A dihydrochalcone and several homoisoflavonoids from Polygonatum odoratum are activators of adenosine monophosphate-activated protein kinase

Adenosine monophosphate (AMP)-activated protein kinase (AMPK) is a major cellular energy sensor and master regulator of metabolic homeostasis; thus, AMPK plays a central role in studies on diabetes and related metabolic diseases. From the rhizomes of Polygonatum odoratum (Mill.) Druce, six homoisoflavonoids (1–6) and one dihydrochalcone (7) were isolated, and the structures of polygonatones A–D (4–7) were elucidated by various spectroscopic analyses. Compounds 1–7 were evaluated for their effect on AMPK activation. The amount of active phosphorylated AMPK and acetyl-CoA carboxylase in rat liver epithelial IAR-20 cells increased when the cells were incubated with the aforementioned compounds. Specifically, (3R)-5,7-dihydroxyl-6-methyl-8-methoxyl-3-(4′-hydroxylbenzyl)-chroman-4-one (1), (3R)-5,7-dihydroxyl-6,8-dimethyl-3-(4′-hydroxylbenzyl)-chroman-4-one (2), (3R)-5,7-dihydroxyl-6-methyl-3-(4′-hydroxylbenzyl)-chroman-4-one (3), and polygonatone D (7) exhibited significant activation effects.     

New cytotoxic dihydrochalcone and steroidal saponins from the aerial parts of Sansevieria cylindrica Bojer ex Hook

A new dihydrochalcone, 2‘,4‘-dihydroxy-3‘-methoxy-3,4-methylenedioxy-8-hydroxymethylene dihydrochalcone 1 and two new steroidal saponins, (25S)-ruscogenin-1-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranoside 2, (25S)-ruscogenin-3-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside 3, together with three known steroidal saponins (25S)-ruscogenin-3-O-β-d-glucopyranoside 4, (25S)-ruscogenin-1-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-α-l-arabinopyranoside 5 and (25R)-26-O-β-d-glucopyranosyl-furost-5-ene-1β,3β,22α,26-tetrol-1-O-α-L-rhamnopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-α-l-arabinopyranoside 6 were isolated from the aerial parts of Sansevieria cylindrica. The structures of the new compounds were established by UV, IR, EI-MS, HR-ESI–MS as well as 1D (¹H,¹³C and DEPT-135) and 2D (HSQC, HMBC and TOCSY) NMR spectral analysis. The isolated compounds 1-6 were assayed for in vitro cytotoxicities against the three human tumor cell lines HT116, MCF7 and HepG2. Compound 1 showed a moderate cytotoxicity against MCF7. Compounds 2, 3 and 6 exhibited moderate cytotoxicities against the three used cell lines and compound 5 showed marked cytotoxicities against all used cell lines.     

Steroidal saponins and homoisoflavanone from the aerial parts of Sansevieria cylindrica Bojer ex Hook.

Phytochemical study on the methanolic extract of Sansevieria cylindrica aerial parts lead to the isolation, characterization and structure elucidation of a new steroidal saponin, 1β-hydroxy-kryptogenin-1-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranoside (1), a new homoisoflavanone, (3S)-3,7-dihydroxy-8-methoxy-3-(3′,4′-methylenedioxybenzyl) chroman-4-one (2) and the known saponin alliospiroside A (3). To the best of our knowledge, the genin 1β-hydroxy-kryptogenin is reported here for the first time. The structures of the new compounds were determined by UV, IR, EIMS, HRESIMS together with 1D (¹H and ¹³C) and 2D (HSQC and HMBC) NMR spectral analysis. The isolated compounds 1–3 were tested for their radical scavenging activity (DPPH). Compound 2 exhibited activity compared to that of ascorbic acid as a standard. The cytotoxicity of the isolated compounds and the standard doxorubicin was tested against the three human tumor cell lines HT116, MCF-7 and PC-3. The results showed that the isolated compounds were inactive.     

An efficient and quick protocol for in vitro multiplication of snake plant,Sansevieria trifasciata var. Laurentii [Prain]

Plant Cell, Tissue and Organ Culture (PCTOC) - Plant germ cells, such as pollen grains, can be affected by exposure to metal nanoparticles (NPs) that have diffused into the environment. The...     

Curvularia asianensis and Curvularia eragrostidis associated with leaf spot of Sansevieria trifasciata in Malaysia

Leaf spot disease was detected on Sansevieria trifasciata in Malaysia. Two Curvularia species namely C. eragrostidis and C. asianensis were isolated as the pathogens. The isolated fungi were identified based on morphology and multigene phylogeny (ITS, GAPDH and TEF1-α). Pathogenicity tests confirmed the roles of both Curvularia isolates in causing leaf spot of S. trifasciata. To our knowledge, this is the first report of C. eragrostidis and C. asianensis causing leaf spot of S. trifasciata in Malaysia.     

Synthesis and in vitro evaluation of homoisoflavonoids as potent inhibitors of nitric oxide production in RAW-264.7 cells

Syntheses of natural homoisoflavonoids, (±)-portulacanones A–C (4, 8 and 9), portulacanone D (6), isolated from Portulaca oleracea L. (POL) and their derivatives (3, 5 and 7) have been achieved for the first time along with the synthesis of known derivatives (1 and 2) and their in vitro inhibitory effect against NO production in LPS-induced RAW-264.7 macrophages was evaluated as an indicator of anti-inflammatory activity. All the compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without obvious cytotoxicity. Compounds 3 (97.2% at 10?μM; IC₅₀?=?1.26?µM) followed by 6 (portulacanone D) (92.5% at 10?μM; IC₅₀?=?2.09?µM), 1 (91.4% at 10?μM; IC₅₀?=?1.75?µM) and 7 (83.0% at 10?μM; IC₅₀?=?2.91?µM) were the most potent from the series. This finding was further correlated with the suppressed expression of iNOS induced by LPS. Our promising preliminary results may provide the basis for the assessment of compound 3 as a lead structure for a NO production-targeted anti-inflammatory drug development and also could support the usefulness of POL as a folklore medicinal plant in the treatment of inflammatory diseases.     

The characteristics of pyrophosphate: D-fructose-6-phosphate 1-phosphotransferases from Sansevieria trifasciata leaves and Phaseolus coccineus stems

Three different molecular forms of pyrophosphate-dependent phosphofructokinase have been isolated: one from Sansevieria trifasciata leaves and two from Phaseolus coccineus stems. The form isolated from S. trifasciata has the molecular weight of about 115,000. The apparent molecular weights for the two forms from mung bean were approximately 220,000 and 450,000. All three forms have the same pH optima, an absolute requirement for Mg2+ ions both in the forward and reverse reaction, but differ in their sensitivity toward fructose 2,6-bisphosphate. Kinetic properties of the partially purified enzymes have been investigated in the presence and absence of fructose 2,6-bisphosphate. Pyrophosphate-dependent phosphofructokinase from S. trifasciata exhibited hyperbolic kinetics with all substrates tested. The saturation curves of the enzyme (form A) from mung bean for pyrophosphate, fructose 6-phosphate and fructose 1,6-bisphosphate were sigmoidal in the absence of fructose 2,6-bisphosphate. In the presence of fructose 2,6-bisphosphate these kinetics became hyperbolic.     

Stimulating the production of homoisoflavonoids in cell suspension cultures of Caesalpinia pulcherrima using cork tissue

It has previously been demonstrated that cork tissue increases the efficiency of the production of lipophilic secondary metabolites in diverse plant cell suspension cultures. In the present study, three new homoisoflavonoids--named dihydrobonducellin, 2'-methoxydihydrobonducellin, and 2'-methoxybonducellin--and bonducellin and isobonducellin were isolated from Caesalpinia pulcherrima cultured cells coincubated with cork tissue. Cork tissue increased the production of 2'-methoxybonducellin by about 7-fold relative to control cells, and more than 80% of the product was recoverable from the cork tissue. When cork tissue and methyl jasmonate or yeast extract were added simultaneously to the medium, the amount of 2'-methoxybonducellin produced increased further. The production of the other four homoisoflavonoids was enhanced by variable amounts. Our results indicate that the addition of cork tissue would be an effective technique for investigating formation of secondary metabolites that usually accumulate only in trace amounts.     

Homoisoflavonoids and xanthones from the tubers of wild and in vitro regenerated Ledebouria graminifolia and cytotoxic activities of some of the homoisoflavonoids

Eleven homoisoflavonoids and two xanthones were isolated and characterized from the bulbs of Ledebouria graminifolia. Five of the homoisoflavonoids are new compounds and were identified as: 5-hydroxy-7-methoxy-3-(4'-hydroxybenzyl)-4-chromanone, 5-hydroxy-6,7-dimethoxy-3-(4'-hydroxybenzyl)-4-chromanone, 5,7,8-trimethoxy-3-(4'-hydroxybenzyl)-4-chromanone, 5-hydroxy-3',4',7-trimethoxyspiro[2H-1-benzopyran-7'-bicyclo[4.2.0]octa-trien]-4-one, 5,7-dihydroxy-3',4'-dimethoxyspiro[2H-1-benzopyran-7'-bicyclo[4.2.0]octa-trien]-4-one. Structures were elucidated by extensive 1D, and 2D NMR spectroscopy and HRMS. A method for tissue culture was developed and the bulbs of mature plants were found to contain all the compounds isolated from the wild specimens of L. graminifolia.     

Homoisoflavonoids from Ophiopogon japonicus Ker-Gawler

From the ethyl acetate extract of the tuberous roots of Ophiopogon japonicus (Liliaceae) eight known and five new homoisoflavonoidal compounds were isolated. The new compounds are 5,7-dihydroxy-8-methoxy-6-methyl-3-(2'-hydroxy-4'-methoxybenzyl)chroman-4-one (1), 7-hydroxy-5,8-dimethoxy-6-methyl-3-(2'-hydroxy-4'-methoxybenzyl)chroman-4-one (2), 5,7-dihydroxy-6,8-dimethyl-3-(4'-hydroxy-3'-methoxybenzyl)chroman-4-one (3), 2,5,7-trihydroxy-6,8-dimethyl-3-(3',4'-methylenedioxybenzyl)chroman-4-one (4) and 2,5,7-trihydroxy-6,8-dimethyl-3-(4'-methoxybenzyl)chroman-4-one (5). Their structures have been elucidated by mass and NMR spectroscopy. Compounds 4 and 5 are the first isolated homoisoflavonoids with a hemiacetal function at position 2.     

Systematics of Ruscaceae/Convallariaceae: a combined morphological and molecular investigation

This paper discusses the intrafamilial systematics of Ruscaccae sensu lata by means of a combined molecular-morphological analysis. Ruscaceae sensu lata (including former Con-vallariaceae. Dracaenaceae and Nolinaccac, as well as Comospermum and Eriospermum ) represent a well-supported clade in other molecular analyses and are further linked by the absence of phytomclan in the seed coat. Within this clade there is an unusual lack of sequence divergence for such a morphologically varied group of taxa, but the combined morphological-molecular analysis indicates some groupings: (1) Eriospermum , (2) Comospermum , (3) nolinoids (former Nolinaceac) plus Ophiopogon and Liriope (Ophiopogonae, excluding Peliosanthes ), (4) dracaenoids (former Dracaenaceae), (5; Polygonatae and (6) a clade comprising Convallarieac (including Aspidistra ) and the ruscoids (Ruscaccae sensu stricto ) plus Peliosanthes. In the morphological analysis Peliosanthes is embedded in Convallarieae, and in the molecular analysis it is sister to all other Ruscaceae except Eriospermum: in neither case does it fall with Ophiopogon and Liriope (Ophiopogonae), with which it was traditionally placed. Peliosanthes has several characters in common with some Convallarieae, e.g. filaments fused into a column surrounding the gynoecium, and a thick, fleshy corona with the stigma more or less filling the narrow floral opening. On the other hand, there arc also some notable differences, such as in karyotype, leaf anatomy, pollen morphology and nectaries. Since there is a considerable range of morphological variation in the taxon currently designated as Peliosanthes. more taxonomic work is needed to establish the monophyly of this genus before there can be confidence in its relationships within Ruscaccae sensu lata.     

三线闭壳龟繁殖生态的研究

在暨南大学爬行动物养殖场对三线闭壳龟的繁殖生态进行了研究。结果显示:三线闭壳龟每年产卵1次,每次产卵平均3.6枚。受精卵长径为48.00±2.63mm,短径为26.42±1.66mm,卵重为23.89±3.34g。未受精卵长径为44.35±4.36mm,短径为25.39±2.71mm,卵重为20.39±4.96g。卵的受精率为50.9%,孵化率为83.3%,孵化期平均88d,估计积温为59.581℃·h。稚龟的背甲长为44.83±2.41mm,背甲宽为36.90±1.86mm,体重为15.85±2.07g。     

A Diterpene Endoperoxide from Microtoena insuavis （Hance） Prain ex Dunn

A novel endoperoxlde diterpene, 7a-hydroxy-abieta-8（14）-en-18-oi 9α,13α-endoperoxide （compound 1）, was isolated from the stems of Microtoena insuavis （Hance） Prain ex Dunn, along with 4,4＇-dlhydroxytruxillic acid （compound 2）, gallic acid （compound 3）, ellaglc acid （compound 4）, 3-O-methylellaglc acid 3＇-O-α- rhamnopyranoslde （compound 5）, 3＂＇-O-methylcrenatoslde （compound 6）, crenatoslde （compound 7）, aptgenin （compound 8）, succinic acid （compound 9）, β-sitosterot （compound 10）, and β-daucosterol （compound 11）. The structures of these compounds were elucidated on the basis of spectral evidence.     

Isolation and Identification of Steroidal Saponins from Dioscorea panthaica Prain et Burkill

Two steroidal saponins have been isolated from the rhizomes of Dioscorea panthaica Prain et Burkill. collected from Sichuan province. They were identified as 3-0-{α-L- rhamnopyranosyl (1→4)- [α-L-rhamnopyranosyl (1→2) ]-β-D-glucopyranosyl } -diosgenin (dioscin) and 3-O-{β-D-glucopyranosyl (1→3)-[α-L-rhamnopyranosyl (1→2)]-β-D-glucopyranosyl}-diosgenin (gracillin) on the basis of mp., m. mp., TLC. acetylation, acid hydrolysis, IR, MS, and 13C NMR.     

Synthesis, structural revision, and antioxidant activities of antimutagenic homoisoflavonoids from Hoffmanosseggia intricata

Intricatinol and intricatin, the two homoisoflavonoids isolated from Hoffmanosseggia intricata, and two analogs have been synthesized from pyrogallol in three steps. The spectral data of synthetic intricatinol are in good agreement with those of natural metabolite, but the spectral data of intricatin are not corroborative with those of the natural product. The structure of intricatin has been thus revised to 8-methoxybonducellin, a compound isolated from Caesalpinia pulcherrima. The antioxidant activity of all the four homoisoflavonoids was determined by superoxide (NBT) and DPPH free radical scavenging methods. The synthetic analog 7,8-dihydroxy-3-[(3,4-dihydroxyphenyl)methylene]chroman-4-one displayed excellent activity in both methods.     

三线闭壳龟18SrRNA基因序列的测定

用分子遗传标记进行物种鉴别准确可靠,本文应用18SrRNA序列测定研究中药材三线闭壳龟的进化与种类鉴定.应用PCR直接测序技术测定三线闭壳龟肌肉18srRNA基因部分核苷酸序列.结果表明,所测序列为678bp,其中GC占多数(54.1%).讨论了DNA测序技术在龟鳖类等中药材鉴定方面的应用.     

Phenylsulfonyl piperazine bridged [1,3]dioxolo[4,5-g]chromenones as promising antiproliferative and antioxidant agents

Two series of sulfonylpiperazines linked [1,3]dioxolo[4,5-g]chromenones were synthesized featuring phenyl (7a-k) and chalcone (12a-k) bridge representing flavones or homoisoflavonoids core. New molecules are synthesized utilizing aldol condensation to inspect as antioxidants against DPPH and ABTS⁺ and antiproliferative agents toward selected human cancer cell lines. Cytotoxicity of new compounds was confirmed using SRB assay against non-cancer MDCK cell line. The results concluded that both individual structures of 7 and 12 were vital for modulating pharmacological potencies and presence of different electron withdrawing and electron donating functional group(s) on the phenylsulfonyl entity yielded varied biological effects. Substituent h (OCF₃) and j, k (OCH₃) were found to play a crucial role scavenging DPPH and ABTS⁺ as well as inhibiting cancer cell lines SK-OV-3 and HT-29. Moreover, molecules bearing halogen atom(s) such as substituent b-g expressed excellent inhibitory potential against HeLa and A-549 cancerous cell lines. Bioassay data displayed some interesting structure-activity relationships which are discussed in this paper. The results justified that tested derivatives are promising antioxidants and cytotoxic agents and warrant further structural optimization and bioassay studies. Spectroscopic techniques such as FT-IR, ¹H NMR, ¹³C NMR and elemental analysis (CHN) were carried out to confirm the final structures.