Cleome

By using an elegant 13C-labeling study that involved incubation of Phoma sp. with 1-13C and 1,2-13C acetate, Oikawa et al. [9], were able to isolate the proposed biosynthetic intermediate phomactatriene (or Sch 49026), with 13C incorporation from singly labeled acetate units as indicated by in Fig. 8.3. Phomactatriene is strikingly reminiscent of taxadiene, a biosynthetic intermediate for Taxol . The net biosynthesis for both involves geranylgeranyl diphosphate (GGDP) cyclization [9]. It is noteworthy that prior to isolation of phomactins, the only known related structure is cleomeolide, a diterpene from the herb Cleome viscosa [10] that remarkably resembles phomactin H. 

Artemisia rupestris Baccharis pilularis Grindelia nana Grindelia tenella Haplopappus hirtellus Haplopappus sonorensis Ozothamnus scutellifolius Senecio viscosa Stevia subpubescens Xanthocephalum gymnoap. Heliotropium pycnophyllum Cleome spinosa... 

Fushiya, S. et al., Flavonoids from Cleome droserifolia supress NO production in activated macrophages in vitro, Planta Med., 65, 404, 1999. 

Wollenweber, E. and Dorr, M., Elavonoid aglycones of Cleome spinosa (Cleomaceae), Phytochem. Bull, 24, 2, 1992. 

Sharaf, M., Mansour, R.M.A., and Saleh, N.A.M., Exudate flavonoids from aerial parts of four Cleome species, Biochem. Syst. Ecol, 20, 443, 1992. 

Cleome spinosa Jacquin C. gynandra L. C. viscosa L. Xi Yang Bai Hua Cai Xiang Tian Huang (Spiderwisp) (seed) Cleomin, lactone, tannins, volatile oils.50 Treat dysentery, gonorrhea, malaria, rheumatoid arthritis. 

Cleome spinosa, C. gynandra, C. viscosa, Eupatorium chinense, E. lindleyanum, E. japonicum, Rhaponticum uniflorum Vitex nequndo... 

The incorporation of [3H]MVA into phospholipids in hamster liver in vivo has been claimed,380 and a possible intermediate, which had similar properties to dolichyl-mannose phosphate, incorporated tracer from tritium-labelled mannose and MV A in the same system. The C45, C50, and C55 polyprenols of leaves of Cleome spinosa that have only three trans double bonds within the molecule are thought381 to be synthesized by successive c/s-addition of isoprene units to all-trans-GGPP. 

Table 2 presents a list of coumarinolignans arranged alphabetically together with their structure numbers, sources and references. The colored photographs of two coumarinolignan-bearing plants, Cleome viscosa and Daphne oleoides are presented in Figs. 3 and 4. 

Ray and coworkers (31) studied the liver protective properties of cleomiscosins A (9), B (10) and C (7), isolated from Cleome viscosa seeds, and found significant activity against D-galactosamine-induced cytotoxicity in primary cultured rat hepa-tocytes, with 10 being the most potent of these substances. Chattopadhyay et al. (33) have patented a hepatoprotective pharmaceutical preparation (Cliv-92), composed of a mixture of three coumarinolignans isolated fi om the seeds of C. viscosa, in the optimized ratio of 3 5 2. 

Cleomiscosins A (9), B (10), and C (7), isolated from the seeds of Cleome viscosa, were shown to have immunomodulatory activity in vivo by Bawankule et al. (84). These coumarinolignans, at a dose of 10 mg kg body weight, enhanced the body immune function by significantly increasing the white blood cell count and hemagglutination antibody titer responses, by reducing the delayed-type hypersensitivity response towards rabbit red blood cells. The same group, led by Chattopadhyay, filed a patent on an immunomodulatory pharmaceutical composition, comprised of cleomiscosins isolated from the seeds of C. viscosa (85). 

USA for granting permission to reproduce the images of respectively, of Cleome viscosa. Daphne oleoides, Sasa veitchii, and Maackia amuremis. Thanks are also due to the Cambridge Crystallographic Data Centre for providing the X-ray crystallographic structure. 

Ray AB, Chattopadhyay SK, Konno C, Hikmo H (1980) Stracture of Cleomiscosin A, a Coumarino-lignoid of Cleome viscosa Seeds. Tetrahedron Lett 21 4477... 

Kumar S, Ray AB, Konno C, Oshima Y, Hikino H (1988) Cleomiscosin D, a Coumarino-Lignan from the Seeds of Cleome viscosa. Phytochemistry 27 636... 

Nair AGR (1979) Cleosandrin, a Novel 7-Phenoxycoumarin from the Seeds of Cleome icosandra. Indian J Chem 17B 438... 

Bawankule DU, Chattopadhyay SK, Pal A, Saxena K, Yadav S, Yadav NP, Mani D, Tripathi AK, Beg SU, Srivastava A, Gupta AK, Khanuja SPS (2007) An in Vivo Study of the Immunomodulatory Activity of Coumarinolignoids from Cleome viscosa. Nat Prod Commun 2 923... 

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