Maurizio Bruno

Abietane diterpenoids from the root of Salvia phlomoides

Abstract From the root of Salvia phlomoides three new abietane diterpenoids, demethylcryptojaponol, 14-deoxycoleon U and salviphlomone, have been isolated, besides the previously known diterpenes 8,13-abietadiene, 8,11,13-abietatriene, royleanone, 7α-acetoxyroyleanone, taxodione, taxodone, cryptojaponol and sugiol. The structures of demethylcryptojaponol (11,12-dihydroxy-8,11,13-abietatrien-7-one), 14-deoxycoleon U (6,11,12-trihydroxy-5,8,11,13-abietatetraen-7-one) and salviphlomone (6α,7β-dihydroxy-8,13-abietadiene-11,12-dione) were established by chemical and spectroscopic means.

Neo-clerodane diterpenoids from Scutellaria columnae

Abstract Three new neo-clerodane diterpenoids, scutecolumnins AC, have been isolated from the acetone extract of the aerial parts of Scutellaria columnae subsp. columnae . The structures of these substances were established by spectroscopic means and by comparison with closely related compounds.

Neo-clerodane diterpenoids from Scutellaria alpina subsp. javalambrensis

Abstract Three new neo-clerodane derivatives, scutalpins B–D, were isolated from the acetone extract of the aerial parts of Scutellaria alpina subsp. javalambrensis . The structures of these compounds were established mainly by spectroscopic means as (11 S )-11,19-diacetoxy-4α,18-epoxy-8β-hydroxy-6α-tigloyloxy-13-neo-cleroden-15,16-olide (scutalpin B), (11 S )-19-acetoxy-4α,18-epoxy-8β,11-dihydroxy-6α-tigloyloxy-13-neo-cleroden-l5,16-olide (scutalpin C) and (13 S )-11β,19-diacetoxy-4α,18;8β,13-diepoxy-6α-tigloyloxy-neo-clerodan-15,16-olide (scutalpin D).

Two C-10 oxygenated neo-clerodane diterpenoids from Teucrium pestalozzae

Abstract From the aerial parts of Teucrium pestalozzae two new neo -clerodane diterpenoids, teupestalins A and B, have been isolated. The structures of teupestalin A (4α,18;15,16-diepoxy-6β,10β-dihydroxy- neo -cleroda-13(16),14-dien-20, 12 S -olide-3α,19-hemiacetal) and teupestalin B (19-acetoxy-4α,18;15,16-diepoxy-6-oxo- neo -cleroda-13(16),14-dien-20, 12 S -olide-3β,10⊝hemiacetal) were established by spectroscopic means and, in the case of teupestalin A, also by an X-ray diffraction analysis. Teupestalins A and B are the first C-10 oxygenated neo -clerodane derivatives found in plants belonging to the genus Teucrium .

Neo-clerodane diterpenoids from Teucrium pyrenaicum and T. subspinosum

Abstract From the aerial parts of teucrium pyrenaicum two new neo-clerodane diterpenoids, teupyrins A and B, have been isolated. The structures of teupyrin A [3β,12S-diacetoxy-4α,18; 15,16-diepoxy-6-keto-neo-cleroda-13(16),14-diene-20R,19-hemiacetal] and teupyrin B [6α-acetoxy-4α,18; 15,16-diepoxy-3β,12ξ,19-trihydroxy-neo-cleroda-13(16),14-diene] were established mainly by spectroscopic means and, in the case of teupyrin A, by X-ray diffraction analysis. The acetone extract of the aerial parts of T. subspinosum yielded four previously known neo-clerodane diterpenoids: teucvin, teuflin, teucrin H2 and 6α-hydroxyteuscordin.

Neo- and seco-Neo-clerodane diterpenoids from Teucrium gracile and T.fruticans

Abstract Two new neo -clerodane diterpenoids, teugracilins D and E, together with the previously known diterpene 19-acetylteulepicin, have been isolated from Teucrium gracile . The structures of teugracilin D [19-acetoxy-40α, 18;15,16-diepoxy-3β,6α-dihydroxy- neo -cleroda-13(16),14-diene-(20- O -acetyl) -20 R , 12 S -hemiacetal] and teugracilin E [3β,6α,12ξ,19,20-pentaacetoxy-4α,18;15,16-diepoxy- neo -cleroda-13(16),14-diene] were determined on spectroscopic grounds. In addition, reexamination of the diterpene composition of T. fruticans allowed the isolation, for the first time from Teucrium species, of a new seco- neo -clerodane derivative, fruticolide. Its structure, 19-acetoxy-4α,18;15,16-diepoxy-5,6-seco- neo -cleroda-13(16),14-dien-6,1α-olide, was established by spectroscopic means, including an X-ray diffraction analysis.

Teucrolivins D–F, neo-clerodane derivatives from Teucrium oliverianum

Abstract Three new neo-clerodane diterpenoids, teucrolivins D–F, have been isolated from the aerial parts of Teucrium oliverianum. Their structures, 3β,7β,19-triacetoxy-4α,18;15,16-diepoxy-6α-hydroxy-neo-cleroda-13(16),14-diene (teucrolivin D), 3β,19-diacetoxy-4α,18;15,16-diepoxy-6α-hydroxy-neo-cleroda-13(16),14-dien-7-one (teucrolivin E) and 6α,19-diacetoxy-4α,18-epoxy-3-oxo-13,14,15,16-tetranor-neo-clerodan-12,10β-olide teucrolivin F), were established by spectroscopic means.

Neo-clerodane diterpenoids from Teucrium oxylepis subsp. Marianum

Abstract Two new neo -clerodane diterpenoids have been isolated from the aerial parts of Teucrium oxylepis subsp. marianum . Their structures, 4α,18;15,16-diepoxy-6β,12S-dihydroxy- neo -clerado-13(16),14-dien-20,19-olide (teucroxylepin) and 12 S -acetoxy-6β,18; 15,16-diepoxy-4α,6α-dihydroxy- neo -cleroda-13(16),14-dien-20,19-olide (12- O -acetylteugnaphalodin), were established by chemical and spectroscopic means. In addition, 10 already known neo -clerodane diterpenoids were also isolated from the same source.

Neo-clerodane diterpenoids from Teucrium pestalozzae, T. Odontites and T. Microphyllum

Abstract From the aerial parts of Teucrium pestalozzae , T. odontites and T. microphyllum several previously known neo -clerodane diterpenoids have been isolated. In addition, T. pestalozzae yielded two natural diterpenes, 40α,18-epoxy-tafricanin A and 20-oxo-teuflavin, already known as synthetic compounds.

Abietane and 20-nor-abietane diterpenoids from the root of Meriandra benghalensis

Abstract From the root of Meriandra benghalensis four abietane diterpenoids have been isolated. Two of these substances, horminone and cryptotanshinone, were previously known compounds and the other ones were the 12-O-methyl derivative of horminone, found for the first time as natural product, and 17-hydroxycryptotanshinone, a new substance whose structure of 14,16-epoxy-17-hydroxy-20-nor-abieta-5(10),6,8,13-tetraene-11,12-dione was established by spectroscopic means.