Guttiferones

Gey, C Kyrylenko, S Hennig, L., Nguyen, L.H., Biittner, A., Pham, H.D. et al. (2007) Phloroglucinol derivatives guttiferone G, aristoforin, and hyperforin inhibitors of human sirtuins SIRTl and SIRT2. Angewandte Chemie, 119, 5311-5314. 

Fig. 19 CD spectra for enantiomers of oxy-guttiferone K (left) and its ent-form (right). Calculations were performed at the MPWlPW91/6-31G(d) level of theory. Reprinted from [217], with permission from Elsevier...

Prenylated natural products of close similarity to hyperforin 10 were also reported from other species of the Guttiferae family. Biogenetically they are classified as polyprenylated benzophenones, however many of them bear a bicyclononane ring system as with hyperforin 10. Xanthochymol 27, which is identical with guttiferone E, was isolated from... 

Although, the absolute configurations of plukenetiones D and E have not been determined Henry et al. suggested that plukenetiones D/E and 7-epinemorosone are the same product. This consideration is logic but, these products could be enatiomers in like manner guttiferone E and camboginol. 

Ethylenic functions in the side chains of PBDs seem to be very sensitive to acid solutions. In organic or inorganic acids converted xanthochymol, guttiferone E, guttiferone F and cambogin to the corresponding pyran ether... 

PBDs have shown different biological properties but, probably the three most important are the cytoprotection against HIV-1 in vitro of guttiferones [3-4], antimicrobial properties [5-11] and cytotoxic activity found in diverse nucleus [12-16]. Interesting bioactivity such as antibacterial activity against methicillin-resistant Straphylococcus aureus [6-8], antioxidant activity [44,59,60] and cytotoxic activity due to induction of apoptosis in human leukemia cells have been reported [61,62],... 

Isoxanthochymol (44), a cyclized derivate of guttiferone E (54), was inactive [3] suggesting that the presence of an enol functionality is necessary for anti-HIV activity. 

Some PBDs have shown cytotoxic activity. The SBDs vismiaguianones B, D and E, cudraphenones A-D and the bicyclo-[3.3.1]-nonane derivatives ochrocarpinones A-C, guttiferones A, E and G, xanthochymol possess this biological activity. 

Also guttiferones A (49) and G (52) were weakly cytotoxic in the A2780 human ovarian cell line, with IC50 values of 6.8 and 8.0 pg mL 1, respectively [15]. Actinomycin D was used as a positive control with an IC50 = 0.003 pg mL 1. 

Guttiferone C Prenyl Oil Prenyl. / prenyl no, 0 °H 670 Symphonia globulifera [881... 

Guttiferone G Prenyl OH Prenyl., Gerar.vl Prenyl 0 OH 670 Garcima macrophylla [93]... 

A number of benzophenones have been assayed for their cytotoxicity towards ovarian [78,93], leukemia [14,82], and CNS [102] cancer cell lines. In addition, the guttiferones (132 and 135-142) have displayed potent cytotoxicity toward leukemia [82] and ovarian cancer cell lines [37,93],... 

The guttiferones (132 and 135-142) displayed partial cytoprotection toward HIV-1 infection in human lymphoblastoid CEM-SS cells however, no decrease in viral replication was observed [88,96], The vismiaphenones were also assayed for their anti-HIV activity in the NCI primary HIV screen only 55 was active [15]. 

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