New Phytochemicals from Dietary Supplements of “Cha de Bugre”, “Arjuna” and “Acai”

“Cha de Bugre” is an appetite suppressant, weight loss product. Twenty three new compounds were obtained from the dried powder of “Cha de Bugre”, including fifteen new diterpenoids, namely, caseatrins A-C, casearins U and V, caseariasides A-E and sylvestrisides A-E, and two C13 nor-isoprenoids, namely, (6S,9S)-6,9-dihydroxy megastiman-4-en-9-O-β-D-glucopyranoside and (6S,9S)-6,9-dihydroxymegastiman- 4-en- 9-O-β-D- apiofuranosyl-(1→6)-β-D-glucopyranoside and six new neolignans casearialignands A-F, together with 28 known compounds, namely, echinophyllin A, (-)-patagonic acid, (-)-hardwickic acid, ent-3β, 18-dihydroxykaur-16-ene, spathulenol, N-methyl-trans-4-hydroxy-L-proline, cinnamic acid, soyacerebroside I, methypheophorbide a, pheophorbide a, chlorophyll a, β-sitosterol, stigmastane-3, 6-diol, daucosterol, β -D-glucopyranoside, (3 β)-stigmast-5-en-3-yl,6-nonadecanoate, oplopanone, 4-(2-hydroxyethyl)phenol (tyrosol), syringaresinol-β-D-glucoside, isoquercitrin, lβ,6α-dihydroxy-4(14)-eudesmene, 1,10-seco-4ξ-hydroxy-muurol- 5-ene-1,10-diketone, icariside B5, byzantionoside B, blumenol B, blumenol C and loliolide. The botanical origin of “Cha de Bugre” was identified as the leaves of Casearia sylvestris, not of Cordial salicifolia. [1–6]

“Arjuna”, the bark of Terminalia arjuna, is a cardio-tonic for heart failure, ischemic cardiomyopathy, atherosclerosis and myocardium necrosis. In our continuing search for therapeutic bio-markers, eight new compounds including five novel 18,19-secooleanane type triterpenoids, namely, arjunasides A-E, two new oleanane type triterpenoids arjunglucosides IV and V, and one new ursane type triterpenoids 2α,3β-dihydroxyurs-12,18-dien-28-oic acid 28-O-β-D-glucopyranosyl ester, together with one known lupane type triterpenoid quadranoside I and nine known oleanane type triterpenoids, namely, arjunglucosides I-III, arjunetin, sericoside, bellericoside, arjunic acid, arjungenin, arjunolic acid, and crataegioside, four known ursane triterpene glycosyl esters, namely, 2α,3β,23-trihydroxyurs-12,18-dien-28-oic acid 28-O-β-D-glucopyranosyl ester, quadranoside VIII, kajiichigoside F1 and 2α,3β,23-trihydroxyurs-12,19-dien-28-oic acid 28-O-β-D-glucopyranosyl ester, as well as four other known compounds, namely, 3-O-methylellagic, 4'-O-α-L-rhamnopyranoside, catechinacid, β-sitosterol and daucosterol were isolated from “Arjuna”. [7–9]

“Acai”, which is the fruit of E. oleracea (Acai), is used to make various beverages and food preparations such as juices and desserts in Brazil, and are used medicinally for the treatment of diarrhea. In the present report, 3 new compounds were obtained from “Acai”, namely, (-)-7R8S-7',8'-dihydroxy-dihydrodehydroconiferyl alcohol-9-O-β-D-glucopyranoside, (+)-7S8R-7',8'- dihydroxy-dihydrodehydroconiferyl alcohol-9-O-β-D- glucopyranoside and 4-hydroxy-2-methoxyphenyl 1-O-[6-(hydrogen 3-hydroxy-3-methylpentanedioate)] - β -D-glucopyranoside together with 6 known compounds, namely, cyanidin 3-glucoside, cyanidin 3-rutinoside, (Z)-4-O-β-D-glucopyranosyl-p-coumaric acid, vanillic acid glucoside and uridine. Their structures were established on the basis of 1D and 2D NMR spectroscopic analyses and comparison with literature data [10]. Acknowledgements: This work was supported by the United States Department of Agriculture Specific Cooperative Research Agreement Number 58–6408–6-067 and the FDA/CFSAN grant entitled “Science Based Authentication of Dietary Supplements” Number 2 U01 FD 002071–07. We thank Dr. Bharathi Avula for recording the HRESIMS spectra and Dr. Shabana Khan for the bioassay. References: [1] Wang W, et al. (2009) Planta Medica 75: 1436–1441. [2] Wang W, et al. (2009) Fitoteropia 80(7) 404–407. [3] Wang W, et al. (2010) Planta Medica 76: 903–908. [4] Wang W, et al. (2010) Fitoterapia 81: 480–484. [5] Wang W, et al. (2010) Helvetica Chimica Acta 93(1): 139–146. [6] Wang W, et al. (2010) Nat Prod Comm 5(5): 771–774. [7] Wang W, et al. (2010) Planta Medica 76: 1751–1754. [8] Wang W, et al. (2010) Planta Medica 76: 1751–1754. [9] Wang W, et al. (2010) Fitoterapia 81: 480–484. [10] Wang W, et al. (2010) Planta Medica 77(3) DOI: 10.1055/s-0031–1273559.