.
Pestalafuranone A (1).
Pestalafuranone A (1): colorless oil; UV (CH3OH) λmax 272 (ε 7800), 265 (ε 6600) nm; IR (Neat) νmax 2962, 1748, 1717, 1448, 1364 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 217.0840 [M+Na]+ (calcd for C11H14O3Na, 217.0835).
Pestalafuranone B (2): pale yellow oil; [α]D −16 (c 0.05, CH3OH); UV (CH3OH) λmax 270 (ε 3300) nm; IR (Neat) νmax 3403 (br), 2932, 1749, 1446 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 217.0842 [M+Na]+ (calcd for C11H14O3Na, 217.0835).
Pestalafuranone C (3): pale yellow oil; UV (CH3OH) λmax 265 (ε 6600), 235 (ε 4300) nm; IR (Neat) νmax 2919, 1752, 1717, 1445, 1365 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 219.0998 [M+Na]+ (calcd for C11H16O3Na, 219.0992).
Pestalafuranone D (4): colorless oil; [α]D +32 (c 0.05, CH3OH); UV (CH3OH) λmax 275 (ε 4460) nm; IR (Neat) νmax 2963, 1751, 1450, 1381 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 217.0846 [M+Na]+ (calcd for C11H14O3Na, 217.0835).
Pestalafuranone D (5): colorless oil; [α]D +16 (c 0.05, CH3OH); UV (CH3OH) λmax 275 (ε 6270) nm; IR (Neat) νmax 2931, 1753, 1446, 1346 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 219.0995 [M+Na]+ (calcd for C11H16O3Na, 219.0992).
Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, China
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Pestalafuranone A (1).
Position | 1 a | 2 a | 3 a | 4 a | 5 a |
---|---|---|---|---|---|
5 | 4.65, s | 4.85, s | 4.63, s | 4.78, s | 4.78, d (17) |
4.71, d (17) | |||||
6 | 6.10, d (16) | 6.26, d (16) | 2.45, t (7.5) | 6.24, d (16) | 2.61, t (7.5) |
7 | 6.86, m | 6.97, m | 1.52, m | 6.85, m | 1.55, m |
8 | 1.86, d (7.0) | 1.89, d (6.7) | 0.93, t (7.5) | 1.81, d (6.5) | 0.94, t (7.5) |
9 | 2.70, m | 6.77, d (16) | 2.67, br s | 2.90, dd (15, 3.6) | 2.86, dd (12, 4.0) |
2.65, dd (15, 6.0) | 2.44, dd (12, 7.0) | ||||
10 | 2.70, m | 6.04, dd (16, 7.7) | 2.67, br s | 2.77, m | 2.75, ddd (7.0, 4.0, 2.0) |
11 | 4.52, m | 2.85, dq (4.5, 2.0) | 2.81, dq (7.5, 2.0) | ||
11-OH | 1.75, br s | ||||
12 | 2.18, s | 1.68, d (7.0) | 2.19, s | 1.24, d (4.5) | 0.93, d (7.5) |
Position | 1 a | 2 a | 3 a | 4 a | 5 a | ||||
---|---|---|---|---|---|---|---|---|---|
2 | 172.9, qC | 173.0, qC | 177.5, qC | 173.0, qC | 174.5, qC | ||||
3 | 123.3, qC | 122.7, qC | 127.9, qC | 123.9, qC | 128.7, qC | ||||
4 | 156.6, qC | 149.4, qC | 158.9, qC | 156.3, qC | 158.5, qC | ||||
5 | 70.8, CH2 | 68.6, CH2 | 71.2, CH2 | 71.7, CH2 | 71.8, CH2 | ||||
6 | 118.1, CH | 118.7, CH | 25.6 CH2 | 119.9, CH | 25.6, CH2 | ||||
7 | 133.0, CH | 134.3, CH | 20.6 CH2 | 132.3, CH | 21.4, CH2 | ||||
8 | 19.3, CH3 | 19.6, CH3 | 13.9, CH3 | 17.4, CH3 | 13.9, CH3 | ||||
9 | 20.4, CH2 | 118.6, CH | 21.3, CH2 | 30.2, CH2 | 29.9 CH2 | ||||
10 | 41.0, CH2 | 140.8, CH | 41.3, CH2 | 57.2, CH | 56.8, CH | ||||
11 | 206.1, qC | 68.3, CH | 206.0, qC | 54.7, CH | 54.5, CH | ||||
12 | 29.8, CH3 | 23.5, CH3 | 29.8, CH3 | 19.1, CH3 | 17.2, CH3 |
Extraction and Isolation
The fermented material was freeze-dried and extracted with methyl ethyl ketone (3 × 500 mL), and the organic solvent was evaporated to dryness under vacuum to afford 5.0 g of crude extract. The extract was fractionated by silica gel column chromatography (5 × 40 cm) using CHCl3–CH3OH gradient elution. The fraction (50 mg) that was eluted with 1% MeOH was further separated by semipreparative reversed-phase HPLC (Kramosil C18 column; 10-µm; 10 × 250 mm, 2 mL/min) to afford pestalafuranone B (2; 1.9 mg, tR 15.3 min; 50% MeOH in H2O over 2 min, 50–72% over 10 min, 72–74% over 13 min). The fraction (180 mg) that was eluted with 2% MeOH was then separated by Sephadex LH-20 column chromatography (CH2Cl2–n-C6H14 = 4:1) to afford six fractions. Fraction 3 (60 mg) was successively separated by semipreparative reversed-phase HPLC (32% MeOH in H2O over 2 min, 32–55% over 60 min) afforded pestalafuranones A (1; 1.6 mg, tR 25.7 min), C (3; 6.0 mg, tR 26.6 min), D (4; 1.5 mg, tR 30.0 min), and E (5; 3.5 mg, tR 31.5 min).Pestalafuranone A (1): colorless oil; UV (CH3OH) λmax 272 (ε 7800), 265 (ε 6600) nm; IR (Neat) νmax 2962, 1748, 1717, 1448, 1364 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 217.0840 [M+Na]+ (calcd for C11H14O3Na, 217.0835).
Pestalafuranone B (2): pale yellow oil; [α]D −16 (c 0.05, CH3OH); UV (CH3OH) λmax 270 (ε 3300) nm; IR (Neat) νmax 3403 (br), 2932, 1749, 1446 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 217.0842 [M+Na]+ (calcd for C11H14O3Na, 217.0835).
Pestalafuranone C (3): pale yellow oil; UV (CH3OH) λmax 265 (ε 6600), 235 (ε 4300) nm; IR (Neat) νmax 2919, 1752, 1717, 1445, 1365 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 219.0998 [M+Na]+ (calcd for C11H16O3Na, 219.0992).
Pestalafuranone D (4): colorless oil; [α]D +32 (c 0.05, CH3OH); UV (CH3OH) λmax 275 (ε 4460) nm; IR (Neat) νmax 2963, 1751, 1450, 1381 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 217.0846 [M+Na]+ (calcd for C11H14O3Na, 217.0835).
Pestalafuranone D (5): colorless oil; [α]D +16 (c 0.05, CH3OH); UV (CH3OH) λmax 275 (ε 6270) nm; IR (Neat) νmax 2931, 1753, 1446, 1346 cm−1; 1H- and 13C-NMR data, see Table 1 and Table 2; HRESIMS obsd. m/z 219.0995 [M+Na]+ (calcd for C11H16O3Na, 219.0992).
SEE
Molecules
2012,
17(12),
14015-14021;
doi:10.3390/molecules171214015
Article
New Furanones from the Plant Endophytic Fungus Pestalotiopsis besseyi
1
Key Laboratory of Bioactive Substances
and Resources Utilization of Chinese Herbal Medicine, Ministry of
Education, Institute of Medicinal Plant Development, Chinese Academy of
Medical Sciences and Peking Union Medical College, Beijing 100193, China
2
Graduate School of Chinese Academy of Sciences, Beijing 100086, China
3
Institute of Microbiology, Beijing 100086, China
4
Biotechnology Center of Shandong Academy of Sciences, Jinan 250014, Shandong, China
5
College of Life Science, Shaanxi Normal University, Xi’an 710062, Shaanxi, China
*
Author to whom correspondence should be addressed; Email: Tel.: +86-010-5783-3281; Fax: +86-010-5783-3290.
Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, China
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