Anti-AIDS Agents, 9. Suberosol, a New C₃₁ Lanostane-Type Triterpene and Anti-HIV Principle from Polyalthia suberosa

Abstract

A new C31 lanostane-type triterpene, assigned the trivial name suberosol [1], has been isolated from Polyalthia suberosa as an anti-HIV principle. The structure has been characterized as 24-methylenelanost-7,9(11)-diene-3 beta, 15 alpha-diol (suberosol) [1], based on spectroscopic evidence. Compound 1 was found to show anti-HIV replication activity in H9 lymphocyte cells with an EC50 of 3 micrograms/ml.

Constituents ofPolyalthia jucunda. and Their Cytotoxic Effect on Human Cancer Cell Lines

“…Though N-trans-feruloyltyramine (3) and 24-methylenelanosta-7, 9(11)-dien-3-b, 15a-diol (4) have been previously isolated from the plants of the genus Polyalthia (Li et al, 1993;Lue et al, 1998;Tuchinda et al, 2000), 4-hydroxy-4,7-dimethyl-a-tetralone (1) and 4,5-dihydroblumenol A (2) were isolated for the first time from this genus. While 4,5-dihydroblumenol A (2) was first isolated from the aerial part of Perrottetia multiflora Lundell (Gonz a alez et al, 1994) and later from leaves of Helianthus annuus var.…”

“…However, we have no access to the spectroscopic data or to the method of isolation of this compound. Interestingly, except for compound 4, which exhibited an anti-HIV replication activity (Li et al, 1993), these compounds have not been investigated for their biological activity.…”

“…The plants of this genus have been found to afford a variety of secondary metabolites, including aporphine (Hamonnière et al, 1977;Jossang et al, 1984;Yang-Chang et al, 1990;Connolly et al, 1996;Kanokmedhakul et al, 2003), azaanthracene (Tuchinda et al, 2000), azafluorene (Yang-Chang et al, 1990), indolosesquiterpene (Hamonnière et al, 1977;Hocquemiller et al, 1981;Okorie, 1981) and protoberberine (Gonzalez et al, 1997, Chung-Yi et al, 2000Faizi et al, 2003) alkaloids; benzopyran derivatives (Zafra-Polo et al, 1996); clerodane (Kijjoa et al,1989(Kijjoa et al, , 1990(Kijjoa et al, , 1993Ma et al, 1994;Hao et al, 1995;Hara et al, 1995), halimane (Hara et al, 1995;Chung-Yi et al, 2000), and labdane diterpenes (Richomme et al, 1991); diynoic acids (Kanokmedhakul et al, 1998;Tuchinda et al, 2001); N-cinnamoyltyramine (Tuchinda et al, 2001) and lanostane-type triterpenes (Li et al, 1993;Lue et al, 1998), and some of these compounds have been found to exhibit interesting biological activity. Whereas some of the aporphine alkaloids and clerodane diterpenes exhibited a cytotoxic effect on human cancer cell lines (Yang-Chang et al, 1990;Ma et al, 1994), the labdane diterpene was found to possess leishmanicidal activity (Richomme et al, 1991).…”

“…Interestingly, the C31 lanostane-type triterpene suberosol and the azaanthracene alkaloid kalasinamide, isolated from Polyalthia suberosa (Roxb.) Thw., were shown to exhibit anti-HIV replication activity (Li et al, 1993;Tuchinda et al, 2001). On the other hand, the dimeric aporphine alkaloids bidebilines C and D, constituents of the roots of Polyalthia debilis (Piere) Finet & Gagnep, were found to exhibit a moderate antimalarial activity against a multidrug-resistant strain of Plasmodium falciparum (Kanokmedhakul et al, 2003).…”

Inedible mushrooms: a good source of biologically active substances

“…44 So far, these compounds have been shown to possess interesting biological activities, such as anti-inflammatory, 45,46 antimicrobial, 47,48 anti-HIV, 49 and DNA polymerase and DNA topoisomerase inhibitory activity. 50 Investigation on the methanolic extract of the Japanese inedible mushroom F. spraguei (Polyporaceae) led to the isolation of five lanostane-type triterpenoids: three new compounds named fomitopsins A ¶C (25)(26)(27), and two known compounds, quercinic acid C (28) and 3α-carboxyacetyl-12β-hydroxyquercinic acid (29) (Fig.…”