Table 1.
Naturally occurring calanolides, their sources and properties.
| Calanolides | Sources | Physical State | Mol. Formula | Mol. Weight | Optical Rotation [a]D |
UV λmax (MeOH) nm | References |
|---|---|---|---|---|---|---|---|
| Calanolide A (1) | Calophyllum lanigerum var. austrocoriaceum | Oil | C22H26O5 | 370.44 | [a]D +60° (c, 0.7 in CHCl3) | 228, 284 and 325 | [1,9,11,16] |
| Calophyllum brasiliense | [4,17,18] | ||||||
| Calophyllum inophyllum | [6,11] | ||||||
| Calophyllum teysmannii | [19] | ||||||
| Clausena excavata | [10] | ||||||
| 12-O-Acetylcalanolide A (2) | Calophyllum lanigerum var. austrocoriaceum | Oil | C24H28O6 | 412.48 | [a]D +20° (c, 0.5 in CHCl3) | 228, 284 and 325 | [1] |
| 12-O-Methylcalanolide A (3) | Calophyllum lanigerum var. austrocoriaceum | Oil | C23H28O5 | 384.47 | [a]D +32° (c, 0.8 in CHCl3) | 228, 284 and 325 | [1] |
| Calanolide B (4) | Calophyllum lanigerum var. austrocoriaceum | Oil | C22H26O5 | 370.44 | [a]D +8° (c, 1.0 in acetone) | 228, 284 and 325 | [1] |
| Calophyllum brasiliense | [5,17] | ||||||
| Calophyllum teysmannii var. inophylloide | [9] | ||||||
| 12-O-Methyl-calanolide B (5) | Calophyllum lanigerum var. austrocoriaceum | Oil | C23H28O5 | 384.47 | [a]D +34° (c, 0.5 in CHCl3) | 228, 284 and 325 | [1] |
| Calanolide C (6) | Calophyllum brasiliense | Oil | C22H26O5 | 370.44 | - | - | [4,5] |
| Calanolide D (7) | Calophyllum brasiliense | Amorphous solid | C22H24O5 | 368.42 | - | - | [6] |
| Calanolide E (10) | Calophyllum lanigerum var. austrocoriaceum | Amorphous powder | C22H28O6 | 388.50 | [a]D +30° (c, 0.7 in acetone) | - | [1,9,20] |
| Calophyllum membranaceum | [21] | ||||||
| Calophyllum molle | [9] | ||||||
| Calophyllum polyanthum | [22] | ||||||
| Calophyllum teysmannii var. inophylloide | [20] | ||||||
| Calophyllum wallichianum | [15] | ||||||
| Calanolide E1 (11) | Calophyllum lanigerum var. austrocoriaceum | Amorphous powder | C22H28O6 | 388.50 | - | - | [9,20] |
| Calophyllum brasiliense | [9,14] | ||||||
| Calophyllum molle | [9] | ||||||
| Calanolide E2 (12) | Calophyllum lanigerum var. austrocoriaceum | Amorphous powder | C22H28O6 | 388.50 | - | - | [9,20] |
| Calophyllum brasiliense Cambess. | [14] | ||||||
| Calophyllum membranaceum | [21] | ||||||
| Calophyllum molle | [9] | ||||||
| Calophyllum polyanthum | [22,23] | ||||||
| Calophyllum teysmannii var. inophylloide | [9,20] | ||||||
| Calanolide F (13) | Calophyllum lanigerum var. austrocoriaceum | Amorphous powder | C22H26O5 | 370.44 | [a]D −51.5 (c, 0.3 in CHCl3) | 227, 283, 322 | [9,20] |
| Calophyllum teysmannii var. inophylloide | [9,20] | ||||||
| Costatolide (14) [(−)-Calanolide B] |
Calophyllum brasiliense | Crystals (M.p. 181–183°) |
C22H26O5 | 370.44 | [a]D −19.9 (c, 0.42 in CHCl3) | 228, 284 and 325 | [4] |
| Calophyllum costatum | [24] | ||||||
| Calophyllum inophyllum L. | [24] | ||||||
| Calophyllum teysmannii var. inophylloide | [9,19,25] | ||||||
| 7,8-Dihydrocalanolide A (15) | Calophyllum lanigerum var. austrocoriaceum | Amorphous solid | C22H28O5 | 372.46 | Negative optical rotation | - | [25] |
| Dihydrocostatolide (16) | Calophyllum costatum | Amorphous solid | C22H28O5 | 372.46 | - | - | [26] |
| Pseudocalanolide C (8) [incorrectly named as calanolide C (6)] | Calophyllum lanigerum var. austrocoriaceum | Amorphous solid | C22H26O5 | 370.44 | [a]D +68° (c, 0.7 in CHCl3) | - | [1,3,9] |
| Pseudocalanolide D (9) [incorrectly named as calanolide D (7)] |
Calophyllum lanigerum var. austrocoriaceum | Amorphous solid | C22H24O5 | 368.43 | [a]D +60° (c, 0.5 in CHCl3) | - | [1,3] |
| Tomentolide B (17) | Calophyllum tomentosa | Amorphous solid (M.p. 158–160o) |
C22H24O5 | 368.43 | Racemic mixture | - | [1,3,9] |