moderate antimicrobic activity against Propionibacterium acnes with MIC values of 31.3 and 3.9µg/mL, respectively.

Steroidal saponins with antimicrobial activity from stems and leaves of Paris polyphylla var. yunnanensis.

Rhizoma Paridis, the root of Paris polyphylla var. yunnanensis (Trilliaceae), is a Chinese traditional medicine, which resources become less and less. However, the aerial parts of this herb, which can regenerate every year, were discarded. In order to expand the resources, detailed chemical investigation on the stems and leaves of Paris polyphylla var. yunnanensis led to isolation of one sapogenin and 24 steroidal saponins (1-25), including 6 new glycosides, named chonglouosides SL-1-SL-6 (1-6). Their structures were elucidated on the basis of detailed analyses of their 1D and 2D NMR spectra and acid hydrolysis. Among them, compounds 3 and 4 are the first 23,27-dihydroxydiosgenin saponin having a sugar chain attached to C-23 or C-27, while compound 6 is the first 27-hydroxyruscogenin glycoside bearing 1, 27-di-O-sugar chains. The known compounds 10, 12, 14, 19, 20, 22, and 25 were isolated from the genus Paris for the first time. Antimicrobial testing activities of the selected compounds showed that compound 2, 3, 6, 8, 9, 11, 13, 17, 18, 21, and 24 were active against Propionibacterium acnes with MIC values of 62.5, 62.5, 3.9, 16.5, 17.2, 7.8, 39.0, 17.2, 31.3, 62.5, and 31.3 µg/ml, respectively.

Tigliane-type diterpenoid glycosides from Euphorbia fischeriana.

Investigation of whole plants of Euphorbia fischeriana afforded three new tigliane-diterpenoid glycosides, fischerosides A-C (1-3), together with 11 known diterpenoids. Fischerosides A-C (1-3) are the first tigliane-type diterpenoid glucosides. Their structures were determined by a combination of 1D and 2D NMR, MS, and acid hydrolysis. Inhibitory activity against HIV-1 was assessed for compounds 1-5. The new compound 3 showed an EC50 value of 0.02 µM and a therapeutic index (TI) of 17.50, while prostratin (4) and 12-deoxyphorbol-13,20-diacetate (5) showed significantly greater anti-HIV-1 activity.

[Effect of BuYangHuanWu recipe on cerebral microcirculation in gerbils with ischemia-reperfusion].

OBJECTIVE: To explore the protective mechanism of BuYangHuanWu recipe on neurofunction in gerbils with cerebral ischemia- reperfusion. METHODS: Gerbils (n = 48) were divided randomly into three groups: animal model group, BuYangHuanWu recipe group, and sham control group. The animal model of cerebral ischemia was established using bilateral common carotid artery occlusion followed by unclamp 45 min after occlusion. The microcirculation was observed with a Laser Doppler. The density of microvascular was measured using Tannic acid ferric chloride mordant dyeing. The BBB (blood brain barrier) permeability was assessed using evan's blue (EB) dye. The water content in brain tissues was tested with wet and dry method. The learning and memory function test was performed with a 4-PTT dry path maze. RESULTS: Compared with the animal model group, BuYangHuanWu recipe increased blood flow in the hippocampal region at 1 and 5 min after occlusion, inhibited hypoperfusion at 15 min after reperfusion, increased blood flow at 30, 60 and 120 min after reperfusion. Meanwhile, BuYangHuanWu recipe inhibited the increase of BBB permeability and water content in brain tissues after reperfusion (P < 0.05). BuYangHuanWu recipe also improved the scores of learning and memory function of the gerbils. CONCLUSION: BuYangHuanWu recipe protects the neurofunction in gerbils with ischemia-reperfusion through modulating cerebral microcirculation damages.

Chloramultiols A-F, lindenane-type sesquiterpenoid dimers from Chloranthus multistachys.

Six new highly complex lindenane-type sesquiterpenoid dimers, chloramultiols A-F (1-6), along with six known analogues, were isolated from the whole plant of Chloranthus multistachys. The structures of 1-6 were elucidated on the basis of mass spectrometry (MS) and 1D and 2D NMR spectroscopic analysis. Among them, compounds 1 and 6 contain a unique 18-membered macrocyclic triester ring. All compounds isolated were evaluated for the inhibition of the growth of five tumor cell lines.

Steroidal saponins from Lysimachia Paridiformis.

A new steroidal saponin, paridiformoside B (1), was obtained from the EtOH extract of the whole plant of Lysimachia Paridiformis Franch, togerher with one steroidal sapogenin (7) and seven known steroidal saponins (2-6, 8-9). Their structures were elucidated using extensive spectroscopic techniques including 1D and 2D NMR spectra.

Five new steroidal compounds from Ypsilandra thibetica.

Five new steroids, including the four new steroidal saponins ypsilandroside B (1), ypsilandroside A (2), isoypsilandroside A (4), and isoypsilandroside B (5), as well as the new steroidal sapogenin isoypsilandrogenin (3), were isolated from the whole plant of Ypsilandra thibetica Franch. Their structures were determined on the basis of spectroscopic analyses, including extensive 2D-NMR techniques. The structure and relative configuration of ypsilandroside B (=(3beta,12alpha,25R)-3-[(alpha-L-rhamnopyranosyl-(1-->2)-beta-D-apiofuranosyl)oxy]spirost-5-ene-12,27-diol; 1) was unequivocally determined by single-crystal X-ray diffraction. The antifungal and antibacterial activities of 1-5 towards various types of fungi and bacteria are reported.

New tirucallane-type triterpenoid saponins from Sapindus mukorossi Gaetn.

Two new tirucallane-type triterpenoid saponins, sapimukoside C (1) and sapimukoside D (2), have been isolated from the roots of Sapindus mukorossi Gaetn. Their structures have been determined, on the basis of spectral and chemical analysis, as 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L- arabinopyranosyl-(1-->3)]-beta-D-glucopyranosyl (21,23R)-epoxyl tirucalla-7,24-diene-(21S)-ethoxyl-3 beta-ol (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl-(1-->3)]- beta-D-glucopyranosyl (21,23R)-epoxyl tirucall-7,24-diene-(21S)-methoxyl-3 beta-ol (2).

Eudesmane sesquiterpene glycosides from Parepigynum funingense.

A new eudesmane sesquiterpene glycoside, pterodontriol D-6-O-beta-D-glucopyranoside (1), together with a known compound, ainsliaside E (2), was isolated from the roots of Parepigynum funingense. The structure of 1 was determined by 1D and 2D-NMR spectroscopy. Compound 2 was isolated from this plant for the first time.