Physalis Alkekengi Research Articles

Calystegins of Physalts alkekengi var. Francheti (Solanaceae). Structure Determination and their Glycosidase Inhibitory Activities

Five calystegins were extracted from the roots of Physalis alkekengi var. francheti (Solanaceae) with hot water and purified to homogeneity by the combination of a variety of ion-exchange column chromato-graphies. Their structures have been determined from the 1H- and 13C-NMR spectral data, and two of the compounds were identified as calystegins A3 and B2, which have been isolated from the roots of Calys-tegia sepium (Convolvulaceae). Two of the remaining three were found to be lα,3α,4β-trihydroxy-nor-tropane and 1α,2α,3α,4β-tetrahydroxy-nor-tropane and given the trivial name calystegins A5 and B3, respectively. The last calystegin was assigned as 1α,2β,3α,6α-tetrahydroxy-nor-tropane, which was the same as the relative configuration proposed in the literature for calystegin B1 isolated from C. sepium. However, the 13C-NMR spectral data for the compound from C. sepium differed substantially from our results. From a personal communication with the authors of the original paper on calystegins, it was clarified that the 13C-NMR chemical shifts of calystegin B1 in the original paper had been erroneous. Since their corrected 13C-NMR data of calystegin b1 and its 1H-NMR chemical shifts in the original paper are very close to our present data, we concluded that both compounds from C. sepium and P. alkekengi are identical. Calystegin B2 has been known to be a potent competitive inhibitor of almond β-glucosidase (Ki= 1.2 μM) and coffee bean α-galactosidase (Ki= 0.86 μM). In this study calystegin B1 (1α,2β,3α,6α-tetrahydroxynor-tropane) proved to be a potent competitive inhibitor of almond β-glucosidase (Ki= 1.9 μM) and bovine liver β-galactosidase Ki= 1.6 μM), but not an inhibitor of α-galactosidases. Calystegin A3 was found to be a weaker inhibitor compared to calystegin B2 but with the same inhibitory spectrum. Calystegin A5, a 2-deoxy derivative of calystegin B2, showed no activity against any glycosidases tested. Since calystegin B3, a 2-epimer of calystegin B2, also exhibited only a weak inhibitory activity, it was concluded that the equatorially oriented OH group at C2 is the essential feature for recognition and strong binding by the active site of glycosidases. Based on the structure/activity relationships for the five calystegins isolated from P. alkekengi var. francheti and calystegin C1 from Morus alba, we propose that the OH group at C6 of calystegin Bi or Ci, in place of the β-glycoside oxygen, is protonated by an acidic group in the active site of the β-glycosidase.

Physalins Possessing an Endoperoxy Structure from Physalis alkekengi var. francheti. Structural Revision of Physalin K

Abstract Physalin K was isolated from Physalis alkekengi var. francheti. Spectroscopic studies and chemical correlations, however, revealed that the reported structure of physalin K at the AB ring moiety, namely, 4α,5α-epoxy-6α-hydroxy-2-en-1-one, should be revised to 2α,5α-epidioxy-6β-hydroxy-3-en-1-one. A new physalin, named physalin Q, was also isolated and identified as the 2β,5β-epidioxy diastereomer of physalin K.

Crystal Structures of 5α,6α-Epoxy and 2,3-Dihydro Derivatives of Physalin B, a 13,14-Seco-16,24-cyclosteroid, and Their 1H NMR Spectral Analysis

Abstract X-Ray crystallographic analysis of two steroid derivatives, 5α,6α-epoxyphysalin B and 2,3-dihydrophysalin B, have been undertaken, revealing their closely similar crystal structures to each other. Their 1H NMR spectra, as well as that of the parent compound physalin B, a 13,14-seco-16,24-cyclosteroid from Physalis alkekengi, have been analyzed based on the crystal structures of these derivatives.

Physalin and neophysalins from Physalis alkekengi var. francheti and their differentiation inducing activity

A methanol extract of Physalis alkekengi var. francheti showed a potent cell differentiation inducing activity toward mouse myeloid leukemia cell line (M1 cells). From the extract, a new physalin and two new neophysalins, 25,27-dihydro-4,7-didehydro-7-deoxyneophysalin A and 4,7-didehydroneophysalin B, were isolated along with physalin A, L and isophysalin B. The structures of physalins and neophysalins were determined by means of NMR, UV, IR and mass spectra. Of these compounds, physalin A showed potent cell differentiation inducing activity.

The Structure of Physalin P, a Neophysalin from Physalis Alkekengi

Abstract The structure of physalin P, a constituent of Physalis alkekengi var. francheti, was determined to be 5α-hydroxy-6,7-didehydro-5,6-dihydroneophysalin B by spectroscopic study and chemical correlation with a known compound.

Fusarium oxysporum f. sp. vasinfectum . [Descriptions of Fungi and Bacteria

Abstract A description is provided for Fusarium oxysporum f. sp. vasinfectum . Information is included on the disease caused by the organism, its transmission, geographical distribution, and hosts. HOSTS: Cotton ( Gossipium spp., including G. hirsutum, G. barbadense, G. arboreum, G. herbaceum ), Chinese lantern ( Physalis alkekengi ), lucerne (alfalfa) ( Medicago sativa ), lupin ( Lupinus luteus ), okra ( Abelmoschus esculentus ), soyabean ( Glycine max ), tobacco ( Nicotiana tabacum ). A wide range of other plants may also be infected without external symptoms (51, 2512). DISEASE: Vascular wilt. GEOGRAPHICAL DISTRIBUTION: Widespread (IMI map 362). Africa: Central African Republic, Congo, Egypt, Ethiopia, Israel, Madagascar, Republic of South Africa, Senegal, Somalia, Sudan, Tanzania, Uganda, Zimbabwe. America: Argentina, Brazil, Chile, Colombia, Guatemala, Mexico, Nicaragua, Paraguay, Peru, Puerto Rico, Salvador, St. Kitts-Nevis, St. Vincent, USA (south eastern states), Venezuela. Asia: Burma, China, India, Iran, Iraq, Pakistan, Taiwan, USSR. Europe: France, Greece, Italy, Romania, Yugoslavia. TRANSMISSION: The fungus is soil borne and may be transmitted by seed (11, 713; 32, 186) and in irrigation water (62, 4911).

Physalins N and O from Physalis alkekengi

The structures of physalins N and O, isolated from Physalis alkekengi var. francheti, were determined as 7α-hydroxyphysalin B and (25 S)-25,27-dihydrophysalin A, respectively.

Phygrine, an alkaloid from Physalis species

A new alkaloid, phygrine, isolated from the roots and aerial parts of Physalis alkekengi has been shown to be bis-hygrine or 1-[1′-methylpyrrolidine-2′-yl]-3-[1″-methyl-2″-(2″-oxopropyl)pyrrolidine-5″-yl]propan-2-one. The alkaloid is also present in P. angulata, P. philadelphica, P. ixocarpa, P. edulis, P. peruviana, P. minima, P. pubescens, P. viscosa and P. pruinosa.

Activated charcoal-mediated hydroxylation under very mild conditions: conversion of physalin B into 25-hydroxyphysalin B

Activated charcoal treatment of physalin B, a 13, 14-seco-16,24-cyclosteroidal constituent of Physalis alkekengi, in MeOH at room temperature yields a product possessing a hydroxy group at the α-position of the δ-lactone carbonyl function, namely 25-hydroxyphysalin B, in high yield.

Effects of an aqueous extract of Physalis alkekengi fruit on estrus cycle, reproduction and uterine creatine kinase BB-isozyme in rats

Intraperitoneal injections of the aqueous extract of winter cherry fruits ( Physalis alkekengi) to female rats produced 100% diestrus. The rats resumed their normal estrus cycle upon withdrawal of this extract. Although there was no significant decrease in the number of implantation sites, the number of pups born to rats decreased by 96% with extract administration. Treatment with this extract had no effect on body weight, uterus weight, plasma protein level or plasma total creatine kinase activity. However, the level of plasma progesterone was diminished by 44%. In addition, uterine creatine kinase BB-isosyme (an estrogen-induced protein) showed a time-dependent inhibition of activity from 55% to 82%.

Structure of Physalin M Isolated from Physalis alkekengi var. francheti

Abstract The structure of physalin M, isolated from Physalis alkekengi var. francheti was determined as 7-deoxyphysalin L by spectroscopic studies and chemica correlation with a known compound. Physalin M exhibitec weak cytotoxicity against tumor cells.

A New physalin from Physalis alkekengi: structure of physalin L

A new physalin, physalin L, and the known physalins E and F were isolated from Physalis alkekengi. Spectroscopic studies and chemical transformation have established the structure of physalin L as 25- epi-3,4-dehydro-2,3,25,27-tetrahydrophysalin A.

Metabolism of hygrine in Atropa, Hyoscyamus and Physalis

Three-month-old plants of Physalis alkekengi, Atropa belladonna and Hyoscyamus niger were fed via the roots with either d( + ) or l( - )-hygrine-[2′- 14C]. The feeding experiments were terminated after 7 days when the following alkaloids were isolated from the paired groups of plants: tigloidine, 3α-tigloyloxytropane and cuscohygrine from Physalis; hyoscyamine from Hyoscyamus and from Atropa. In contrast to Datura these genera appear to use both hygrine enantiomers in the biosynthesis of the tropane ring.

Chromoplast Ultrastructure in Fruit of Solanum pseudocapsicum and Fruit and Sepals of Physalis alkekengi

The chromoplasts of ripe fruit of Solanum pseudocapsicum contain mostly β-carotene, with lesser amounts of lutein, antheraxanthin, zeaxanthin, mutatochrome and violaxanthin. The ultrastructure of these plastids reveals that the carotenoids appear to crystallize out from the plastoglobules into many small slabs. In addition, fibrils are also present and develop from plastoglobules. In fruit from wild plants, they consist of a single microfibril with a diameter of 21.3 ± 1.4 nm ( ± SD), while those from an ornamental cultivar, Solanum Christmas Cherry Jubilee, contain fibrils consisting of several small microfibrils, with an average centre-to-centre distance of 4.9 ± 0.5 nm (±SD). The chromoplasts of ripe fruit of Physalis alkekengi are remarkably similar to those of S. pseudocapsicum with respect to their ultrastructure, although they contain mainly zeaxanthin dipalmitate and β-carotene. Fruit from one plant contain the electron-transparent crystalloids described for S. pseudocapsicum, as well as fibrils consisting of one or more large microfibrils. Fruit from a second plant contain crystalloids and the short, small fibrils composed of several microfibrils with a centre- to-centre distance of 4.1 ± 0.2 nm (± SD ) . Treatment of mature green fruit of S. pseudocapsicum with CPTA, which inhibits β-carotene accumulation, prevents the formation of crystalloids and both types of fibrils. It is suggested that the crystalloids are the site of β-carotene deposition in S. pseudocapsicum, and of zeaxanthin di- palmitate in P. alkekengi. Furthermore, it is postulated that there are different types of plasto- globules, one type generating crystalloids and the other fibrils.

Growth of Various Powdery Mildew Fungi on the Barley Leaves Infected Preliminarily with the Barley Powdery Mildew Fungus

Young colonies of the barley powdery mildew fungus growing on barley leaves were rubbed off with water-drenched absorbent cotton and then the leaves were inoculated secondarily with the powdery mildew fungi collected from wheat and Agropyron ciliare Franch, var. minus Ohwi and 49 powdery mildew fungi from dicotyledons. The haustoria of the barley powdery mildew fungus, torn off from the hyphae and remaining in the barley epidermal cells, survive for many days. Out of the 51 fungi, 45 grew close to the colonies of the barley fungus on the barley leaves and 30 produced conidia, though the hyphal growth and conidial formation were different in their degree according to the fungi. The powdery mildew fungi from wheat, Agropyron, cucumber, Physalis alkekengi L. var. francheti Hort. form. bunyardii Makino, etc. grew nearly as well as on their respective proper host plants at least for the first several days after inoculation. Some dicotyledonous species, such as Plantago asiatica L., Lycium chinense Mill., Euonymus japonicus Thunb., etc., were also proved to be susceptible to some secondarily inoculated fungi. For example, the powdery mildew fungi from cucumber, buckwheat and barley produced conidia on Lycium, but neither the cucumber fungus nor barley fungus grew at all on buckwheat.

In Vitro Formation of Plants from Leaves of Several Species of the Solanaceae Family

Isolated leaves of Solanum nigrum, Solanum dulcamara, Physalis peruviana and Physalis alkekengi were grown on synthetic media in vitro conditions, and the effect of kinetin and IAA on bud formation has been studied. Numerous buds were formed in the presence of kinetin alone or in the combination with IAA. In the presence of IAA only roots arose from the levaes. The leaf buds of Solanum dulcamara, S. nigrum and Physalis peruviana were capable to develop into shoots and seedlings.

Inhibitory Effect of Tea Catechins on Some Plant Virus Diseases

To develope a new use of tea, inhibitory effects of water-soluble components of tea on plant viruses were investigated in 1966-1968.The aqueous solutions of them were injected into the soil around the base of the plants. The combinations of viruses and host plants were as follows :TMV : Physalis alkekengi L. ; N. tobacum (Bright Yellow-4) ; Tomato ; N. glutinosaCMV : N. tobacum (KY-57) ; vigna sinensis SAVI.In experiments of systemic, infection by TMV, free catechins, catechin mixture and aqueous extract of tea seemed to be slightly inhibitory. Free catechins and catechin mixture were also a little effective for the inhibition of CMV Infectivity.In local infections by TMV and CMV, it was observed that the number of lesions on the inoculated leaves of plants treated with tea catechins (free, ester and their mixture) and caffein was compared to less than the untreated ones.

On a New Strain of Henbane mosaic virus from Physalis alkekengi

On a New Strain of Henbane mosaic virus from Physalis alkekengi

ChemInform Abstract: STRUKTUR VON PHYSALIN C, EINEM BITTERPRINZIP AUS PHYSALIS ALKEKENGI VAR. FRANCHETI

Chemischer Informationsdienst. Organische ChemieVolume 1, Issue 33 Isocyclic Compounds ChemInform Abstract: STRUKTUR VON PHYSALIN C, EINEM BITTERPRINZIP AUS PHYSALIS ALKEKENGI VAR. FRANCHETI M. KAWAI, M. KAWAISearch for more papers by this authorT. MATSUURA, T. MATSUURASearch for more papers by this author M. KAWAI, M. KAWAISearch for more papers by this authorT. MATSUURA, T. MATSUURASearch for more papers by this author First published: August 18, 1970 https://doi.org/10.1002/chin.197033416Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume1, Issue33August 18, 1970 RelatedInformation

ChemInform Abstract: STRUKTUREN VON PHYSALIN A UND B, 13,14‐SECO‐16,24‐CYCLO‐STEROIDE AUS PHYSALIS ALKEKENGI VAR. FRANCHETI VORL. MITT.

Chemischer Informationsdienst. Organische ChemieVolume 1, Issue 23 Natural Products ChemInform Abstract: STRUKTUREN VON PHYSALIN A UND B, 13,14-SECO-16,24-CYCLO-STEROIDE AUS PHYSALIS ALKEKENGI VAR. FRANCHETI VORL. MITT. T. MATSUURA, T. MATSUURASearch for more papers by this authorM. KAWAI, M. KAWAISearch for more papers by this authorR. NAKASHIMA, R. NAKASHIMASearch for more papers by this authorY. BUTSUGAN, Y. BUTSUGANSearch for more papers by this author T. MATSUURA, T. MATSUURASearch for more papers by this authorM. KAWAI, M. KAWAISearch for more papers by this authorR. NAKASHIMA, R. NAKASHIMASearch for more papers by this authorY. BUTSUGAN, Y. BUTSUGANSearch for more papers by this author First published: June 9, 1970 https://doi.org/10.1002/chin.197023357Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume1, Issue23June 9, 1970 RelatedInformation