Dihydrochalcone derivatives

Majumder, P.L., Lahiri, S., and Mukhoti, N., Chalcone and dihydrochalcone derivatives from the orchid Lusia volucris. Phytochemistry, 40, 271, 1995. 

Benosman, A. et al.. New terpenylated dihydrochalcone derivatives isolated from Mitrella kentii, J. Nat. Prod, 60, 921, 1997. 

Latex from the wood of Antiaris toxicaria, a toxic Indonesian plant, has been used for arrow poison. From the root bark of the plants, antiarones A (17) and B (18) [39], the first examples of isoprenylated aurone derivative, have been isolated along with the unique dihydrochalcone derivatives, antiarones J (19) and K (20) [40], Fig. (2). These compounds (19 and 20) are biogenetically considered to be formed... 

Horowitz RM, Gentili B. Dihydrochalcone derivatives and their use as sweetening agents. US Patent No. 3,087,821 1963. 

Bohlmann, F., C. Zdero, W.R. Abraham, A. Suwita, and M. Grenz Naturally Occurring Terpene Derivatives. Part 256. New Diterpene and new Dihydrochalcone Derivatives Together with Further Components from Helichrysum species. Phytochemistry 19, 873 (1980). 

Chalcones and dihydrochalcones have been reported in a restricted number of foods (Robards and others 1999 Tomas-Barbcran and Clifford 2000). Chalconaringenin occurs in tomato skin, but the acid extraction conditions of the usual polyphenol analyses convert the chalcone to the corresponding flavanone (naringenin) in the tomato. The most common dihydrochalcones found in foods are phloretin glucoside (phloridzin) and phloretin xylogalactoside, which are characteristic of apples (see Table 2.2) and derived products such as apple juice, cider, and pomace (Robards and others 1999 Tomas-Barbcran and Clifford 2000). 

Fronza, G. et al.. Structural features of the (3-CD complexes with naringin and its dihydrochalcone and aglycone derivatives by IH NMR, J. Inclusion Phenom. Macrocyclic Chem., 44, 225, 2002. 

Rao et al. revised the structure of crotaramosmin (286), formerly described as a prenyl-flavanone, to 2, 4-dihydroxy-6",6"-dimethylpyrano[2",3" 4, 3 ]dihydrochalcone. Two derivatives of crotaramosmin, crotaramin (287) and crotin (292), were later isolated from the same source, Crotalaria ramosissima (cited incorrectly as Crotolaria ramosissima) Kanzo-nol Y (294) is an uncommon diprenylated a-hydroxydihydrochalcone found in cultivated licorice (Glycyrrhiza glabraf for which the absolute configuration was determined by... 

B-rings of their constituent dihydrochalcone monomers. A concise synthesis of verbenachal-cone (316) by catalytic copper-mediated coupling of phenol and aryl halides has been reported by Xing et al., who also prepared two further derivatives for preliminary structure-activity studies. One of the latter, the corresponding bichalcane (deoxo) derivative of verbenachalcone showed no activity in the neural outgrowth stimulation bioassay mentioned above. 

This checklist of chalcones, dihydrochalcones, and aurones contains compounds of these classes reported in the literature as natural products to the end of 2003. Compounds published before 1992 are cross-referenced to numbered entries in volumes 1 and 2 of the Handbook of Natural Flavonoidf using the abbreviations H1 and H2, respectively. Compounds published from 1992 to 2003 are cross-referenced to Table 16.1-Table 16.15 using numbers in bold type. The compounds are listed according to the system outlined in Section 16.1.1, with the exception that isoprenylated derivatives are included under the heading of aglycones. Bn, benzyl. 

Dihydrochalcones (DHCs) are characteristic of apples and derived products (apple juice, cider, pomace etc.), and their content depends on... 

Ahmed, M., Khaleduzzaman, M., and Islam, M.S., Isoflavan-4-ol, dihydrochalcone and chal-cone derivatives from Polygonum lapathifolium, Phytochemistry, 29, 2009, 1990. 

The phenolic composition of apple consists of cinnamic acids, flavonols, dihydrochalcones, and flavan-3-ols (50,56). In the apple fruit processing industry, hydroxycinnamic acid derivatives and flavan-3-ols are important due to their contribution to the astringency, haze, and browning in apple juice and cider. Chlorogenic acid represents the major hydroxycinnamic acid derivative. The flavan-3-ols (catechins) are present in the monomeric form as well as in oligomeric and polymeric forms (procyanidins) in apple and apple products (56). 

Two natural product derived semisynthetic compounds are utilized as a limited basis, namely, perillartine [28] and neohesperidin dihydrochalcone [45]. Perillartine is an a-jy -oxime and synthesized from perillaldehyde, a constituent of the volatile oil of Perilla frutescens (L.) Britton (Labiatae), and used in Japan as a sweetener for tobacco [28]. Neohesperidin dihydrochalcone is a dihydrochalcone glycoside prepared from a flavanone constituent of Citrus aurantium L. (Rutaceae), which is permitted for use in chewing gum and certain beverages in Belgium and elsewhere [45]. 

Increasing research has developed several new noncaloric sweeteners the dihydrochalcone group of disaccharide, glycyrrhizin (licorice extract), especially its ammoniated derivative dulcin (4-ethoxy-phenylurea), the glycoprotein of miracle fruit and a polypeptide from a tropical fruit called the serendipity berry, said to be 3000 times sweeter than sucrose. Aspartame (C14H18N205) has been approved by FDA. 

Furobenzo-y-pyrone (furochromen-4-one) derivatives are shown in the chalcone-flavone and flavone-chalcone series. These series includes (I-P,0,II-7 I-a, II-6)-chalcone-flavone dimers (310,311) (1-6,0,Il-a I-7,II-P)-flavone-chalcone dimers (312-314) and (I-6,0,II-P I-7,II-a)-flavone-chalcone dimers (315). Fm-o[2,3-/]chromanone derivatives comprise a (I-6,II-a I-5,0,II-P)-flavanone-chalcone dimer (316) dihydrofuro[3,2-g]chromanone derivatives comprise (I-7,0,II-P I-6,II-a)-flavanone-dihydrochalcone dimers (317) and furo[2,3-/ ]benzopyran derivatives (I-a,II-8 I-p,0,II-7)-chalcone-flavan dimers (318,319). 

Natural Diels-Alder-type adducts, including substituted cyclohexene derivatives, prenylbrflavonoids (ketalized Diels-Alder-type adducts), and 2-arylbenzofuran-ketalized Diels-Alder adducts, comprise the fourth main group of structures. Substituted cyclohexene derivatives include (1-a,11-3 ,1-p,11-6 )-dihydrochalcone-dehydrogeranylflavone (393) and (1-a,11-3 ,1-P,11-6 )-dihydrochalcone-dehydrogeranylflavanone (394, 395). 

---