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Volume 4. Issue 4. Pages 457-590. 2009 ISSN 1934-578X (printed); ISSN 1555-9475 (online) www.naturalproduct.us
Volume 4. Issue 4. Pages 457-590. 2009 ISSN 1934-578X (printed); ISSN 1555-9475 (online)
www.naturalproduct.us
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NPC Natural Product Communications
EDITOR-IN-CHIEF
DR. PAWAN K AGRAWAL Natural Product Inc. 7963, Anderson Park Lane, Westerville, Ohio 43081, USA [email protected] EDITORS
PROFESSOR ALESSANDRA BRACA Dipartimento di Chimica Bioorganicae Biofarmacia, Universita di Pisa, via Bonanno 33, 56126 Pisa, Italy [email protected]
PROFESSOR DEAN GUO State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China [email protected]
PROFESSOR J. ALBERTO MARCO Departamento de Quimica Organica, Universidade de Valencia, E-46100 Burjassot, Valencia, Spain [email protected]
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HONORARY EDITOR
PROFESSOR GERALD BLUNDEN The School of Pharmacy & Biomedical Sciences,
University of Portsmouth, Portsmouth, PO1 2DT U.K.
Glycowithanolides accumulation in in vitro Shoot Cultures of Indian Ginseng (Withania somnifera Dunal) Ashok Ahujaa, Devinder Kaurb, Mallubhotla Sharadac, Arun Kumara, Krishan Avtar Suria and Prabhu Dutta
aIndian Institute of Integrative Medicine (CSIR), Jammu 180 001, India bInstitute of Himalayan Bioresource Technology (CSIR) Palampur, 176 061, India cSchool of Biotechnology, Shri Mata Vaishno Devi University (SMVDU), Kakryal 182 320, India [email protected] Received: August 11th, 2008; Accepted: February 18th, 2009
Phytochemical investigations of multiple shoot cultures of selected accessions AGB002 and AGB025 of Withania somnifera. established in vitro utilizing shoot tip apices cultured on Murashige and Skoog’s medium supplemented with BAP (1 mg/L) have been carried out. This has lead to isolation of four glycowithanolides viz. Withanoside IV (WSG-3), Withanoside VI (WSG-3A), Physagulin D (WSG-P) and Withastraronolide (WSC-O).The structures of these have been confirmed on the basis of spectroscopic data. Multiple shoot cultures could be an alternative renewable resource for production of these biologically active molecules. Keywords: Ashwagandha, Glycowithanolides, Indian Ginseng, Shoot cultures, Withania somnifera. Withanolides and Glycowithanolides are a group of pharmacologically active compounds isolated from different plants of the family Solanaceae such as Withania somnifera, Withania coagulans, Acnistus australis and Datura metal. These biomolecules have received considerable attention in recent years owing to their wide potential of biological activities which include adaptogenic, anti-inflammatory, antitumor, immunomodulator, antioxidant and antistress properties [1-4]. Among various plant sources of withanolides and glycowithanolides Withania somnifera (L) Dunal commonly known as Ashwagandha is one of the important source for these biologically active molecules. The plant is native to India and Africa. It is widely distributed in arid subtropical regions is now cultivated around the world. It is also called ‘Indian Ginseng’ for its rejuvenating properties [5]. Production of bioactive metabolites from in vitro cultures has gained considerable attention in recent years. This approach holds great promise as an attractive alternative source to whole plant for
production of high-value low volume phytochemicals [6,7]. Extraction of bioactive compounds from plant tissue cultures is simpler than extraction from organized complex tissues of plants. From a review of the literature [8-10] it was found that tissue cultures of Withania somnifera have been investigated extensively for production of withanolides, however, in vitro cultures have not been phytochemically investigated for the production of glycowithanolides. Glycowithanolides are withanolide glycosides which may be further acylated to sitoindosides containing a glucose molecule at carbon-27. Antistress benefits, antioxidant [11] anxiolytic, antidepressant and immunomodulatory activity [12-14] associated with Withania somnifera have been attributed to the presence of glycowithanolides. Several glycowithanolides have been isolated and identified in Withania somnifera [15]. The present communication reports for the first time potential of in vitro established proliferative multiple shoot cultures of W. somnifera to synthesize biologically active glycowithanolide molecules.
NPC Natural Product Communications 2009 Vol. 4 No. 4
479 - 482
480 Natural Product Communications Vol. 4 (4) 2009 Ahuja et al.
Table 1: Glycowithanolides content in proliferative multiple shoot cultures (selected accessions, AGB002 and AGB025) of Withania somnifera based on HPLC analysis.
Rt=Retention Time:*% dry wt basis;**age 30 days after planting (DAP).
Figure 1: Chromatogram of Standadrd Glycowithanolides Withanoside IV (WSG-3), Withanoside VI (WSG-3A), Physagulin D (WSG-P) and
Withastraronolide (WSC-O).
Figure 2: HPLC Chromatogram representative of Withania somnifera
shoot cultures extracts (AGB002 line). The HPLC data shown in Table 1 and HPLC chromatograms (Figure 1, 2) expresses the content of glycowithanolides detected in shoot culture lines of two accessions AGB 002 and AGB 025 of Withania somnifera. The HPLC analysis revealed the presence of four glycowithanolides eluted in order of Withanoside IV (WSG-3), Physagulin D (WSG-P), Withastraronolide (WSC-O) and Withanoside VI (WSG-3A). Both the shoot culture lines accumulated all four glycowithanolides but in differing proportions. The content of WSG-3 was recorded to be highest. On comparing data for the parent plant and respective shoot culture lines it was found that quantitative difference in glycowithanolide content did exist between the parent and in vitro regenerated shoots. However the glycowithanolide profile remained the same. Multiple shoot cultures of medicinal plants provide a good source for the production of biomolecules, higher product yield, stability and growth of shoot cultures offers good
alternative over the intact plant [6,16]. Besides, the shoot cultures i) provide a homogenous and genetically uniform material, ii) may be propagated at any time in large quantities iii) form good uniform system for feeding experiments with possible precursors of biosynthesis under controlled conditions for attaining enhanced product yield and (iv) provide an ideal uniform system for a genomic based pathway dissection. The present study establishes for the first time the in vitro shoot culture based production of glycowithanolides in W. somnifera. This study suggests that the biosynthetic pathway for the glycowithanolides was not affected by adopting in vitro culture conditions. Experimental
Multiple Shoot Cultures: Shoot apices were collected from uniformly grown plants of selected accessions AGB002 and AGB025 available in Ashwagandha Germplasm Repository of IIIM, Jammu. The plant material was washed thoroughly under running tap water for 1 hr and the excised shoot apices explants were soaked in 1% (v/v) Tween-20 (Sigma St. Louis, USA) solution for 30 min and washed thoroughly under running tap water for 1 hr. Surface sterilization was achieved with Dithane-M45 [0.3% w/v] for 4 min and subsequently with 0.25% (w/v) HgCl2 treatment for 3 min followed by a final rinse (3-4 times) with sterile distilled water. Shoot apices dissected to a size of 3-4 mm each were cultured on 3% (w/v) sucrose, Murashige and Skoog’s [17] agar solidified medium supplemented with and BAP, IAA, IBA, NAA and 2,4-D, either singly or in various combinations, using various concentrations (0.5-1.0 mg/L). The pH of medium was adjusted to 5.8-5.9 prior to the addition of agar 0.8% (w/v). The medium was sterilized by autoclaving at 15 psi at 121oC for 20 min. the cultures were incubated at 25±2oC under 16 hr day/night photoperiod provided by white fluorescent tubes. The in vitro well adapted proliferative shoots culture lines established on MS medium containing
Glycowithanolide Content* AGB 002 AGB 025
Glycowithanolide Identified Rt (min)
Parent Plant** Shoot Culture Parent Plant** Shoot Culture Withanoside IV (WSG-3) 21.991 0.213±0.016 0.229±0.022 0.070±0.006 0.103±0.028 Physagulin D (WSG-P) 23.266 0.205±0.024 0.071±0.018 0.339±0.034 0.083±0.008 Withastraronolide (WSC-O) 24.397 0.011±0.008 0.040±0.008 0.013±0.006 0.027±.0.016 Withanoside VI (WSG-3A) 26.145 0.207±0.026 0.013±0.005 0.103±0.018 0.016±0.006
Glycowithanolides in vitro shoot cultures of Withania somnifera. Natural Product Communications Vol. 4 (4) 2009 481
BAP (1.0 mg/L) were maintained by regular subculture after every 4 weeks. After six subcultures four weeks old shoot cultures lines were harvested for withanolides and glycowithanolides analysis. The leaf material of parent plants, thirty days old from date of planting (DAP) was also utilized for this purpose. Glycowithanolides and withanolides Isolation: Dried and powdered samples of shoot cultures were homogenized and extracted with ethanol: water (1:1) (3 times) for 3 hours by mechanical stirring at room temperature. Combined extracts were then filtered and evaporated to dryness in vacuo at 60±2oC. HPLC Analysis: Accurately weighed residue of the 50% alcoholic extract was dissolved in a fixed volume of HPLC grade methanol: water (1:1) solution. The solutions were filtered through a Millipore filter (0.45 µm) before injection into the HPLC system. The analysis was carried out on a Waters, USA system consisted of a quaternary gradient pump, an auto-sampler, an automatic thermostatic column, a photodiode array detector, a
temperature control module and a computer with Empower software. The column used for analysis was an RP-18e, 5 µm column using two mobile phases, methanol: water (60:40) for isocratic system and acetonitrile: water for gradient system at the flow rate of 0.7 ml/min. the retention time was 30 min in isocratic system and 60 min in gradient system. The percentage compositions were computed from their respective peak areas. Identification of Glycowithanolides and Withanolides: The identification was verified by TLC analysis and retention time [RT] of HPLC separation and compared with standards. TLC was via pre-coated silica gel plates (CHCl3:MeOH (96:4)) and visualizing with vanillin reagent [vanillin: boric acid: methanol: sulphuric acid in the ratio of 0.5 g: 50 g: 500 cm3:10 cm3 (50%)] Acknowledgements - Authors are thankful to the Director, Indian Institute of Integrative Medicine, Jammu for providing facilities and advice during study. We also thank CSIR, Govt. of India for financial support under NMITLI programme.
References
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Natural Product Communications 2009
Volume 4, Number 4
Contents
Original Paper Page
Monoterpene Hydrocarbons May Serve as Antipredation Defensive Compounds in Boisea trivittata, the Boxelder Bug Maria C. Palazzo and William N. Setzer 457
Three Novel Sesquiterpene Esters from Celastrus angulatus Shaopeng Wei, Mingan Wang, Jiwen Zhang, Yong Qian, Zhiqin Ji and Wenjun Wu 461
Sesquiterpenes with Quinone Reductase-Inducing Activity from Liriodendron chinense Ying Dong, Dong Liang, Jianjin Huang and Peng Zhang 467
First Evidence for an Anxiolytic Effect of a Diterpenoid from Salvia cinnabarina Francesco Maione, Maria Camela Bonito, Mariantonella Colucci, Virginia Cozzolino, Angela Bisio, Giovanni Romussi, Carla Cicala, Stefano Pieretti and Nicola Mascolo 469
Variation of Major Limonoids in Azadirachta indica Fruits at Different Ripening Stages and Toxicity against Aedes aegypti Bina Shaheen Siddiqui, Syed Kashif Ali, Syed Tariq Ali, Syed Naeem ul Hassan Naqvi and Rajput Muhammad Tariq 473
Cycloartane-type Glycosides from two Species of Astragalus (Fabaceae) Jens Linnek, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Olivier Duchamp, Jean-François Mirjolet
and Marie-Aleth Lacaille-Dubois 477
Glycowithanolides accumulation in in vitro Shoot Cultures of Indian Ginseng (Withania somnifera Dunal) Ashok Ahuja, Devinder Kaur, Mallubhotla Sharada, Arun Kumar, Krishan Avtar Suri and Prabhu Dutt 479
Structure Activity Studies on the Crinane Alkaloid Apoptosis-inducing Pharmacophore James McNulty, Jerald J. Nair, Jaume Bastida, Siyaram Pandey and Carly Griffin 483
HPLC and NMR Studies of Phenoxazone Alkaloids from Pycnoporus cinnabarinus Daniel A. Dias and Sylvia Urban 489
A new Pyranone Derivative from the Leaves of Livistona australis Samy K. El-Desouky, Mona E. S. Kassem, Zarag I. A. Al - Fifi and Amira M. Gamal El-Deen 499
Isolation, Structure Elucidation and Apoptosis-inducing Activity of New Compounds from the Edible Fungus Lentinus striguellus Yongbiao Zheng, Baobing Zhao, Chunhua Lu, Xinjian Lin, Zhonghui Zheng and Wenjin Su 501
New Benzophenone O-Glucoside from Hypericum ellipticum Elyse Petrunak, Andrew C. Kester, Yunbao Liu, Camile S. Bowen-Forbes, Muraleedharan G. Nair and Geneive E. Henry 507
Structures of New Phenolic Glycosides from the Seeds of Cucurbita moschata Li Fa-Sheng, Xu Jing, Dou De-Qiang, Chi Xiao-Feng, Kang Ting-Guo and Kuang Hai Xue 511
Myricarborin A and n-Butyl-α-L-rhamnopyranoside, Two Novel Compounds from the Bark of Myrica rubra Zhiguo Liu, Shuang Ji, Yuchuan Zhang, Dali Meng and Xian Li 513
Continued inside back cover
