Roseanolone: A New Diterpene from Hypoestes rosea

Abstract

Roseanolone is a new diterpene from the African plant Hypoestes rosea (Acanthaceae). The isolation is described; the structure has been determined to be 1,2,3,3a,4,5,6,6a,7,8,9,10a-dodecahydro-5-hydroxy-3-isopropyl-3a, 6-oxa-6,9,10a-trimethyl-dicyclopenta[a,d] cycloocten-1-one by X-ray crystallography.

AfroDb: A Select Highly Potent and Diverse Natural Product Library from African Medicinal Plants

“…Other promising cytotoxic agents included are six aporphines ( 05 – 10 ) from Cassytha filiformis , among which actinodaphnine ( 05 ), cassythine ( 06 ), and dicentrine ( 07 ) were also shown to possess antitrypanosomal properties in vitro on Trypanosoma brucei brucei [43]. Hypoestoxide (HE, 11 ), a natural diterpenoid [a bicyclo (9, 3, 1) pentadecane], derived from Hypoestoes rosea growing in Nigeria [44] has been reported to be a potent nonsteroidal anti-inflammatory drug. This compound is also reported to be non mutagenic and possesses antiangiogenic and antitumor activities, also inhibiting the activity of IκB kinase [45], [46].…”

The structure, stereochemistry, and biosynthetic origin of a diterpenoid fungal metabolite, traversianal, established by 1H, 2H, and 13C magnetic resonance

“…It may be noted that the vicinal coupling between the 9-proton at 6 2.27 and H-10 is small, J = 1 .O Hz. Enhancement of the H-10 pattern (6 1.84) was observed upon saturation of the multiplet at 6 3.03 (H- 14) and of that at 6 1.34 (H-1), which is strongly coupled to H-2, J = 12.3 Hz, indicative of an antiperiplanar interaction. The H-1 pattern (6 1.34) was enhanced by saturation of the secondary methyl protons (0.78) that also affected the multiplets for H-3 (6 2.29) and the 4-methylene proton at 6 2.52.…”

“…The tricyclic carbon skeleton of 1 is the same as that in other diterpenes, namely the fusicoccanes and cotylenins from Fusicoccum amygdali (10) and a Cladosporium (1 l), respectively, as represented by fusicoccin A (4), the fusicoplagins (12) and anadensin (1 3) from liverworts, as represented by fusicoplagin A (9, and several compounds such as roseanolone (6) and roseadione (7) from the higher plant Hypoestes rosea (14). The same tricyclic skeleton having an extended side chain is also found in the sesterterpenoid ophiobolins such as ophiobolin A (8) and 6-epiophiobolin A from Cochliobolus (Helminthosporium) and Cephalosporium spp (6,15), ophiobolin G (9) from Aspergillus ustus (5, 7); as well as ceroplastol (10) and related compounds from the scale insect Ceroplastes albolineatus (16).…”

Pericolactines A–C, a New Class of Diterpenoid Alkaloids with Unusual Tetracyclic Skeleton

“…Fusicoccane diterpenoids usually possessing a tricyclic (5-8-5) ring system (such as brassicicenes, cyclooctatins, fusicoccins, and periconicins) are biogenetically generated from geranylgeranyl diphosphate (GGDP) 18 , which are found from various natural sources, including bacteria 19 20 , fungi 21 22 23 24 , liverworts 25 26 , algas 27 , and higher plants 28 29 . Fusicoccane diterpenoids exhibit diverse biological activities, such as plant growth regulating activity (fusicoccins) 30 , lysophospholipase inhibitory activity (cyclooctatin) 31 , antimicrobial activity (periconicins) 32 33 , nitrification inhibitory activity (brachialactone) 34 , cytotoxicity against tumor cells (cotylenins) 35 , inhibiting insulin-stimulated GLUT4 fusion activity (fusicoccins) 35 , and so on.…”