2-Geranyl-1,4-naphthoquinone,a Possible Intermediate of Anthraquinones in a Sesamum indicum Hairy Root Culture

2-Geranyl-1,4-naphthoquinone was isolated from the hairy root culture of Sesamum indicum. The structure was determined to be 2-[(E)-3,7-dimethylocta-2,6-dienyl]-1,4-naphthoquinone on the basis of spectroscopic evidence and chemical synthesis. The production of anthrasesamones A, B and C by the hairy root culture was also confirmed for the first time.     

Anthrasesamones D and E from Sesamum indicum Roots

Two anthraquinone derivatives, named anthrasesamones D and E, were isolated from the roots of Sesamum indicum. Their respective structures were determined to be 1,2,4-trihydroxy-3-(4-methylpent-3-enyl)anthraquinone and 1,2-dihydroxy-3-(4-methylpent-3-enyl)anthraquinone on the basis of spectroscopic evidence.     

A Rennin-like Enzyme from Penicillium expansum

dl-(1,3/2)-3-Acetamido-1,2-di-O-benzylcyclohex-4-enediol (IIIa) and dl-(1,3/4)-1-acetamido-3,4-di-O-benzylcyclohex-5-enediol (IIIb) were synthesized from dl-trans-1,2-di-O-benzylcyclohex-3-enediol (I) via the corresponding azide derivatives (IIa-b) prepared by bromination and subsequent treatment with sodium azide in N,N-dimethylformamide. Compounds (IIIa and IIIb) were converted into a variety of deoxyinosamine and deoxyinosadiamine derivatives via epoxides (VIII and IX) or by cis-hydroxylation with osmium tetroxide. Hexaacetyl-rac-inosamine-1 (XVIIIc) was synthesized from dl-(1,3,4/2,5)-3-acetamido-1,2-di-O-benzyl-5-bromocyclohexanetriol (VIa) via conduramine derivatives (XVIIa-c). Conformationai analysis of partially O-benzylated aminocyclitol derivatives were studied by means of NMR spectroscopy.     

Biosynthesis of anthraquinone derivatives in a Sesamum indicum hairy root culture

In order to investigate the intermediacy of 2-(4-methylpent-3-en-1-yl)anthraquinone (MPAQ), a possible intermediate for the biosynthesis of anthraquinone derivatives in sesame (Sesamum indicum), ²H-labeled MPAQ was administered to a hairy root culture of S. indicum. Efficient conversion of fed MPAQ to 2-[(Z)-4-methylpenta-1,3-dien-1-yl]anthraquinone ((Z)-MPDEAQ) was observed. Furthermore, administration experiment with ²H-labeled 2-geranyl-1,4-naphthohydroquinone, another possible intermediate, showed that it was converted to MPAQ and (Z)-MPDEAQ. The results clearly demonstrated that these substrates are the actual precursors for the production of (Z)-MPDEAQ. In contrast, neither MPAQ nor 2-geranyl-1,4-naphthohydroquinone was converted to anthrasesamone B and 2,3-epoxyanthrasesamone B, other anthraquinone derivatives in the hairy roots, suggesting that these substrates may not be the common precursors in the biosynthesis of anthraquinone derivatives.     

Anthrasesamone F from the Seeds of Black Sesamum indicum

A new anthraquinone derivative, named anthrasesamone F, was isolated from the seeds of Sesamum indicum. Its structure was determined to be (Z)-6,7-dihydroxy-2-(6-hydroxy-4-methyl-3-pentenyl)anthraquinone on the basis of spectroscopic evidence.     

Anthrasesamones from roots of Sesamum indicum

Three anthraquinones, named anthrasesamones A, B and C, were isolated from the roots of Sesamum indicum, and their respective structures were determined to be 1-hydroxy-2-(4-methylpent-3-enyl)anthraquinone, 1,4-dihydroxy-2-(4-methylpent-3-enyl)anthraquinone and 2-chloro-1,4-dihydroxy-3-(4-methylpent-3-enyl)anthraquinone on the basis of spectroscopic evidence. Two known anthraquinones were also isolated for the first time from S. indicum roots and characterized as 2-(4-methylpent-3-enyl)anthraquinone and (E)-2-(4-methylpenta-1,3-dienyl)anthraquinone. Anthrasesamone C is a rare chlorinated anthraquinone in higher plants.     

不同理化因子对雪莲毛状根生长和总黄酮生物合成的影响

在 1 2MS液体培养基上研究了不同理化因子对水母雪莲毛状根生长和总黄酮生物合成的影响。实验结果表明 :氮源总浓度 (包括NH+4和NO-3)为 30mmol L ;NH⁺₄ NO^-₃比例为 5∶2 5 ;2 %蔗糖和 3%葡萄糖组合 ;0.5mg LGA₃和 0.5mg LIBA ;pH5.8;18h d的光照 (光强为 35.0.0lx) ;2.4℃ ;摇床转速为 100rmin有利于毛状根生长及总黄酮的生物合成。在此培养条件下 ,经过21d的培养毛状根生长量达到 12.8g L(DW) ,总黄酮合成量为 192.2mg L ,即总黄酮含量占毛状根干重的 15 % ,约为干重野生水母雪莲植株总黄酮含量的 2.5倍。     

Ovicidal activity of Sesamum indicum (L.) oil against Spodoptera littoralis (Boisd.)

In the research for alternative tools and botanical products to control Spodoptera littoralis (Boisduval) (Lepidoptera: Noctuidae). Sesamum indicum (L.) (Lamiales: Pedaliaceae) oil was assayed as an ovicide. The mortality increased with existence of fatty acids. Chemical analysis of S. indicum oil using GLC analysis showed palmitic acid as the major fatty acid (51.27%), while the major hydrocarbon and sterols were found to be heneicosane (58.63%) and β-sitosterol (2.60%), respectively. Generally, the values of LC₅₀s indicated that one-day-old egg masses are more susceptible than three-day-old eggs. Also, the leaf dip technique is more efficient than the spraying one. Results showed several features of chorionic surface deformation treated with sesame and KZ oils than control using scanning electron microscopy. Meanwhile, the tested oils caused significant reduction in both total soluble protein and transaminase enzymes as compared to control. Additionally, the oils elongated the incubation period and larval duration than control.     

重金属对芝麻种子萌发及幼苗生长的影响

采用培养皿滤纸发芽法研究镉(Cd2+)、镍(Ni2+)、铬(Cr6+)、汞(Hg2+)、铅(Pb2+)等5种重金属离子对芝麻Sesamum indicum种子萌发及幼苗生长的影响。结果表明,重金属离子胁迫对芝麻种子露白萌发影响较小,对胚根生长影响最大;随着重金属离子浓度增加,芝麻幼苗芽长、根长和鲜重减小;在Cd2+、Ni2+和Cr6+浓度20 mg·L-1,Hg2+浓度50 mg·L-1,Pb2+浓度100 mg·L-1时,芝麻种子萌发后胚根基本不生长,难以成苗,这些浓度可视为对应重金属离子对芝麻种子萌发毒害的致死浓度。综合比较,5种重金属离子对芝麻种子萌发及芽期幼苗生长的毒害程度依次为Ni2+ > Cr6+ > Cd2+ > Hg2+ > Pb2+。     

Control of hypocotyl phototropism by phytochrome in a dicotyledonous seedling (Sesamum indicum L.)

Abstract The phototropic response in stems of higher plants is brought about by blue/UV light. The problem studied here is to what extent long-wavelength light, which is absorbed by phytochrome, affects the phototropic response. A refined measurement of phototropism — a curvature index — was applied to the hypocotyl of the sesame seedling (Sesamum indicum L.). The time course of the phototropic response was followed in continuous unilateral weak blue light (B, 460 nm, 8 mW m^?2). Long term red light (R) pretreatments, operating through phytochrome, strongly increase the rate and extent of the phototropic response once it is elicited by unilateral B, while the pretreatments decrease the sensitivity towards B. If a R pulse is given immediately prior to the onset of unilateral B, the rate of the response is strongly reduced compared to the time course of curvature observed when the pretreatment was terminated with a long wavelength far-red light (FR) pulse. R and FR were then applied simultaneously with unilateral B to manipulate the status of the phytochrome system during actual curvature. It was found that a low Pfr/P ratio (established by FR) stimulates the phototropic response far above the control (B alone), while a high Pfr/P ratio (established by R) reduces the response below the control. During bending a positive effect of phytochrome on the rate and extent of the phototropic response, which is saturated at a low level of Pfr, appears to be counteracted by an inhibitory effect which dominates at higher levels of Pfr, such as established by omnilateral R. However, if R is applied unilaterally from the same direction as B, R increases the rate of curvature. Apparently the sesame seedling is capable of detecting the direction of R relative to the direction of B. While a mechanistic explanation of these effects cannot be advanced at present, it is clear that the seedling is capable of super-imposing information about the actual light conditions during bending on a ‘memory’ of the light conditions prior to the onset of bending. Thus, the previous as well as the actual light conditions determine its phototropic responsiveness.     

Biological effects of low-energy C ion implantation on sesame (Sesamum indicum L.)

Field cultivation experiments on white sesame (Sesamum indicum L.)seeds implanted with low-energy C ion showed that different dosages of C ion implantation produce different biological effects.Sesame plants in 6 different dosage groups with C ion density respectively at 1×1011,1×1012,1×1015,5×1015,1×1016,5×1016 ion/cm2 were superior to the control group in plant height,leaf number,stalk diameter and leaf size.Further,sesame plants in these groups flower and seed earlier than those in the control group,and single plant yield also increased.Of all the groups,the 5×1015 ion/cm2 dosage group yielded the best effect,whereas the 1×1017/cm2 dosage group showed an evident inhibitory effect of ion implantation on the germination and growth of the sesame seeds.     

真菌诱导子对青蒿发根细胞生长和青蒿素积累的影响

３种真菌诱导子（大菌丽花轮枝孢（Ｖｅｒｔｉｃｉｌｌｉｕｍ ｄａｈｉａｅ Ｋｌｅｂ．）、葡枝根霉（Ｒｈｉｚｏｐｕｓ ｓｔｏｌｏｎｉｆｅｒ（Ｅｈｒｅｎｂ．ｅｘＦｒ．）Ｖｕｉｌｌ）和束状刺盘孢（Ｃｏｌｌｅｔｏｒｉｃｈｕｍ ｄｅｍａｔｉｕｍ（Ｐｅｒｓ．）Ｇｒｏｖｅ）处理青蒿（Ａｒｔｅｍｉｓｉａ ａｎｎｕａＬ．）的发根,均能促进发根中青蒿素的积累,其中以大丽花轮枝孢的诱导效果最好;对细胞生长均没有明显影响,     

Cysteine Formation from Methionine in Pseudomonas melanogenum and Mechanism of Methionine-inhibition of l-DOPA Production by the Bacterium

Using a Dowex 50–X2 column and eluting with a 1 mm sodium acetate buffer (pH 2.6), three l-β-aspartamido-carbohydrate (Asn-carbohydrate) fractions have been isolated in 19% yield from the pronase digest of a 7S soybean protein. The Asn-carbohydrates were composed of one asparagine, two glucosamine and seven, eight and nine mannose residues. Further, 1-l-β-aspartamido-2-acetamido-1,2-dideoxy-β-d-glucose (Asn-GlcNAc), which is derived from the protein-carbohydrate linkage, was produced by partial hydrolysis of the Asn-carbohydrates.     

Calcium application enhances growth and alleviates the damaging effects induced by Cd stress in sesame (Sesamum indicum L.)

In this study, the effects of calcium (Ca²⁺) application on acquired systemic tolerance mechanism to cadmium (Cd) stress in sesame (Sesamum indicum L.) were studied. The Cd stress reduced the root and shoot growth of sesame, and plant contents of photosynthetic pigments; however, the application of Ca²⁺ improved these parameters under Cd stress condition. The hydrogen peroxide, malondialdehyde and soluble sugar contents were higher under Cd stress, and were reduced by Ca²⁺ treatment. The antioxidant enzyme activities in the leaves of sesame, superoxide dismutase (SOD), peroxidase (POD), catalase (CAT), ascorbate peroxidase (APX) and glutathione reductase (GR) were higher under Cd stress, whereas reduced concentration was observed in Ca²⁺-treated plants. Cd stress increased the contents of diacylglycerol and sterol ester; however Ca²⁺ treatment resulted in a significant increase in phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, phosphatidylinositol and phosphatidylserine. Our results indicated that application of calcium enables sesame plants to withstand the deleterious impact of cadmium through upregulating acquired systemic tolerance system as lipid fractions (galactolipids, phospholipids, neutral lipids), antioxidant enzymes (SOD, POD, CAT, APX, GR) hence protect membrane functions.     

Effects of Fungal Elicitors on Cell Growth and Artemisinin Accumulation in Hairy Root Cultures of Artemisia annua

The artemisinin accumulation in the hairy root cultures of Artemisia annua L. was enhanced via a treatment of three fungal elicitors separately ( Verticillium dahliae Kleb., Rhizopus stolonifer (Ehrenb. ex Fr. ) Vuill and Colletotrichum dematium (Pers.) Grove). Among these three elicitors, V. dahliae had the highest inducing efficiency, but none of them manifests any noticeable effects on the cell growth of the hairy root cultures. The artemisinin content of the hairy root cultures treated with V. dahliae elicitor was 1.12 mg/g DW, which was 45% higher than the control (0.77 mg/g DW). The results showed that elicitation was dependent on the elicitor concentration, the incubation period and the physiological stage at which the hairy root cultures were treated. In addition, the authors found that for V. dahliae, the optimum concentration was 0.4 mg carbohydrate per millilitre medium, the strongest response of A. annua hairy root cultures to the elicitation was at the late exponential growth stage, and the highest artemisinin content of the hairy root cultures was on the 4th day post treatment.     

Biotransformation of 4-Hydroxybenzen Derivatives by Hairy Root Cultures of Polygonum multiflorum Thunb.

The biotransformation of four 4-hydroxybenzen derivatives （1,4-benzenediol （compound 1）, 4-hydroxybenzaldehyde （compound 2）, 4-hydroxybenzyl alcohol （compound 3） and 4-hydroxybenzoic acid （compound 4）） by the hairy root cultures of Polygonum multiflorum Thunb. as a new biocatalyst was investigated. It was found that the substrates were transformed to their corresponding glucosides, 4-hydroxyphenyl β-D-glucopyranoside （arbutin, compound la）, 4-hydroxymethylphenyl β-D-glucopyranoside （gastrodin, compounds 2a, 3a） and 4-carboxyphenyl α-D- glucopyranoside （compound 4a）, respectively. In the meantime, the hairy roots of P. multiflorum were able to stereoselectively and regioselectively glucosylate phenolic hydroxyl groups of compounds 1-4, but the cultures could not glucosylate the aldehyde group of compound 2 or the benzyllc hydroxyl group of compound 3, and no glucosyl esterification of carboxyl groups of compound 4 was detected. On the other hand, the result also showed that the hairy roots of P. multiflorum were able to reduce the 4-hydroxybenzaldehyde to its corresponding alcohol. This is the first report that substrate 4 has been converted into its α-D-glucopyranoside by a plant biotransformα- tion system.     

Identification of sesame (Sesamum indicum L.) chromosomes using the BAC‐FISH system

• Sesame (Sesamum indicum L.; Pedaliaceae) is a commercially valuable oilseed crop with high oil content. Its small genome size favours the genomic analysis of key biological processes, such as oil synthesis and metabolism. However, the 13 chromosome pairs of sesame have not been characterised because of technological limitations and their small size.
• We constructed a BAC library comprising 57,600 BAC clones for sesame. The estimated genome coverage of the sesame BAC library was 13.8×. The successive double colour fluorescence in situ hybridisation (FISH) with bacterial artificial chromosomes (BACs) for sesame was established in this study.
• Subsequently, the 13 sesame chromosome pairs were individually differentiated using 17 specific BACs for the first time. The schematic of the sesame chromosome set was drawn according to the chromosome relative length and relative position of the BAC signal. The cytogenetic characteristics of sesame chromosomes were also explored.
• The results provide the technical background required for further cytogenetic map construction, genome assembly and localisation of the DNA sequence in sesame.

     

西洋参发根的诱导及不同外源物质对发根生长和皂苷含量的影响

利用发根农杆菌A4菌株在西洋参根外植体上直接诱导产生发根,并分析不同浓度的植物激素6-BA、NAA,前体物醋酸镁(Mg(Ac)2)、L-亮氨酸和诱导子茉莉酸甲酯(MJA)、水杨酸(SA)对西洋参(Panax quinquefolium L.)发根生长和皂苷含量的影响。同时,研究MJA与SA组合作用对皂苷含量的影响。采用高效液相色谱法测定发根中单体皂苷Rb1的含量。结果显示,适宜浓度的外源物质均可促进皂苷含量的增加,MJA尤其明显。