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DOI: 10.1055/s-0043-1775429
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Natural Products and Bioactive Small Molecules

Novel 4,5-seco-Abietane-Type Diterpenes from Salvia prattii

Yan-Ling Li‡
,
Fei-Fei Xiong‡
,
Yu Zhou‡
,
Fan Xia∗
,
Gang Xu∗
We thank the National Natural Science Foundation of China (32070392 and 82104041), the Yunnan Fundamental Research Projects (202301AU070029 and 202401AT070198), and DR Plant for financial support.
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Abstract

Eight new 4,5-seco-abietane-type diterpenes, salpratones B–I, along with two analogues, featuring diverse 6/5/6, 6/6/6, 6/6/7, and 6/6/8 ring systems, were isolated from Salvia prattii. Notably, salpratone B is the first example of a 4,5;13,14-bis-seco-abietane diterpene characteristic with a rare rearranged 6/5/6 tricyclic core skeleton. Their structures were determined by comprehensive NMR spectroscopy, single-crystal X-ray diffraction, and electronic circular dichroism. Moreover, salpratones B–D were resolved into optically pure enantiomers. Partial diterpenes were evaluated for their in vitro anticoagulant activities. While salpratones B, E, F can weakly prolong the clotting times of human plasma in the activated partial thromboplastin time (APTT) assays with concentrations of 100 μM, showing no appreciable anticoagulant activities.

Key words

Salvia prattii - 4,5-seco-abietane-type diterpene - anticoagulant activity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775429. Included are: general experimental procedures; detailed extraction and isolation process; detailed crystal data for 1–4; the details of ECD calculation for compounds 1–3; anticoagulant activity; the original 1D/2D NMR, and HRMS spectra for compounds 1–10.
  • Supporting Information


Publication History

Received: 26 October 2024

Accepted after revision: 29 November 2024

Article published online:
23 January 2025

© 2025. Thieme. All rights reserved

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  • 22 Salpratone B (1) Colorless crystals; mp 174–176 °C. UV (MeOH): λmax (log ε): 200 (4.69), 248 (2.31), 266 (2.63) nm. IR (KBr): νmax = 3397, 3339, 2967, 2919, 1709, 1469, 1384, 1194, 1057, 914, 822 cm–1. HRMS (ESI): m/z calcd for C20H28O5Na: 371.1829; found: 371.1837 [M + Na]+. [α]D 21  + 17  (c  0.24,  MeOH)  for  (+)-1;  [α]D 21 –20 (c  0.24,  MeOH) for (–)-1. CD (0.00039 M, MeOH): λmax (Δε): 195 (+8.25), 201 (+15.33), 233 (–3.46), 300 (+1.07) nm for (+)-1; CD (0.00036 M, MeOH): λmax (Δε): 195 (–7.73), 201 (–13.17), 233 (+4.90), 300 (–0.15) nm for (–)-1. Salpratone C (2) Colorless crystals; mp 96–97 °C. UV (MeOH): λmax (log ε): 203 (4.33), 242 (4.20), 280 (3.22), 334 (3.67) nm. IR (KBr): νmax = 3441, 2963, 2927, 1632, 1383, 1046, 581 cm–1. HRMS (ESI): m/z calcd for C20H26O3Na: 337.1774; found: 337.1780 [M + Na]+. [α]D 21 +2.2 (c 0.12, MeOH) for (+)-2; [α]D 21 –32.2 (c 0.12, MeOH) for (–)-2. CD (0.00086 M, MeOH): λmax (Δε): 195 (–9.19), 220 (+8.37), 244 (–4.74), 337 (–2.70), 380 (+1.31) nm for (+)-2. CD (0.00079 M, MeOH): λmax (Δε): 195 (+7.36), 220 (–7.97), 244 (+3.92), 337 (+2.26), 380 (–1.60) nm for (–)-2. Salpratone D (3) Colorless crystals; mp 162–164 °C. UV (MeOH): λmax (log ε): 204 (4.45), 237 (4.02), 265 (3.95), 306 (3.60) nm. IR (KBr): νmax = 3415, 2964, 2938, 1619, 1571, 1361, 1265, 1112, 1026 cm–1. HRMS (ESI): m/z calcd for C20H25O3, 313.1804; found: 313.1803 [M + H]+. ECD (MeOH): λmax (Δε): 195 (–10.78), 208 (–6.51), 213 (–6.81), 237 (–2.37), 253 (–3.46), 282 (+0.74), 320 (+6.84), 360 (+0.09) nm. [α]D 21 +3.6 (c 0.08, MeOH) for (+)-3; [α]D 21 –27.5 (c 0.08, MeOH) for (–)-3. CD (0.00102 M, MeOH): λmax (Δε): 207 (+5.59), 240 (–5.58), 295 (–1.78), 325 (+4.65), 363 (–3.54), 450 (–0.27) nm for (+)-3. CD (0.001 M, MeOH): λmax (Δε): 207 (–6.61), 240 (+6.45), 295 (+1.89), 325 (–5.87), 363 (+3.71), 450 (–0.28) nm for (–)-3. Salpratone E (4) Colorless crystals; mp 197–200 °C; [α]D 19 –104.2 (c 0.03, MeOH). UV (MeOH): λmax (log ε): 197 (4.18), 236 (3.78), 274 (3.19), 322 (3.43) nm. IR (KBr): νmax = 3388, 2960, 2920, 2851, 1683, 1261, 1097, 1029, 802 cm–1. HRMS (ESI): m/z calcd for C20H22O3Na, 333.1461; found: 333.1467 [M + Na]+. Salpratone F (5) Colorless gum; [α]D 20 –75.6 (c 0.05, MeOH). UV (MeOH): λmax (log ε): 197 (4.77), 220 (4.29), 242 (4.55), 269 (3.46), 335 (4.06) nm. IR (KBr): νmax = 3418, 2960, 2927, 1693, 1460, 1383, 1072, 969 cm–1. HRMS (EI): m/z calcd for C21H26O3, 326.1882; found: 326.1883 [M]+. Salpratone G (6) Colorless solid; [α]D 19 –119.7 (c 0.06, MeOH). UV (MeOH): λmax (log ε): 197 (4.57), 221 (4.08), 242 (4.34), 270 (3.23), 335(3.85) nm. IR (KBr): νmax = 3412, 2960, 2925, 2852, 1693, 1462, 1383, 1260, 966, 815 cm–1. HRMS (ESI): m/z calcd for C20H24O3Na, 335.1618; found: 335.1615 [M + Na]+. Salpratone H (7) Colorless gum; UV (MeOH): λmax (log ε): 204 (4.54), 226 (4.39), 265 (3.96), 294 (4.05), 357 (3.98) nm. IR (KBr): νmax = 2961, 2926, 1606, 1563, 1433, 1287, 1136 cm–1. HRMS (EI): m/z calcd for C20H22O2, 294.1620; found: 294.1635 [M]+. Salpratone I (8) Colorless solid; [α]20 DD 20 +460 (c 0.06, MeOH). UV (MeOH): λmax (log ε): 202 (4.64), 2.32 (4.12), 247 (4.22), 271 (3.24), 338 (4.08) nm. IR (KBr): νmax = 3427, 2962, 2930, 1651, 1466, 1386, 1080, 986 cm–1. HRMS (ESI): m/z calcd for C20H26O3Na, 337.1774; found: 337.1779 [M + Na]+. Crystallographic Data Crystallographic data of 1–4 were collected at 100 K on a Bruker APEX DUO diffractometer equipped with an APEX II CCD using Cu Kα radiation. CCDC 2333505 (1), CCDC 2333506 (2), CCDC 2333510 (3), and CCDC 2333511 (4) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures