Actinidia polygama

In the cyclopentanoid monoterpene family, compounds containing an iridoid-structure exhibit various bioactivities in Nature. For example, dehydroiridodiol, isolated from dry leaves of the cat-attracting plant Actinidia polygama Miq., is known to be an attractant for the male adults of the Chrysopidae and shows activity in amounts as small as lO"" pg [35]. Dehydroiridodial, a more oxidized product, was isolated as a pungent principle of Actinidia polygama Miq. and was characterized by T. Sakan et al. in 1978 [36]. 

Neonepetalactone, 61 (Fig. 1.2.3), a bioactive compound found to be quite attractive to cats [41], was isolated in 1965 from the leaves and galls of Actinidia polygama by T. Sakan et al. and its absolute configuration was determined in 1980 [41b]. As some syntheses of the racemic mixture or ex-chiral-pool syntheses had already been reported, we realized that our SAMP/RAMP hydrazone methodology would make it possible to develop a very short asymmetric synthesis of this bioactive 8-lactone. 

Actinidia polygama (Sieb. et Zucc.) Planch ex Maxim. China Matatabic acid, iridomyrmecin, actinidine, allomatatabiol, iridomyrmecin, neo-nepetalactone, dihydronepetalactol, matatabiether, isoneomatatabiol, matatabistic acid, neomatabiol, vitamin C, vitamin B.48-50 52 Used for escophageal and liver cancers, rheumatoid arthritis, arthralgia, urinary stones, fever. 

V. oreophilum, Vitex labrusca, V. agnus-castus Actinidia polygama Belamcanda chinensis Belamcanda chinensis Chaenomeles speciosa Lemna minor... 

Actinidia polygama, Citrus aurantium, Prunella vulgaris, Raphanus sativus, Sesamum indicum Avena sativa, Daucus carota, Hippophae rhamnoides, Rosa canina, R. damascena, R. gallica Lycium barbarum, Moms alba, Picrasma excelsa, Ribes nigmm Lycium barbarum... 

The (+)-enantiomer (40) of actinidine, an alkaloid of Valeriana officinalis and Actinidia polygama, has been synthesized as outlined in Scheme 7, the starting material being obtained from (+)-pulegone.35... 

S. Ito et al. utilized the aza-Claisen rearrangement of carboxamide enolates for the enantioselective total synthesis of (-)-isoiridomyrmecin, which is a constituent of Actinidia polygama and exhibits unique bioactivity. The rearrangement of the (S,S) stereoisomer was conducted under standard conditions, and the product was isolated as a single [R,R) stereoisomer in 77% yield. 

A review by CavilP summarises the earlier literature of the simpler iridoids. From the chrysope-attracting plant Actinidia polygama several ethers have been obtained, some of which have been synthesised by two groups. The... 

The dial (3/ ,85)-(109), named dehydroiridodial, has been isolated from Actinidia polygama and synthesized from (—)-limonene u/a (45,85)-p-menth-1-en-9-ol of known absolute configuration the diastereoisomeric chrysomeli-dial [(35,85)-(109)] (Vol. 8, p. 35) has been synthesized similarly from... 

On the other hand, some iridoids are able to attract certain felines, like iridolactones from Actinidia polygama [16] o Nepeta cataria [17]. 

CioH.jN, Mr 147.22, oil, bp. 100-103 °C(1 kPa),[a]i, -7.2° (CHCI3), a monoterpene alkaloid ( iridoids) from the east Asian creeper Actinidia polygama and other Actinidiaceae, Bignoniaceae, and Valerianaceae. It is a component of the defensive secretion of black beetles, ants, grasshoppers, and flies. Only the (5) enantiomer occurs in nature. A. exhibits antimicrobial properties and a deterrent effect against birds and arthropods , while cats are strongly attracted Synthesis There are various syntheses of the racemate and the unnatural (/I) enantiomer, but only three for the (5) enantiomer. The biosynthesis presumably proceeds from iridodial. 

CioHijO, Mr 152.24, bp. 67 C (1.6 kPa), [a]o -150° (CCI4). A C,o- iridoid with an unusual structure. (-)-M. is isolated from the leaves and galls of the East Asian plant Actinidia polygama (Actinidiaceae). The name of the compound is derived from the Japanese name for the plant Matatabi . The plant has an attracting effect on cats (Felidae) and lacewing flies (Chry-sopidae). 

When the unripe fruits of Actinidia polygama (Actinidiaceae) are stabbed by the insect Pseudosphondylia matatabi, a gall is formed. The gall is collected, treated with boiling water, and dried to yield mokutenryou, which is used in Kampo medicine for analgesia and to prevent diarrhea. 

Plants of Actinidia polygama (Actinidiaceae) have an excitatory effect on cats and odier Felidae. This plant is also used in folk medicine in Japan. Several iridoid monoterpenes have been isolated [iridomyrmecin (1), isoiridomyrmecin (44), dihydronepetalactone (31), isodihydronepetalactone... 

Sakan, T., S. Isoe, and S. B. Hyeon, The chemistry of attractants for Chrysopidae from Actinidia polygama Miq., in Control of Insect Behavior by Natural Products (D. L. Wood, R. M. Sil-... 

Hop ether (136) and karahana ether (139) are monoterpenoid compounds which occur in Japanese hop (Shinshu-wase) 426), while the occurrence of (-h)-matatabi ether (138) and of its isomer (137) is limited to the essential oil of Actinidia polygama Franch. et Sav. (Ternstroemiaceae) 261, 716). 

Among the monoterpenoid lactones, derivatives of the iridane series 600) have acquired limited importance as aroma substances. Nepetalactone (143) occurs in quantities of up to 78% in American oil of catnip Nepeta cataria L.) 490), while epinepetalactone (144) is the major constituent (70%) of the essential oil of Nepeta mussini L. 490). The essential oil of this species was also found to contain neonepetalactone (146) as well as the two saturated compounds a- and 5-dihydronepetalactones (147) and (148) 490, 518) and 5,9-dehydronepetalactone (145) 528). Both dihydro compounds (147) and (148) are structurally closely related to the iri-domyrmecins from Actinidia polygama 515, 516). Lactones (143) to (150) are aroma compounds which have a strong odor and which exert an attracting effect on Felidae 518, 519). 

Sakan, T., F. Murai, S. Isoe, S. BeHyeon, and Y. Hayashi Biologically Active Cg-, Cio- and Cn-Terpenes from Actinidia polygama, Boschniakia rossica, and Menyanthes. J. Chem. Soc. Japan90,507 (1969) (Jap.) Chem. Abstr. 71,53479k(1969). 

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