NMR Spectra of Triterpenoids. II. Hopenes and Migrated Hopenes.

Ageta, Hiroyuki; Shiojima, Kenji; Arai, Yôko; Suzuki, Hideki; Kiyotani, Tamiko

doi:10.1248/cpb.42.39

CHEMICAL & PHARMACEUTICAL BULLETIN

1994

DOI: 10.1248/cpb.42.39

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NMR Spectra of Triterpenoids. II. Hopenes and Migrated Hopenes.

Hiroyuki Ageta¹,

Kenji Shiojima²,

Yôko Arai³

et al.

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Cited by 35 publications

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“…In fact, 3 and 4 are the first examples of oleanane compounds from Adiantum ferns. This paper deals with the isolation and structure elucidation of these new compounds.The constituents of the crude hexane extract of these fronds were purified by various chromatographic techniques (see Experimental) to give nineteen triterpenoids, seventeen of which were known: olean-18-en-3-one (3),3) olean-12-en-3-one (4), 3) ferrn-9(11)-ene (5), 4) ferna-7,9(11)-diene (6), 4) fern-7-ene (7), 4) hop-22(29)-ene (8), 4) filic-3-ene (9), 4) neohop-12-ene (10), 4) adiantoxide (11), 1) adiantone (12), 5) fern-9(11)-en-12-one (13), 5) 28-hydroxyfern-9(11)-ene (14), 1) isoadiantone (15), 6) isoglaucanone (16), 5) hydoxyhopane (17), 5) isoadiantol (18) 5) and hydroxyadiantone (19). …”

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“…3) olean-12-en-3-one (4), 3) ferrn-9(11)-ene (5), 4) ferna-7,9(11)-diene (6), 4) fern-7-ene (7), 4) hop-22(29)-ene (8), 4) filic-3-ene (9), 4) neohop-12-ene (10), 4) adiantoxide (11), 1) adiantone (12), 5) fern-9(11)-en-12-one (13), 5) 28-hydroxyfern-9(11)-ene (14), 1) isoadiantone (15), 6) isoglaucanone (16), 5) hydoxyhopane (17), 5) isoadiantol (18) 5) and hydroxyadiantone (19).…”

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confidence: 99%

“…fern-7-ene (7), 4) hop-22(29)-ene (8), 4) filic-3-ene (9), 4) neohop-12-ene (10), 4) adiantoxide (11), 1) adiantone (12), 5) fern-9(11)-en-12-one (13), 5) 28-hydroxyfern-9(11)-ene (14), 1) isoadiantone (15), 6) isoglaucanone (16), 5) hydoxyhopane (17), 5) isoadiantol (18) 5) and hydroxyadiantone (19). 5) Compound 1 was obtained as colorless needles, and its high resolution HR-MS showed M ϩ at m/z 442.3804 suggesting the molecular formula to be C 30 H 50 O 2 (Calcd, 442.3810).…”

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“…Each eluate was further subjected to silica gel CC and HPLC repeatedly and furnished 1, 2 and the known compounds, viz. 5 (mp 170-171°C, 13 mg), 4) 6 (mp 200-202°C, 0.5 mg), 4) 7 (mp 213-214°C, 3 mg), 4) 8 (mp 211-212°C, 1 mg), 4) 9 (mp 232-234°C, 0.5 mg), 4) 10 (mp 210-212°C, 0.5 mg), 4) 11 (mp 227-229°C, 47 mg), 1) 12 (mp 229-231°C, 90 mg), 5) 13 (mp 229-231°C, 1 mg), 5) 14 (mp 159-161°C, 4 mg), 1) 15 (mp 236-237°C, 7 mg), 5) 16 (mp 243-245°C, 4 mg), 5) 17 (mp 253-255°C, 1 mg), 4) 18 (mp 213-215°C, 20 mg) 5) and 19 (trace).…”

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Fern Constituents: Triterpenoids from Adiantum capillus-veneris.

Nakane

Maeda

Ebihara

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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In preceding papers of this series, 1,2) we reported the isolation of twenty-two triterpenoids, including nine new compounds from the fresh fronds of Adiantum capillus-veneris L. (Adiantaceae) collected in Japan. Further investigation of A. capillus-veneris L. collected in China and Egypt has resulted in the isolation of two new triterpenoids; viz. 4a-hydroxyfilican-3-one (1) and fern-9(11)-en-12b-ol (2) of Chinese origin, and two oleanane triterpenoids; olean-12-en-3-one (3) and olean-18-en-3-one (4) of Egyptian origin (Chart 1). In fact, 3 and 4 are the first examples of oleanane compounds from Adiantum ferns. This paper deals with the isolation and structure elucidation of these new compounds.The constituents of the crude hexane extract of these fronds were purified by various chromatographic techniques (see Experimental) to give nineteen triterpenoids, seventeen of which were known: olean-18-en-3-one (3),3) olean-12-en-3-one (4), 3) ferrn-9(11)-ene (5), 4) ferna-7,9(11)-diene (6), 4) fern-7-ene (7), 4) hop-22(29)-ene (8), 4) filic-3-ene (9), 4) neohop-12-ene (10), 4) adiantoxide (11), 1) adiantone (12), 5) fern-9(11)-en-12-one (13), 5) 28-hydroxyfern-9(11)-ene (14), 1) isoadiantone (15), 6) isoglaucanone (16), 5) hydoxyhopane (17), 5) isoadiantol (18) 5) and hydroxyadiantone (19). 5)Compound 1 was obtained as colorless needles, and its high resolution HR-MS showed M ϩ at m/z 442.3804 suggesting the molecular formula to be C 30 H 50 O 2 (Calcd, 442.3810). Its IR spectrum indicated the presence of a hydroxyl and a carbonyl group. The 1 H-NMR spectrum of 1 displayed signals for six tertiary and two secondary methyl groups, and the chemical shifts of methyl protons (H-25-H-30) resembled those of filican-3-one (20) ( Table 1). The 13 C chemical shifts of 1 were also very close to those of 20 (Table 2), except for those of C-2, C-4, C-5, C-6 and C-24. The large down field shifts of C-4 by 22.8 ppm suggested that the hydroxyl group of 1 was located at C-4.The heteronuclear multiple bond correlation (HMBC) spectrum of 1 also fully corroborated the above observation (Fig. 1) (25), and 191 (c) (27) (Chart 2) which also supported the assigned structure. The orientation of the hydroxyl group was deduced from the nuclear Overhauser enhancement spectroscopy (NOESY) spectrum of 1, which exhibited NOE correlations between the H 3 -23 and b-oriented H 3 -24, H 3 -24 and b-oriented H 3 -25, H 3 -25 and H 3 -26, and H 3 -27 and a-oriented H 3 -28 (Fig. 2), and therefore the OH group at C-4 must be a-oriented. Thus, the structure of 1 was established as 4a-hydroxyfilican-3-one.Compound 2 was obtained as a colorless needles, and its IR spectrum suggested the presence of hydroxyl group in the molecule. Its molecular formula was deduced to be C 30 (44) and 134 (e) (79) (Chart 2) in its MS indicated that 2 is a fernene derivative with a hydroxyl group at ring A, B or C of the molecule. The 1 H-NMR spectrum of 2 indicated the presence of six tertiary methyl groups, two secondary methyl groups, one trisubstituted vinylic methine ...

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Fern Constituents: Triterpenoids from Adiantum capillus-veneris.

Nakane

Maeda

Ebihara

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…1,8) But the chemical shifts of C-17 to C-22 and C-28 to C-30 in the ring E moiety differed from those of 9 and pteron-14-ene, migrated hopane triterpenoid. 16) Therefore 1 might be a migrated lupane triterpenoid with D 14 double bond rather than a migrated hopane triterpenoid. The fragment ions in the low resolution (LR) MS at m/z 344, 257 and 204 ( Fig.…”

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Composite Constituent: Lactucenyl Acetate, a Novel Migrated Lupane Triterpenoid from Lactuca indica Revision of Structure of Tarolupenyl Acetate

Shinozaki

Nakane

Onodera

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Migrated Hopene Synthases from Colysis pothifolia and Identification of a Migration Switch Controlling the Number of 1,2‐Hydride and Methyl Shifts

et al. 2015

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Ferns are known to produce triterpenes, derived from squalene, that are synthesized by squalene cyclases (SCs). Among these, Colysis species produce onoceroids, the bis-cyclic skeleton of which can be cyclized from both termini of squalene. To gain insight into the molecular basis of triterpene structural diversity, cDNA cloning of SCs from C. elliptica and C. pothifolia was performed; this leads to the isolation of five SC cDNAs. Functional analysis of these clones revealed their enzymatic products to be hop-22(29)-ene, α-polypodatetraene, and hop-17(21)-ene. One of these clones (CPF) is a transcribed pseudogene with a 22-nucleotide deletion causing a nonsense mutation. To predict the inherent function of CPF, we constructed an insertion mutant of CPF that successfully converted inert CPF to the active SC, the product of which is fern-9(11)-ene. Subsequent mutations identified active-site residues that control the number of 1,2-hydride and methyl shifts.

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NMR Spectra of Triterpenoids. II. Hopenes and Migrated Hopenes.

Cited by 35 publications

References 0 publications

Fern Constituents: Triterpenoids from Adiantum capillus-veneris.

Fern Constituents: Triterpenoids from Adiantum capillus-veneris.

Composite Constituent: Lactucenyl Acetate, a Novel Migrated Lupane Triterpenoid from Lactuca indica Revision of Structure of Tarolupenyl Acetate

Migrated Hopene Synthases from Colysis pothifolia and Identification of a Migration Switch Controlling the Number of 1,2‐Hydride and Methyl Shifts

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